PHENOLIC COMPOUNDS and PARTHENOLIDE PRODUCTION from in Vitro CULTURES of Tanacetum Parthenium Revista Mexicana De Ingeniería Química, Vol
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Revista Mexicana de Ingeniería Química ISSN: 1665-2738 [email protected] Universidad Autónoma Metropolitana Unidad Iztapalapa México Nieto-Trujillo, A.; Buendía-González, L.; García-Morales, C.; Román-Guerrero, A.; Cruz- Sosa, F.; Estrada-Zúñiga, M.E. PHENOLIC COMPOUNDS AND PARTHENOLIDE PRODUCTION FROM in vitro CULTURES OF Tanacetum parthenium Revista Mexicana de Ingeniería Química, vol. 16, núm. 2, 2017, pp. 371-383 Universidad Autónoma Metropolitana Unidad Iztapalapa Distrito Federal, México Available in: http://www.redalyc.org/articulo.oa?id=62052087004 How to cite Complete issue Scientific Information System More information about this article Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Journal's homepage in redalyc.org Non-profit academic project, developed under the open access initiative Vol. 16, No. 2 (2017) 371-383 Revista Mexicana de Ingeniería Química PHENOLIC COMPOUNDS AND PARTHENOLIDECONTENIDO PRODUCTION FROM in vitro CULTURES OF Tanacetum parthenium Volumen 8, número 3, 2009 / Volume 8, number 3, 2009 ´ ´ PRODUCCI ON DE COMPUESTOS FENOLICOS Y PARTENOLIDA EN CULTIVOS in vitro DE Tanacetum parthenium 213 DerivationA. and Nieto-Trujillo application of1 ,the L. Stefan-Maxwell Buend´ıa-Gonz equationsalez´ 2, C. Garc´ıa-Morales2, A. Roman-Guerrero´ 1, F. Cruz-Sosa1*, M.E. Estrada-Zu´niga˜ 3 1Departamento de(Desarrollo Biotecnolog´ıa,Universidad y aplicación de las ecuaciones Aut´onomaMetropolitana-Iztapalapa. de Stefan-Maxwell) Av. San Rafael Atlixco N° 186, Col. Stephen Whitaker Vicentina C.P. 09340, M´exicoD.F. 2 Facultad de Ciencias, Universidad Aut´onomadel Estado de M´exico,Campus El Cerrillo, Piedras Blancas. Carretera Toluca-Ixtlahuaca Km. 15.5, C.P. 50200, Toluca, Estado de M´exico,M´exico. 3Centro de Investigaci´onenBiotecnología Recursos / Biotechnology Bi´oticos-Facultad de Ciencias, Universidad Aut´onomadel Estado de M´exico,Carretera Toluca-Ixtlahuaca Km 14.5, San Cayetano C.P. 50295, Toluca, Estado de M´exico,M´exico. 245 Modelado de la biodegradación en biorreactores de lodos de hidrocarburos totales del petróleo Received December 28, 2016; Accepted February 28, 2017 intemperizados en suelos y sedimentos Abstract (Biodegradation modeling of sludge bioreactors of total petroleum hydrocarbons weathering in soil Tanacetum parthenium has gained attention for drug development due to its production of bioactive secondary metabolites, and sediments) such as phenolic compounds (PHEC) and parthenolide (PTN). This work investigated the differences in the production of those compoundsS.A. among Medina-Moreno,in vitro cultures S. Huerta-Ochoa, (organs from C.A. plantlets Lucho-Constantino, and roots cultures) L. Aguilera-Vázquez, of T. parthenium A. Jiménez-. Results showed that the in vitro culturesGonzález produced y M. Gutiérrez-Rojas PHEC and PTN, which depended on the type of culture and the incubation time. The content of secondary259 Crecimiento, metabolites sobrevivencia was higher y in adaptación shoots of de plantlets Bifidobacterium (S-ivPL), infantis followed a condiciones by root cultures ácidas (R-ivC) and roots of plantlets (R-ivPL). The PHEC and PTN production was enhanced in plantlets by applying a combination of plant growth regulators (PGRs: (Growth,α-naphtalenacetic survival and acid adaptation [NAA] of atBifidobacterium 0.27 µM with infantis kinetin to acidic [KIN] conditions) at 2.32 µ M). The highest content of secondary metabolitesL. Mayorga-Reyes, (62.54 mg gallic P. acidBustamante-Camilo, equivalents g− 1A.; 4.261Gutiérrez-Nava, and 4.973 E. mg Barranco-Florido chlorogenic acid y gA.−1 ;Azaola- 0.858 and 1.015 − − − mg caffeic acid g Espinosa1; 1.931 mg salicylic acid g 1; 0.071 mg PTN g 1) was found in the PGRs-treated S-ivPL samples. Also, morphogenesis265 Statistical and growth approach of plantlets to optimization was enhanced of ethanol by these fermentation PGRs. by Saccharomyces cerevisiae in the Keywords: Tanacetum parthenium, parthenolide, phenolic compounds, in vitro cultures, bioactive secondary metabotiles presence of Valfor® zeolite NaA Resumen Tanacetum parthenium (Optimizaciónha ganado estadística la atenci deon´ la para fermentación el desarrollo etanólica de f armacos´de Saccharomyces por su capacidad cerevisiae para en presencia producir de metabolitos secundarios bioactivos,zeolita tales Valfor® como zeolite compuestos NaA) fenolicos´ (CFEN) y partenolida (PTN). El presente trabajo investigo´ las diferencias en la produccion´ de dichos metabolitos entre cultivos in vitro (organos´ de plantulas´ y cultivos de ra´ıces) de G. Inei-Shizukawa, H. A. Velasco-Bedrán, G. F. Gutiérrez-López and H. Hernández-Sánchez T. parthenium. Los resultados mostraron que los cultivos in vitro produjeron CFEN y PTN, la cual dependio´ del tipo de cultivo y del tiempo de incubacion.