LGAC-Alimentos Funcionales y Nutracéuticos (AFyN)

La línea de investigación de Alimentos Funcionales y Nutracéuticos tiene como objetivo el identificar y purificar principios activos en productos naturales, desarrollando con la aplicación de nuevas tecnologías, nutracéuticos, alimentos y bebidas funcionales de relevancia para la salud, demostrando su eficacia con estudios de biología celular, biología molecular y estudios preclínicos para facilitar el tránsito hacia la evaluación clínica. La línea de investigación en su origen fue constituida por los profesores investigadores: Dr. José Alberto Gallegos Infante, Dra. Nuria Elizabeth Rocha Guzmán y el Dr. Rubén Francisco González Laredo. En años recientes se ha sumado al grupo, fortaleciéndolo, la Dra. Martha Rocío Moreno Jiménez. El perfil académico, especialidad y experiencia de los integrantes es diverso pero complementario, ya que va de la Fisicoquímica de Alimentos, hasta la Biología Molecular y Celular, pasando por la Química de Productos Naturales. Por lo anterior la integración de los mencionados se ha dado de manera natural, su sinergia de trabajo ha sido virtuosa, siendo un ejemplo de trabajo en equipo a nivel local y nacional, además de promover múltiples colaboraciones a nivel nacional e internacional. En el caso de publicaciones científicas, de 2013 a la fecha se han publicado un total de 49 artículos de investigación por la totalidad de los integrantes de la LGAC. PRODUCCIÓN ASOCIADA A LOS PTCMIEMBROS DE LA LGAC ALIMENTOS FUNCIONALES Y NUTRACÉUTICOS. ALIMENTOS FUNCIONALES Y NUTRACÉUTICOS

1 Moreno-Jiménez, M. R., Rocha-Guzmán, N. E., Rutiaga-Quiñones, J. G., Medrano-Núñez, D., Rojas-Contreras, J. A., & Alberto, R. F. G. L. J. (2018). Polyphenolic Profile, Sugar Consumption and Organic Acids Generation along Fermentation of Infusions from Guava (Pisidium guajava) by the Kombucha Consortium. Recent Research in Science and Technology, 16-22. 2 Guillén-Román, C. J., Guevara-González, R. G., Rocha-Guzmán, N. E., Mercado-Luna, A., & Pérez-Pérez, M. C. I. (2018). Effect of nitrogen privation on the phenolics contents, antioxidant and antibacterial activities in Moringa oleifera leaves. Industrial Crops and Products, 114, 45-51. 3 Gamboa-Gómez, C. I., Simental-Mendía, L. E., González-Laredo, R. F., Alcantar-Orozco, E. J., Monserrat-Juarez, V. H., Ramírez-España, J. C., ... & Rocha-Guzmán, N. E. (2017). In vitro and in vivo assessment of anti-hyperglycemic and antioxidant effects of Oak leaves (Quercus convallata and Quercus arizonica) infusions and fermented beverages. Food Research International, 102, 690-699. 4 García-Villalba, R., Espín, J. C., Tomás-Barberán, F. A., & Rocha-Guzmán, N. E. (2017). Comprehensive characterization by LC-DAD-MS/MS of the phenolic composition of seven Quercus leaf teas. Journal of Food Composition and Analysis, 63, 38-46. 5 Ruiz-Rodríguez, M. A., Vedani, A., Flores-Mireles, A. L., Cháirez-Ramírez, M. H., Gallegos-Infante, J. A., & González- Laredo, R. F. (2017). In silico prediction of the toxic potential of lupeol. Chemical research in toxicology, 30(8), 1562- 1571. 6 Pérez-Beltrán, Y. E., Becerra-Verdín, E. M., Sáyago-Ayerdi, S. G., Rocha-Guzmán, N. E., García-López, E. G., Castañeda-Martínez, A., ... & Montalvo-González, E. (2017). Nutritional characteristics and bioactive compound content of guava purees and their effect on biochemical markers of hyperglycemic and hypercholesterolemic rats. Journal of Functional Foods, 35, 447-457. 7 Minjares-Fuentes, R., Rodríguez-González, V. M., González-Laredo, R. F., Eim, V., González-Centeno, M. R., & Femenia, A. (2017). Effect of different drying procedures on the bioactive polysaccharide acemannan from Aloe vera (Aloe barbadensis Miller). Carbohydrate polymers, 168, 327-336. 8 Fregoso-Madueño, J. N., Goche-Télles, J. R., Rutiaga-Quiñones, J. G., González-Laredo, R. F., Bocanegra-Salazar, M., & Chávez-Simental, J. A. (2017). Alternative uses of sawmill industry waste. Revista Chapingo. Serie Ciencias Forestales y del Ambiente, 23(2). 9 Rosales-Castro, M., González-Laredo, R. F., Rivas-Arreola, M. J., & Karchesy, J. (2017). Chemical analysis of polyphenols with antioxidant capacity from pinus durangensis bark. Journal of Wood Chemistry and Technology, 37(5), 393-404. 10 Vázquez-Cabral, B.D., Larrosa-Pérez, M., Gallegos-Infante, J.A., Moreno-Jiménez, M.R., González-Laredo, R.F., Rutiaga-Quiñones, J.G., Gamboa-Gomez C.I., Rocha-Guzmán, N.E. (2017) Oak Kombucha protects againts oxidative stress and inflammatory processes. Chemico-Biological Interaction272 1-9 11 D. Jasso de Rodríguez, D.A. Carrillo-Lomelí, N.E. Rocha-Guzmán, M.R. Moreno-Jiménez, R. Rodríguez-García, M.L.V. Díaz-Jiménez, M.L. Flores-López, J.A. Villarreal-Quintanilla. (2017). Antioxidant, anti-inflammatory and apoptotic effects of Flourensia microphylla on HT-29 colon cancer cells. Industrial Crops and Products. http://dx.doi.org/10.1016/j.indcrop.2017.03.034 12 Breglia, Raffaella; Ruiz-Rodríguez M; Vitriolo, Alessandro; González-Laredo RF; De Gioia, Luca; Greco, Claudio; Bruschi, Maurizio, ( 2017)Theoretical insights into [NiFe]-hydrogenases oxidation resulting in a slowly reactivating inactive state, JBIC Journal of Biological Inorganic Chemistry, Vol.22, Pag.137-151. 13 D. Jasso De Rodríguez, L.C. García-Hernández, N.E. Rocha-Guzmán, M.R. Moreno-Jiménez, R. Rodríguez-García, M.L.V. Díaz-Jiménez, M.L. Flores-López, J.A. Villarreal-Quintanilla, F.M. Peña-Ramos, D.A. Carrillo-Lomelí. 2017. Hypoglycemic and anti-inflammatory effects of Psacalium paucicapitatum corms infusions. http://dx.doi.org/10.1016/j.indcrop.2017.04.022 14 Cháirez-Ramírez M.H., Moreno-Jiménez M.R., González-Laredo R.F., Gallegos-Infante J.A., Rocha-Guzmán N.E. (2016). Lupane-type triterpenes and their anti-cancer activities against most common malignant tumors: A review. EXCLI Journal. 15. 758-771. 15 Díaz-Rivas J.O., Rocha-Guzmán N.E., Gallegos-Infante J.A., Moreno-Jiménez M.R., González-Laredo R.F. (2016). Gastroprotective activities of Buddleja scordioides – Role of polyphenols against inflammation. Journal of chemical biology & therapeutics. 1(2), 1-8. 16 Gamboa-Gómez C.I., González-Laredo R.F., Gallegos-Infante J.A., Larrosa-Pérez M., Moreno-Jimenez M.R., Flores- Rueda A.G., Rocha-Guzmán N.E. (2016). Antioxidant and angiotensin-converting enzyme inhibitory activity of Eucalyptus camaldulensis and Litsea glaucescens infusions fermented with Kombucha Consortium. Food Technol. Biotechnol. 54(3) 367-374. 17 Vázquez-Cabral B.D., Valdez-Fragoso A., Rocha-Guzmán N.E., Moreno-Jiménez M.R., González-Laredo R.F., Morales- Martínez P.S., Rojas-Contreras J.A., Mujica-Paz H., Gallegos-Infante J.A. (2016). Effect of pulsed electric field (PEF)- treated kombucha analogues from Quercus obtusata infusions on bioactive and microorganisms. Innovative Food Science & Emerging Technologies. 34. 171-179. 18 Mendoza-Sánchez M.M., Guevara-González R.M., Castaño-Tostado E., Mercado-Silva E.M., Acosta-Gallegos J.A., Rocha-Guzmán N.E., Reynoso-Camacho R. (2016). Effect of chemical stress on germination of cv Dalia bean (Phaseolus vulgaris L) as an alternative to increase antioxidant and nutraceutical compounds in sprouts. Food Chemistry. 212, 128 – 137. 19 Rosales-Castro M., González-Laredo R.F., Rocha-Guzmán N.E., Gallegos-Infante J.A., Peralta-Cruz J., Karchesy J.J. (2016). Evaluación química y capacidad antioxidante de extractos polifenólicos decortezas. 15(3). 87 - 105. 20 Gamboa-Gómez C.I., Muñoz-Martínez A., Rocha-Guzmán N.E., Gallegos-Infante J.A., Moreno-Jiménez M.R., González- Herrera S.M., Soto-Cruz N.O., González-Laredo R.F. (2016). Changues in phytochemical and antioxidant potential of Tempeh common bean flour from two selected cultivars influenced by temperature and fermentation time. Journal of food processing and preservation. 40. 270 – 278. 21 Medina-Torres L., Calderas F., Minjares R., Femenia A., Sanchez-Olivares G., Gonzalez-Laredo R.F., Santiago-Adame R., Ramirez-Nuñez D.M., Rodríguez-Ramírez J., Manero O. (2016) Structure preservation of Aloe vera (barbadensis Miller) mucilage in a spray drying process. LWT - Food Science and Technology. 66. 93-100. 22 Minjares-Fuentes R., Femenia A., Comas-Serra F., Rosselló C., Rodríguez-Gonzá lez V.M., Gonzá lez-Laredo R.F., Gallegos-Infante J.A., Medina-Torres L. (2016). Effect of different drying procedures on physicochemical properties and flow behavior of Aloe vera (Aloe barbadensis Miller) gel. LWT - Food Science and Technology. 74. 378-386. 23 Medina-Torres L., Santiago-Adame R., Calderas F., Gallegos-Infante J.A., González-Laredo R.F., Rocha-Guzmán N.E., Núñez-Ramírez D.M., Bernard-Bernard M.J., Manero O. (2016). Microencapsulation by spray drying of laurel infusions (Litsea glaucescens) with maltodextrin. Industrial Crops and Products. 90. 1 – 8. 24 Santiago-Adame R., Medina-Torres L., Gallegos-Infante J.A., Calderas F., González-Laredo R.F., Rocha-Guzmán N.E., Ochoa-Martínez L.A., Bernad-Bernad M.J. (2016). Spray drying-microencapsulation of cinnamon infusions (Cinnamomum zeylanicum) with maltodextrin. LWT-Food Science and Technology. 64(2) 571-577. 25 Blanca D. Vázquez-Cabral; Martha R. Moreno-Jiménez; Nuria E. Rocha-Guzmán; José A. Gallegos-Infante; Silvia M. González-Herrera; Claudia I. Gamboa-Gómez; Rubén F. González-Laredo (2016). Mexican oaks as a potential non- timber resource for Kombucha beverages. Revista Chapingo Serie Ciencias Forestales y del Ambiente, 22(1), 73-86. 26 Cháirez-Ramírez, M.H., Sánchez-Burgos, J.A., Gomes C., Moreno-Jiménez, M.R., González-Laredo, R.F., Bernad- Bernad, M. J., Medina-Torres, L., Ramírez-Mares, M.V., Gallegos-Infante, J.A., Rocha-Guzmán, N.E. (2015). Morphological and release characterization of nanoparticles formulated with poly (dl-lactide-co-glycolide) (PLGA) and lupeol: In vitro permeability and modulator effect on NF-κβ in CaCo-2 cell system stimulated with TNFα. Food and Chemical Toxicology. 85. 2 – 9 27 Sánchez-Burgos J.A., Ramírez-Mares M.V., Gallegos-Infante J.A., González-Laredo R.F., Moreno-Jiménez M.R., Cháirez-Ramírez M.H., Medina-Torres L., Rocha-Guzmán N.E. (2015). Isolation of Lupeol from Species of White Oak and their anti-inflammatory activity. Industrial Crops & Products. 77. 827-832. 28 Herrera-Carrera E., Moreno-Jiménez M.R., Rocha-Guzmán N.E., Gallegos-Infante J.A., Díaz-Rivas J.O., Gamboa- Gómez C.I., González-Laredo R.F. (2015). Phenolic composition of selected herbal infusions and their anti- inflammatoty effect on a colonic model in vitro in HT-29 cells. Cogent Food & Agriculture. 1. 2-15. 29 Rosales-Castro M., Honorato-Salazar J.A., Reyes-Navarrete M.G., González-Laredo R.F. (2015). Antioxidant phenolic compounds of ethanolic and aqueous extracts from pink cedar (Acrocarpus fraxinifolius Whight & Arn.) bark at two tree ages. Journal of Wood Chemistry and Technology 35(4). 270-279. 30 Moreno-Jiménez M.R., Trujillo-Esquivel F., Gallegos-Corona M.A., Reynoso-Camacho R., González-Laredo R.F., Gallegos-Infante J.A., Rocha-Guzmán N.E., Ramos-Gomez M. (2015). Antioxidant, anti-inflammatory and anticarcinogenic activities of edible red oak (Quercus spp.) infusions in rat colon carcinogenesis induced by 1,2- dimethylhydrazine. Food and Chemical Toxicology. 80. 144-153. 31 Narváez-Flores M., Sá nchez-Madrigal M.A., Quintero-Ramos A., Paredes-Lizá rraga M.A., Gonzá lez-Laredo R.F., Ruiz- Gutié rrez M.G., Piñó n-Castillo H.A., Melé ndez-Pizarro C.O. (2015) Ultrasound assisted extraction modeling of fructans from agave (Agave tequilana Weber var. Azul) at different temperatures and ultrasound powers. Food and Bioproducts Processing. 96. 232–239. 32 Gamboa-Gómez C.I., Rocha-Guzmán N.E., Gallegos-Infante J.A., Moreno-Jiménez M.R., Vázquez-Cabral B.D., González-Laredo R.F. (2015). Plants with potential use on obesity and its complications. EXCLI Journal. 14. 809- 831. 33 Díaz-Rivas J.O., Herrera-Carrera E., Gallegos-Infante J.A., Rocha-Guzmán N.E., González-Laredo R.F., Moreno- Jiménez M.R., Ramos-Gómez M., Reynoso-Camacho R., Larrosa-Pérez M., Gallegos-Corona M.A. (2015). Gastroprotective potential of Buddleja scordioides Kunth Scrophulariaceae infusions; effects into the modulation of antioxidant enzymes and inflammation markers in an in vivo model. Journal of Ethnopharmacology 169. 280–286. 34 Pérez-Ramírez I.F., Castaño-Tostado E., Rocha-Guzmán N.E., Ramírez-de León J.A., and Reynoso-Camacho R. (2015). Effect of stevia and citric acid on the stability of phenolic compounds and in vitro antioxidant and antidiabetic capacity of a roselle (Hibiscus sabdariffa L.) beverage. Food Chemistry 172, 885-892. 35 Camarena-Tello J.C., Rocha-Guzmán N.E., Gallegos-Infante J.A., González-Laredo R.F., Pedraza-Bucio F.E., López- Albarrán P., Herrera-Bucio R., Rutiaga-Quiñones J.G., (2015). Chemical composition of biomass generated in the Guava tree pruning. EXCLI Journal. 14. 204-212. 36 Moreno-Jiménez M.R., Cervantes-Cardoza V., Gallegos-Infante J.A., González-Laredo R.F., Estrella I., García-Gasca T. De J., Herrera-Carrera E., Díaz-Rivas O., Rocha-Guzmán N.E. (2015). Phenolic composition changes of processed common beans: their antioxidant and anti-inflammatory effect in intestinal cancer cells. Food Research International. 76. 79-85. 37 González-Laredo R.F., Rosales-Castro M ., Rocha-Guzmán N.E., Gallegos-Infante JA, Moreno-Jiménez M.R., Karchesy J.J. (2015). Wood preservation using natural products. Madera y Bosques 21(num. esp.):63-76. 38 Figueroa-Pérez M., Rocha-Guzmán N., Pérez-Ramírez I., Mercado-Silva E., Reynoso-Camacho R. (2014). Metabolite profile, antioxidant capacity, and inhibition of digestive enzymes in infusions of peppermint (Mentha piperita) grown under drought stress. Journal of Agricultural and Food Chemistry. 62. 12027-12033. 39 Figueroa-Pérez M.G., Rocha-Guzmán N.E., Mercado-Silva E., Loarca-Piña G., Reynoso-Camacho R. (2014). Effect of chemical elicitors on peppermint (Mentha piperita) plants and their impact on the metabolite 40 Vázquez-Cabral B.D., González-Herrera S.M., González-Laredo R.F., Moreno-Jiménez M.R., Córdova-Moreno I.T., Gallegos-Infante J.A., Rocha-Guzmán N.E. (2014). Chemical and sensory evaluation of a functional beverage obtained from infusions of oak leaves (Quercus resinosa) inoculated with the Kombucha consortium at different processing conditions. Nutrafoods. 13. 169-178. 41 Arce-Arce E.,Gallegos-Infante J.A., Rocha-Guzmán, N.E., González-Laredo R.F., Moreno-Jiménez R., Figueroa- Cárdenas J.D., Montelongo-Montelongo A.N. (2014). Effect of infrared heating on the physicochemical properties of common bean (Phaseolus vulgaris L.) flour. CyTA-Journal of Food, 12(3): 242-248. 42 Cervantes-Martínez C.V., Medina-Torres L., González-Laredo R.F., Calderas F., Sánchez-Olivares G, Herrera- Valencia EE, Gallegos Infante J.A., Rocha-Guzmán N.E., Rodríguez-Ramírez J. (2014). Study of spray drying of the Aloe vera mucilage (Aloe vera barbadensis Miller) as a function of its rheological properties. LWT Food Science and Technology, 55(2): 426–435 43 Rocha-Amador O.G., Gallegos-Infante J.A., Huang Qingrong, Rocha-Guzmán N.E., Moreno-Jiménez M.R., González- Laredo R.F. (2014). Influence of Commercial Saturated Monoglyceride, Mono-/Diglycerides Mixtures, Vegetable Oil, Stirring Speed, and Temperature on the Physical Properties of Organogels. International Journal of Food Science, Article ID 513641, 8pp. 44 Sánchez-Burgos J.A., Ramírez-Mares M.V., Larrosa M.M., Gallegos-Infante J.A., González-Laredo R.F., Medina Torres L., Rocha-Guzmán N.E. (2013). Antioxidant, antimicrobial, antitopoisomerase and gastroprotective effect of herbal infusions from four Quercus species. Industrial Crops and Products, 42: 57-62. 45 García-Andrade M., González-Laredo R.F., Rocha-Guzmán N.E., Gallegos-Infante J.A., Rosales-Castro M., Medina- Torres L. (2013). Mesquite leaves (Prosopis laevigata), a natural resource with antioxidant capacity and cardioprotection potential. Industrial Crops and Products, 44: 336–342 46 Gamboa-Gómez C.I., Hernández-Saavedra D., Gallegos-Infante J.A., González-Laredo R.F., Manzocco L., Rocha- Guzmán N.E. (2013). Polyphenolic content and antioxidant activity of leaf extracts from Quercus durifolia, Quercus eduardii, Quercus sideroxyla and Quercus resinosa. Journal of Medicinal Plants Research, 7(35): 2564- 2573. 47 Rocha-Guzmán N.E.,Gallegos-Infante J.A., González-Laredo R.F., Cardoza-Cervantes V. , Reynoso- Camacho R., Ramos-Gomez M., García-Gasca T., De Anda-Salazar A. (2013). Evaluation of culinary quality and antioxidant capacity for Mexican beans (Phaseolus vulgaris L.) canned in pilot plant. International Food Research Journal, 20(3): 1087-1093 48 Gallegos-Infante J.A., Rocha-Guzmán N.E., González-Laredo R.F., García-Casas M.A. (2013). Efecto del procesamiento térmico sobre la capacidad antioxidante de pinole a base de vainas de mezquite(Prosopis laevigata). CyTA – Journal of Food, 11(2): 162-170. 2013. 49 Medina-Torres L., García-Cruz E.E., González-Laredo R.F., Gallegos-Infante J.A., Rocha-Guzmán N.E., Rodríguez- Ramírez J., Calderas F. (2013). Microencapsulation by spray drying of gallic acid with nopal mucilage (Opuntia ficus indica). LWT – Food Science and Technology, 50(2): 642–650.

Recent Research in Science and Technology 2018, 10: 16-22 doi: 10.25081/rrst.2018.10.3399 http://updatepublishing.com/journal/index.php/rrst/

ISSN: 2076-5061

R E G U L A R A R T I C L E

POLYPHENOLIC PROFILE, SUGAR CONSUMPTION AND ORGANIC ACIDS GENERATION ALONG FERMENTATION OF INFUSIONS FROM GUAVA (PISIDIUM GUAJAVA) BY THE KOMBUCHA CONSORTIUM MARTHA ROCÍO MORENO-JIMÉNEZa, NURIA ELIZABETH ROCHA-GUZMÁNa, RUTIAGA-QUIÑONES, JOSÉ GUADALUPEb, DANIELA MEDRANO-NÚÑEZa, JUAN ANTONIO ROJAS-CONTRERASa, RUBÉN FRANCISCO GONZÁLEZ-LAREDOa, JOSÉ ALBERTO GALLEGOS-INFANTEa* aTecNM/Instituto Tecnológico de Durango, Dpto. de Ings. Química y Bioquímica, UPIDET, Blvd. Felipe Pescador 1830 Ote. Col Nueva Vizcaya, 34080 Durango, Dgo, México bFacultad de Ingeniería en Tecnología de la Madera. Universidad Michoacana de San Nicolás de Hidalgo. Apartado Postal 580. 58000 Morelia, Michoacán. México ABSTRACT The kombucha beverage is usually prepared from black tea, with sucrose, inoculated with previously fermented liquid broth and/or tea fungus pellicle, and incubated. Alternative sources have been used for kombucha beverages. Guava leaves have been used for long time as traditional medicine. It is found in many commercially available botanical supplements in form of decoction, milled and used as comprises. They are rich in polyphenolic compounds. Several changes are produced during fermentation of the beverages. The main objective of the present work is to characterize fermentation process of guava leaves infusions by kombucha and studying possible chemical changes in their polyphenolic profile. Infusions from guava leaves were prepared and fermented by the kombucha consortium. The pH, titrable acidity, polyphenolic compounds, sugar consumption, organic acid along the fermentation was made by UPLC-ESI-MS. Kombucha from Camellia sinensis (CS) was made as a control. Higher rate of sucrose consumption was observed for Kombucha made with CS, also, higher production of organic acids (acetic and succinic acid) was observed too. Both behaviors were related to the content of glucose. The flavan-3-ols were diminishing along the fermentation time, with the exception of epigallocatechin in Camellia sinensis, Flavan-3-ol content in Guava leaves was low. Higher content of dicaffeoyl quinnic acid was observed for both systems in special for CS, falling after a maximum peak; minor constituents of hydroxycinnamic acids were stable along the fermentation for both systems. Keywords: Fermentation, Guava leaves, Kombucha, Polyphenols

INTRODUCTION infection, and its tannin content may promote healing. Indigenous people from Southeast Asian countries Guava (Psidium guajava) is a fruit that grows in tropical consumed the fruit to reduce or prevent hypertension and countries. The variety of fruit dictates its shape (i.e. round, to fight influenza infection. In Malaysia, guava leaves are oval, or pear-shaped), diameter (approximately 1–4 in), and color (i.e. pink, white, yellow, salmon, or deep red color) [1]. used in an astringent solution to treat diarrhea and stomach Psidium guajava L. (guava) leaves have been used for a long ache. Researchers have also reported the use of guava leaves time as traditional medicine in form of decoction, milled to expel the placenta during child birth [5]. Other health and used as comprises, etc., currently they are still conditions related to guava use were reviewed by [6] who employed [2]. Guava leaves after drying is suitable as a suggested that different plant constituents, usually the botanical supplement. Several biological activity studies leaves, may exhibit antidiabetic, antimicrobial, showed that guava leaves have important beneficial healthy antidiarrheal, and anti-cough properties. effects as anti-inflammatory, hypoglycemic, antibacterial, Similarly, some in vivo studies have proved the anti- antidiarrheal and antioxidant properties [3-5] indicated inflammatory action of extracts, essential oils, or steam that in India, guava leaves were used to treat skin wounds and alleviate toothaches. distilled components of guava leaf [7, 8]. About studies on its phytochemical profile, several authors report presence of The leaves contain antimicrobial components effective flavonoids, in special, quercetin [9, 10] in guava leaves. In against Staphylococcus aureus that may ward off contrast, the guava leaves fermentation process showed

Received 26 December 2017; Accepted 28 February 2018 *Corresponding Author Jose Alberto Gallegos Infante TecNM/Instituto Tecnológico de Durango, Dpto. de Ings. Química y Bioquímica, UPIDET, Blvd. Felipe Pescador 1830 Ote. Col Nueva Vizcaya, 34080 Durango, Dgo, México Email: [email protected] ©This article is open access and licensed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted, use, distribution and reproduction in any medium, or format for any purpose, even commercially provided the work is properly cited. Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made.

