Review Article Recent Applications of Mass Spectrometry in the Study of Grape and Wine Polyphenols
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LC–MS/MS and UPLC–UV Evaluation of Anthocyanins and Anthocyanidins During Rabbiteye Blueberry Juice Processing
beverages Article LC–MS/MS and UPLC–UV Evaluation of Anthocyanins and Anthocyanidins during Rabbiteye Blueberry Juice Processing Rebecca E. Stein-Chisholm 1, John C. Beaulieu 2,* ID , Casey C. Grimm 2 and Steven W. Lloyd 2 1 Lipotec USA, Inc. 1097 Yates Street, Lewisville, TX 75057, USA; [email protected] 2 United States Department of Agriculture, Agricultural Research Service, Southern Regional Research Center, 1100 Robert E. Lee Blvd., New Orleans, LA 70124, USA; [email protected] (C.C.G.); [email protected] (S.W.L.) * Correspondence: [email protected]; Tel.: +1-504-286-4471 Academic Editor: António Manuel Jordão Received: 11 October 2017; Accepted: 1 November 2017; Published: 25 November 2017 Abstract: Blueberry juice processing includes multiple steps and each one affects the chemical composition of the berries, including thermal degradation of anthocyanins. Not-from-concentrate juice was made by heating and enzyme processing blueberries before pressing, followed by ultrafiltration and pasteurization. Using LC–MS/MS, major and minor anthocyanins were identified and semi-quantified at various steps through the process. Ten anthocyanins were identified, including 5 arabinoside and 5 pyrannoside anthocyanins. Three minor anthocyanins were also identified, which apparently have not been previously reported in rabbiteye blueberries. These were delphinidin-3-(p-coumaroyl-glucoside), cyanidin-3-(p-coumaroyl-glucoside), and petunidin-3-(p- coumaroyl-glucoside). Delphinidin-3-(p-coumaroyl-glucoside) significantly increased 50% after pressing. The five known anthocyanidins—cyanidin, delphinidin, malvidin, peonidin, and petunidin—were also quantitated using UPLC–UV. Raw berries and press cake contained the highest anthocyanidin contents and contribute to the value and interest of press cake for use in other food and non-food products. -
Identification of Compounds with Potential Therapeutic Uses From
International Journal of Molecular Sciences Article Identification of Compounds with Potential Therapeutic Uses from Sweet Pepper (Capsicum annuum L.) Fruits and Their Modulation by Nitric Oxide (NO) Lucía Guevara 1, María Ángeles Domínguez-Anaya 1, Alba Ortigosa 1, Salvador González-Gordo 1 , Caridad Díaz 2 , Francisca Vicente 2 , Francisco J. Corpas 1 , José Pérez del Palacio 2 and José M. Palma 1,* 1 Group of Antioxidant, Free Radicals and Nitric Oxide in Biotechnology, Food and Agriculture, Department of Biochemistry, Cell and Molecular Biology of Plants, Estación Experimental del Zaidín, CSIC, 18008 Granada, Spain; [email protected] (L.G.); [email protected] (M.Á.D.-A.); [email protected] (A.O.); [email protected] (S.G.-G.); [email protected] (F.J.C.) 2 Department of Screening & Target Validation, Fundación MEDINA, 18016 Granada, Spain; [email protected] (C.D.); [email protected] (F.V.); [email protected] (J.P.d.P.) * Correspondence: [email protected]; Tel.: +34-958-181-1600; Fax: +34-958-181-609 Abstract: Plant species are precursors of a wide variety of secondary metabolites that, besides being useful for themselves, can also be used by humans for their consumption and economic benefit. Pepper (Capsicum annuum L.) fruit is not only a common food and spice source, it also stands out for containing high amounts of antioxidants (such as vitamins C and A), polyphenols and capsaicinoids. Citation: Guevara, L.; Particular attention has been paid to capsaicin, whose anti-inflammatory, antiproliferative and Domínguez-Anaya, M.Á.; Ortigosa, A.; González-Gordo, S.; Díaz, C.; analgesic activities have been reported in the literature. -
Isolation of Anthocyanins by High-Speed Countercurrent