´ El contenido de los metabolitos secundarios fue mayor en brotes de plantulas´ (B-ivPL), seguido de cultivosIngeniería de ra de´ıces procesos (R-ivC) / Process y ra´ıces engineering de plantulas´ (R-ivPL). La produccion´ de CFEN y PTN fue potenciada en las plantulas´ al271 aplicar Localización una combinaci de una on´planta de reguladoresindustrial: Revisión de crecimiento crítica y vegetaladecuación (RCVs: de losacido´ criteriosα-naftalenac empleadosetico´ en 0.27 µM −1 y cinetina 2.32 µM.esta Los decisión mejores contenidos de metabolitos secundarios (62.54 mg equivalentes de acido´ galico´ g de fenoles totales; 4.261 y 4.973 mg acido´ clorogenico´ g−1; 0.858 y 1.015 mg acido´ cafeico g−1; 1.931 mg acido´ salic´ılico (Plant site selection: Critical review and adequation criteria used in this decision) g−1; 0.071 mg PTN g−1) fueron encontrados en B-ivPL tratados con RCVs. Tambien,´ la morfogenesis´ y el crecimiento de J.R. Medina, R.L. Romero y G.A. Pérez las plantulas´ fueron potenciadas con los RCVs. Palabras clave : Tanacetum parthenium, compuestos fenolicos,´ partenolida, cultivos in vitro, metabolitos secundarios bioactivos. * Corresponding author. E-mail: mail: [email protected] Tel. 52-55-5804-4714; fax: 52-55-5804-4712 Publicado por la Academia Mexicana de Investigacion´ y Docencia en Ingenier´ıa Qu´ımica A.C. 371 Nieto-Trujillo et al./ Revista Mexicana deIngenier ´ıaQu ´ımica Vol. 16, No. 2 (2017) 371-383 1 Introduction effects against cancer, diabetes, cardiovascular and neurodegenerative diseases (Pisoschi and Pop, 2015). Tanacetum parthenium (L.) Schultz-Bip (Asteraceae) In T. parthenium, the content of total phenolic is a species that has gained great attention for compounds from extracts affects the antioxidant drug development, based on its outstanding uses in activity (Wu et al., 2006). However, it is well known folk medicine against migraine, asthma, rheumatoid that the production of secondary metabolites in arthritis, gynecological problems, insect bites, plants is regulated by different factors (Karuppusamy psoriasis and fevers (Awang et al., 1991; Pareek 2009; Verpoorte et al., 2002). In T. parthenium, the et al., 2011). Pharmacological and phytochemical production of parthenolide depends on the organ used studies on this species have contributed to validate to obtain extracts, stages of cultivation, environmental scientifically its medicinal potential (e.g. on cancer, factors, genotype and developmental stage (Awang migraine, inflammatory diseases, etc.) (Andonova 1991; Fonseca et al., 2005; Heptinstall et al., 1992; et al., 2016; Eardie et al., 1992; Ernst and Pittler Hojati et al., 2016; Majdi et al., 2013, 2015). 2000; Ferro et al., 2012; Pfaffenrath et al., 2002). Plant tissue and organ culture has become The phytochemical results have elucidate bioactive a feasible biotechnological technique to produce compounds belonging to terpenoid (essential oils bioactive compounds since it allows controlling the and sesquiterpene lactones) and phenolic (flavonoids, conditions to produce secondary metabolites and phenolic acids and coumarins) secondary metabolites morphogenesis (Dias et al. 2016). Reports about in type (Majdi et al., 2011; Pareek et al., 2011; Wu vitro cultures of T. parthenium have demonstrated et al., 2006). Sesquiterpene lactones are one of that the production of parthenolide is affected by the the most important biologically active principles; type of cultured tissue, carbon source, PGRs and more than 30 types of them have been identified, chemicals (El-Shamy et al., 2007; Rateb et al., 2007; being PTN the most abundant (Pareek et al., 2011; Stojakowska and Kisiel 1997). Furthermore, it has Cretnik 2005). PTN exerts cytotoxic activity against been determined that in vitro cultures of T. parthenium several human cancer cell lines (e.g. breast, leukemia, can produce other types of secondary metabolites. osteosarcoma, human cervical) (Al-Fatlawi et al., In hairy root cultures, dyacetylenes and coumarins 2015; D’Anneo et al., 2013; Lesiak et al., 2010; Pei et (Stojakowska et al., 2002, 2008) have been identified, al., 2012). Its mechanism of action has been associated while in callus coniferaldehyde derivatives (Sy and with the inhibition of growth and the induction of Brown 1999) and coumarin isofraxidin are detected apoptosis without having an effect on normal cells (Banthorpe and Brown 1990). However, there is no (Al-Fatlawi et al., 2015; Cijo et al., 2012; Mathema et evidence reporting the simultaneous production of al., 2012). Additional biological effects have been parthenolide and phenolic compounds from in vitro described for PTN, which includes antimigraine cultures of T. parthenium. The aim of the present (Tassorelli et al., 2005), anti-inflammatory