16 ,QGXVWULDO &URSV & 3URGXFWV 114 (2018) 45²51

Contents lists available at ScienceDirect

Industrial Crops & Products

journal homepage: www.elsevier.com/locate/indcrop

Effect of nitrogen privation on the phenolics contents, antioxidant and antibacterial activities in Moringa oleifera leaves Cesiah J. Guillén-Romána, Ramón G. Guevara-Gonzálezb, Nuria E. Rocha-Guzmánc, b a,⁎ Adán Mercado-Luna , Ma. Cristina I. Pérez-Pérez a Instituto Tecnológico de Celaya, Departamento de Ingeniería Bioquímica, Calle Antonio Garcia Cubas 600, 38010 Celaya, Gto, Mexico b Universidad Autónoma de Querétaro, Ingeniería en Biosistemas, Cerro de las Campanas S/N, Colonia las Campanas, Querétaro, Qro, Mexico c Instituto Tecnológico de Durango, Departamento de Ingenierías, Química y Bioquímica, Durango, Dgo, Mexico

A R T I C L E I N F O A B S T R A C T

Keywords: Moringa oleifera has an exceptional composition in nutrients and different medicinal compounds. Phenolic Nitrogen privation compounds present in Moringa plant could prevent chronic non-communicable diseases. An increase in the Plant growth secondary metabolites of Moringa oleifera could improve its functional properties. One possible strategy to in- Antioxidant activity crease functional properties in plants is to cultivate them under fertilizer deficit regimes as elicitation treatment Antimicrobial activity (i.e: nitrogen). The present study aimed to evaluate the effect of four nitrogen levels on the phenolic compounds profiles as well as on plant growth and functional properties in Moringa oleifera leaves. Total phenols and fla- vonoids, antioxidant and bactericidal activities of Moringa oleifera leaves extracts were evaluated. Our results displayed that reduce fertirrigation until 0.7 mg/L of N-NO3 (T0) had a positive impact on total phenols and flavonoids with 355 ± 4.9 μg CA/mg dry extract and 316 ± 8 μg Q/mg dry extract respectively, whereas the fertirrigation with 294.7 mg/L of N-NO3 (T100) It was found only 157 ± 8.1 μg CA/mg dry extract and 54 ± 0.1 μg Q/mg dry extract respectively. The higher values of phenolic content were improved the anti- oxidant activity and antibacterial properties of Moringa oleifera leaves extracts, nevertheless plant growth was affected.

1. Introduction Pacific Islands. In the Americas it is found from southern Florida (USA) to Argentina (Fahey, 2005; Olson, 2010; Kumar, 2013; Lim, 2015; Agricultural research for development over the past decades has Zheng et al., 2016). Particularly in Mexico the distribution of Moringa focused on increasing productivity in order to feed a growing popula- oleifera is in the Pacific coast, from southern Sonora to Chiapas, in- tion and alleviate food shortage (Garcia-Mier et al., 2014; Tálos-ne- cluding the south of the peninsula of Baja California, the south of the behaj et al., 2017). Current agricultural research is focusing on the yield Istmo de Tehuantepec, villages in the area of Infiernillo and in the vi- in the production as well as on the increase of bioactive compounds cinity of Apatzingán, Mezcala, Iguala and Tequesquitengo (Olson and contents (secondary metabolites or phytochemicals). For decades, the Fahey, 2011). Moringa oleifera is recognized as a high producer of decline of non-communicable diseases (NCDs) as neurodegenerative beneficial phytochemicals for pharmaceutical, agricultural and food diseases, heart disease, diabetes, cancer, etc, has been linked to the industries (Gopalakrishnan et al., 2016; Zheng et al., 2016). For Mor- consumption of fruits and vegetables (Awad and De Jager, 2002; Del inga oleifera, several studies have recently been carried out in order to Rio et al., 2013; Garcia-Mier et al., 2014). The latter effect is associated improve extractions to increase yield and quality in phytochemicals for to a wide range of phytochemicals present in fruits and vegetables industrial purposes (Nouman et al., 2016; Fakayode and Ajav, 2016; (Garcia-Mier et al., 2014). The major categories of phytochemicals in- Zheng et al., 2016; Chen et al., 2017). Moreover, several biotechnolo- clude phenolics, carotenoids, isoflavones, flavonoids, indols, lignans, gical strategies have been used to enhance the production of phyto- saponins, monoterpenes, glucosinolates, etc (Crozier and Clifford, chemicals in several plant species (García-Mier et al., 2014). Accumu- 2006; Kurmukov, 2013; Variyar et al., 2014). Moringa oleifera is a plant lation of phytochemicals occurs in plants subjected to biotic and abiotic species originated from India, western Himalaya, and is now widely stresses, because they constitute biochemical defenses to cope with distribute in Southeast Asia, Western Asia, West, East and South Africa, them (Mejía-Teniente et al., 2013). To manage stress conditions in

⁎ Corresponding author. E-mail address: [email protected] (M.C.I. Pérez-Pérez). https://doi.org/10.1016/j.indcrop.2018.01.048 Received 9 March 2017; Received in revised form 15 January 2018; Accepted 19 January 2018 $YDLODEOH RQOLQH 16 )HEUXDU\ 2018 0926-6690/ ‹ 2018 (OVHYLHU %.9. $OO ULJKWV UHVHUYHG.

Subscriber access provided by NEW YORK UNIV Article IN SILICO PREDICTION OF THE TOXIC POTENTIAL OF LUPEOL Manuel Antonio Ruiz-Rodríguez, Angelo Vedani, Ana Lidia Flores-Mireles, Manuel Humberto Chairez-Ramirez, Jose Alberto Gallegos-Infante, and Ruben F. Gonzalez-Laredo Chem. Res. Toxicol., Just Accepted Manuscript • DOI: 10.1021/acs.chemrestox.7b00070 • Publication Date (Web): 27 Jun 2017 Downloaded from http://pubs.acs.org on June 29, 2017

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Journal of Wood Chemistry and Technology

ISSN: 0277-3813 (Print) 1532-2319 (Online) Journal homepage: http://www.tandfonline.com/loi/lwct20

Chemical analysis of polyphenols with antioxidant capacity from pinus durangensis bark

Martha Rosales-Castro, Rubén F. González-Laredo, María José Rivas-Arreola & Joseph Karchesy

To cite this article: Martha Rosales-Castro, Rubén F. González-Laredo, María José Rivas- Arreola & Joseph Karchesy (2017): Chemical analysis of polyphenols with antioxidant capacity from pinus durangensis bark, Journal of Wood Chemistry and Technology, 001: 10.1080/02773813.2017.1310898

To link to this article: http://dx.doi.org/10.1080/02773813.2017.1310898

Published online: 22 May 2017.

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Food Research International

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In vitro and in vivo assessment of anti-hyperglycemic and antioxidant effects of Oak leaves (Quercus convallata and Quercus arizonica) infusions and fermented beverages

Claudia I. Gamboa-Gómeza,b, Luis E. Simental-Mendíab, Rubén F. González-Laredoa, Esteban J. Alcantar-Orozcoa, Victor H. Monserrat-Juareza, Julio C. Ramírez-Españaa, a a a,⁎ Jose Alberto Gallegos-Infante , Martha R. Moreno-Jiménez , Nuria E. Rocha-Guzmán a Instituto Tecnológico de Durango, Felipe Pescador 1830 Ote., 34080 Durango, Dgo., Mexico b Biomedical Research Unit Mexican Social Security Institute, 34067 Durango, Mexico

A R T I C L E I N F O A B S T R A C T

Keywords: The aim of this study was to evaluate the anti-hyperglycemic and antioxidant effects of oak leaves infusions and Fermented beverages fermented beverages from Quercus convallata and Q. arizonica in vitro and in vivo. Female C57BL/6 mice fed with high Kombucha saturated fat and fructose diet-induced obesity were treated with oak leaves beverages (200 μL/per day equivalent Anti-hyperglycemic activity to 15 mg of lyophilized sample/Kg of body weight for infusions and 31 mg of lyophilized sample/Kg of body weight Antioxidant activity for fermented beverages) for 3 months and an oral glucose tolerance test (OGTT) was performed. Blood plasma was Oak leaves obtained for determination of glucose, lipid profile, and oxidative stress markers (ABTS, nitric oxide, and ORAC assays). Insulin resistance was estimated using the product of triglycerides and glucose (TyG). Oak leaves infusions and fermented beverages exhibited exerted inhibition of α-amylase (8–15% and 5–9%, respectively) and α- glucosidase (98% and 99%, respectively) enzymes. After OGTT, the groups treated with either oak leaves infusions or fermented beverages showed lower glucose levels compared with the obesity control group (18%) and a similar glucose tolerance to healthy control group. On long-term evaluation, inter- vention groups showed a significant reduction in fasting glucose concentrations (41–50% for oak leaves infu- sions and 52–66% for fermented beverages) and TyG index (4.2–4.6% for oak leaves infusions and 5.9–7.5% for fermented beverages) compared with the obese control group. Oak leaves infusions and fermented beverages had antioxidant potential in vitro and scavenging activity for radicals such as peroxyl and peroxynitrite anions. Our results suggest anti-hyperglycemic and antioxidant effects of beverages prepared with leaves of Quercus species in vitro and in vivo.

1. Introduction On over-nutrition condition, a large amount of glucose is oxidized during the tricarboxylic cycle, leading to an increased production of Obesity is a highly prevalent metabolic disorder characterized by an electron donors in the mitochondrial electron transport chain. Thus, the excess of visceral adiposity. Furthermore, it has been associated with process of electron donation to molecular oxygen promotes the pro- dyslipidemia, hyperglycemia, insulin resistance, and oxidative stress duction of superoxide ions (Brownlee, 2005). In addition, an excess of through several mechanisms, leading to metabolic syndrome (Alberti et free fatty acids increases the oxidation level in the mitochondria. Both, al., 2009). Regard, oxidative stress is an imbalance of reactive oxygen β-oxidation of fatty acids and oxidation of free fatty acids-derived acetyl species (ROS) and antioxidant defenses. The cells are protected against CoA by the tricarboxylic cycle, produce the same electron donors the excess of ROS by antioxidant enzymes (e.g. catalase, glutathione (NADH and FADH2) as in glucose oxidation; thus, an increased free peroxidase (GPX), superoxide dismutase (SOD), and other anti- fatty acid oxidation results in mitochondrial overproduction of ROS oxidants). However, when ROS overwhelms antioxidant capacity, the (Brownlee, 2005). cell functions are affected by this imbalance (Matsuda & Shimomura, Several studies have reported a correlation between ROS and glu- 2013). cose metabolism disturbances, such as hyperglycemia and insulin

Abbreviations: QCi, Quercus convallata infusion; QCk, Quercus convallata fermented beverage; QAi, Quercus arizonica infusion; QAk, Quercus arizonica fermented beverage ⁎ Corresponding author. E-mail address: [email protected] (N.E. Rocha-Guzmán). http://dx.doi.org/10.1016/j.foodres.2017.09.040 Received 6 June 2017; Received in revised form 14 September 2017; Accepted 17 September 2017 $YDLODEOH RQOLQH 23 6HSWHPEHU 2017 0963-9969/ ‹ 2017 (OVHYLHU /WG. $OO ULJKWV UHVHUYHG. Chemico-Biological Interactions 272 (2017) 1e9

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Chemico-Biological Interactions

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Oak kombucha protects against oxidative stress and inflammatory processes B.D. Va'zquez-Cabral a, M. Larrosa-Pe'rez b, J.A. Gallegos-Infante a, M.R. Moreno-Jime'nez a, R.F. Gonza'lez-Laredo a, J.G. Rutiaga-Quin~ones c, C.I. Gamboa-Go'mez a, a, * N.E. Rocha-Guzma'n a Research Group on Functional Foods and Nutraceuticals, Departamento de Ingenierías Química y Bioquímica, TecNM/Instituto Tecnolo'gico de Durango, Felipe Pescador 1830 Ote., 34080 Durango, Dgo., Mexico b School of Doctoral Studies & Research, European University of Madrid, Calle Tajo, s/n, Villaviciosa de Odo'n, ES-28670 Madrid, Spain c Facultad de Ingeniería en Tecnología de la Madera, Edificio D, Ciudad Universitaria, Universidad Michoacana de San Nicola's de Hidalgo, Av. Fco. J. Múgica S/N. Col. Felicitas de Río, Morelia, Michoaca'n C.P. 58040, Mexico

a r t i c l e i n f o a b s t r a c t

Article history: Black tea infusion is the common substrate for preparing kombucha; however other sources such as oak leaves Received 20 March 2017 infusions can be used for the same purpose. Almost any white oak species have been used for medicinal Received in revised form applications by some ethnic groups in Mexico and could be also suitable for preparing kombucha analogues 27 April 2017 from oak (KAO). The objective of this research was to investigate the antioxidant activity and anti-inflammatory Accepted 1 May 2017 effects of KAO by examining its modulation ability on macrophage- derived TNF-alpha and IL-6. Herbal Available online 3 May 2017 infusions from oak and black tea were fermented by kombucha consortium during seven days at 28 oC.

Chemical composition was determined by LC-ESI-MS/MS. The antioxidant activity of samples against Keywords: oxidative damage caused by H 2O2 in monocytes activated (macrophages) was explored. Additionally, it was Antioxidant fl Kombucha determined the anti-in ammatory activity using lipopolysaccharide (LPS) - stimulated macrophages; in Quercus particular, the nitric oxide (NO), TNF-alpha, and IL-6 production was assessed. Levels of pro-inflammatory Anti-inflammatory cytokines IL-6 and TNF-alpha were signifi- cantly reduced by the sample treatment. Likewise, NO Fermented beverages production was lower in treatment with kom- bucha and KAO compared with LPS-stimulated macrophages. Fermented beverages of oak effectively down-regulated the production of NO, while pro-inflammatory cytokines (TNF-alpha and IL-6) in macrophages were stimulated with LPS. Additionally, phytochemical compounds present in KAO decrease oxidative stress. © 2017 Elsevier B.V. All rights reserved.

1. Introduction floating biofilm of cellulose and the sour liquid broth [4]. Several positive effects have been reported, including gastro protective effect Some fermented foods have transcended their sources to become of the culture broth and probiotic potential of the Kombucha everyday products in more than one continent; fermen- tations microbiome [1,13]. In particular, in the culture broth the main involved in these foods are of enormous complexity, and their study metabolites identified are gluconic and glucuronic acids, glycerol, has provided us a wealth of biotechnology knowledge. An attractive phenolic acids and caffeine; some are associated with beneficial bioprocess consists on the degradation of glucose and fructose effects on health. The two main classes of involved polyphenols are through the fermentation action of a bacterial and yeast consortium flavonoids and phenolic acids. Their chemical and structural mod- called Kombucha [6]. This Kombucha is a fermented beverage that ifications are due to biotransformation and metabolism by the has been traditionally consumed in China for over 2200 years. This kombucha consortium action, and have not been taken into ac- count ancient beverage is composed of two portions: a in previous studies of kombucha analogues obtained from other sources. The biotransformation of flavonoids has been a topic of research due to the interest in explaining the correlation be- tween * Corresponding author. the beneficial properties of flavonoids and the structures of the active E-mail address: [email protected] (N.E. Rocha-Guzm'an). compounds. In Kombucha obtained from black tea, the

http://dx.doi.org/10.1016/j.cbi.2017.05.001 0009-2797/© 2017 Elsevier B.V. All rights reserved. Carbohydrate Polymers 168 (2017) 327–336

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Carbohydrate Polymers

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Effect of different drying procedures on the bioactive polysaccharide acemannan from Aloe vera (Aloe barbadensis Miller) Rafael Minjares Fuentesa, Víctor Manuel Rodríguez Gonzálezb, Rubén Francisco González Laredoc, Valeria Eima, María Reyes González Centenoa, a ∗ Antoni Femenia , a Department of Chemistry, University of the Balearic Islands, Ctra Valldemossa Km 7.5, 07122, Palma de Mallorca, Spain b Facultad de Ciencias Químicas, Universidad Juárez del Estado de Durango, Av. Articulo 123 s/n Fracc Filadelfia, 35010, Gómez Palacio, Dgo, Mexico c Departamento de Ingenierías Química y Bioquímica, TecNM Instituto Tecnológico de Durango, Blvd. Felipe Pescador 1830 Ote., 34080, Durango, Dgo, Mexico

a r t i c l e i n f o a b s t r a c t

Article history: The main effects of different drying procedures: spray , industrial freeze , refractance window and radi Received 8 January 2017 ant zone drying, on acemannan, the main bioactive polysaccharide from Aloe vera gel, were investigated. Received in revised form 17 March 2017 All the drying procedures caused a considerable decrease in the acemannan yield (∼40%). Degradation Accepted 27 March 2017 affected not only the backbone, as indicated by the important losses of (1 → 4) linked mannose units, Available online 29 March 2017 but also the side chains formed by galactose. In addition, methylation analysis suggested the deacetyla tion of mannose units (>60%), which was confirmed by 1 H NMR analysis. Interestingly, all these changes Keywords: were reflected in the functional properties which were severely affected. Thus, water retention capacity Aloe vera Acemannan values from processed samples decreased ∼50%, and a reduction greater than 80% was determined in Drying procedures swelling and fat adsorption capacity values. Therefore, these important modifications should be taken Acetylation into consideration, since not only the functionality but also the physiological effects attributed to many Functional properties Aloe vera based products could also be affected.

© 2017 Elsevier Ltd. All rights reserved.

1. Introduction the Aloe vera (Campestrini, Silveira, Duarte, Koop, & Noseda, 2013; Chokboribal et al., 2015; Ni et al., 2004). Acemannan, the major polysaccharide found in Aloe vera gel, Acemannan is a storage polysaccharide located within the pro is mainly composed of large amounts of partially acetylated man toplast of the parenchymatous cells of the Aloe vera gel, and not nose units (Man >60%), followed by glucose (Glc ∼20%) and, to a a component of the cell walls (Femenia et al., 1999). Interestingly, minor extent, galactose (Gal <10%) (Choi & Chung, 2003; Chow, this polymer has been reported as the main bioactive substance Williamson, Yates, & Goux, 2005; Femenia, Sánchez, Simal, & present in Aloe vera gel, being responsible for most of the benefi Rosselló, 1999; Talmadge et al., 2004). Structurally, the aceman cial properties attributed to Aloe vera (Hamman, 2008; McAnalley, nan polysaccharide, with a molecular weight of around 40–50 kDa, 1993; Reynolds, 1985; Reynolds & Dweck, 1999; t’Hart, van den could be represented by a single chain of í3 (1 → 4) mannose with Berg, Kuis, van Dijk, & Labadie, 1989), such as the reduction in í3 (1 → 4) glucose inserted into the backbone; a (1 → 6) galactose blood glucose, blood pressure and the improvement of lipid profile units may also be found as side chains (Chokboribal et al., 2015; in diabetic patients, among many others (Choudhary, Kochhar, & Chow et al., 2005; Femenia et al., 1999; Talmadge et al., 2004). Sangha, 2011; Pothuraju, Sharma, Onteru, Singh, & Hussain, 2016). The acetyl groups are the unique non sugar functional groups These beneficial effects have been attributed to the high molecular present in acemannan and seem to play a key role not only in the weight fractions of acemannan which are degraded by the intestinal physico chemical properties but also in the biological activity of microbiota to form oligosaccharides that inhibit intestinal glucose absorption (Boban, Nambisan, & Sudhakaran, 2006; Jain, Gupta, & Jain, 2007; Yagi et al., 2001, 2009). Furthermore, several studies have demonstrated that the acetyl groups of acemannan are mainly responsible not only for the interaction of acemannan with other ∗ Corresponding author. biomolecules but also for enabling the transport of other bioac E mail address: [email protected] (A. Femenia).

http://dx.doi.org/10.1016/j.carbpol.2017.03.087 0144 8617/© 2017 Elsevier Ltd. All rights reserved.

Revista Chapingo. Serie Ciencias Forestales y del Ambiente ISSN: 2007-3828 [email protected] Universidad Autónoma Chapingo México

Fregoso-Madueño, Jesús N.; Goche-Télles, José R.; Rutiaga-Quiñones, José G.; González-Laredo, Rubén F.; Bocanegra-Salazar, Melissa; Chávez-Simental, Jorge A. Alternative uses of sawmill industry waste Revista Chapingo. Serie Ciencias Forestales y del Ambiente, vol. XXIII, núm. 2, mayo- agosto, 2017, pp. 243-260 Universidad Autónoma Chapingo Chapingo, México

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Industrial Crops & Products

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Influence of water deficit on the main polysaccharides and the rheological properties of Aloe vera (Aloe barbadensis Miller) mucilage Rafael Minjares-Fuentesa,d, Luis Medina-Torresb, Rubén Francisco González-Laredoc, d a a,⁎ Víctor Manuel Rodríguez-González , Valeria Eim , Antoni Femenia a Department of Chemistry, University of the Balearic Islands, Ctra Valldemossa Km 7.5, 07122, Palma de Mallorca, Spain b Facultad de Química, Universidad Nacional Autónoma de México, 04510 México D.F., Mexico c Departamento de Ingenierías Química y Bioquímica, TecNM-Instituto Tecnológico de Durango, Blvd. Felipe Pescador 1830 Ote., 34080, Durango, Dgo., Mexico d Facultad de Ciencias Químicas, Universidad Juárez del Estado de Durango, Av. Articulo 123 s/n Fracc Filadelfia, 35010, Gómez Palacio, Dgo, Mexico

A R T I C L E I N F O A B S T R A C T

Keywords: The aim of this study was to evaluate the effect of water deficit on the composition of the main polysaccharides and Aloe vera rheological behaviour from Aloe vera (Aloe barbadensis Miller) mucilage. In particular, plants with 0 (D0), 40 Rheological behaviour (D40) and 60% (D60) water deficits were used. Water-soluble polysaccharides were isolated and subjected to Acemannan carbohydrate and glycosidic linkage analysis. The steady-shear and linear oscillatory flows were studied, not only Pectin in fresh but also in reconstituted mucilages. Acemannan and pectic substances were the predominant Water deficit polysaccharides in the Aloe vera mucilage, being the bioactive polymer acemannan the most affected by water deficit. Thus, increasing the water deficit by up to 60% promoted a mannose decrease of 41%, although a significant increase in its average molecular weight, from 54 to 98 kDa, was detected. Interestingly, acemannan did not undergo deacetylation as a consequence of the water deficits applied. All Aloe vera mucilages, either fresh or reconstituted, exhibited a shear-thinning flow behaviour (n < 1). However, water deficit affected the me- chanical

properties, changes being more noticeable in the reconstituted mucilages. Thus, the viscosity (η1) of reconstituted mucilages increased, from 0.12 to 0.28 Pa·s, as water deficit increased, whereas their flow index (n) decreased from

0.57 to 0.47. Further, D40 and D60 reconstituted mucilages exhibited an Ea of 17.4 and 17.6 kJ/ mol, respectively,

whilst, for D0, Ea was 16.7 kJ/mol. Interestingly, only the D40 reconstituted mucilage showed a crossover point at 7.39 rad/s between viscous and elastic modulus. The understanding of the influence of water deficit on the main physico-chemical characteristics of Aloe vera polysaccharides and, in turn, of its effect on the rheology of the mucilages could be a useful tool for the design, development and control of biologically active ingredients based on the Aloe vera plant.