ition & F tr oo u d N f S č o c Veli kovska et al., J Nutr Food Sci 2013, 3:6 l i e a n n c r e DOI: 10.4172/2155-9600.1000243 u s o J Journal of Nutrition & Food Sciences ISSN: 2155-9600 Research Article Open Access Isolation of Anthocyanins by High-Speed Countercurrent Chromatography and Application of the Color Activity Concept to Different Varieties of Red Grape Pomace from Macedonia Sanja Kostadinović Veličkovska1*, Hamed Mirhosseini2 and Elena Bogeva3 1Faculty of Agriculture, University “Goce Delčev”, Krste Misirkov bb, 2000 Štip, Macedonia 2Department of Food Technology, Faculty of Food Science and Technology, University Putra Malaysia, Sri Serdang, 43400 UPM Serdang, Selangor, Malaysia 3Experimental laboratory of wines and wine-making, Elenov winery, Demir Kapija, Macedonia Abstract Anthocyanins of Macedonian grape pomace from three varieties “Pinot noir”, “Merlot” and “Vranec” were isolated by high speed countercurrent chromatography. After purification of the fractions by means of preparative high performance liquid chromatography the structures of isolated pigments were elucidated by electrospray ionization multiple mass spectrometry (ESI-MSn) and nuclear magnetic resonance (NMR) spectroscopy. The major anthocyanin malvidin-3-glucoside and the minor pigments delphinidin-3-glucoside, cyaniding-3-glucoside, petunidin-3-glucoside, and malvidin-3-p-coumarоyl-glucoside were isolated. The “Color activity concept” was applied and visual detection thresholds of isolated anthocyanins were determined. The results of the “color activity value” of the isolated pigments and their detection thresholds were in good agreement with the color shade of the different varieties of red grape pomace. Keywords: Red grape pomace; HSCCC; NMR; Anthocyanins; Color using NMR spectroscopy confirmed the structure of the most abundant activity concept pigments in plants [11-20]. -
Chemistry and Pharmacology of Kinkéliba (Combretum
CHEMISTRY AND PHARMACOLOGY OF KINKÉLIBA (COMBRETUM MICRANTHUM), A WEST AFRICAN MEDICINAL PLANT By CARA RENAE WELCH A Dissertation submitted to the Graduate School-New Brunswick Rutgers, The State University of New Jersey in partial fulfillment of the requirements for the degree of Doctor of Philosophy Graduate Program in Medicinal Chemistry written under the direction of Dr. James E. Simon and approved by ______________________________ ______________________________ ______________________________ ______________________________ New Brunswick, New Jersey January, 2010 ABSTRACT OF THE DISSERTATION Chemistry and Pharmacology of Kinkéliba (Combretum micranthum), a West African Medicinal Plant by CARA RENAE WELCH Dissertation Director: James E. Simon Kinkéliba (Combretum micranthum, Fam. Combretaceae) is an undomesticated shrub species of western Africa and is one of the most popular traditional bush teas of Senegal. The herbal beverage is traditionally used for weight loss, digestion, as a diuretic and mild antibiotic, and to relieve pain. The fresh leaves are used to treat malarial fever. Leaf extracts, the most biologically active plant tissue relative to stem, bark and roots, were screened for antioxidant capacity, measuring the removal of a radical by UV/VIS spectrophotometry, anti-inflammatory activity, measuring inducible nitric oxide synthase (iNOS) in RAW 264.7 macrophage cells, and glucose-lowering activity, measuring phosphoenolpyruvate carboxykinase (PEPCK) mRNA expression in an H4IIE rat hepatoma cell line. Radical oxygen scavenging activity, or antioxidant capacity, was utilized for initially directing the fractionation; highlighted subfractions and isolated compounds were subsequently tested for anti-inflammatory and glucose-lowering activities. The ethyl acetate and n-butanol fractions of the crude leaf extract were fractionated leading to the isolation and identification of a number of polyphenolic ii compounds. -
Plant Phenolics: Bioavailability As a Key Determinant of Their Potential Health-Promoting Applications
antioxidants Review Plant Phenolics: Bioavailability as a Key Determinant of Their Potential Health-Promoting Applications Patricia Cosme , Ana B. Rodríguez, Javier Espino * and María Garrido * Neuroimmunophysiology and Chrononutrition Research Group, Department of Physiology, Faculty of Science, University of Extremadura, 06006 Badajoz, Spain; [email protected] (P.C.); [email protected] (A.B.R.) * Correspondence: [email protected] (J.E.); [email protected] (M.G.); Tel.: +34-92-428-9796 (J.E. & M.G.) Received: 22 October 2020; Accepted: 7 December 2020; Published: 12 December 2020 Abstract: Phenolic compounds are secondary metabolites widely spread throughout the plant kingdom that can be categorized as flavonoids and non-flavonoids. Interest in phenolic compounds has dramatically increased during the last decade due to their biological effects and promising therapeutic applications. In this review, we discuss the importance of phenolic compounds’ bioavailability to accomplish their