1. Introduction Tiku, 2016; Pothuraju et al., 2016; Radha and Laxmipriya, 2015). Aloe vera mucilage is the aqueous extract of the hydroparenchyma Nowadays there is an ongoing search for new biomaterials that may cells present in the succulent leaves of Aloe vera plant (Javed and Atta- be used in the development of functional ingredients able to substitute Ur-Rahman, 2014). This mucilage consists of about 98.5%–99.5% synthetic molecules which are, increasingly, being considered as po- water, the remaining solids being composed mainly of polysaccharides tentially harmful for human health (Avila-de la Rosa et al., 2015). (∼60% w/w), in particular acemannan and pectic substances (Femenia Different plant materials have been investigated in order to obtain et al., 1999). Acemannan, considered as the main bioactive component natural components that could be used as these functional ingredients. of the Aloe vera mucilage, is a storage polymer located within the Within this context, Aloe barbadensis Miller (Aloe vera) may be con- protoplast of the parenchymatous cells (Femenia et al., 1999). This sidered as a potential and valuable source of gums and hydrocolloids, polysaccharide is mainly composed of partially acetylated mannose which are present in the mucilage of Aloe vera (Kiran and Rao, 2016). units linked by β−(1 → 4) glycosidic bonds (Chokboribal et al., 2015; The widespread use of Aloe vera mucilage as a source of functional Chow et al., 2005; Femenia et al., 1999; McAnalley, 1993). On the other ingredients is mainly due to the considerable number of beneficial hand, pectic substances are the main component of the cell walls, mostly properties attributed to this plant (Huseini et al., 2012; Kumar and made up of a very high percentage of galacturonic acid units

⁎ Corresponding author. E-mail address: [email protected] (A. Femenia). http://dx.doi.org/10.1016/j.indcrop.2017.09.016 Received 23 May 2017; Received in revised form 25 August 2017; Accepted 10 September 2017 $YDLODEOH RQOLQH 21 6HSWHPEHU 2017 0926-6690/ ‹ 2017 (OVHYLHU %.9. $OO ULJKWV UHVHUYHG. Journal of Functional Foods 35 (2017) 447–457

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Journal of Functional Foods

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Nutritional characteristics and bioactive compound content of guava purees and their effect on biochemical markers of hyperglycemic and hypercholesterolemic rats

Yolanda E. Pérez-Beltrán a, Eduardo Mendeleev Becerra-Verdín b, Sonia G. Sáyago-Ayerdi a, Nuria E. Rocha-Guzmán c, Emma G. García-López d, Alfonso Castañeda-Martínez b, b e a,⇑ Rubén Montalvo-González , Cristian Rodríguez-Aguayo , Efigenia Montalvo-González a Laboratorio Integral de Investigación en Alimentos, Instituto Tecnológico de Tepic, Av. Tecnológico No. 2595, Lagos del Country, 63175 Tepic Nayarit, Mexico b Laboratorio de Investigación Clínica e Histología, Universidad Autónoma de Nayarit, Ciudad de la Cultura Amado Nervo S/N, 63155 Tepic Nayarit, Mexico c Departamento de Ingenierías Química y Bioquímica, Instituto Tecnológico de Durango, Felipe Pescador 1830 Ote., 34080 Durango, Durango, Mexico d Purés y Derivados de Nayarit, Carr. Tepic-Camichin Km 3.4, 3155 Camichin de Jauja, Nayarit, Mexico e Department of Experimental Therapeutics, The University of Texas MD Anderson Cancer Center, Houston, TX 77030, United States

a r t i c l e i n f o a b s t r a c t

Article history: The nutritional characteristics and bioactive compound content in purees elaborated with guava- Received 25 February 2017 strawberry, guava-blackberry, guava-soursop or guava-passion fruit were evaluated as well as their effect Received in revised form 5 June 2017 on biochemical markers of hyperglycemic and hypercholesterolemic rats. Over a 4-week period, the effects Accepted 7 June 2017 of each puree were examined. All purees presented a high content of indigestible fraction (70.6–82.3 g/100 Available online 12 June 2017 g), vitamin C (500–534.6 mg/100 g), soluble polyphenols (32.8–33 mg/g) and antioxi- dant capacity. Several phenolic acids and flavonoids were identified. The addition of purees in the diet increased the body Keywords: weight of hyperglycemic rats (rv7%), but decreased the body weight of hypercholes- terolemic rats Nutritional characteristics (rv15%). All the purees decreased the levels of plasma glucose, urea and creatinine in hyper- glycemic rats, Bioactive compounds as well as the total cholesterol and triacylglycerol levels in hypercholesterolemic rats. The hepatic damage Guava purees Hyperglycemia was reduced for all purees. These guava-purees represent a therapeutic alternative for individuals with diet- Hypercholesterolemia related diseases problems such as hyperglycemia and hypercholesterolemia. © 2017 Elsevier Ltd. All rights reserved.

1. Introduction these pathologies decrease with the consumption of fresh fruits and vegetables due to the significant amounts of vitamins, miner- Noncommunicable diseases (NCDs) are defined as chronic dis- als, dietary fibre, indigestible fraction and bioactive compounds eases that are not transmitted from person to person. Alarmingly, that they have; which turn can control and prevent non- these diseases are increasing worldwide, affecting all age groups degenerative diseases. Moreover the diets that are rich in these (WHO, 2015). NCDs include obesity, hyperglycemia, hypercholes- vegetables may cause lower rates of mortality caused by NCDs terolemia, hyperlipidemia, arteriosclerosis, diabetes mellitus (DM) (Elleuch et al., 2011). type II, hypertension and other cardiovascular diseases (WHO, Therefore many fruits and their components (stem, leaves, seeds 2015). These metabolic disorders are known as a metabolic and by-products) have been investigated to study their effects on syndrome, which increases the morbidity and mortality that along health issues that include anti-hyperglycemic, hepatic steatosis, anti- with an increasingly aging society, creates a serious medical and inflammatory, anti-cancer, cardioprotective, anti-obesity, among socioeconomic problem (Elleuch et al., 2011). It is known that others. The fruits that have been most studied are: guava (Huang, Yin, & Chiu, 2011; Liu, Wang, Hsieh, Lu, & Chiang, 2015), ber- ries (Afrin et al., 2016; Aqil et al., 2016; Mazzoni et al., 2016), passion fruit (Kandandapani, Balaraman, & Ahamed, 2015) and soursop fruit ⇑ Corresponding author. E-mail addresses: [email protected] (Y.E. Pérez-Beltrán), qfb_mendel@ya- (Coria-Téllez, Montalvo-Gónzalez, Yahia, & Obledo-Vázquez, 2016). hoo.com.mx (E.M. Becerra-Verdín), [email protected] (S.G. Sáyago-Ayerdi), These fruits are widely accepted by the consumers and are an impor- [email protected] (N.E. Rocha-Guzmán), [email protected] (E.G. Gar- cía- tant source of vitamin C, vitamin E, pigments (anthocyanins or car- López), [email protected] (A. Castañeda-Martínez), montalvogonza- otenoids), dietary fibre (DF) and polyphenols (Huang et al., 2011; [email protected] (R. Montalvo-González), [email protected] (C. Rodríguez- Meireles et al., 2015; USDA, 2011). Aguayo), [email protected] (E. Montalvo-González).

http://dx.doi.org/10.1016/j.jff.2017.06.022 1756-4646/© 2017 Elsevier Ltd. All rights reserved. -RXUQDO RI )RRG &RPSRVLWLRQ DQG $QDO\VLV 63 (2017) 38²46

Contents lists available at ScienceDirect

Journal of Food Composition and Analysis

journal homepage: www.elsevier.com/locate/jfca

Original research article

Comprehensive characterization by LC-DAD-MS/MS of the phenolic composition of seven Quercus leaf teas Rocío García-Villalbaa,⁎, Juan Carlos Espína, Francisco A. Tomás-Barberána, b Nuria Elizabeth Rocha-Guzmán a Laboratory of Food & Health, Research Group on Quality, Safety and Bioactivity of Plant Foods, Department of Food Science and Technology, CEBAS-CSIC, 30100 Campus de Espinardo, Murcia, Spain b Research Group on Functional Foods and Nutraceuticals, Departamento de Ingeniería Química y Bioquímica, Instituto Tecnológico de Durango, Felipe Pescador 1830 Ote., 34080 Durango, Dgo., Mexico

A R T I C L E I N F O A B S T R A C T

Keywords: A complete characterization of the phenolic profile of leaves infusions from seven Mexican Quercus species was Food analysis developed using different LC-DAD-MS/MS methodologies. The main families of phenolic compounds identified and Food composition quantified were: hydrolyzable tannins and flavonol glycosides, based on their fragmentation patterns and UV Quercus spectra, analyzed after acid-catalysis in the presence of phloroglucinol, and phenolic acids Polyphenols evaluated using UPLC-triple quadrupole mass spectrometer (QqQ). White oak species showed the largest amount Proanthocyanidins of total phenols (830–2956 mg/L) with hydrolyzable tannins as the predominant group (60–96%), mainly Hydrolyzable tannins vescavaloninic acid, vescalagin, and castalagin. Red species (total phenolics 129–280 mg/L), showing proan- Phloroglucinolysis LC– MS/MS thocyanidins as the dominant family, consisted of units of , gallocatechin and in less amount and and larger percentages of phenolic acids (10–19%).

1. Introduction enzymes relevant for hyperglycemia and Alzheimeŕs disease were also observed in hydromethanolic and aqueous extracts of leaves of other In recent years, the interest and consumption of herbal infusions Quercus species (Custodio et al., 2015; Haidi et al., 2017; Nugroho et al., (commonly called teas or tisanes) from a great diversity of edible plants 2016). has increased considerably among the Mexican population. These plant These biological activities are thought to be associated, at least in species include the genus Quercus, which has its diversification center in part, with the presence of phenolic compounds. Polyphenols, as a group Mexico, because of 450 species estimated worldwide, about 135–150 are of secondary metabolites broadly distributed in plant-derived products, from this country, and 86 are considered endemic (Nixon, 1998; Zavala, have been shown to be responsible for many health benefits, including 1998). Forty-one Quercus species (22 white and 19 red) occur in Durango cardio-protective, anti-cancer, anti-diabetic, anti-aging and neuropro- forest. For many civilizations, local ethnic groups (Mixtecos, tective effects (Scalbert et al., 2005). Therefore, the characterization of Tepehuanos, Totonacas and Tepehuas) have used Quercus species for polyphenols is of great importance, to confirm the potential health medicinal and food purposes (Luna-José et al., 2003). The use of these benefits attributed to Quercus teas. herbal infusions as antioxidant nutraceuticals in traditional medicine is From a phytochemical point of view, Quercus tree is very interesting a common practice. because of the presence of different families of polyphenols. Different Recently, tisanes prepared with the leaves of Mexican Quercus spe- parts of the tree (wood, bark, cork, acorns) have been extensively in- cies (Q. resinosa, Q. sideroxyla, Q. eduardii and Q. durifolia) have been vestigated (Cantos et al., 2003; Castro-Vázquez et al., 2013; Fernandes reported to exhibit antioxidant activity (Rocha-Guzmán et al., 2012) as et al., 2011; Fernández de Simón et al., 2006) due to their important role well as cardioprotective (Rivas-Arreola et al., 2010), anti-carcinogenic in the maturation of wines inside oak barrels, in the wood industry and (Rocha-Guzmán et al., 2009), anti-inflammatory (Moreno-Jiménez et human and animal nutrition (Haidi et al., 2017). al., 2015), antimicrobial and anti-topoisomerase potential (Sánchez- Bark and woods, mainly used in cooperages, are especially rich in Burgos et al., 2013). Antioxidant activity and inhibitory activity of key ellagitannins (castalagin, vescalagin, grandinin and roburins A–E) and

⁎ Corresponding author at: Research Group on Quality, Safety and Bioactivity of Plant Foods, Department of Food Science and Technology, CEBAS−CSIC, 30100 Campus de Espinardo, Murcia, Spain. E-mail address: [email protected] (R. García-Villalba). http://dx.doi.org/10.1016/j.jfca.2017.07.034 Received 17 April 2017; Received in revised form 14 June 2017; Accepted 19 July 2017 $YDLODEOH RQOLQH 24 -XO\ 2017 0889-1575/ ‹ 2017 (OVHYLHU ,QF. $OO ULJKWV UHVHUYHG. G Model ARTICLE IN PRESS Industrial Crops and Products xxx (2017) xxx–xxx

Contents lists available at ScienceDirect

Industrial Crops and Products

journal homepage: www.elsevier.com/locate/indcrop

Antioxidant, anti-inflammatory and apoptotic effects of Flourensia microphylla on HT-29 colon cancer cells D. Jasso de Rodrígueza,∗, D.A. Carrillo-Lomelía, N.E. Rocha-Guzmánb, M.R. Moreno-Jiménezb, R. Rodríguez-Garcíaa, M.L.V. Díaz-Jiménezc, M.L. Flores-Lópeza, a J.A. Villarreal-Quintanilla a Universidad Autónoma Agraria Antonio Narro, Calzada Antonio Narro 1923, Col. Buenavista, CP 25315 Saltillo, Coahuila, Mexico b Instituto Tecnológico de Durango, Blvd. Felipe Pescador 1830 Ote., Col. Nueva Vizcaya, 34080 Durango, Dgo., Mexico c Cinvestav-Saltillo Carretera Saltillo-Monterrey, Km 13, CP 25900 Ramos Arizpe, Coahuila, Mexico

a r t i c l e i n f o a b s t r a c t

Article history: Colon cancer is one of the most common cancer types, causing major health problems worldwide. In Received 17 January 2017 Mexico, colon cancer occupies the third place on incidence among all cancer types. Flourensia species Received in revised form 20 March 2017 have been used in traditional medicine, and recently, these have been studied due to their biological prop- Accepted 22 March 2017 erties such antibacterial and antifungal. Therefore, the aims of this work were to study the antioxidant, Available online xxx anti-inflammatory, and apoptotic effects of two extracts (ethanol and acetone) of Flourensia microphylla. The leaves of F. microphylla were collected in the wild site (25◦07 1 131 1 N latitude and 101◦07 1 241 1 W longi- Keywords: tude, 2383 maslaltitude) at Southeastof Coahuila, Mexico. Thephenolic contentandantioxidant activity Flourensia microphylla Antioxidant and anti-inflammatory weredeterminedinethanolandacetone extracts. Chemicalcomposition wasanalyzedwith LC–MS/MS activities and GC–MS. Cellular viability were analyze by 3-(4,5-di-methylthiazol-2-yl)-2,5,-dephenyl-2 tetrazolium Apoptotic bromide (MTT) assay and evaluated on HT-29 cells. Western blot assay was carried out to measure the Anticancer inflammatorymarkersexpression andapoptotic assaywasconducted withahumanapoptosis antibody array. Results showed that F. microphylla extracts are a great source of phenolic compounds withantiox- idant activity. Acetone extract presented anti-inflammatory effect due to the inhibition of interleukin 8 (IL-8). Also, acetone extract showed activation of the intrinsic pathway of apoptosis by the increment of the Bax/Bcl-2 ratio. Ethanol extract activated the extrinsic pathway as the expression of the TNF fam- ily proteins, such as Fas and TRAIL, was observed. Both extracts demonstrated apoptotic activity by the expression of caspase 3 (Cas-3), the initiator caspase of apoptosis. Thus, F. microphylla extracts can be a potential natural alternative to prevent colon cancer. © 2017 Elsevier B.V. All rights reserved.

1. Introduction Theimportant role that inflammationplays on the development and progression of cancer has been widely reported (Candido and Cancer is a genetic disease resulting from dynamic changes Hagemann, 2013; Elinav et al., 2013). Inflammation is a biologi- that involves the transformation of a normal cell to a malignant, cal process of defense and repair by the human’s immune system. which begins to grow uncontrollably invading organs (Hanahan This allows to protect an organism against noxious agents such as and Weinberg, 2000). Nowadays, cancer is one of the main causes pathogens, toxins, and damaged cells (Jungbauer and Medjakovic, of mortality in the world (Bayala et al., 2014); among which, colon 2012). But, the deregulation of this immune system’ component cancer is the most important public health problem (Altobelli et al., (e.g. chronic inflammation) predisposes the organism to diverse 2014). In Mexico, colon cancer ranks third place on incidence with cancer types (Colotta et al., 2009). In fact, the chronic inflamma- 4656 and 3995 reported cases in men and women, respectively tory bowel disease has been known in the past as ulcerative colitis, (World Health Organization, 2014). a risk factor for colon cancer development (Grivennikov, 2013). Apoptosis is a type of programmed cell death characterized by the control of the cell autodigestion; it is regulated by molecular mechanisms that activate astereotyped program causing cell death (Manosroi et al., 2012). But cancer cells apoptosis mechanism is ∗ Corresponding author. E-mail address: [email protected] (D. Jasso de Rodríguez). blockedallowingthecancercellstomultiplyindefinetily.Apoptosis

http://dx.doi.org/10.1016/j.indcrop.2017.03.034 0926-6690/© 2017 Elsevier B.V. All rights reserved.

Please cite this article in press as: Jasso de Rodríguez, D., et al., Antioxidant, anti-inflammatory and apoptotic effects of Flourensia microphylla on HT-29 colon cancer cells. Ind. Crops Prod. (2017), http://dx.doi.org/10.1016/j.indcrop.2017.03.034

J Biol Inorg Chem DOI 10.1007/s00775-016-1416-1

ORIGINAL PAPER

Theoretical insights into [NiFe]‑hydrogenases oxidation resulting in a slowly reactivating inactive state

Raffaella Breglia1 · Manuel Antonio Ruiz‑Rodriguez2 · Alessandro Vitriolo3 · Rubén Francisco Gonzàlez‑Laredo2 · Luca De Gioia3 · Claudio Greco1 · 1 Maurizio Bruschi

Received: 29 July 2016 / Accepted: 9 November 2016 © SBIC 2016

Abstract [NiFe]-hydrogenases catalyse the relevant The results presented in this work show that, among all + − H2 → 2H + 2e reaction. Aerobic oxidation or anaero- bic plausible isomers featuring various protonation patterns and oxidation of this enzyme yields two inactive states oxygenic ligands, the one corresponding to the crys- called Ni-A and Ni-B. These states differ for the reactiva- tallographic structure recently reported by Volbeda et al. (J tion kinetics which are slower for Ni-A than Ni-B. While Biol Inorg Chem 20:11–22, 19)—featuring a bridging there is a general consensus on the structure of Ni-B, the hydroxide ligand and the sulphur atom of Cys64 oxidized to nature of Ni-A is still controversial. Indeed, several crys- bridging sulfenate—is the most stable. However, iso- mers tallographic structures assigned to the Ni-A state have been with cysteine residues oxidized to terminal sulfenate are proposed, which, however, differ for the nature of the very close in energy, and modifications in the network of H- bridging ligand and for the presence of modified cysteine bond with neighbouring residues may alter the stabil- ity residues. The spectroscopic characterization of Ni-A has order of such species. been of little help due to small differences of calculated spectroscopic parameters, which does not allow to dis- Keywords [NiFe]-hydrogenase · Oxidative inactivation · criminate among the various forms proposed for Ni-A. Here, Ni-A state · Protein S-sulfenation · Density functional we report a DFT investigation on the nature of the Ni-A theory state, based on systematic explorations of confor- mational and configurational space relying on accurate energy calculations, and on comparisons of theoretical geometries Introduction with the X-ray structures currently available. Hydrogenases are enzymes involved in the metabolism of dihydrogen, and are expressed by several eukaryotic and Electronic supplementary material The online version of this prokaryotic microorganisms. In particular, two hydroge- article (doi:10.1007/s00775-016-1416-1) contains supplementary nases classes—the [NiFe] and [FeFe]-hydrogenases—are material, which is available to authorized users. able to catalyse the reversible oxidation of H2, following the reaction [1–4]: * Maurizio Bruschi [email protected] H → 2H+ + 2e−. 2 1 Department of Earth and Environmental Science, University [NiFe]-hydrogenases represent the most widespread of Milano-Bicocca, Piazza Della Scienza 1, 20126 Milan, hydrogenase class in Nature; this fact, as well as the very Italy interesting reactivity promoted by such enzymes, has led 2 Departamento de Ingeniería Química y Bioquímica, Instituto researchers to spend increasing efforts in the study of Tecnológico de Durango, Felipe Pescador Ote, Durango, Mexico [NiFe]-hydrogenases. In particular, the development of green-chemistry approaches for the evolution of molecu- lar 3 Department of Biotechnology and Biosciences, University of Milano-Bicocca, Piazza della Scienza 2, 20126 Milan, hydrogen would enable to employ H2 as a clean energy Italy carrier.

13

Industrial Crops & Products xxx (xxxx) xxx–xxx

Contents lists available at ScienceDirect

Industrial Crops & Products

journal homepage: www.elsevier.com/locate/indcrop

Hypoglycemic and anti-inflammatory effects of Psacalium paucicapitatum corms infusions ⁎ D. Jasso De Rodrígueza, , L.C. García-Hernándeza, N.E. Rocha-Guzmánb, M.R. Moreno-Jiménezb, R. Rodríguez-Garcíaa, M.L.V. Díaz-Jiménezc, M.L. Flores-Lópeza, J.A. Villarreal-Quintanillaa, a a F.M. Peña-Ramos , D.A. Carrillo-Lomelí a Universidad Autónoma Agraria Antonio Narro, Calzada Antonio Narro 1923, Col. Buenavista, CP 25315 Saltillo, Coahuila, Mexico b Instituto Tecnológico de Durango, Blvd. Felipe Pescador 1830 Ote., Col. Nueva Vizcaya, 34080 Durango, Durango, Mexico c Cinvestav-Saltillo, Carretera Saltillo-Monterrey Km 13, CP 25900 Ramos Arizpe, Coahuila, Mexico

A R T I C L E I N F O A B S T R A C T

Keywords: Diabetes mellitus is an important health problem worldwide. This disease is characterized by the hyperglycemia Psacalium paucicapitatum normally accompanied by obesity. Several studies indicated the relation between low-grade inflammation and Hypoglycemic diabetes. Psacalium paucicapitatum [(B.L. Rob. & Greenm.) H. Rob. & Brettell], is an endemic plant of Mexico used Anti-inflammatory effect in traditional medicine to control diabetes. Thus, the aims of this work were to evaluate the anti-inflammatory Diabetes effect in vitro, and the hypoglycemic effect in vivo of infusions of P. paucicapitatum corms. The plants were Fructooligosaccharides collected at two sites of Ixtlán de Juárez at Sierra Norte of Oaxaca, Mexico: Cuachirindoó and Rancho Texas. The phenolic and flavonoid contents and antioxidant capacity were determined. Chemical composition was carried out by LC–MS/MS. Cytotoxic effect was evaluated on HT-29 cells by 3-(4,5-di-methylthiazol-2-yl)-2,5,-diphenyl- 2 tetrazolium bromide (MTT) assay. Inflammation markers were measured by Western blot technique and the hypoglycemic effect was assessed by the Glucose Tolerance Test (GTT). The results evidenced the anti- inflammatory effect of P. paucicapitatum on HT-29 cells and its hypoglycemic effect in mice C57BL/6. These activities can be attributed to the fructooligosaccharides found in the corms of the plant. P. paucicapitatum corms infusions can be a potential natural alternative to the treatment of diabetes and inflammatory disorders.

1. Introduction Several studies have indicated the association of oxidative stress and low-grade inflammation with the development of obesity and DM2 Diabetes mellitus (DM) is a chronic disease which incidence is (Zozulinska and Wierusz-Wysocka, 2006). The inflammation can be growing in the world, with 336 million cases reported, and it is expected activated on an altered metabolic context, which it is produced by that by 2030 the number will be increased to 552 million, in both several pro-inflammatory cytokines markers such as tumor necrosis developing and developed countries (Schwandt, 2012). The DM affects factor-α (TNF-α) and interleukins (IL) in DM2 (Fève and Bastard, 2012; a large proportion of adults in Mexico, as it was the leading cause of Sun et al., 2012). Also, Duncan et al. (2003) reported that the death in 2012 with 14.5% (87600 deceased) and it is estimated that by inflammatory markers: sialic acid, orosomucoid, IL-6, and protein c- 2025, 11.7 million Mexicans will be diagnosed with DM (World Health reactive, are related with the development of DM2, being predicted its Organization, 2015). incidence by the occurrence of a low-grade inflammation. The main characteristic of DM is the hyperglycemia, that results Plant extracts have traditionally been used as infusions for the from defects in the insulin secretion or its action (Patel et al., 2012). control of DM in Mexico, highlighting the species of the genus Psacalium Diabetes is classified in two types: type-1 diabetes (DM1) that is insulin (Family Asteraceae, Tribe Senecioneae) (Jimenez-Estrada et al., 2006; dependent and results from the destruction of pancreatic islet-cell, Alarcon-Aguilar et al., 2010). The root decoction of P. decompositum has usually presented in childhood or in adolescence (Ashcroft and showed hypoglycemic activity associated to the presence of cacalol, Rorsman, 2012); and type 2 diabetes (DM2) characterized by insulin cacalone, maturin, alcaloids and sugars (Alarcon-Aguilar et al., 1997). resistance and obesity, usually presented in adulthood (Stumvoll et al., Merino-Aguilar et al. (2014), reported the decreasing of cholesterol, 2005). triglycerides and also, a significant reduction of inflammatory cytokines

⁎ Corresponding author. E-mail address: [email protected] (D.J. De Rodríguez). http://dx.doi.org/10.1016/j.indcrop.2017.04.022 Received 30 January 2017; Received in revised form 7 April 2017; Accepted 13 April 2017 0926-6690/ © 2017 Elsevier B.V. All rights reserved.

Please cite this article as: RODRÍGUEZ, D.J.D., Industrial Crops & Products (2017), http://dx.doi.org/10.1016/j.indcrop.2017.04.022 EXCLI Journal 2016;15:758-771 – ISSN 1611-2156 Received: September 14, 2016, accepted: October 30, 2016, published: November 30, 2016

Review article:

LUPANE-TYPE TRITERPENES AND THEIR ANTI-CANCER ACTIVITIES AGAINST MOST COMMON MALIGNANT TUMORS: A REVIEW

MH Cháirez-Ramírez, MR Moreno-Jiménez, RF González-Laredo, JA Gallegos-Infante, NE Rocha-Guzmán*

Instituto Tecnológico de Durango, Departamento de Ingenierías Química y Bioquímica, Blvd. Felipe Pescador 1830 Ote., Col Nueva Vizcaya, 34080 Durango, Dgo., México

* corresponding author: Nuria Elizabeth Rocha-Guzmán Laboratory of Functional Foods and Nutraceuticals, Instituto Tecnológico de Durango, Unidad de Posgrado, Investigación y Desarrollo Tecnológico (UPIDET), Blvd. Felipe Pescador 1830 Ote., 34080 Durango, Dgo., México. E-mail: [email protected]; [email protected]; Tel: + 52 (618) 8186936 ext 112; + 52 (618) 8185402 ext 112

http://dx.doi.org/10.17179/excli2016-642

This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/).

ABSTRACT In recent times, a great deal of interest has been motivated on plant derived compounds known as nutraceuticals. These compounds exert important beneficial activities that improve people’s health status when are consumed regularly, and now they appear as a viable option to explore their possible therapeutic effects against diseases like cancer. Particularly, lupane-type triterpenes have shown great ability to modulate multiple cancer-related signaling pathways and processes, including NF-κB, Wnt/β-catenin, PI3K/Akt, apoptosis, and many other routes related to proliferation or cell death, which are uncontrolled in malignant tumors. These investigations have promoted in vitro and in vivo studies, searching their mechanisms of action; although more research is still need- ed to prove its potential in human clinical trials. This review focuses on the ability of betulin, betulinic acid and lupeol to show benefits against the most common types of malignant tumors, which are considered a major glob- al threat for public health.

Keywords: lupeol, betulin, betulinic acid, cancer, signaling pathway

INTRODUCTION year; 75 % of these deaths (28 million) occur In present times, non-communicable commonly in third world countries. chronic diseases are responsible for about 63 Cancer is a generic term that comprises a % of deaths worldwide. This group in- cludes large number of diseases that affect distinct parts of the human body. It is characterised by diabetes mellitus (DM), cardiovascu- lar diseases (CVD), chronic respiratory dis- eases uncontrolled cell growth, and is capable to (CRD) and cancer, being responsible for disseminate to different tissues from where it approximately 38 million of deaths per was originated (metastasis), leading to people´s death. Cancer is responsible for

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Journal of Chemical Biology

o Díaz Rivas et al., J Chem Biol Ther 2016, 1:2 & Therapeutics

Review Article Open Access

Gastroprotective Activities of Buddleja scordioides-Role of Polyphenols against Inflammation Díaz Rivas JO, Rocha Guzmán NE, Gallegos Infante JA*, Moreno Jiménez MR and González Laredo RF Department of Chemistry and Biochemistry Ings, UPIDET, Durango, Mexico *Corresponding author: Gallegos Infante JA, Department of Chemistry and Biochemistry Ings, Durango Institute of Technology, UPIDET, Durango, Mexico, Tel: 526188186936; E-mail: [email protected] Received date: Jun 13, 2016; Accepted date: Aug 25, 2016; Published date: Aug 29, 2016 Copyright: © 2016 Díaz Rivas JO, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

Abstract

Medicinal plants show great interest today because of its multiple physiological effects. They contain a diversity of chemical compounds, phytochemicals, with demonstrated important biological activities. Buddleja scordioides Kunth is a plant that shows a wealth of important phytochemicals, which could contribute towards the prevention of various health problems such as gastrointestinal disorders. The main causes of gastrointestinal pathology are mediated by inflammatory processes caused by several factors. B. scordioides HBK (KUNTH) is commonly used for the treatment of diarrhea and stomach pain (colic). Several studies shown presence of flavonoids such as rutin, quercetin and quercetrin and kaempferol (also found in Buddleja genus). Other isolated compounds include some hidroxicinnamic and hidroxibenzoic acids, verbascosides, siringin, some iridoids, sesquiterpenes and fenilpropanoids. All of them related with anti-inflammatory activity. The present review is an opinion of the state of art anti-inflammatory activity of B. scordioides and gastrointestinal disorders.

Keywords: Anti-Inflammation Buddleja scordioides; In Mexico in 2008, the incidence of ulcers, gastritis and duodenitis Gastroprotection; Phytochemicals were larger than the states of Nayarit, Tabasco and Durango (3396.11, 3212.11 and 2193.78 cases per 100,000 population, respectively) [2]. In Introduction general, these problems are associated with inflammator processes, which are part of a non-specifi response of tissues that occurs in Medicinal plants show great interest today because of its multiple reaction to any type of injury, which is an immune response to physiological effects The contain a diversity of chemical compounds, pathogens, damaged, irritating cells, etc. [3]. phytochemicals, with demonstrated important biological activities. Thes compounds are produced by the secondary metabolism of Th main symptoms of inflammator processes are: Redness, heat, plants, which have evolved from differen biotic or abiotic factors, and pain and tumor and also these symptoms can cause high cellular usedbytheplant fordefense or survival. However, multiple studies on metabolism, vasodilatation, and high blood flo [4]. In some diseases these compounds have provenbeneficia tohumanhealth [1]. the inflammatio process under normal conditions is restrictive; it becomes chronic dysfunctions that develop subsequently. In Phytochemicals have multiple properties such as antioxidant and inflammator processes, it can be distinguished two steps of anti-inflammatory which can be used as a preventive means to protect inflammation 1) Acute inflammatio that is the immediate response against the development of health problems. The may interact with to vascular changes, where widespread effect of inflammatio molecules that can inhibit the genesis of this type of pathologies or mediators cause pain, heat and swelling; these symptoms are usually conversely, interact with biomarkers that enhance the protective short-lived. 2) Chronic inflammatio is self-prolonged that and can capabilities of the organism. last for weeks, months andeven years, and canbedeveloped as aresult Medicinal properties of many plants are mainly attributed to the ofrecurrent or progressive acuteinflammatio [5]. presence of flavonoids but these effect may also be promoted by other Th main causes of gastrointestinal pathology are mediated by organic and inorganic compounds such as coumarins, alkaloids, inflammator processes caused by invading microorganisms ingested terpenes, tannins, antioxidant phenolic acids and micronutrients, for in the diet, use of medications that hurt the mucosa such as non- example, Cu, Mn and Zn. Buddleja scordioides Kunth is a plant that steroidal anti-inflammator drugs (NSAIDs), milk and dairy fats, shows a wealth of important phytochemicals, which could contribute alcohol, stress and nervousness are responsible for many digestive towards the prevention of various health problems such as disorders [6]. Thei presence of symptoms is varied, may include gastrointestinal disorders. Nowadays these diseases have been stomach or abdominal pain accompanied by cramps, diarrhoea, considered a health problem around the world due to its high dehydration, abdominal bloating, increased intestinal gas, lawn blood, incidence. fever, tires, loss of appetite and weight loss, weakness and constipation, among others [7]. Gastrointestinal disease and inflammatory response Once developed an inflammator process focused on the Gastrointestinal diseases are one of the most common health gastrointestinal tract, the mucosa in charge of maintenance and problems that affec people of all ages and social condition, although integrity causing activation of immune cells, which begin to produce the most vulnerable groups are children and the elders. differen proteins (cytokines) by expressing differen molecules in

JChem Biol Ther anopen access journal Volume 1 • Issue 2 • 1000109 C.I. GAMBOA-GÓMEZ et al.: ACE Inhibition of Kombucha-Fermented Infusions, Food Technol. Biotechnol. 54 (3) 367–374 (2016) 367

ISSN 1330-9862 preliminary communication doi: 10.17113/ftb.54.03.16.4622

Antioxidant and Angiotensin-Converting Enzyme Inhibitory Activity of Eucalyptus camaldulensis and Litsea glaucescens Infusions Fermented with Kombucha Consortium

Claudia I. Gamboa-Gómez1, Rubén F. González-Laredo1, José Alberto Gallegos-Infante1, Mª del Mar Larrosa Pérez2, Martha R. Moreno-Jiménez1, Ana G. Flores-Rueda1 and Nuria E. Rocha-Guzmán1* 1Durango Institute of Technology, Felipe Pescador 1830 Ote., MX-34080 Durango, Durango, Mexico 2European University of Madrid, Calle Tajo, s/n, Villaviciosa de Odón, ES-28670 Madrid, Spain Received: January 26, 2016 Accepted: May 11, 2016

Summary Physicochemical properties, consumer acceptance, antioxidant and angiotensin-con- verting enzyme (ACE) inhibitory activities of infusions and fermented beverages of Euca- lyptus camaldulensis and Litsea glaucescens were compared. Among physicochemical param- eters, only the pH of fermented beverages decreased compared with the unfermented infusions. No relevant changes were reported in consumer preference between infusions and fermented beverages. Phenolic profile measured by UPLC MS/MS analysis demonstrat- ed significant concentration changes of these compounds in plant infusions and fermented beverages. Fermentation induced a decrease in the concentration required to stabilize 50 % of DPPH radical (i.e. lower IC50). Additionally, it enhanced the antioxidant activity mea- sured by the nitric oxide scavenging assay (14 % of E. camaldulensis and 49 % of L. glauce- scens); whereas relevant improvements in the fermented beverage were not observed in the lipid oxidation assay compared with unfermented infusions. The same behaviour was ob- served in the inhibitory activity of ACE; however, both infusions and fermented beverages had lower IC50 than positive control (captopril). The present study demonstrated that fer- mentation has an influence on the concentration of phenolics and their potential bioactivity. E. camaldulensis and L. glaucescens can be considered as natural sources of biocompounds with antihypertensive potential used either as infusions or fermented beverages.

Key words: herbal infusions, fermented beverages, kombucha, antioxidant activity, polyphe- nols

tant source of bioactive compounds such as polyphenols. Introduction It has been shown that these compounds can act by di- In recent years, the consumption of herbal infusions verse mechanisms providing significant protection against around the world has increased due to their beneficial chronic diseases (2). For example, the consumption of health effects. These beverages are prepared by placing a some herbal polyphenols with antioxidant activity may small amount of the selected plant material in freshly regulate hypertension through inhibition of the angio- boiled water, allowing the preparation to steep for a short tensin-converting enzyme (ACE), a key component in the period of time (1). Although herbal infusions do not have renin-angiotensin aldosterone system which regulates any particular nutritional value, they represent an impor- blood pressure (3).

*Corresponding author: Phone: +52 (618) 818 5402; 818 6936 Ext. 112; E-mail: [email protected] Innovative Food Science and Emerging Technologies 34 (2016) 171–179

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Effect of pulsed electric field (PEF)-treated kombucha analogues from Quercus obtusata infusions on bioactives and microorganisms D. Vazquez-Cabral a, A. Valdez-Fragoso b, N.E. Rocha-Guzman a,⁎, M.R. Moreno-Jimenez a, R.F. Gonzalez-Laredo a, P.S. Morales-Martinez a, J.A. Rojas-Contreras a, H. Mujica-Paz c, J.A. Gallegos-Infante a,⁎ a Instituto Tecnológico de Durango, Departamento de Ingenierías Química y Bioquímica, Blvd. Felipe Pescador 1830 Ote., Col. Nueva Vizcaya, 34080 Durango, Dgo., Mexico b Centro de Biotecnología FEMSA, Escuela de Ingeniería y Ciencias, Tecnológico de Monterrey, Av. Eugenio Garza Sada 2501 Sur, Col. Tecnológico, 64849 Monterrey, NL, Mexico c Departamento de Biotecnología e Ingeniería de Alimentos, Instituto Tecnológico de Estudios Superiores de Monterrey, Av. Eugenio Garza Sada 2501 Sur, Col. Tecnológico, 64849 Monterrey, NL, Mexico

a r t i c l e i n f o a b s t r a c t

Article history: Pulsed electric field (PEF) is a promising non-thermal food preservation technology. The objective was to study Received 4 November 2015 inactivation of yeasts in PEF-treated kombucha analogues prepared from Quercus obtusata infusions. Fermentation Received in revised form 12 January 2016 conditions of infusions from Q. obtusata were time (7 days), sugar (10%), starting culture (10%), and inoculum Accepted 25 January 2016 (2.5%, at 25 °C). The PEF treatment considered using square waves, an electric field strength (37.3–53.4 kV/cm), Available online 12 February 2016 PEF processing time (445.3–1979.2 μs), an output temperature (18.31 ± 0.98 °C), an input energy (21.2 - 136.5 KJ/L), and two feed flow rates (51.42 and 102.85 L/h). pH, °Brix, color determinations, microbiological testing, Keywords: total phenolic, flavonoidcontent, DPPH test, and UPLC/ESI/MS/MSanalysiswere done. No changes at different PEF Flavonoids Topic: conditions were observed for pH and °Brix. Higher color changes were observed at higher specific energies. Acid- Kombucha acetic bacteria were more sensitive to PEF than yeasts. Lower specific energies render products with higher polyphe- Oak leaves nolic content and antioxidant capacity. Pulse electric fields Industrial relevance: Pulse electric field is an interesting alternative to preserve kombucha analogues from oak leave Functional beverages infusions with minimal changes in physicochemical characteristics, antioxidant activity and bioactive compounds. Phenolic The present work describes the effect of feed flow and specific energy on the several characteristics of fermented beverages, determining conditions for best processing. © 2016 Elsevier Ltd. All rights reserved.

1. Introduction (2001) indicate that the main process parameters that affect microbial inactivation by PEF are electric field strength, pulse length, pulse shape, Thermal treatments are effective on enzyme inactivation and microbi- number of pulses, and start temperature (MacGregor, Farish, Fouracre, ological control. However, they imply an important loss of nutrients and Rowan, & Anderson, 2000). Also, type of microorganism, species, strains, phytochemicals such as phenolic compounds (Manzocco, Mastrocola, & size and shape are related with the efficiency of PEF to inactivate micro- Nicoli, 1998), although several reports have claimed opposite results organisms (Wouters et al., 2001). (Manzocco, Anese, & Nicoli, 1998; Nicoli, Anese, Parpinel, Franceschi, & Electric field strength and treatment time are the most studied pa- Lerici, 1997). rameters related with microbial inactivation by PEF. The main process The conventional way to determine the efficiency of a thermal parameters that affect microbial inactivation by PEF are electric field process is based on the assumption that survival curves of microbial strength, pulse length, pulse shape, number of pulses, and starting tem- cells and bacterial spores are governed by a first-order kinetic law perature (Barbosa-Canovas, Pothakamury, Gongora-Nieto, & Swanson, (Mafart, Couvert, Gaillard, & Leguerinel, 2002). As a complement to or 1999; Saldaña, Álvarez, Condón, & Raso, 2014; Siemer, Toepfl, & Heinz, replacement of traditional thermal pasteurization, pulsed electric field 2014). In general, increasing the intensity of these factors enhances (PEF) is a promising non-thermal food preservation technology (Toepfl, microbial inactivation; however, their relationship with the survival Heinz, & Knorr, 2007). Several investigations have been performed in fraction is unclear (Wouters et al., 2001). Not only process parameters various fruit juices to evaluate microbial resistance to PEF treatments are important, but also product parameters are significant too. (Raso, Calderón, Góngora, Barbosa-Cánovas, & Swanson, 1998a, 1998b; PEF treatment has been applied to a range of different products as Timmermans et al., 2013). Wouters, Alvarez, & Raso fruit juices, milk, liquid eggs, and dry herbs (Barba et al., 2015). Also the influence of pH and conductivity has been studied by several groups. * Corresponding authors. Wouters et al. (2001) found that a change in the medium conductivity E-mail addresses: [email protected] (N.E. Rocha-Guzman), affected the pulse energy; Vega-Mercado, Pothakamury, Chang, [email protected] (J.A. Gallegos-Infante). Barbosa-Cánovas, & Swanson (1996), concluded that it is better to

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Effect of chemical stress on germination of cv Dalia bean (Phaseolus vularis L) as an alternative to increase antioxidant and...

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ARTÍCULO DE INVESTIGACIÓN Evaluación química y capacidad antioxidante de extractos polifenólicos de cortezas de Pinus cooperi, P. engelmannii, P. leiophylla y P. teocote

Chemical evaluation and antioxidant capacity of polypehenolic extracts from bark of Pinus cooperi, P. engelmannii, P. leiophylla and P. teocote

Martha Rosales-Castro1, Rubén Francisco González-Laredo2, Nuria Elizabeth Rocha-Guzmán2, José Alberto Gallegos-Infante2, Javier Peralta-Cruz3 y Joseph J. Karchesy4

RESUMEN

Se evaluó la concentración de fenoles totales, flavonoides y proantocianidinas en extractos de acetona acuosa 70% (extracto crudo) y extractos semipurificados por partición líquido-líquido con acetato de etilo (extracto orgánico), de cortezas de Pinus cooperi, Pinus engelmannii, Pinus leiophylla y Pinus teocote, asimismo se determinó la actividad antioxidante de los extractos por las técnicas de radical ácido 2,2´-azinobis-3-etilbenzotiazolin-6-sulfónico (ABTS•+), desoxi-d-ribosa (atrapamiento de radical hidroxilo), y por la inhibición de la oxidación de lipoproteínas de baja densidad (LDL). Se realizó una comparación cromatográfica de los extractos por Cromatografía Líquida de Alta Resolución (HPLC). La concentración de fenoles fue de 491 mg g-1 a 604 mg g-1, los extractos orgánicos presen- taron mayor concentración de flavonoides (292 mg g-1 a 385 mg g-1) que los extractos crudos (259 mg g-1 a 314 mg g-1), mientras que la concentración de proantocianidinas fue mayor en el extracto crudo (186 mg g-1a 286 mg g-1) que en el orgánico (70 mg g-1a 151 mg g-1). La capacidad de captura del radical ABTS fue de 49,48% a 57,44%, similares al que presentó el estándar catequina (57,92%). La capacidad de captura del radical hidroxilo varió de 25,85% a 48,46% y fue mayor en el extracto orgánico en todas las especies. La inhibición de oxidación de LDL fue de 64,41% a 89,39%, con valores más altos en el extracto orgánico. Los cromatogramas de HPLC muestran semejanza de los compuestos químicos en las cuatro especies. Se identificó el flavanol catequina a baja concentra- ción en todas las especies. El compuesto principal en P. cooperi, P. engelmannii, y P. teocote, es similar en las tres especies y por espectro de UV corresponde a una flavanona.

PALABRAS CLAVE: ABTS, corteza, Lipoproteínas de Baja Densidad (LDL), Pinus, polifenoles.

1 Centro Interdisciplinario de Investigación para el Desarrollo Integral Regional Unidad Durango. Instituto Poli- técnico Nacional. Av. Sigma 119 fraccionamiento 20 de noviembre II, Durango Durango. C.P. 34220. [email protected]. Becaria de COFAA-IPN. 2 Instituto Tecnológico de Durango. Departamento de Ingeniería Química y Bioquímica. [email protected]. 3 Escuela Nacional de Ciencias Biológicas. Instituto Politécnico Nacional. Becario de COFAA-IPN. 4 Oregon State University. Department of Wood Science and Engineering. Corvallis, OR 97331, USA. Journal of Food Processing and Preservation ISSN 1745-4549

CLAUDIA I. GAMBOA-GÓMEZ, ABIGAIL MUÑOZ-MARTÍNEZ, NURIA E. ROCHA-GUZMÁN, J. ALBERTO GALLEGOS-INFANTE, MARTHA R. MORENO-JIMÉNEZ, SILVIA M. GONZÁLEZ-HERRERA, 1 OSCAR SOTO-CRUZ and RUBÉN F. GONZÁLEZ-LAREDO

Chemical and Biochemical Engineering, Instituto Tecnológico de Durango, Felipe Pescador 1830 Ote., Durango, 34080 Durango, Mexico

1 Corresponding author. TEL: 52-618-818-5402, 52-618-818-6936 Ext. 113; Processing option such as fungal fermentation (tempeh) improves legume FAX: 52-618-8185401 Ext. 112; nutraceutical properties. The aim of this work was to evaluate the physicochemical EMAIL: [email protected] and antioxidant potential of common bean tempeh flour from two varieties: Bayo victoria (BV) and Pinto durango (PD) processed at two different temperature and Received for Publication July 28, 2015 Accepted for Publication September 14, 2015 fermentation times. Results showed differences between cultivars followed by changes in temperature and fermentation times, being more significant at 35C for doi:10.1111/jfpp.12604 40 h. The phenolic content in both cultivars varied considerably after cooking, being higher in raw flour (0.4–3.0-fold for BV and 0.35–0.5-fold for PD). The highest phenolic content was for BV fermented at 35C and 40 h, whereas for PD was at 30C and 40 h. Antioxidant capacity was evaluated by 2,2-diphenyl-1- picrylhydrazyl, low-density lipoprotein oxidation and hydroxyl radical-scavenging assays. Results showed different antioxidant capacity for each test. The major dif- ferences in results were shown between cultivars than the processing variations of temperature and fermentation time.