physiological functions, and highlight main factors affecting such parameter throughout metabolism of phenolics, from absorption to excretion. Besides, we give an updated overview of the health benefits of phenolic compounds, which are mainly linked to both their direct (e.g., free-radical scavenging ability) and indirect (e.g., by stimulating activity of antioxidant enzymes) antioxidant properties. Such antioxidant actions reportedly help them to prevent chronic and oxidative stress-related disorders such as cancer, cardiovascular and neurodegenerative diseases, among others. Last, we comment on development of cutting-edge delivery systems intended to improve bioavailability and enhance stability of phenolic compounds in the human body. Keywords: antioxidant activity; bioavailability; flavonoids; health benefits; phenolic compounds 1. Introduction Phenolic compounds are secondary metabolites widely spread throughout the plant kingdom with around 8000 different phenolic structures [1]. -
Structure Assignment and H/D-Exchange Behavior of Several Glycosylated Polyphenols Andreas H
University of the Pacific Scholarly Commons College of the Pacific aF culty Articles All Faculty Scholarship 1-1-2014 Structure assignment and H/D-exchange behavior of several glycosylated polyphenols Andreas H. Franz University of the Pacific, [email protected] Ilona Serebnitskaya University of the Pacific Gurbir Gudial University of the Pacific Christopher Wallis San Joaquin Valley Agricultural Sciences Center Follow this and additional works at: https://scholarlycommons.pacific.edu/cop-facarticles Part of the Chemistry Commons Recommended Citation Franz, A. H., Serebnitskaya, I., Gudial, G., & Wallis, C. (2014). Structure assignment and H/D-exchange behavior of several glycosylated polyphenols. ARKIVOC, 2014(5), 1–29. DOI: 10.3998/ark.5550190.p008.583 https://scholarlycommons.pacific.edu/cop-facarticles/143 This Article is brought to you for free and open access by the All Faculty Scholarship at Scholarly Commons. It has been accepted for inclusion in College of the Pacific aF culty Articles by an authorized administrator of Scholarly Commons. For more information, please contact [email protected]. General Papers ARKIVOC 2014 (v) 94-122 Structure assignment and H/D-exchange behavior of several glycosylated polyphenols Andreas H. Franz,a* Ilona Serebnitskaya,a Gurbir Gudial,a and Christopher Wallisb a Department of Chemistry, University of the Pacific, 3601 Pacific Avenue, Stockton, CA 95211, USA b Crop Diseases, Pests, and Genetics Research Unit, USDA-ARS San Joaquin Valley Agricultural Sciences Center, 9611 S. Riverbend Ave, Parlier, CA 93648, USA E-mail: [email protected] DOI: http://dx.doi.org/10.3998/ark.5550190.p008.583 Abstract The NMR-structures of six polyphenols, resveratrol (1), (-)-epicatechin (2), pelargonidin chloride (3), cyanidin chloride (4), cyanin chloride (5), and keracyanin chloride (6), were fully assigned. -
Delphinidin and Cyanidin Exhibit Antiproliferative and Apoptotic
Integrative Cancer Science and Therapeutics Research Article ISSN: 2056-4546 Delphinidin and cyanidin exhibit antiproliferative and apoptotic effects in MCF7 human breast cancer cells Jessica Tang1,2*, Emin Oroudjev1, Leslie Wilson1 and George Ayoub1 1Department of Molecular, Cellular & Developmental Biology, University of California, Santa Barbara, USA 2School of Medicine, Medical Sciences, Indiana University, Bloomington, USA Abstract Fruits high in antioxidants such as berries and pomegranates have been shown to have many biological effects, including anticancer activity. We previously reported that bilberry (European blueberry) extract exhibited cytotoxic effects on MCF7-GFP-Tubulin breast cancer cells. To delve further into the mechanism of action of bilberry extract, we focused on two of the most abundant anthocyanins found in bilberry, delphinidin and cyanidin. In this study, we examined the radical scavenging activity, antiproliferative, and apoptotic effects of delphinidin and cyanidin on MCF7 breast cancer cells in comparison to Trolox, a vitamin E analog. DPPH radical scavenging activity assay showed at 50% antioxidant activity, an IC50 of 80 µM, 63 µM, 1.30 µM for delphinidin, cyanidin, and Trolox, respectively. As determined by SRB assay, delphinidin, cyanidin, and Trolox were shown to inhibit MCF7 cell proliferation at IC50 of 120 µM, 47.18 µM, and 11.25 µM, respectively. Immunofluorescence revealed that delphinidin, cyanidin, and Trolox caused apoptotic features such as rounding up of cell, retraction of pseudopodes, condensation of chromatin, minor modification of cytoplasmic organelles, and plasma membrane blebbing. Together, these results show that delphinidin and cyanidin have significant radical scavenging activity, inhibit cell proliferation, and increase apoptosis of MCF7 breast cancer cells. -