Phaseolus vulgaris is one of the most important grain legumes for human con- sumption attributable to its nutritional properties, low cost and health promoter effects. However, the nutraceutical properties of this legume have changed due to process variables such as temperature and time of cooking. It has been demon- strated experimentally that fungal fermentation or tempeh production can be an efficient strategy to improve the phenolic content and antioxidant activity of common beans, becoming a favored alternative as an ingredient/supplement development for the prevention and control of degenerative diseases. However, little information is available on the effect of temperature, fermentation time and common bean cultivars in relation with their nutraceutical properties. The present investigation demonstrated that the major effects were between cultivars rather than processing variations of temperature and fermentation time. Therefore, con- sidering cultivars and processing variables, common bean tempeh flour may be an efficient strategy to enhance the antioxidant activity of this seed.

Phaseolus vulgaris is grown in a variety of eco-agricultural regions and distributed in multiple forms, such as whole Common bean (Phaseolus vulgaris L.) is one of the most unprocessed seeds, as part of mixed, canned products, or as important grain legumes for human consumption. It gluten-free wheat flour substitute (Câmara et al. 2013). comprises 50% of the grain legumes consumed worldwide. Common beans have been studied due to their bioactive It is the primary source of dietary protein in developing components, which include antioxidants, dietary fiber frac- countries (Mitchell et al. 2009). tions, resistant starch and oligosaccharides present in the

Journal of Food Processing and Preservation (2015) ••–•• © 2015 Wiley Periodicals, Inc. LWT - Food Science and Technology 66 (2016) 93e100

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Structure preservation of Aloe vera (barbadensis Miller) mucilage in a spray drying process L. Medina-Torres a, *, F. Calderas b, R. Minjares c, A. Femenia c, G. S'anchez-Olivares b, F.R. Go'nzalez-Laredo d, R. Santiago-Adame d, D.M. Ramirez-Nun~ez e, f g J. Rodríguez-Ramírez , O. Manero a Facultad de Química, Universidad Nacional Auto'noma de Me'xico (UNAM), M'exico, D.F. 04510, Mexico b CIATEC, A.C., Omega 201, Leo'n Gto., 37545, Mexico c Ingeniería Agroalimentaria, Departamento de Química, Universitat de les Illes Balears, Spain d Departamento de Ingenierías Química y Bioquímica, Instituto Tecnolo'gico de Durango, Blvd. Felipe Pescador 1830 Ote., 34080, Durango, Dgo., Mexico e Facultad de Ciencias Químicas, Universidad Jua'rez del Estado de Durango (UJED), Avenida veterinaria, s/n, Circuito Universitario, C.P. 34120, Durango, Dgo., Mexico f Centro Interdisciplinario de Investigacio'n para el Desarrollo Integral Regional Unidad Oaxaca, Hornos No. 1003, Col. Noche Buena, Santa Cruz Xoxocotla'n, C.P. 71230, Oaxaca, Mexico g Instituto de Investigaciones en Materiales, Universidad Nacional Auto'noma de Me'xico (UNAM), M'exico, D.F. 04510, Mexico

a r t i c l e i n f o a b s t r a c t

Article history: Aloe vera (barbadensis Miller) mucilage in powder form was obtained by spray-drying following by suspension Received 9 April 2015 in aqueous solution, to enable microstructure recovery. The rheological behavior of the reconstituted mucilage Received in revised form was evaluated as a function of mucilage concentration, temperature, pH and ionic- strength. Mucilage solutions 5 October 2015 exhibited shear-thinning non-Newtonian behavior. The viscosity was found dependent on ionic-strength. This Accepted 6 October 2015 dependence is more evident when divalent cations are used, although a strong rise in viscosity upon increasing Available online xxx pH is observed. Linear viscoelastic data show a predominant viscous behavior, but with a crossover point (storage module G0 ¼ loss module G00) sug- gesting a change in molecular conformation to a random-coil Keywords: arrangement of the mucilage micro- structure. The spray-dried powders were compared with fresh mucilage, Rheology with regard to chemical composition and mechanical flow behavior. Results reveal a small structure modification Molecular-weight Viscoelastic properties during the spray-drying process, evidencing preservation of the mucilage microstructure when optimum spray- o Viscosity drying conditions are used, i.e., 1.5 L/h inlet flow, temperature of 150 C and atomization rate of 27,500 Polysaccharides rpm. © 2015 Published by Elsevier Ltd.

1. Introduction molecular weight. Spray-drying (SD) is a process widely used to produce powders Polysaccharides are used in the food industry for their ability to due to several advantages such as capacity to produce powders of a modify the functional properties of food systems (Medina-Torres, specific particle size and moisture content, continuous operation, ' Brito-de La Fuente, Torrestiana-Sanchez, & Katthain, 2000). Since short production times, cost effectiveness, and flexibility (Keshani, polysaccharides impart a functional property to a specific product, Daud, Nourozi, Namvar, & Ghasemi, 2015 and references therein). the economics and availability of polysaccharides are important in Examples of recent studies of SD food products are: Blackberry the final formulation (Whistler, 1993). A very popular plant in the (Ferrari, Germer, & de Aguirre, 2012), coffee oil (Frascareli, Silva, Cactaceae family is Aloe vera (AV) (barbadensis Miller) which has Tonon, & Hubinger, 2012), Yoghurt (Sakin-Yilmazer, Koç, Balkir, & been widely studied due to its healing properties. AV is a hetero- Kaymak-Ertekin, 2014), among others. However, the relative high polysaccharide (it is formed by several polysaccharides) of high temperatures used in the SD process can negatively affect the properties of the powders causing degradation and oxidation of the product. Thus, finding the best process conditions is of paramount * Corresponding author. importance to obtain powders with optimum properties. For E-mail address: [email protected] (L. Medina-Torres). example, it was found that the increase in inlet air-temperature

http://dx.doi.org/10.1016/j.lwt.2015.10.023 0023-6438/© 2015 Published by Elsevier Ltd. Accepted Manuscript

Effect of different drying procedures on physicochemical properties and flow behavior of Aloe vera (Aloe Barbadensis Miller) gel

R. Minjares-Fuentes, A. Femenia, F. Comas-Serra, C. Rosselló, V.M. Rodríguez- González, R.F. González-Laredo, J.A. Gallegos-Infante, L. Medina-Torres

PII: S0023-6438(16)30471-6 DOI: 10.1016/j.lwt.2016.07.060 Reference: YFSTL 5634

To appear in: LWT - Food Science and Technology

Received Date: 28 March 2016 Revised Date: 26 July 2016 Accepted Date: 27 July 2016

Please cite this article as: Minjares-Fuentes, R., Femenia, A., Comas-Serra, F., Rosselló, C., Rodríguez- González, V.M., González-Laredo, R.F., Gallegos-Infante, J.A., Medina-Torres, L., Effect of different drying procedures on physicochemical properties and flow behavior of Aloe vera (Aloe Barbadensis Miller) gel, LWT - Food Science and Technology (2016), doi: 10.1016/j.lwt.2016.07.060.

This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Industrial Crops and Products 90 (2016) 1–8

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Microencapsulation by spray drying of laurel infusions (Litsea glaucescens) with maltodextrin

L. Medina-Torresa,∗, R. Santiago-Adameb, F. Calderasc, J.A. Gallegos-Infanted, R.F. González-Laredo d, N.E. Rocha-Guzmán d, D.M. Nún˜ ez-Ramírez e, a b M.J. Bernad-Bernad , O. Manero a Facultad de Química, Universidad Nacional Autónoma de México, México, D.F., 04510, Mexico b Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, México, D.F., 04510, Mexico c CIATEC, A.C. Omega 201, Fracc. Industrial Delta, CP 37545, León, Guanajuato, Mexico d Instituto Tecnológico de Durango, Felipe Pescador Ote, CP 34080, Durango, Mexico e Facultad de Ciencias Químicas, Universidad Juárez del Estado de Durango (UJED), Avenida Veterinaria, s/n, Circuito Universitario, C.P. 34120, Durango, Mexico

a r t i c l e i n f o a b s t r a c t

Article history: The effect of maltodextrin as an encapsulating agent on spray dried (SD) laurel infusions was studied (inlet Received 17 February 2016 temperatures: 140, 160 and 180 ◦C, and feed rate: 8 and 10 mL/min at fixed flow atomization). In the SD Received in revised form 18 May 2016 samples, the phenolic content (TPC), antioxidant capacity (DPPH*), morphology (SEM), chemical structure Accepted 6 June 2016 (FTIR), rheology properties and release profiles were studied. The results show that laurel infusion had 42.10 (±0.23) mg gallic acid equivalent/g of laurel and EC50 of 0.40 (±0.10) mg laurel/mL of DPPH*, the SD Keywords: microparticles showed defined morphologies. Encapsulation of laurel infusion was achieved with an efficiency Microencapsulation of ∼70%. The reconstituted SD powders solutions showed a shear-thinning rheological behavior (n < 1). The Litsea glauscecens Laurel infusions ( ) ◦ Spray-drying results evidenced that the best conditions for laurel encapsulation by SD were 160 C inlet Rheological properties and release profile temperature and 8 mL/min feed rate.

© 2016 Elsevier B.V. All rights reserved.

1. Introduction affects their stability and reduce the antioxidant benefits, so that their protection with encapsulation vectors becomes crucial for the Laurel (Litsea spp.) is one of the most used spices in the world. preparation of functional food (D’Archivio et al., 2010; Ersus and Thesespices are commonly usedasfood additives, provide flavors, Yurdagel, 2007; Jafari et al., 2008). The most common microen- scents, colors and even help in food preservation. It is commonly capsulation process is spray drying (SD), which has proven to be known as“baylaurel” and it hasbeen reported to impart antimicro- an effective technology inprotecting polyphenolic compounds. SD bial and antioxidant properties to food. Laurel hasbeen reported to consists inconverting water suspensions into powdered micropar- be used as an aid in gastrointestinal disorders, inflammation prob- ticles, which are composed of a wall material (shell) and a core lems and atherosclerosis (Shan et al., 2007; Cherrat et al., 2014). (encapsulated material) (Reineccius, 1988). Carbohydrates, such as The laurel spice has been used since ancient times in traditional maltodextrins are one of the main wall materials used as encap- Chinese medicine (Xie and Yu, 1996). All these benefits are related sulating materials to protect polyphenolic compounds (Desai and to the phytochemicals that compose laurel which include polyphe- Park, 2005; Ersus and Yurdagel, 2007; Jafari et al., 2008). Maltodex- nols such as phenolic acids and flavonoids (Kong et al., 2015; Tsai trins are hydrolyzed starch, they have a low cost and possess high and Lee, 2011). The phenolic compounds (polyphenols) in Laurel water solubility ( > 75%) and low viscosity in aqueous solutions. spiceprovidenatural antioxidantcapacitiestotrapfreeradicalsand Maltodextrins form a coating film minimizing oxygen contact of inhibit oxidative processes in the body (Shan et al., 2005). However, the encapsulated material (Pourashouri et al., 2014). Microparti- polyphenols are extremely labile at ambient conditions (Ultravio- cles obtained from SD are able to last for longer periods of time let, radiation, temperature, oxygen, stomach digestion, etc.) which and they have been reported to release the encapsulated materials under simulated conditions of the digestive tract (Medina-Torres et al., 2013) SD is the ideal process to achieve mechanical stability

∗ Corresponding author. of encapsulated polyphenols particles and preserve their bioactiv- E-mailaddresses: [email protected], [email protected] (L. Medina-Torres). ity (Mahdavi et al., 2014; Khazaei et al., 2014). There have been

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Spray drying-microencapsulation of cinnamon infusions (Cinnamomum zeylanicum) with maltodextrin R. Santiago-Adame a, L. Medina-Torres b, *, J.A. Gallegos-Infante a, F. Calderas c, a a a b R.F. Gonza'lez-Laredo , N.E. Rocha-Guzma'n , L.A. Ochoa-Martínez , M.J. Bernad-Bernad a Departamento de Ing. Química y Bioquímica, Instituto Tecnolo'gico de Durango., Blvd. Felipe Pescador 1830 Ote., 34080, Durango, Dgo., Mexico b Facultad de Química, Universidad Nacional Aut'onoma de M'exico (UNAM), M'exico, D.F., 04510, Mexico c CIATEC, A.C. Omega 201, Fracc. Industrial Delta, CP 37545, Leo'n, Gto., Mexico

a r t i c l e i n f o a b s t r a c t

Article history: The effect of temperature and feed rate on spray dried cinnamon infusions (SDCInf) using maltodextrin Received 4 March 2015 as an encapsulating agent was studied (inlet temperature: 140, 160, and 180 oC; feed rate: 8 and 10 mL/ min). Received in revised form Total phenolic content (TPC), antioxidant capacity (DPPH*), morphology (SEM), chemical (FTIR) and 3 June 2015 rheological properties, and releasing profiles were assessed in SDCInf. Cinnamon infusions (CInf) resulted in Accepted 6 June 2015 29.32 (±0.70) mg of GAE/g of cinnamon. As for DPPH* inhibition, EC 50 was 0.291 (±0.09) mg of cin- Available online 18 June 2015 namon/mL. Microparticles showed a deflated-balloon like shape, encapsulating up to ~85% of the cin- namon infusion, and a simple shear-thinning behavior (n < 1). Results show that powdered SDCInf obtained at 160 Keywords: and 180 oC and 10 mL/min yielded the best protection for cinnamon infusions. Microencapsulation © 2015 Elsevier Ltd. All rights reserved. Cinnamon infusions (Cinnamomum zeylanicum) Spray-drying Rheological properties and release profile

1. Introduction comprised of a wall material and a core. Carbohydrates, such as maltodextrins, are among major wall materials; they are used as Spices are commonly used food additives. They provide flavor, encapsulating materials that protect the core (Desai & Park, 2005; aroma, color, and food preservative capabilities. Cinnamon is the Jafari, Assadpoor, He, & Bhandari, 2008). Maltodextrins are ob- second most important spice (just behind black pepper) in the USA tained from starch hydrolysis. They are cheap, highly water soluble and Europe (Jayaprakasha, Negi, Jena, & Rao, 2007). Its consump- (>75%), and aqueous solutions containing them have commonly low tion is related to health benefits, such as: antimicrobial activity, viscosity. This material has the ability to form a cover for the core, inhibition of cancer cells proliferation, protection against common encapsulating aromas and flavors, minimizing exposure to oxygen flu, and glucose control in diabetes (Anderson et al., 2004). Among (Pourashouri et al., 2014). Microparticles obtained by spray drying the compounds related to these effects are polyphenols. Poly- are able to protect cores for long periods and release them under phenols possess characteristic properties, such as free-radical digestive conditions. Therefore, this process is suitable for increasing scavenging and inhibition of oxidizing processes in the body. polyphenols stability during long-term storage while preserving Phenolic compounds are important because they provide cinna- their biological activity (Khazaei, Jafari, Ghorbani, & Kakhki, 2014; mon with natural antioxidant capacity (i.e. scavenging of free rad- Mahdavi, Jafari, Ghorbani, & Assadpoor, 2014). Thus, these icals). However, they are extremely sensitive to environmental microparticles are studied in relation to their total phenolic content, conditions (e.g. UV radiation, temperature, oxygen, digestion, etc.). chemical configuration (FTIR-analysis), morphology (Scanning Microencapsulation processes, such as spray drying, have proved to Electron Microscopy), particle size homo- geneity (Particle Size be an effective technology for protecting this sort of compounds. Distribution, PSD), rheological properties, and release profile. There This technology turns suspensions into powdered microparticles, are several studies on the non-polar fraction of cinnamon, yet only a few for the aqueous fraction. The aim of this study was to assess the effect of temperature and feed rate on the properties of SDCInf encapsulated with maltodextrin in order to find the best spray * Corresponding author. E-mail address: [email protected] (L. Medina-Torres). drying conditions to achieve the highest total

http://dx.doi.org/10.1016/j.lwt.2015.06.020 0023-6438/© 2015 Elsevier Ltd. All rights reserved. Review article doi: 10.5154/r.rchscfa.2015.04.014

Mexican oaks as a potential non-timber resource for Kombucha beverages Encinos mexicanos, un recurso no maderable con potencial para elaborar bebidas tipo Kombucha

Blanca D. Vázquez-Cabral; Martha R. Moreno-Jiménez; Nuria E. Rocha-Guzmán; José A. Gallegos-Infante; Silvia M. González-Herrera; Claudia I. Gamboa-Gómez; Rubén F. González-Laredo*.

Instituto Tecnológico de Durango. Felipe Pescador núm. 1830 Ote., col. Nueva Vizcaya. C. P. 34080. Durango, Dgo., México. Correo-e: [email protected] Tel.: +52 18 8185402 ext. 113 (*Autor para correspondencia).

Abstract

aks (Quercus spp.) are some of the world’s most important and abundant trees in nearly all temperate forests of the northern hemisphere. There are two diversity O centers for this genus: one is in Southeast Asia, and the other is in Mexico. Studies on the use of oak have mainly highlighted its timber applications. However, its non-timber value is still unappreciated. Ethnobotanical tradition shows infusions from Quercus leaves, alone or in combination with other plants, which have anticarcinogenic effects in gastric cancer patients. Sensorial studies on oak herbal infusions have shown that a higher phenolic content decreases their acceptability. Therefore, a significant alternative for encouraging use of herbal teas is fermentation with the Kombucha culture (black tea fungus). Kombucha drink is reported as a potential health promoter. It is a slightly acidic beverage from fermentation of sweetened black tea with Kombucha consortium, which consists mainly of acetic acid bacteria and yeasts. The phenolic composition and content gradually changes over fermentation time, producing a beverage rich in antioxidants. Metabolic conversion of Keywords: Nutraceutical, polyphenols may be due to glucuronidation of original flavonoid compounds. This process herbal infusion, functional enhances the bioavailability of phytochemicals, which include a wide range of bioactive drinks, polyphenols, Quercus. ellagitannins and flavonoids, in oaks.

Resumen

os encinos (Quercus spp.) son algunos de los árboles más importantes y abundantes en casi todos los bosques templados del hemisferio norte. El sudeste asiático y México L destacan como centros de diversidad del género. La investigación sobre el encino se ha enfocado principalmente en sus aplicaciones maderables, siendo poco reconocido su valor como recurso no maderable. La tradición etnobotánica muestra que las infusiones de hojas de encino, solas o combinadas con otras plantas, presentan efectos contra el cáncer gástrico; sin embargo, el análisis sensorial de las infusiones ha mostrado relación inversa entre su aceptabilidad y su contenido fenólico. Por lo anterior, el hongo del té (Kombucha) es una alternativa para fermentar infusiones de encino, mejorando su aceptabilidad y carácter profiláctico. La bebida Kombucha es ligeramente ácida debido a que se prepara a partir de té negro endulzado que es fermentado por el consorcio microbiano Kombucha. El consorcio se forma por bacterias ácido acéticas y levaduras que cambian gradualmente la composición Palabras clave: Bebidas fenólica del sustrato, produciendo una bebida rica en antioxidantes. La conversión metabólica nutracéuticas, bebidas de los polifenoles puede deberse a su glucuronidación, que es un proceso que libera y realza funcionales, infusión herbal, la biodisponibilidad de los fitoquímicos presentes en el encino, incluyendo elagitaninos y polifenoles, Quercus. flavonoides bioactivos.

Please cite this article as follows (APA 6): Vázquez-Cabral, B. D., Moreno-Jiménez, M. R., Rocha-Guzmán, N. E., Gallegos- Infante, J. A., González-Herrera, S. M., Gamboa-Gómez, C. I., & González-Laredo, R. F. (2016). Mexican oaks as a potential non-timber resource for kombucha beverages. Revista Chapingo Serie Ciencias Forestales y del Ambiente, 22(1), 73- 86. doi: 10.5154/r.rchscfa.2015.04.014 Received: April 14, 2015 / Accepted: December 01, 2015. www.chapingo.mx/revistas/forestales

Food and Chemical Toxicology xxx (2015) 1e8

Contents lists available at ScienceDirect

Food and Chemical Toxicology

journal homepage: www.elsevier.com/locate/foodchemtox

Morphological and release characterization of nanoparticles formulated with poly (DL-lactide-co-glycolide) (PLGA) and lupeol: In vitro permeability and modulator effect on NF-kB in Caco-2 cell system stimulated with TNF-a M.H. Cha'irez-Ramírez a, J.A. Sa'nchez-Burgos a, C. Gomes b, M.R. Moreno-Jime'nez a, R.F. Gonza'lez-Laredo a, M.J. Bernad-Bernad c, L. Medina-Torres c, M.V. Ramírez-Mares d, a, * a, ** J.A. Gallegos-Infante , N.E. Rocha-Guzma'n a Instituto Tecnolo'gico de Durango, Departamento de Ingenierías Química y Bioquímica, Blvd. Felipe Pescador 1830 Ote, Col Nueva Vizcaya, 34080 Durango, Dgo, Mexico b Texas A&M, Dept. of Biological and Agriculture Engineering, 201 Scoates Hall I 2117 TAMU, College Station, TX 77843, USA c Facultad de Química, Departamento de Ingeniería Química, Conjunto E, Universidad Nacional Auto'noma de M'exico, CU, 04510 Me'xico, DF, Mexico d Instituto Tecnolo'gico de Morelia, Departamento de Ingenierías Química y Bioquímica, Ave. Tecnolo'gico 1500, Col. Lomas de Santiaguito, 58120 Morelia Mich, Mexico

a r t i c l e i n f o a b s t r a c t

Article history: Lupeol exhibits anti-inflammatory effects; unfortunately it shows low water solubility. An alternative to Received 29 May 2015 overcome this is the development of nanomaterials. Several methods for nanomaterial production are available. Received in revised form One of them is emulsification/solvent-evaporation. The objective of the present work was to evaluate physical 23 July 2015 properties, transport and in vitro modulator effects on NF-kB of poly (lactide-co-gly- colide) (PLGA) Accepted 2 August 2015 nanoparticles loaded with lupeol. Nanonutraceuticals were prepared with 16% (w/v) of lupeol. Size Available online xxx distribution and morphology were measured by particle size analyzer and TEM. In vitro release of lupeol was studied by three different models: Higuchi, Siepmann & Peppas, and Power law. Transport of Keywords: nanonutraceutical was studied in a Caco-2 cell model and by GCeMS. Modulator effect on NK-kB was studied fl Anti-in ammation by western blot analysis. Nanonutraceuticals were 10% larger than the nanoparticles without lupeol (372 vs Lupeol 337 nm) and presented a broader size distribution (0.28 vs 0.22 ). TEM results displayed spherical structures Nanoparticles with a broader size distribution. Entrapment ef ficiency of lupeol was 64.54% and it in vitro release data fitted NF-kB Transport well to the Power law and Higuchi equation (R > 0.84e0.84). Strong regulation of NF-kB of nanonutraceutical was observed. It was not observed any transport across the Caco-2 cell model at the different experimental conditions. © 2015 Published by Elsevier Ltd.

1. Introduction comprising 5 six-membered rings (ursanes and lanostanes) or 4 six-membered rings and 1 five-membered ring (lupanes and Several natural compounds show biological effects, as the pen- hopanes) (Wal et al., 2011). They can be found in the balsam, and tacyclic triterpenes. They are based on a 30-carbon skeleton plant resins (Muffler et al., 2011); and usually in the diet, where a consumption of 250 mg per day is estimated for this compound (Saleem, 2009). One of them is lupeol, a lupane-type pentacyclic triterpene present indiverse plants suchas Japanese pear, aloeleaf, * Corresponding author. Laboratory of Natural Products Instituto Tecnol'ogico de Durango, Unidad de Posgrado, Investigacio'n y Desarrollo Tecnolo'gico (UPIDET), mango pulp extract, ginseng oil, etc. (Siddique and Saleem, 2011). Blvd. Felipe Pescador 1830 Ote., 34080 Durango, Dgo, Mexico. Regarding to its anti-inflammatory effect, lupeol has shown ** Corresponding author. Laboratory of Functional Foods and Nutraceuticals inhibitory activities on pro-inflammatory cytokines such as IL-2, ' ' Instituto Tecnologico de Durango, Unidad de Posgrado, Investigacion y Desarrollo IFN-g and TNF-a (Bani et al., 2006; Ahmad et al., 2010), IL-4, IL-5, Tecnol'ogico (UPIDET), Blvd. Felipe Pescador 1830 Ote., 34080 Durango, Dgo, Mexico. eosinophils reduction (Vasconcelos et al., 2008) and effect against E-mail addresses: [email protected] (J.A. Gallegos-Infante), nrocha@ pro-inflammatory enzymes like iNOS and COX-2 (Saleem et al., itdurango.edu.mx, [email protected] (N.E. Rocha-Guzma'n). 2004; Sa'nchez-Burgos et al., 2013).

http://dx.doi.org/10.1016/j.fct.2015.08.003 0278-6915/© 2015 Published by Elsevier Ltd.

Please cite this article in press as: Cha'irez-Ramírez, M.H., et al., Morphological and release characterization of nanoparticles formulated with poly (DL-lactide-co-glycolide) (PLGA) and lupeol: In vitro permeability and modulator effect on NF-kB in Caco-2 cell system stimulated with TNF-a, Food and Chemical Toxicology (2015), http://dx.doi.org/10.1016/j.fct.2015.08.003 Industrial Crops and Products 77 (2015) 827–832

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Industrial Crops and Products

journal homepage: www.elsevier.com/locate/indcrop

Isolation of lupeol from white oak leaves and its anti-inflammatory activity

a b a a J.A. Sánchez-Burgos , M.V. Ramírez-Mares , J.A. Gallegos-Infante , R.F. González-Laredo , M.R. Moreno-Jiméneza, M.H. Cháirez-Ramíreza, L. Medina-Torresc, ,∗ N.E. Rocha-Guzmána

a Research Group on Functional Foods and Nutraceuticals, Departamento de Ingenierías Química y Bioquímica, Tecnológico Nacional de México—Instituto Tecnológico de Durango, Felipe Pescador 1830 Ote., 34080 Durango, Dgo., Mexico b Universidad del Mar Campus Puerto Ángel, Cd. Universitaria Puerto Ángel, Distrito de San Pedro Pochutla, Oaxaca, Mexico c Facultad de Química Edif. E. Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico

a r t i c l e i n f o a b s t r a c t

Article history: Lupeol [lup-20(29)-en-2-ol] is found mainly on the surface of plant barks, stems, leaves and fruits waxes. This Received 21 July 2015 research explored oaks leaves of several species (Quercus resinosa, Q. grisea, Q. laeta and Q. obtusata) as Received in revised form ◦ potential source of lupeol. It was extracted from Quercus leaves by maceration with CHCl3 at 35 C, 20 September 2015 followed by a purification in silica column (normal phase), and using as mobile phase hexane (100%), Accepted 22 September 2015 hexane:ethyl acetate (90:10) and hexane:ethyl acetate (80:20). Lupeol in oak leaves was identified by 13C NMR

and quantified by GC–MS. Quercus obtusata leaves were an abundant source of lupeol (173.59 µg/g of sample). Keywords: Anti-cyclooxygenase activity has been used for determining bioactivity of lupeol in this research. Lupeol Anti-cyclooxygenase activity © 2015 Elsevier B.V. All rights reserved. Purification Chromatography

1. Introduction involve the use of nonsteroidal anti-inflammatory drugs (NSAIDs). However, the low enzymatic selectivity of these drugs and the Nutraceuticals are recognized as biologically active substances abuse in their consumption cause health problems. This is due to present in natural products and foods that when consumed in con- the non-selective inhibition of NSAIDs on cyclooxygenase cyto- centrated form have demonstrated beneficial effects on the health. quines. Therefore, it is justified to explore natural alternatives, Plants are the most commonly sources of natural bioactive com- which involve the use of bioactive nutraceuticals without side pounds, which may specifically be helpful in the treatment of effects as the associated with the prolonged use of NSAIDs(Kumari certain diseases. Quercus speciescommonly known as oaks have an and Kakkar,2012). important distribution in Mexico. Particularly the state of Durango, Among the nutraceutical recognized with major biological Mexico, possesses large forest areas with 41 Quercus species, from potential as anti-inflammatory activity are triterpenes. Lupeol is which 22 are whites and 19 are reds (Rosales-Castro et al., 2011). As a pentacyclic triterpene found in many medicinal plants and some reported, Quercus spp. leaves contain tannins, alkaloids, saponins, fruits (Deyrup et al., 2014; Hernández-Vázquez et al., 2010). This cardiac glycosides and steroids (Sánchez-Burgos et al., 2013), and chemical constituent has shown diverse biological effects such as: haveshownantioxidant,antimicrobial,antitopoisomeraseandgas- antioxidant, anti-topoisomerase, antitumor, anti-inflammatory, troprotective effects. Infusions of Quercus species has been used among other activities (Santiago and Mayor, 2014; Zhang et al., in folk medicine as treatment for several inflammatory diseases 2015; Kumari and Kakkar, 2012). (Maxia et al., 2005). Lupeol is distributed along the plant kingdom, and is found in Inflammatory diseases are one of the major problems in many olive fruit, mango fruit, Aloe leaves, Elm Plant, Japanese pear, Gin- pathophysiologies such as gastrointestinal disorders. There are seng oil (Saleem, 2009) and fig (Santiago and Mayor, 2014) among many alternatives to treat inflammatory processes, some of which others, in concentrations between 3 and 880 µg/g of sample. Con- sidering the health benefits that this triterpene provides, the main objective of the present work was to explore new natural sources to obtain lupeol from several white oak species. In addition, a second ∗ Corresponding author. E-mail address: [email protected] (N.E. Rocha-Guzmán).

http://dx.doi.org/10.1016/j.indcrop.2015.09.056 0926-6690/© 2015 Elsevier B.V. All rights reserved.

Herrera-Carrera et al., Cogent Food & Agriculture (2015), 1: 1059033 http://dx.doi.org/10.1080/23311932.2015.1059033

FOOD SCIENCE & TECHNOLOGY | RESEARCH ARTICLE

Phenolic composition of selected herbal infusions

and their anti-inflammatory effect on a colonic

model in vitro in HT-29 cells

Received: 05 February 2015 Elda Herrera-Carrera1, Martha Rocío Moreno-Jiménez1*, Nuria Elizabeth Rocha-Guzmán1, Accepted: 02 June 2015 José Alberto Gallegos-Infante1, Jesús Omar Díaz-Rivas1, Claudia Ivette Gamboa-Gómez1 and Published: 13 July 2015 Rubén Francisco González-Laredo1*

*Corresponding authors: Martha Rocío Moreno-Jiménez and Rubén Francisco Abstract: Some herbal infusions used in folk medicine in Mexico to treat gastroin- González-Laredo, Departamento de Ingenierías Química y Bioquímica, testinal disorders were evaluated. Antioxidant activity and phenolic compounds Instituto Tecnológico de Durango, Felipe were analyzed on the lyophilized aqueous crude extracts (LACE) of arnica (Aster Pescador 1830 Ote, 34080 Durango, Durango, Mexico gymnocephalus), chamomile (Chamaemelum nobile), cumin (Cominum cyminum), E-mails: [email protected]. desert resurrection plant (DRP) (Selaginella lepidophylla), laurel (Listea glaucescens), mx(Martha Rocío Moreno-Jiménez); [email protected] marjoram (Origanum majorana), mint (Mentha spicata), salvilla (Buddleia scordioides) (Rubén Francisco González-Laredo) and yerbaniz (Tagetes lucida). Total phenolic content ranged from 8.0 to 70.7 μg GAE/ Reviewing editor: mg for DRP and laurel respectively. Major phenolic compounds were identified by gas Fatih Yildiz, Middle East Technical University, Turkey chromatography–mass spectrometry and high-performance liquid chromatography. The IC determined by the degradation of the deoxy-d-ribose ranged from 2,452.53 Additional information is available at 50 the end of the article to 5,097.11 μg/mL. The cytoprotective effect of the LACE alone and on indometha- cin- induced oxidative stress in HT-29 cells was tested. The tetrazolium dye MTT assay was performed in concentrations of 0.125–10 mg/mL allowing choosing the lowest

concentration for this experimentation. Inflammation markers were measured by

© 2015 The Author(s). This open access article is distributed under a Creative Commons Attribution (CC-BY) 4.0 license.

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Antioxidant Phenolic Compounds of Ethanolic and Aqueous Extracts from Pink Cedar (Acrocarpus fraxinifolius Whight...

Article in Post Communist Economies · July 2015 DOI: 10.1080/02773813.2014.946619

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Food and Chemical Toxicology ■■ (2015) ■■–■■

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1 Antioxidant, anti-inflammatory and anticarcinogenic activities of 2 edible red oak (Quercus spp.) infusions in rat colon carcinogenesis 3 induced by 1,2-dimethylhydrazine 4 5 Martha Rocío Moreno-Jimenez a, Fátima Trujillo-Esquivel b, Marco A. Gallegos-Corona c, 6 Rosalia Reynoso-Camacho b, Rubén Francisco González-Laredo a, 7 José Alberto Gallegos-Infante a, Nuria Elizabeth Rocha-Guzmán a, 8 Minerva Ramos-Gomez b,*

9 a Departamento de Ings. Química y Bioquímica, Instituto Tecnológico de Durango, Blvd. Felipe Pescador 1830 Ote., Col. Nueva Vizcaya, 34080 Durango, Dgo., 10 Mexico 11 b Posgrado en Alimentos (PROPAC), Facultad de Química, Universidad Autónoma de Querétaro, Cerro de las Campanas, S/N, Col. Centro, 76010 Querétaro, 12 Qro., Mexico 13 c Laboratorio de Histoptología, Facultad de Medicina, Universidad Autónoma de Querétaro, Clavel 200, Col. Prados de la Capilla, 76017 Querétaro, Qro., 14 Mexico 15 16 17 A R T I C L E I N F O A B S T R A C T 18 2190 Article history: Red oak (Quercus spp.) leaves are traditionally used as food in Mexico, and some of their infusions have 212 Received 25 September 2014 potential anticarcinogenic and anti-inflammatory effects; however, these properties have not yet been 234 Accepted 12 March 2015 scientifically tested. The aim of this work was to explore the anti-inflammatory activity in HT-29 cells Available online 256 and anticarcinogenic effect in 1,2-dimethylhydrazine (DMH)-induced colon carcinogenesis of red oak 278 infusions. Quercus infusions were prepared and administered as the sole source of drink to male Sprague- Keywords: 29 Dawley rats (1% w/v) for the entire 26-week experimental period. On week 4, rats received 8 subcutaneous 30 Quercus sideroxyla 31 injections of DMH (21 mg/kg body weight) once a week. The results showed that mean tumor (0.9 ± 0.2 vs. 332 Anticarcinogenic activity 345 Anti-inflammatory 2.6 ± 0.3) and multiplicity (1.2 ± 0.1 vs. 2.0 ± 0.23), and β-catenin protein level (2.2-fold) in adenocarcinomas 367 Colon cancer were significantly lower in Quercus sideroxyla-treated group compared with DMH group. By contrast, Quercus 389 Herbal infusions durifolia and Quercus eduardii infusions had no protective effect. Additionally, the experiments in HT-29 cells 410 Polyphenols confirmed that Q. sideroxyla infusion effectively decreased the levels of the inflammatory markers COX-2 42 and IL-8 by modulating the expression of NF-κB. These results highlight some of the molecular mechanisms 43 related to the chemopreventive effect of Q. sideroxyla infusion and its potential value as a source of 44 bioactive compounds. 45 © 2015 Published by Elsevier Ltd.

46

47 1. Introduction proto-oncogenes, such as K-ras and CTNNB1, the gene coding for 63 48 β-catenin, and genetic alterations in tumor suppressor genes, 64

49 Colorectal cancer (CRC) is the third most common malignant including the APC gene, a suppressor of β-catenin signaling (Bos 65 et 50 neoplasm worldwide (Altobelli et al., 2014; Matsuda and Machii, al., 1987; Morin et al., 1997). Mutations in the K-ras gene and in 66 51 2013). In Mexico, according to the 1998–2002 cancer registry data, CTNNB1 can also be detected in colonic tumors of rats induced with 67 52 CRCrepresents 3.8% of newcancer cases, a 36% increase during this the colonic procarcinogen 1,2-dimethylhydrazine (DMH), or its 68 53 period; furthermore, CRCmortalityhasalsoincreasedoverthe same proximate metabolite, azoxymethane (AOM) (Perše and Cerar, 2011; 69 54 period (Verastegui and Mohar, 2010). CRC is the end result of a Takahashi and Wakabayashi, 2004). 70 55 stepwise process involving transition of preneoplastic lesions Inflammation-related processes have also been shown to be in- 71 56 (polyps) to moreadvancedstages (adenocarcinomas) (Tanaka, 2009). volved in the development of both human and DMH/AOM-induced 72 57 Colonic malignant transformation involves activating mutations in colon carcinogenesis (Rogler, 2014; Takahashi and Wakabayashi, 73 2004). Nuclear factor kappa B (NF-κB) is a transcription factor that 74 58 plays a crucial role in regulation of pro-inflammatory cytokines, such 75

as tumor necrosis factor α (TNF-α), chemokines, anti-apoptotic pro- 76 59 77 60 * Corresponding author. C.U., Cerro de las Campanas S/N, Col. Centro. 76010 teins and growth factors (Shen and Tergaoankar, 2009); therefore, 61 Querétaro, Qro. México. Tel.: +52 442 192 1307; fax: +52 442 192 1304. NF-kB modulation by dietary constituents is of major importance 78 62 E-mail address: [email protected] (M. Ramos-Gomez). in cancer chemoprevention. 79

http://dx.doi.org/10.1016/j.fct.2015.03.011 0278-6915/© 2015 Published by Elsevier Ltd.

Please cite this article in press as: Martha Rocío Moreno-Jimenez, et al., Antioxidant, anti-inflammatory and anticarcinogenic activities of edible red oak (Quercus spp.) infusions in rat colon carcinogenesis induced by 1,2-dimethylhydrazine, Food and Chemical Toxicology (2015), doi: 10.1016/j.fct.2015.03.011

Accepted Manuscript

Title: Ultrasound assisted extraction modeling of fructans from agave (Agave tequilana Weber var. Azul) at different temperatures and ultrasound powers

Author: Mart´ın Narva´ez-Flores Miguel A´ . Sa´nchez-Madrigal Armando Quintero-Ramos Marco A. Paredes-Liza´rraga Rube´n F. Gonza´lez-Laredo Martha G. Ruiz-Gutie´rrez Hilda A. Pin˜o´ n- Castillo Carmen O. Mele´ndez-Pizarro

PII: S0960-3085(15)00109-1 DOI: http://dx.doi.org/doi:10.1016/j.fbp.2015.08.007 Reference: FBP 641

To appear in: Food and Bioproducts Processing

Received date: 2-4-2015 Revised date: 3-8-2015 Accepted date: 30-8-2015

Please cite this article as: Narva´ez-Flores, M., Sa´nchez-Madrigal, M.A´ ., Quintero- Ramos, A., Paredes-Liza´rraga, M.A., Gonza´lez-Laredo, R.F., Ruiz-Gutie´rrez, M.G., Pin˜o´ n-Castillo, H.A., Mele´ndez-Pizarro, C.O.,Ultrasound assisted extraction modeling of fructans from agave (Agave tequilana Weber var. Azul) at different temperatures and ultrasound powers, Food and Bioproducts Processing (2015), http://dx.doi.org/10.1016/j.fbp.2015.08.007

This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. EXCLI Journal 2015;14:809-831 – ISSN 1611-2156 Received: February 11, 2015, accepted: June 16, 2015, published: July 09, 2015

Review article:

PLANTS WITH POTENTIAL USE ON OBESITY AND ITS COMPLICATIONS

Claudia I. Gamboa-Gómez, Nuria E. Rocha-Guzmán, J. Alberto Gallegos-Infante, Martha R. Moreno-Jiménez, Blanca D. Vázquez-Cabral, Rubén F. González-Laredo*

Instituto Tecnológico de Durango, Felipe Pescador 1830 Ote., 34080 Durango, Dgo., México

* Corresponding author: Tel.: +52 (618) 818-5402, 818-6936 Ext. 113. E-mail address: [email protected]

http://dx.doi.org/10.17179/excli2015-186

This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/).

ABSTRACT Obesity is the most prevalent nutritional disease and a growing public health problem worldwide. This disease is a causal component of the metabolic syndrome related with abnormalities, including hyperglycemia, dyslipidem- ia, hypertension, inflammation, among others. There are anti-obesity drugs, affecting the fundamental processes of the weight regulation; however they have shown serious side effects, which outweigh their beneficial effects. Most recent studies on the treatment of obesity and its complications have focused on the potential role of differ- ent plants preparation that can exert a positive effect on the mechanisms involved in this pathology. For instance, anti- obesity effects of green tea and its isolated active principles have been reported in both in vitro (cell cul- tures) and in vivo (animal models) that possess healthy effects, decreasing adipose tissue through reduction of adipocytes differentiation and proliferation. A positive effect in lipid profile, and lipid and carbohydrates metab- olisms were demonstrated as well. In addition, anti-inflammatory and antioxidant activities were stud- ied. However, the consumption of green tea and its products is not that common in Western countries, where other plants with similar bioactivity predominate; nevertheless, the effect extension has not been analyzed in depth, despite of their potential as alternative treatment for obesity. In this review the anti-obesity potential and reported mechanisms of action of diverse plants such as: Camellia sinensis, Hibiscus sabdariffa, Hypericum per- foratum, Persea americana, Phaseolus vulgaris, Capsicum annuum, Rosmarinus officinalis, Ilex paraguariensis, Citrus paradisi, Citrus limon, Punica granatum, Aloe vera, Taraxacum officinale and Arachis hypogaea is sum- marized. We consider the potential of these plants as natural alternative treatments of some metabolic alterations associated with obesity.

Keywords: Obesity, obesity complications, anti-obesity plants, phytochemicals, alternative treatments

INTRODUCTION Overweight is an established risk factor Obesity is now the most prevalent nutri- for type 2 diabetes and cardiovascular dis- tional disease and a growing public health eases, where the central and causal compo- problem worldwide. The disease has ac- nent is the metabolic syndrome (Montague quired epidemic proportions projected to and O’Rahilly, 2000). This is a series of reach 2.3 billion of overweight adults and 700 metabolic abnormalities including hypergly- million obese adults, respectively by 2015 cemia, dyslipidemia, hypertension, inflam- (Malik et al., 2013). mation, oxidative stress, among others (Grundy et al., 2004).

809 Author's Accepted Manuscript

Gastroprotective potential of Buddleja scor- dioides Kunth Scrophulariaceae infusions; effects into the modulation of antioxidant in enzymes and inflammation markers in an vivo model

J.O. Díaz-Rivas, E. Herrera-Carrera, J.A. Gallegos-Infante, N.E. Rocha-Guzmán, R.F.

González-Laredo, M.R. Moreno-Jiménez, M. Ramos-Gómez, R. Reynoso-Camacho, M. www.elsevier.com/locate/jep Larrosa-Pérez, M.A. Gallegos-Corona

PII: S0378-8741(15)00290-1 DOI: http://dx.doi.org/10.1016/j.jep.2015.04.024 Reference: JEP9467

To appear in: Journal of Ethnopharmacology

Received date: 27 September 2014 Revised date: 16 April 2015 Accepted date: 16 April 2015

Cite this article as: J.O. Díaz-Rivas, E. Herrera-Carrera, J.A. Gallegos-Infante, N. E. Rocha-Guzmán, R.F. González-Laredo, M.R. Moreno-Jiménez, M. Ramos- Gómez, R. Reynoso-Camacho, M. Larrosa-Pérez, M.A. Gallegos-Corona, Gastroprotective potential of Buddleja scordioides Kunth Scrophulariaceae infusions; effects into the modulation of antioxidant enzymes and inflammation markers in an in vivo model, Journal of Ethnopharmacology, http: //dx.doi.org/10.1016/j.jep.2015.04.024

This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting galley proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Accepted Manuscript

Effect of stevia and citric acid on the stability of phenolic compounds and in vitro antioxidant and antidiabetic capacity of a roselle (Hibiscus sabdariffa L.) beverage

Iza F. Pérez-Ramírez, Eduardo Castaño-Tostado, José A. Ramírez-de León, Nuria E. Rocha-Guzmán, Rosalía Reynoso-Camacho

PII: S0308-8146(14)01511-8 DOI: http://dx.doi.org/10.1016/j.foodchem.2014.09.126 Reference: FOCH 16482

To appear in: Food Chemistry

Received Date: 20 May 2014 Revised Date: 15 August 2014 Accepted Date: 22 September 2014

Please cite this article as: Pérez-Ramírez, I.F., Castaño-Tostado, E., Ramírez-de León, J.A., Rocha-Guzmán, N.E., Reynoso-Camacho, R., Effect of stevia and citric acid on the stability of phenolic compounds and in vitro antioxidant and antidiabetic capacity of a roselle (Hibiscus sabdariffa L.) beverage, Food Chemistry (2014), doi: http:// dx.doi.org/10.1016/j.foodchem.2014.09.126

This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. EXCLI Journal 2015;14:204-212 – ISSN 1611-2156 Received: October 23, 2014, accepted: December 12, 2014, published: February 04, 2015

Original article:

CHEMICAL COMPOSITION OF BIOMASS GENERATED IN THE GUAVA TREE PRUNING

Julio César Camarena-Tello1, Nuria Elizabeth Rocha-Guzmán2, José Alberto Gallegos- Infante2, Rubén Francisco González-Laredo2, Fabiola Eugenia Pedraza-Bucio1, 1 1 1* Pablo López-Albarrán , Rafael Herrera-Bucio , José Guadalupe Rutiaga-Quiñones

1 Facultad de Ingeniería en Tecnología de la Madera, Edificio D, Ciudad Universitaria, Universidad Michoacana de San Nicolás de Hidalgo, Av. Fco. J. Múgica S/N. Col. Felicitas de Río, Morelia, Michoacán, C.P. 58040, México 2 Departamento de Ingenierías Química y Bioquímica, Instituto Tecnológico de Durango, Blvd. Felipe Pescador 1830 Ote., Col. Nueva Vizcaya, Durango, Durango, C.P. 34080, México * Corresponding autor: [email protected]; Telephone: +52 (443) 3260379 http://dx.doi.org/10.17179/excli2014-647

This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/).

ABSTRACT Psidium guajava L. (Myrtaceae) is a native plant of Central America and is now widely cultivated in many trop- ical regions of the world for the fruit production. In Mexico, in the guava orchards common practices to control fruit production are: water stress, defoliation and pruning. In this study, we report the chemical composition of the biomass (branches and leaves) generated in the pruning practices. The results ranged as follows: pH (4.98- 5.88), soda solubility (39.01-70.49 %), ash (1.87-8.20 %); potassium and calcium were the major inorganic ele- ments in ash. No heavy metals were detected in the studied samples; total solubility (15.21-46.60 %), Runkel lignin (17.77- 35.26 %), holocellulose (26.56 -69.49 %), α-cellulose (15.53-35.36 %), hemicelluloses (11.02- 34.12 %), tannins in aqueous extracts (3.81-9.06 %), and tannins in ethanolic extracts (3.42-15.24 %).