Food Chemistry 218 (2017) 440–446
Food Chemistry 218 (2017) 440–446 Contents lists available at ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem Antiradical activity of delphinidin, pelargonidin and malvin towards hydroxyl and nitric oxide radicals: The energy requirements calculations as a prediction of the possible antiradical mechanisms ⇑ Jasmina M. Dimitric´ Markovic´ a, , Boris Pejin b, Dejan Milenkovic´ c, Dragan Amic´ d, Nebojša Begovic´ e, Miloš Mojovic´ a, Zoran S. Markovic´ c,f a Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia b Department of Life Sciences, Institute for Multidisciplinary Research – IMSI, Kneza Višeslava 1, 11030 Belgrade, Serbia c Bioengineering Research and Development Center, 34000 Kragujevac, Serbia d Faculty of Agriculture, Josip Juraj Strossmayer University of Osijek, Kralja Petra Svacˇic´a 1D, 31000 Osijek, Croatia e Institute of General and Physical Chemistry, Studentski trg 12-16, 11000 Belgrade, Serbia f Department of Chemical-Technological Sciences, State University of Novi Pazar, Vuka Karadzˇic´a bb, 36300 Novi Pazar, Serbia article info abstract Article history: Naturally occurring flavonoids, delphinidin, pelargonidin and malvin, were investigated experimentally Received 24 August 2015 and theoretically for their ability to scavenge hydroxyl and nitric oxide radicals. Electron spin resonance Received in revised form 28 August 2016 (ESR) spectroscopy was used to determine antiradical activity of the selected compounds and M05-2X/6- Accepted 16 September 2016 311+G(d,p) level of theory for the calculation of reaction enthalpies related to three possible mechanisms Available online 17 September 2016 of free radical scavenging activity, namely HAT, SET-PT and SPLET. The results obtained show that the molecules investigated reacted with hydroxyl radical via both HAT and SPLET in the solvents investi- Chemical compounds studied in this article: gated. -
Research Focus 2016-3B
Research News from Cornell’s Viticulture and Enology Program Research Focus 2016-3b RESEARCH FOCUS Comparing Red Wine Color in V. vinifera and Hybrid Cultivars Claire Burtch and Anna Katharine Mansfield Department of Food Science, Cornell University, New York State Agricultural Experiment Station, Geneva, NY KEY CONCEPTS • The color of red wine comes from pigments called anthocyanins. • Wines produced from V. vinifera have antho- cyanin-3-monoglucosides, which polymerize with other wine compounds to form stable color. • Wine produced from interspecific hybrids usu- Bench-top anthocyanin kinetic experiments help researchers ally contain high concentrations of anthocyan- describe color formation in red hybrid wines. Photo by Claire Burtch in-3,5-diglucosides. Red hybrid grapes have a broader and more varied col- • Anthocyanin-3,5-diglucosides don't form poly- lection of phenolic compounds than their Vitis vinifera meric pigment as quickly as monoglucosides. counterparts, and consequently show greater diversity in wine color, structure, and mouthfeel. Hybrid red • Hybrid cultivars have less extractable tannins. wine quality, however, is often measured through com- parison to more familiar V. vinifera varietal wines, so • Interspecific hybrid wines will have low con- obvious color differences may detract from perceived centrations of stable color, polymeric pigment, quality. Winemakers complain that hybrid red wines due to high anthocyanin-3,5-diglucoside con- vary from V. vinifera in color density, hue, and develop- centration and low tannin concentration. ment during aging, but the reasons for these differences have not been extensively studied. To determine the nins. For this reason, understanding the rate and types source of the differences in hybrid and V. -
Cyanidin-3-O-Glucoside Is an Important Anthocyanin in Several Clones of Vitis Vinifera L