Keywords: Psidium guajava, pH, ash, extractives, polysaccharide, tannins

INTRODUCTION gapeo (2,500 hectares), Benito Juárez (1,500 Psidium guajava L. belongs to the Myr- hectares) and Zitácuaro (1,000 hectares) taceae family. It is a native of Central Amer- (Mendoza Lopez et al., 2005). In these guava ica but is now widely cultivated, distributed orchards common practices to control fruit and the fruits enrich the diets of millions of production are: water stress, defoliation and people in the world tropics (Rathish and Su- pruning; pruning is the most used activity. mitra, 2007; El-Mahmood, 2009). In Mexi- P. guajava is a well known traditional co, the States with the largest fruit produc- medicinal plant used in some indigenous sys- tion are Michoacan (42 %), Aguascalientes tems throughout the world. All parts of this (35 %) and Zacatecas (15 %), the rest (8 %) tree, including roots, bark, leaves, seeds, and belongs to other states (González Gaona et al., the fruits have been used for treatment gas- 2002). In Michoacan, the maximum fruit trointestinal problems. Leaves, pulp and seeds production falls into three municipalities lo- are used as an antispasdomic, anti- cated in the eastern area of the state: Jun- inflammatory, and anti-diarrheic, to treat

204

Phenolic composition changes of processed common beans: Their antioxidant and anti-inflammatory effects in intestinal cancer cells

Martha R. Moreno-Jime´nez, Vero´ nica Cervantes-Cardoza, Jose´ A. Gallegos- Infante, Rube´n F. Gonza´lez-Laredo, Isabel Estrella, Teresa de J. Garc´ıa-Gasca, Elda Herrera-Carrera, Jesu´ s O. D´ıaz-Rivas, Nuria E. Rocha-Guzma´n

PII: S0963-9969(14)00773-X DOI: doi: 10.1016/j.foodres.2014.12.003 Reference: FRIN 5605

To appear in: Food Research International

Received date: 25 September 2014 Revised date: 2 December 2014 Accepted date: 6 December 2014

Please cite this article as: Moreno-Jim´enez, M.R., Cervantes-Cardoza, V., Gallegos- Infante, J.A., Gonza´lez-Laredo, R.F., Estrella, I., Garc´ıa-Gasca, T.J., Herrera-Carrera, E., D´ıaz-Rivas, J.O. & Rocha-Guzm´an, N.E., Phenolic composition changes of processed common beans: Theirantioxidant and anti-inflammatory effects in intestinal cancer cells, Food Research International (2014), doi: 10.1016/j.foodres.2014.12.003

This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. 2015

Woodpreservation using natural products

Preservación de la madera usando productos naturales

Rubén Francisco González-Laredo1,2*, Martha Rosales-Castro3, Nuria Elizabeth Rocha-Guzmán2, José Alberto Gallegos-

2 2 4 Infante , Martha Rocío Moreno-Jiménez and Joseph J. Karchesy

1 Instituto Tecnológico de Durango. Depto. Ingenierías 2 Facultad de Ciencias Forestales. Universidad Juárez 4 Oregon State University. College of Forestry. Depart- Química y Bioquímica. Felipe Pescador 1830 Ote., del Estado de Durango. Durango, Dgo. México ment of Wood Science & Engineering. Corvallis OR, 34080 Durango, Dgo. México 3CIIDIR-IPN Durango. Biotechnology Group. Sigma 119 USA 997331 * Corresponding author. [email protected] Fracc. 20 de Noviembre, 34220 Durango, Dgo. México

AbstrAct

It is a current concern in the wood preservation field to avoid the use of toxic chemicals and develop new technologies based on low environmental impact agents and sustainable principles. Under this expectation, an intended state-of-the-art is introduced on the appli- cation of natural products such as traditional tar and wood oils as well as tannins and plant extracts. A particular revision to heartwood chemical components is offered. The combined methods of using natural and chemical components are reviewed, considering as out- standing the mixtures of natural organic constituents with cooper and boron salts that seem to be under encouraging experimentation. Fungicides and anti-termite applications are commented as well the leaching problem of inorganic salts. Chemical modification of wood structure through the formation of adducts and the treatment with nanomaterials are promising tools that will change the actual view and performance of wood preservation techniques.

Keywords: bark, biocides, extract, fungicide, oil, phenolics, tannins, termites. resumen Una de las prioridades actuales en el campo de la preservación de madera es evitar el uso de materiales tóxicos, desarrollando nuevas tecnologías fundamentadas en principios sustentables y empleando agentes de bajo impacto ambiental. Con esta expectativa se plantea una revisión del estado del arte sobre la aplicación de productos naturales, tales como taninos, alquitrán, aceites y extractos vegetales. Se presenta en particular una revisión sobre los componentes químicos contenidos en el duramen de maderas naturalmente resistentes. Se analizan los métodos combinados de ingredientes naturales y químicos, resaltando las mezclas de componentes naturales orgánicos con sales de cobre y boro que parecen representar una opción experimental confiable. Se comentan también las aplicaciones fungicidas y anti termitas, así como los problemas de lixiviación de sales inorgánicas. Opciones como la modificación química de la madera vía la formación de aductos y por tratamiento con nanomateriales son procesos promisorios que cambiaran eventualmente la manera de ver y aplicar la tecnología actual de preservación de maderas.

Palabras clave: corteza, biocidas, extracto, fungicidas, aceite, compuestos fenólicos, taninos, termitas.

IntroductIon chemical preservatives containing metals for wood treat- Wood as a natural renewable resource plays an important ment and their disposal problems have urged the search for role in the world economy, particularly in the construc- tion more ecologically friendly technologies. The current and furniture fields. The expectation for better options in progress and implementation of new technologies has been preserving wood from biodegradation during storage, limited due to variability between the laboratory and the transportation, manufacturing, and in service is actual. field performances of natural products alternatives, and Environmental issues from the conventional toxic legal problems derived from the lack of globally

63

Article pubs.acs.org/JAFC

Metabolite Profile, Antioxidant Capacity, and Inhibition of Digestive Enzymes in Infusions of Peppermint (Mentha piperita) Grown under Drought Stress Marely G. Figueroa-Peŕez,† Nuria Elizabeth Rocha-Guzmań,‡ Iza F. Peŕez-Ramírez,† † ,† Edmundo Mercado-Silva, and Rosalía Reynoso-Camacho* †Research and Graduate Studies in the Department of Food Science, School of Chemistry, Universidad Autónoma de Queretaro, Centro Universitario, Cerro de las Campanas S/N, Queretaro, Queretaro 76010, Mexico ‡Department of Graduate Studies, Research, and Technology Development (UPIDET), Instituto Tecnologico de Durango, Boulevard Felipe Pescador 1830 Oriente, Durango, Durango 34080, Mexico

ABSTRACT: Peppermint (Mentha piperita) infusions represent an important source of antioxidants, which can be enhanced by inducing abiotic stress in plants. The aim of this study was to evaluate the effect of drought stress on peppermint cultivation as well as the metabolite profile, antioxidant capacity, and inhibition of digestive enzymes of resulting infusions. At 45 days after planting, irrigation was suppressed until 85 (control), 65, 35, 24, and 12% soil moisture (SM) was reached. The results showed that 35, 24, and 12% SM decreased fresh (20%) and dry (5%) weight. The 35 and 24% SM treatments significantly increased total phenolic and flavonoid contents as well as antioxidant capacity. Coumaric acid, quercetin, luteolin, and naringenin were detected only in some drought treatments; however, in these infusions, fewer amino acids and unsaturated fatty acids were identified. The 24 and 12% SM treatments slightly improved inhibition of pancreatic lipase and α-amylase activity. Therefore, induction of moderate water stress in peppermint is recommended to enhance its biological properties.

INTRODUCTION Nevertheless, the use of drought stress as a strategy to improve ■ phytochemicals in plants should be carefully applied to avoid Herbal infusions are widely consumed because of the phenolic the detrimental effects of excessive ROS production, such as compounds that they contain. These compounds are 7 considered the most abundant natural antioxidants in food and cellular damage and death. Therefore, the aim of this study was are recommended for inclusion in the diet because of the to cultivate peppermint (M. piperita) at different levels of health benefits that they can produce. One of the most popular drought stress and to evaluate the effect on plant growth as well herbal preparations is peppermint (Mentha piperita) infusion. as on the metabolite profile, antioxidant capacity, and inhibitory This plant has a phenolic compound content in leaves of activity on digestive enzymes of resulting infusions. approximately 19−23% dry weight, of which 12% are flavonoids, such as eriocitrin, rosmarinic acid, hesperidin, and ■ MATERIALS AND METHODS luteolin.1 Approximately 75% of these compounds can be Reagents and Biological Materials. The peppermint plants were extracted in the preparation of an infusion, and many of them purchased from a local plant nursery, Floraplant S.A. de C.V. (Mexico) have been shown to have antioxidant, hypolipidemic, and taxonomically identified in the herbarium “Dr. Jerzy Rzedowski” of 2,3 the Natural Science Department of Universidad Autoónma de antidiabetic, and antitumoral properties. Other important Queretaro. 1,1-Diphenyl-2-picrylhydrazyl radical, 2,20-azinobis(3- components found in peppermint leaves are fatty acids, volatile ethylbenzthiazoline-6-sulfonic acid), sodium nitroprusside, lipase compounds, chlorophyll, α- and γ-tocopherols, and ascorbic from porcine pancreas (type II), 4-nitrophenyl butyrate, α-amylase, p- 1 acid. nitrophenyl-α-D-glucopyranoside, α-glucosidase, caffeic, coumaric, Several studies have demonstrated that peppermint extracts sinapic, and rosmarinic acids, eriocitrin, naringenin, rutin, vanillin, decrease glucose, total cholesterol, triacylglycerols, very low- luteolin, quercetin, and hesperidin were purchased from Sigma-Aldrich density lipoprotein (VLDL ), and low-density lipoprotein (St. Louis, MO). (LDL) levels, thus decreasing the atherogenic index in diabetic Plant Growth Conditions and Measurement of Growth P e 4,5 arameters. The plants were grown in a greenhous at the Universidad rats. These health benefits can be enhanced using preharvest Autónoma de Queretaro in pots with a diameter of 40 cm, with strategies to increase bioactive compounds in the peppermint irrigation every 3 days [85% soil moisture (SM)] during the fi first 45 days. Mean daily temperature inside the greenhouse was within leaves. In a wide variety of plant species, de cit irrigation has 1 been shown to enhance the synthesis of several phytochemicals, optimal ranges for peppermint growth (19−25 °C). Fertilization was including phenolic acids, flavonoids, and tannins, as a response to stress constraints.6 Under stress conditions, increased Received: July 30, 2014 reactive oxygen species (ROS) production is observed in Revised: November 12, 2014 different cellular compartments, leading to the activation of the Accepted: November 22, 2014 antioxidant system, which synthesizes phenolic compounds. Published: December 2, 2014

© 2014 American Chemical Society 12027 dx.doi.org/10.1021/jf503628c | J. Agric. Food Chem. 2014, 62, 12027−12033

Food Chemistry 156 (2014) 273–278

Contents lists available at ScienceDirect

Food Chemistry

journal homepage: www.elsevier.com/locate/foodchem

Effect of chemical elicitors on peppermint (Mentha piperita) plants and their impact on the metabolite profile and antioxidant capacity of resulting infusions Marely G. Figueroa Pérez a, Nuria Elizabeth Rocha-Guzmán b, Edmundo Mercado-Silva a, ⇑ Guadalupe Loarca-Piña a, Rosalía Reynoso-Camacho a, a Research and Graduate Studies in Food Science, School of Chemistry, Universidad Autonoma de Queretaro, C.U., Cerro de las Campanas S/N, Queretaro, Queretaro 76010, Mexico b Department of Graduate Studies, Research, and Technology Development (UPIDET), Instituto Tecnologico de Durango, Blvd. Felipe Pescador 1830 Ote., Durango, Dgo. 34080, Mexico

a r t i c l e i n f o a b s t r a c t

Article history: Infusions are widely consumed all over the world and are a source of dietary antioxidants, which can be Received 29 September 2013 improved in plants using elicitors. The aim of this study was to evaluate the foliar applica tion of salicylic acid Received in revised form 17 December 2013 (SA) (0.5, 1 and 2 mM) or hydrogen peroxide (H2O2) (0.05, 0.1 and 0.5 mM) on peppermint (Mentha piperita) Accepted 27 January 2014 plants and its effect on the metabolite profile and antioxidant capacity of resulting infusions. Whereas 2 mM Available online 7 February 2014 SA treatment improved plant growth parameters and metabolite profile (carbohydrates and amino acids), 0.5 and 1 mM SA treatments increased phenolic compound concentration. Sinapic acid, Keywords: rutin and naringin were detected only in SA treatments; antioxidant capacity was also improved. Regard- Peppermint ing H O treatments, no differences in plant growth parameters, metabolite profile or antioxidant capac-

2 2 Elicitor Salicylic acid ity were found. Therefore, the application of SA to peppermint is recommended in order to improve Hydrogen peroxide bioactive compounds and the antioxidant capacity of infusions.

© 2014 Elsevier Ltd. All rights reserved.

1. Introduction compounds can be extracted in an infusion (McKay & Blumberg, 2006). It has been reported that flavonoids exert many beneficial Herbal infusions are aromatic beverages prepared by pouring hot effects on health which is linked to their known biological functions or boiling water over dry parts of plants. These infusions are some as antioxidants, due to their free radical scavenging and metal of the most widely consumed beverages in the world, provid- ing a chelating properties (Pawlak et al., 2010). major source of dietary phenolic compounds, which are considered Phenolic compounds are involved in various plant processes the most abundant natural antioxidants. In Mexico, approximately such as growth and reproduction and are also synthesized as a de- 80% of the population consumes infusions on a regular basis, and fence mechanism against biotic or abiotic stress (Cohen & Kennedy, one of the most popular is prepared from peppermint (Mentha 2010); therefore, their production can be enhanced by treatment with piperita) (Rivera et al., 2008). certain compounds, termed elicitors, which are defined as a Among the major components found in peppermint leaves are substance that, when introduced in small concentrations to a living fatty acids such as linoleic, linolenic and palmitic acid. A variety of system, initiates or improves the biosynthesis of specific com- volatile compounds, mainly menthol, menthone and isomenth- one pounds (Edreva et al., 2008; Ferrari, 2010). Salicylic acid (SA) is a have also been identified along with b-carotene, chlorophyll, a- and phenolic compound that shows great potential as an elicitor in c-tocopherols and ascorbic acid. Other important com- pounds plants. It occurs naturally in plants in small amounts and partici- found in peppermint are phenolic compounds. The propor- tion of pates in the regulation of physiological processes such as stomatal phenolic compounds found in peppermint leaves is approximately closure, nutrient uptake, chlorophyll and protein synthesis, tran- 19–23% dry weight, of which 12% belongs to the flavonoids group, spiration and photosynthesis (Raskin, 1992). Low concentrations of including eriocitrin, rosmarinic acid, hesperidin and luteolin 7-O- exogenously applied SA interact with stress-signalling mecha- nisms rutinoside, among others. 75 percent of these and induce phenolic compound synthesis (Gharib, 2007; Ghasemzadeh & Jaafar, 2012; Khandaker, Akond, & Oba, 2011). Catalase and ascorbate peroxidase are the main enzymes involved in ⇑ Corresponding author. Tel.: +52 (442) 1921300x5576; fax: +52 (442) 1921304. the removal of H2O2 in plants and their activities can be E-mail address: [email protected] (R. Reynoso-Camacho).

http://dx.doi.org/10.1016/j.foodchem.2014.01.101 0308-8146/© 2014 Elsevier Ltd. All rights reserved. Nutrafoods (2014) 13:169-178 DOI 10.1007/s13749-014-0035-0

Original Research

Chemical and sensory evaluation of a functional beverage obtained from infusions of oak leaves (Quercus resinosa) inoculated with the kombucha consortium under different processingconditions Blanca D. Vázquez-Cabral, Nuria E. Rocha-Guzmán, José A. Gallegos-Infante, Silvia M. González-Herrera, Rubén F. González-Laredo, Martha R. Moreno-Jiménez, Indira T.S. Córdova-Moreno Correspondence to: Nuria E. Rocha Guzman [email protected]

Received: 17 January 2014 / Accepted: 20 June 2014 © Springer – CEC Editore 2014

Abstract tion with the kombucha consortium significantly The potential use of non-timber products as alter- increased the product’s acceptability (up to 5 units) native sources of functional beverages such as kom- and decreased its pH (2 units). bucha analogues was evaluated. The fermentation of sweetened oak herbal infusions (Quercus resinosa) Introduction with the kombucha consortium was explored. The Kombucha is a popular beverage that originated in following conditions of the fermentation process Northeast China or Manchuria and then spread to induced by the action of the kombucha consortium Russia, Germany and the rest of the world [1]. Kom- were assessed: sensory acceptability and pH, colour bucha tea is an effervescent and sour drink that is a and chemical changes (phenolic composition). The product of the biotransformation of sweetened black chemical analysis showed the presence of hydroxy- tea (Camellia sinensis) by means of the sym- biotic benzoic and hydroxycinnamic acid derivatives, action of a consortium formed by acetic acid bacteria flavonoids, flavonols and flavanones, which are re- (Bacterium xylinum, B. xylinoides, B. glucon- icum, lated to the antioxidant capacity of the product among others) and yeasts (Saccharomyces lud- wigii, S. obtained. The metabolic consumption of flavan-3- apiculatus varieties, Schizosaccharomyces pombe, ols and hydroxybenzoic acid derivatives as well as among others) [2]. The symbiosis of the kombucha the production of organic acids (succinic acid) has consortium may vary depending on ge- ographic and decreased the astringency and bitterness, improving climatic conditions as well as on the local species of the product’s quality and acceptability. Fermenta- wild yeasts and bacteria [3]. The fermentation process involves the activity of yeasts that ferment glucose and fructose to ethanol,

Blanca D. Vázquez-Cabral, Nuria E. Rocha-Guzmán (•), which is then oxidised to acetic acid by acetic acid José A. Gallegos-Infante, Silvia M. González-Herrera, bacteria. The main source of carbon in this process is Rubén F. González-Laredo, Martha R. Moreno-Jiménez, sucrose. The sugar is hydrolysed by the enzyme Indira T.S. Córdova-Moreno Research Group on Functional Foods and Nutraceuticals invertase from yeast present in the kombucha con- Departamento de Ingenierías Química y Bioquímica sortium, producing ethanol via the metabolic path- InstitutoTecnológico de Durango Felipe Pescador 1830 Ote., 34080 Durango, Dgo., Mexico way of glycolysis, with a preference for fructose as the [email protected] substrate. Subsequently, acetic bacteria convert

13

CyTA - Journal of Food

ISSN: 1947-6337 (Print) 1947-6345 (Online) Journal homepage: http://www.tandfonline.com/loi/tcyt20

Effect of infrared heating on the physicochemical properties of common bean (Phaseolus vulgaris L.) flour

Estrella Edith Arce-Arce, José Alberto Gallegos-Infante, Nuria Elizabeth Rocha-Guzmán, Rubén Francisco González-Laredo, Rocío Moreno-Jiménez, Juan de Dios Figueroa-Cárdenas & Argelia Nazdira Montelongo-Montelongo

To cite this article: Estrella Edith Arce-Arce, José Alberto Gallegos-Infante, Nuria Elizabeth Rocha-Guzmán, Rubén Francisco González-Laredo, Rocío Moreno-Jiménez, Juan de Dios Figueroa-Cárdenas & Argelia Nazdira Montelongo-Montelongo (2014) Effect of infrared heating on the physicochemical properties of common bean (Phaseolus vulgaris L.) flour, CyTA - Journal of Food, 12:3, 242-248, DOI: 10.1080/19476337.2013.834978

To link to this article: http://dx.doi.org/10.1080/19476337.2013.834978

© 2013 Taylor & Francis Published online: 05 Dec 2013.

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Date: 26 May 2017, At: 04:36 LWT - Food Science and Technology 55 (2014) 426e435

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LWT - Food Science and Technology

journal homepage: www.elsevier. com/locate/ lwt

Study of spray drying of the Aloe vera mucilage (Aloe vera barbadensis Miller) as a function of its rheological properties C.V. Cervantes-Martínez a, L. Medina-Torres b,*, R.F. González-Laredo a, F. Calderas b, G. Sánchez-Olivares c, E.E. Herrera-Valencia b, J.A. Gallegos Infante a, N.E. Rocha-Guzman a, d J. Rodríguez-Ramírez a Departamento de Ingenierías Química y Bioquímica, Instituto Tecnológico de Durango, Blvd. Felipe Pescador 1830 Ote., 34080, Durango, Dgo., Mexico b Facultad de Química, Departamento de Ingeniería Química, Conjunto E Universidad Nacional Autónoma de México (UNAM), México D.F., 04510, Mexico c CIATEC, A.C., Omega 201, León, Gto., 37545, Mexico d Centro Interdisciplinario de Investigación para el Desarrollo Integral Regional Unidad Oaxaca, Hornos No. 1003, Col. Noche Buena, Santa Cruz Xoxocotlán, C.P. 71230, Oaxaca, Mexico

a r t i c l e i n f o a b s t r a c t

Article history: Spray Drying(SD) was used to obtain Aloe vera powderfrom fresh plants. Thepowder was reconstituted Received 8 July 2013 inanaqueous medium and its rheological properties, particle size distribution (PSD), thermal properties Received in revised form (differential scanning calorimetry, DSC), and morphology (scanning electron microscopy, SEM) were 4 September 2013 evaluated in order to find an alternative to natural gum to be used in the food industry. Rheological Accepted 27 September 2013 measurements were conducted at 25 .C in aqueous concentrations of 3 g/100 mL and 6 g/100 mL. A 23 factorial design was used with three central points to evaluate yield, efficiency and the rheological Keywords: properties of reconstituted powders, results were compared with a liophilized (FD) sample of A. vera Rheological properties mucilage. Experimental results showed that the shear viscosity decreased with the increase of the inlet Viscoelasticity air temperature and the speed of atomization, and it increased with increasing feed flow in SD. Addi- Mucilage Aloe vera tionally, most powders obtained in all treatments have an average particle diameter of w10 mm with a Spray drying modal distribution (PSD). The best conditions of SD in order to obtain a good thickening agent were: 150 .C inlet temperature, 1.5 L/h feed rate and atomization speed of 275,000 rpm, and with rheological properties very close to those of the FD sample. © 2013 Elsevier Ltd. All rights reserved.

1. Introduction sensitive to separation methods and they can be significantly altered with the drying process (Wang, Wang, Li, Xue, & Mao, 2009). It has Due to the concern and current interest of people in their health been shown that this plant can provide nutritional components as and quality of life, there has been an increasing demand for natural feedstock for the production of functional products, considered the products, which has impelled pharmaceutical and natural products chemistry of the future (Vega, Ampuero, Díaz, & Lemus, 2005). A. industries to focus their research on products with functional Vera is a plant that has great range for adapta- tion to the properties. A raw material that currently has potential in this field is environment due to its high rate of water retention, allowing it to A. vera, a kind of cactus from which cosmetics, pharmaceuticals and form a dense layer of gel, which contains 99.4 g/100 g water and 0.6 chemistry products can be obtained. A. vera is considered to be a g/100 g of solids, there are at least four different partially acetalized potential source of gums and/or hydrocolloids (Sánchez González, sugars in its composition that differ in the radius of the glucose and Vargas, González-Martínez, Cháfer, & Chiralt, 2008). The selection mannose (Vega, Uribe, Lemus, & Miranda, 2007). This plant has a of new sources of biopolymers requires a thorough understanding composition of equal proportions of D- glucose and D-mannose (76 of the rheological properties and physicochemical characteristics of g/100 g), with 24 g/100 g of uronic acid, the juice contains 55.2 mg of natural chemistries (García-Cruz, Rodríguez-Ramírez, Méndez- polysaccharides per 100 mL of juice. The approximate total mass of Lagunas, & Medina-Torres, 2013). These properties of the gum are polysaccharides is 788 mg/L (Rodríguez-González, Femenia, Minjares-Fuentes, & González-Lar- edo, 2010). Femenia, Sánchez, Simal, and Rosselló (1999) and Femenia, García-Pascual, Simal and * Corresponding author. Tel.: þ52 5556225360; fax: þ52 5556225329. Rosselló (2003) reported that the polysaccharides contained in the E-mail address: [email protected] (L. Medina-Torres). parenchyma of the Aloe are of

0023-6438/$ e see front matter © 2013 Elsevier Ltd. All rights reserved. http://dx.doi.org/10.1016/j.lwt.2013.09.026 LWT - Food Science and Technology 55 (2014) 426e435

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Study of spray drying of the Aloe vera mucilage (Aloe vera barbadensis Miller) as a function of its rheological properties C.V. Cervantes-Martínez a, L. Medina-Torres b,*, R.F. González-Laredo a, F. Calderas b, G. Sánchez-Olivares c, E.E. Herrera-Valencia b, J.A. Gallegos Infante a, N.E. Rocha-Guzman a, d J. Rodríguez-Ramírez a Departamento de Ingenierías Química y Bioquímica, Instituto Tecnológico de Durango, Blvd. Felipe Pescador 1830 Ote., 34080, Durango, Dgo., Mexico b Facultad de Química, Departamento de Ingeniería Química, Conjunto E Universidad Nacional Autónoma de México (UNAM), México D.F., 04510, Mexico c CIATEC, A.C., Omega 201, León, Gto., 37545, Mexico d Centro Interdisciplinario de Investigación para el Desarrollo Integral Regional Unidad Oaxaca, Hornos No. 1003, Col. Noche Buena, Santa Cruz Xoxocotlán, C.P. 71230, Oaxaca, Mexico

a r t i c l e i n f o a b s t r a c t

Article history: Spray Drying(SD) was used to obtain Aloe vera powderfrom fresh plants. Thepowder was reconstituted Received 8 July 2013 inanaqueous mediumand its rheological properties, particle size distribution (PSD), thermal properties Received in revised form (differential scanning calorimetry, DSC), and morphology (scanning electron microscopy, SEM) were 4 September 2013 evaluated in order to find an alternative to natural gum to be used in the food industry. Rheological Accepted 27 September 2013 measurements were conducted at 25 .C in aqueous concentrations of 3 g/100 mL and 6 g/100 mL. A 23 factorial design was used with three central points to evaluate yield, efficiency and the rheological Keywords: properties of reconstituted powders, results were compared with a liophilized (FD) sample of A. vera Rheological properties mucilage. Experimental results showed that the shear viscosity decreased with the increase of the inlet Viscoelasticity air temperature and the speed of atomization, and it increased with increasing feed flow in SD. Addi- Mucilage Aloe vera tionally, most powders obtained in all treatments have an average particle diameter of w10 mm with a Spray drying modal distribution (PSD). The best conditions of SD in order to obtain a good thickening agent were: 150 .C inlet temperature, 1.5 L/h feed rate and atomization speed of 275,000 rpm, and with rheological properties very close to those of the FD sample. © 2013 Elsevier Ltd. All rights reserved.

1. Introduction sensitive to separation methods and they can be significantly altered with the drying process (Wang, Wang, Li, Xue, & Mao, 2009). It has Due to the concern and current interest of people in their health been shown that this plant can provide nutritional components as and quality of life, there has been an increasing demand for natural feedstock for the production of functional products, considered the products, which has impelled pharmaceutical and natural products chemistry of the future (Vega, Ampuero, Díaz, & Lemus, 2005). A. industries to focus their research on products with functional Vera is a plant that has great range for adapta- tion to the properties. A raw material that currently has potential in this field is environment due to its high rate of water retention, allowing it to A. vera, a kind of cactus from which cosmetics, pharmaceuticals and form a dense layer of gel, which contains 99.4 g/100 g water and 0.6 chemistry products can be obtained. A. vera is considered to be a g/100 g of solids, there are at least four different partially acetalized potential source of gums and/or hydrocolloids (Sánchez González, sugars in its composition that differ in the radius of the glucose and Vargas, González-Martínez, Cháfer, & Chiralt, 2008). The selection mannose (Vega, Uribe, Lemus, & Miranda, 2007). This plant has a of new sources of biopolymers requires a thorough understanding composition of equal proportions of D- glucose and D-mannose (76 of the rheological properties and physicochemical characteristics of g/100 g), with 24 g/100 g of uronic acid, the juice contains 55.2 mg of natural chemistries (García-Cruz, Rodríguez-Ramírez, Méndez- polysaccharides per 100 mL of juice. The approximate total mass of Lagunas, & Medina-Torres, 2013). These properties of the gum are polysaccharides is 788 mg/L (Rodríguez-González, Femenia, Minjares-Fuentes, & González-Lar- edo, 2010). Femenia, Sánchez, Simal, and Rosselló (1999) and Femenia, García-Pascual, Simal and * Corresponding author. Tel.: þ52 5556225360; fax: þ52 5556225329. Rosselló (2003) reported that the polysaccharides contained in the E-mail address: [email protected] (L. Medina-Torres). parenchyma of the Aloe are of

0023-6438/$ e see front matter © 2013 Elsevier Ltd. All rights reserved. http://dx.doi.org/10.1016/j.lwt.2013.09.026 Hindawi Publishing Corporation International Journal of Food Science Volume 2014, Article ID 513641, 8 pages http://dx.doi.org/10.1155/2014/513641

Research Article Influence of Commercial Saturated Monoglyceride, Mono-/Diglycerides Mixtures, Vegetable Oil,Stirring Speed, and Temperature on the Physical Properties of Organogels

Omar Gerardo Rocha-Amador,1 Jose Alberto Gallegos-Infante,1 2 1 Qingrong Huang, Nuria Elizabeth Rocha-Guzman, 1 1 Martha Rocio Moreno-Jimenez, and Ruben F. Gonzalez-Laredo 1 Unidad de Posgrado, Investigacio´n y Desarrollo Tecnolo´gico, Departamento de Ings Qu´ımica y Bioqu´ımica, Instituto Tecnolo´gico de Durango, Bulevar Felipe Pescador 1830 Ote., Colonia Nueva Vizcaya, 34080 Durango, DGO, Mexico 2DepartmentofFood Science, SchoolofEnvironmentaland BiologicalSciences, RutgersUniversity, Th NewJersey StateUniversity,65Dudley Road,NewBrunswick, NJ08901,USA

Correspondence should be addressed to Jose Alberto Gallegos-Infante; [email protected]

Received 11May 2014; Revised 25 July 2014; Accepted 16August 2014; Published 21September 2014

Academic Editor: Jose M. Prieto

Copyright © 2014 Omar Gerardo Rocha-Amador et al. Thi is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Th objective of this study was to evaluate the influence of gelator, vegetable oil, stirring speed, and temperature on the physical properties of obtained organogels. They were prepared under varying independent conditions and applying a fractional experimental design. From there a rheological characterization was developed. The physical characterization also included polarized light microscopy and calorimetric analysis. Once these data were obtained, X-Ray diffraction was applied toselected samples and a microstructure lattice was confi med. Commonly, the only conditions that affect crystallization have been analyzed (temperature, solvent, gelator, and cooling rate). Wefound that stirring speed is the most important parameter in the organogel preparation.

1. Introduction system. Gel is a system consisting of molecules, particles, and chains, which are partially connected to each other in a Gels have been described as materials that are “easier to fluid medium by crosslinks tothe macroscopic dimensions. recognize than defin ” [1]. Most of the times this problem The the loss of fluidity is the result of connectivity. Both comes from industry, which develops products with a gel are operational definitions and may have the possibility of name, just to be attractive to consumers [2]. However, exclusions [2]. gels have been accepted as semisolid materials comprising Organogels have been attracting much attention in low concentrations (<15%) of gelator molecules to form a biomedical and pharmaceutical fields, where the erosion network self-assembly that entraps the solvent (in organogels of gels in stomach and intestines is important for drug both nonpolar components), preventing fl w due to surface delivery [4, 5]; therefore gels erosion has been applied for tension [3]. this purpose [6]. As oils are safe materials and are suitable Gels can be defi ed both from a rheological behavior for lipophilic components [7], they are considered a good and from a structural feature. In a rheological point of view, option for organogels elaboration. That is why food industry a gel is a system that does not flow and has the presence is very interested in this type of systems as a replacement of a plateau region of storage modulus and a low tan훿 of hydrogenated fats [8]. Thus, understanding organogels, (<0.1) at an angular frequency from 1−03 to 10 2rad/s. The defin tion is closely related to their characteristics and their structural defin tion is based on the connectivity of the crucial potential to develop new applications. Industrial Crops and Products 42 (2013) 57–62

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Industrial Crops and Products

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Antioxidant, antimicrobial, antitopoisomerase and gastroprotective effect of herbal infusions from four Quercus species J.A. Sánchez-Burgosa, M.V. Ramírez-Maresb, M.M. Larrosac, J.A. Gallegos-Infantea, ,∗ R.F. González-Laredoa, L. Medina-Torresd, N.E. Rocha-Guzmána a Instituto Tecnológico de Durango, Unidad de Posgrado, Investigación y Desarrollo Tecnológico (UPIDET), Blvd. Felipe Pescador 1830 Ote., 34080 Durango, Dgo., Mexico b Instituto Tecnológico de Morelia, Departamento de Ings. Química y Bioquímica, Ave. Tecnológico 1500, Col. Lomas de Santiaguito, 58120 Morelia, Mich., Mexico c Centro de Edafología y Biología Aplicada del Segura (CEBAS-CSIC), Murcia, E-30100, Spain d Facultad de Química, Edif. E, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico

a r t i c l e i n f o a b s t r a c t

Article history: Leaves from four species of white oaks (Quercus resinosa, Quercus laeta, Quercus grisea, and Quercus Received 18 April 2012 obtusata) were investigated for the evaluation and comparison of their antioxidant, antimicrobial, anti- Received in revised form 9 May 2012 topoisomerase, and anti-proliferative activities. DPPH and hydroxyl radical scavenging capacities were Accepted 14 May 2012 tested in vitro. Results indicated thataqueousextractsfromleaves of Quercus laeta and Q. grisea displayed higher radical scavenging activity, while extracts from Q. grisea and Q. obtusata were more efficient in Keywords: inhibiting the degradation of deoxyribose, preventing the formation of hydroxyl radicals. Polar extracts Quercus showed different degrees of antimicrobial activity, presenting Q. resinosa leaves a broader spectrum. In DPPH Q. resinosa Deoxyribose the anti-topoisomerase assay only leaves infusions showed activity. The investigation indicates Anti-topoisomerase activities that the biological activity of aqueous extracts from oak leaves promises a more rational and effective application of this resource in the near future.

© 2012 Elsevier B.V. All rights reserved.

1. Introduction with dietary substances is an important area of research and entails using non-toxic substances to interfere with carcinogen- Quercus trees, commonly known as oaks, belong to the family esis (Johnson et al., 2010). There are worldwide efforts to discover Fagaceae. They comprise 450 species worldwide, with an impor- anticancer agents from plants (Demain and Vaishnav, 2011). Some tant distribution in Mexico, where are present 135–150 species, 86 phytochemicals as ellagitanins (type of polyphenols) have shown of them are considered endemic (Luna-José et al., 2003). The state antioxidant, gastroprotective (Beserra et al., 2011) and anticancer of Durango, Mexico, possesses extent woodland resources properties (Umesalma and Sudhandiran, 2011). covered by template speciesmainly represented by mixed pine and Several methods have been proposed to link biochemical oaks forests (Corral and Navar Chaidez, 2005). In Durango, Mexico mechanism to carcinogenesis (Shureiqi et al., 2000). An exam- forests inhabit 41 Quercus species, from which 22 are white and 19 ple is topoisomerase inhibitors which constitute a class of agents are red (Rosales-Castro et al., 2011). that inhibit carcinogenesis via their antiproliferative or cell- Research on natural products with potential therapeutic bene- differentiating action and are considered an attractive targeting fits represents an area of great interest in which herbal products had strategy in chemotherapy and chemoprevention (Cho et al., 2000). been the most important source. Phytochemical compounds allow The aim of this work was to investigate the in vitro antioxidant, us to understand plant physiology and biochemical pathways and antitopoisomerase, antimicrobial, anticiclooxigenase and antipro- propose a sustainable handling for each particular product. This liferative activities of herbal infusions (teas) from the leaves of potential source for non-timber products, including nutraceutical Quercus resinosa, Quercus grisea, Quercus laeta and Quercus obtusata. ingredients, has not been explored. In Mexican traditional medicine the use of plants on the form of infusion or plasters is a common practice. Chemoprevention 2. Material and methods

2.1. Biological material

Saccharomyces cerevisiae mutant cells JN362a, JN394, JN394 t− , ∗ Corresponding author. Tel.: +52 618 8186936x112; fax: +52 618 8186936x112. 1 E-mail addresses: [email protected], JN394t2–4 and JN394t2–5 were kindly provided by Dr. John Nitiss of [email protected] (N.E. Rocha-Guzmán). St. Jude Children’s Research Hospital, Memphis, TN, USA. Standard

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Mesquite leaves (Prosopis laevigata), a natural resource with antioxidant capacity and cardioprotection potential

M. García-Andradea, R.F. González-Laredoa,∗, N.E. Rocha-Guzmána, J.A. Gallegos-Infantea, b,1 c M. Rosales-Castro , L. Medina-Torres a Instituto Tecnológico de Durango, Dpto. Ingenierías Química y Bioquímica, Blvd. Felipe Pescador 1830 Ote., 34080 Durango, Dgo., Mexico b CIIDIR-IPN Unidad Durango, Sigma 119 fracc. 20 de noviembre, 43220 Durango, Dgo., Mexico c Facultad de Química, Depto. Ingeniería Química, Conjunto E, UNAM, 04510 México, D.F., Mexico

a r t i c l e i n f o a b s t r a c t

Article history: The antioxidant activity of acetone extracts and purified fractions from Prosopis laevigata leaves were evaluated Received 14 September 2012 as well its cardioprotection potential in vitro. Mezquite leaves were dewaxed with petroleum ether and Received in revised form 9 November 2012 extracted with aqueous acetone (70%); the polar extract was purified in Sep-Pak® Cartridges and their Accepted 19 November 2012 fractions evaluated. Significant differences among fractions and crude extracts were found in total phenolic content (Folin Ciocalteu), antioxidant capacity by scavenging hydroxyl and DPPH radi- cal assays. Keywords: Purified fractions showed antihypertensive effects inhibiting angiotensin converting enzyme and Antioxidant cardioprotection inhibiting low density lipoprotein oxidation. The HPLC profile displayed phenolic Cardioprotection Mesquite compounds such as gallic acid, catechin, gallocatechin, epicatechin gallate, rutin, and luteolin that may explain Polyphenols these antioxidant and biological properties. Mesquite leaves can be a source of bioactive phenolics as Prosopis nutraceutical ingredients.

© 2012 Elsevier B.V. All rights reserved.

1. Introduction structure and its parts from being damaged by free radicals and reactive species, avoiding diseases such as atherosclerosis (Han et Currently, there is a generalized interest for balanced diets rich al., 2007). Plant phenols, as named in industry, are used as the in fruits and vegetables and their direct relationship with human active principles in many actual formulations (Quideau et al., 2011). health and well-being. The contribution of natural phytochemi- cals Hence, there is interest in searching for bioactive plant antioxidant present in foods to reduce the risk of chronic diseases is being sources that might prevent from oxidative stress-induced degra- continuously reported (De La Rosa et al., 2010). Cell damage from dation or fight its negative effects in biological systems. unbalance of free radicals that endures as an oxidative stress disor- Mesquite (Prosopis spp.) is an endemic tree that belongs to the der affects the cellular structure and its components. Then tissues Leguminosae family and Mimosaceae subfamily, and com- prises 44 and organs become disturbed as a result of the metabolic syndrome, species distributed at arid and semiarid regions over one third of which is often characterized by oxidative stress that eventually pro- the earth surface (Burkart, 1976). In Mexico there are 11 Prosopis motes the appearance of degenerative conditions such as cancer, species: P. odorata, P. glandulosa, P. velutina, P. articulata, P. diabetes and cardiovascular diseases (Roberts and Sindhu, 2009). tamaulipana, P. yaquiana, P. vidaliana, P. mezcalana, P. mayana, P. Plants, herbs and spices have been used as remedies in tra- juliflora, and P. laevigata (Cedillo and Mayoral, 1997). Mesquite is an ditional medicine and attained a wide recognition as sources of ecologically important plant because it fixes nitro- gen in soil, bioactive phytochemicals with prophylactic benefits. A distinctive promoting the growing of associated shrub and bushes species, property of these active principles is their antioxidant capac- ity, which diminishes soil erosion (Golubov et al., 2001). Its stem and which is common in many secondary metabolites from the plant branches are used for wood and charcoal production, and as kingdom (Yadav et al., 2012). The major natural antioxidants are firewood; from its pods a kind of honey and other edi- ble polyphenols, although antioxidation is not a property limited products are obtained, and the pods along the leaves are also used as only to them. Polyphenols protect macromolecules from the cell forage for cattle and small ruminants (Rodriguez-Franco and Maldonado-Aguirre, 1996). Heartwood from Prosopis species has shown resistance against fungal attack, mainly suggesting −( )- mesquitol as the bioactive flavanol compound (Pizzo et al., 2011). ∗ Corresponding author. Tel.: +52 618 8185402x113; fax: +52 618 8186936x112. However, it cannot be considered as the unique and definite factor E-mail address: [email protected] (R.F. González-Laredo). to explain the durability of this woody material. 1 Becario COFAA-IPN.

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Vol. 7(35), pp. 2564-2573, 17 September, 2013 DOI: 10.5897/JMPR12.997 ISSN 1996-0875 ©2012 Academic Journals Journal of Medicinal Plants Research http://www.academicjournals.org/JMPR

Full Length Research Paper Polyphenolic content and antioxidant activity of leaf extracts from Quercus durifolia, Quercus eduardii, Quercus sideroxyla and Quercus resinosa

C. I. Gamboa-Gómez1, D. Hernández-Saavedra1, J. A. Gallegos-Infante2, R. F. González- Laredo2, Manzocco L.3 and N. E. Rocha-Guzmán2*

1Department of Molecular Biochemistry, Research and Graduate Studies in Food Science, School of Chemistry, Universidad Autónoma de Querétaro, Querétaro, México. 2Department of Chemical and Biochemical Engineering. Instituto Tecnológico de Durango. UPIDET. 34080 Durango, Dgo, México. 3Dipartimenti di Scienze degli Alimenti, Universitá di Udine, Via Sondrio, 2/A - 33100, Udine, Italy.

Accepted 8 September, 2013

The phenolic content and antioxidant activities of extracts from Quercus durifolia, Quercus resinosa, Quercus eduardii and Quercus sideroxyla leaves were studied. Extracts were obtained by successive extraction with aqueous acetone (70%) followed by methanol (50%). Antioxidant activities were determined using a single electron transfer (SET) and hydrogen atom transfer (HAT) based assays. For SET-based the assays performed were, 2,2-diphenyl-1-picryl hydrazine (DPPH) inhibition expressed as IC50, redox potential, as mV, inhibition of the low density lipoprotein (LDL) oxidation, as % of inhibition. For HAT-based assay, crocin bleaching technique was applied; a kinetics approach was used for the evaluation of total antioxidant capacity and the results presented in terms of equivalence by weight of a reference antioxidant. Acetone extracts (PFQA) from leaves of all Quercus species showed the best antioxidant capacity. Q. resinosa (PFQr) exhibited the best antioxidant capacity among the Quercus species analyzed either in acetone or methanol extracts (PFQM). Distinctive results are: DPPH IC50, PFQrA = 78.3 µg/g, PFQrM = 250.7 µg/g; In Redox potential, PFQrA = 147.0 mV, PFQrM = 201.6 mV; In LDL oxidation inhibition: 98.2% and in inhibition of crocin bleaching, PFQrA = 1.08 g, PFQrM = 0.98 g. In conclusion, Quercus leaves might be used as potential source of polyphenolic antioxidants.

Key words: Quercus sp., SET-based assay, HAT-based assay, phenolic compounds, antioxidant activity.

INTRODUCTION

On recent times the use of plants, vegetables, herbs and compounds with evidenced biological activity, among spices used in folk and traditional medicine have gained a which are natural antioxidants. These compounds can wide acceptance as an important source for new prevent the damage to macromolecules and cells by chemicals discovery (Afolayan et al., 2008). Currently, interfering with free radicals, usually implicated in the there is an increased interest for new sources of etiology of several diseases such as atherosclerosis,

*Corresponding author. E-mail: [email protected]. Tel (Fax) : 52-618-8186936 ext-112.

International Food Research Journal 20(3): 1087-1093 (2013) Journal homepage: http://www.ifrj.upm.edu.my

Evaluation of culinary quality and antioxidant capacity for Mexican common beans (Phaseolus vulgaris L.) canned in pilot plant

1Rocha-Guzman, N. E., 2*Gallegos-Infante, J. A., 2Gonzalez-Laredo, R. F., 2Cardoza-Cervantes, V., 1Reynoso-Camacho, R., 1Ramos-Gomez, M., 3Garcia-Gasca, T. and 4De Anda Salazar, A.

1Universidad Autónoma de Querétaro, Facultad de Química, Departamento de Investigación y Posgrado en Alimentos (DIPA), Centro Universitario, Cerro de las Campanas s/n, Querétaro, México 2Instituto Tecnológico de Durango, Departamento de Ingeniería Química y Bioquímica, Felipe Pescador 1830 Ote., Col. Nueva Vizcaya, 34080, Durango, Dgo., México 3Universidad Autónoma de Querétaro, Facultad de Ciencias Naturales, Av. de las Ciencias s/n. Juriquilla, Querétaro, México 4Universidad Autónoma de San Luis Potosí, Facultad de Ciencias Químicas. Ave. Manuel Nava 5, Zona Universitaria, San Luis Potosí, SLP., México

Article history Abstract

Received: 24 August 2012 Common beans are rich in bioactive phytochemicals such as polyphenolic compounds. Received in revised form: Unfortunately, they need to be thermally processed to be consumed. The health benefits 12 December 2012 related to common beans comsumption depends mainly on their thermal processing. Accepted:13 December 2012 The objective of this work was to evaluate the effect of thermal processes on the antioxidant capacity and industrial quality of four Mexican common beans cultivars (Black bean 8025, Pinto Saltillo, Pinto Durango, and Bayo Victoria). The common beans were thermally processed by two methods: sterilization (canning), and open pan

Keywords cooking. Optimal cooking time and Fo parameter (Defined as being equivalent, in sterilizing capacity, to the cumulative lethal effect of all time/temperature combinations Canning experienced at the slowest heating point) were obtained for each cultivar. Grain size, common beans water absorption capacity (WAC), oil absorption capacity, integrity and color were the polyphenols physical parameter evaluated. Chemical parameters analyzed were total phenolic quality content (TPC), and DPPH radical scavenging activity. Bayo beans showed biggest size, radical scavenging activity Pinto beans, medium size, and Black beans, the smallest size. Lowest optimal cooking time (open pan) was observed in Pinto Saltillo cultivar. Lowest Fo parameter of the container during the thermal process was observed for Bayo Victoria cultivar. Higher WAC values were observed in Bayo Victoria and Black bean cultivar (open and canned). Higher value of integrity was found for Bayo Victoria beans. After any thermal processing L* value was lower in all cultivars. Higher values of TPC in cooked common

beans cultivars were observed in Black beans and Bayo Victoria cultivars. Lower IC50 value in DPPH test was observed in canned Black beans and Bayo Victoria cultivars.

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Introduction which show antioxidant capacity (Dueñas et al., 2005; Oomah et al., 2005). Common edible beans (Phaseolus vulgaris L.) In vitro antioxidant activities and phenolic are one of the basic foods in Africa, India, and Latin compounds in raw (unprocessed) pinto and black America. Pinto beans are preferred in the North of beans, yellow and black soybeans have been reported Mexico and the Southwestern of United States, while in several studies (Madhujith et al., 2004; Oomah et Central and South of Mexico, Central America and al., 2005; Xu and Chang, 2007). They indicate that South America eat mostly colored beans (including common beans may serve as an excellent dietary black beans). Common bean is a legume considered source of natural antioxidants for disease prevention a functional food because it contains bioactive and health promotion. However, the health-promoting phytochemicals, such as polyphenols and tannins, capacities of common beans could depend on their

*Corresponding author. Email: [email protected]