LOGAN ET AL., CYANIDIN-3-O-GLUCOSIDE IN PINOT NOIR FRUITS AND WINE, P.1 CYANIDIN-3-O-GLUCOSIDE IS AN IMPORTANT ANTHOCYANIN IN SEVERAL CLONES OF VITIS VINIFERA L. PINOT NOIR FRUITS AND RESULTING WINE FROM MICHIGAN AND NEW ZEALAND. Gerard A. LOGAN 1* , G. Stanley HOWELL 2, Muraleedharan G. NAIR 3 1* Corresponding Author: Gerard A. Logan [Tel.: +64 6 974 8000, Ext.: 5832; Fax.: +64 6 974 8910; E-mail.: [email protected] ]. Lecturer in Viticulture, School of Viticulture & Wine, Faculty of Science & Technology, Eastern Institute of Technology, Gloucester Street, Private Bag 1201, Taradale, Hawkes Bay, New Zealand. 2 G. Stanley Howell, Emeritus Professor, Program of Viticulture and Enology, Department of Horticulture, Michigan State University, East Lansing, Michigan 48824, USA. 3 Muraleedharan G. Nair, Professor, Bioactive Natural Products and Phytoceuticals, Department of Horticulture and National Food Safety and Toxicology Center, Michigan State University, East Lansing, Michigan 48824, USA. Abstract In the cool winegrowing regions of Michigan, USA and Canterbury, New Zealand, Vitis vinifera L. Pinot noir is an economically important red winegrape cultivar. Both regions have problems with the color of Pinot noir wines based on anthocyanin concentration. Thus, anthocyanin concentration of V. vinifera L. Pinot noir fruit was investigated using three clones and two growing locations, Canterbury, New Zealand and Michigan, USA. Wines were made from Michigan sample vines, and analyzed for anthocyanin. Utilizing HPLC (High Pressure Liquid Chromatography) techniques, the five main anthocyanins (1-5), in the fruit and wine were identified and quantified based on cyanidin-3-O-glucoside (4, C3G), and total anthocyanin concentration in grapes and wine was compared. -
Anthocyanins, Vibrant Color Pigments, and Their Role in Skin Cancer Prevention
biomedicines Review Anthocyanins, Vibrant Color Pigments, and Their Role in Skin Cancer Prevention 1,2, , 2,3, 4,5 3 Zorit, a Diaconeasa * y , Ioana S, tirbu y, Jianbo Xiao , Nicolae Leopold , Zayde Ayvaz 6 , Corina Danciu 7, Huseyin Ayvaz 8 , Andreea Stanilˇ aˇ 1,2,Madˇ alinaˇ Nistor 1,2 and Carmen Socaciu 1,2 1 Faculty of Food Science and Technology, University of Agricultural Sciences and Veterinary Medicine, 400372 Cluj-Napoca, Romania; [email protected] (A.S.); [email protected] (M.N.); [email protected] (C.S.) 2 Institute of Life Sciences, University of Agricultural Sciences and Veterinary Medicine, Calea Mănă¸stur3-5, 400372 Cluj-Napoca, Romania; [email protected] 3 Faculty of Physics, Babes, -Bolyai University, Kogalniceanu 1, 400084 Cluj-Napoca, Romania; [email protected] 4 Institute of Chinese Medical Sciences, State Key Laboratory of Quality Research in Chinese Medicine, University of Macau, Taipa, Macau 999078, China; [email protected] 5 International Research Center for Food Nutrition and Safety, Jiangsu University, Zhenjiang 212013, China 6 Faculty of Marine Science and Technology, Department of Marine Technology Engineering, Canakkale Onsekiz Mart University, 17100 Canakkale, Turkey; [email protected] 7 Victor Babes University of Medicine and Pharmacy, Department of Pharmacognosy, 2 Eftimie Murgu Sq., 300041 Timisoara, Romania; [email protected] 8 Department of Food Engineering, Engineering Faculty, Canakkale Onsekiz Mart University, 17020 Canakkale, Turkey; [email protected] * Correspondence: [email protected]; Tel.: +40-751-033-871 These authors contributed equally to this work. y Received: 31 July 2020; Accepted: 25 August 2020; Published: 9 September 2020 Abstract: Until today, numerous studies evaluated the topic of anthocyanins and various types of cancer, regarding the anthocyanins’ preventative and inhibitory effects, underlying molecular mechanisms, and such. -
Effects of Anthocyanins on the Ahr–CYP1A1 Signaling Pathway in Human
Toxicology Letters 221 (2013) 1–8 Contents lists available at SciVerse ScienceDirect Toxicology Letters jou rnal homepage: www.elsevier.com/locate/toxlet Effects of anthocyanins on the AhR–CYP1A1 signaling pathway in human hepatocytes and human cancer cell lines a b c d Alzbeta Kamenickova , Eva Anzenbacherova , Petr Pavek , Anatoly A. Soshilov , d e e a,∗ Michael S. Denison , Michaela Zapletalova , Pavel Anzenbacher , Zdenek Dvorak a Department of Cell Biology and Genetics, Faculty of Science, Palacky University, Slechtitelu 11, 783 71 Olomouc, Czech Republic b Institute of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacky University, Hnevotinska 3, 775 15 Olomouc, Czech Republic c Department of Pharmacology and Toxicology, Charles University in Prague, Faculty of Pharmacy in Hradec Kralove, Heyrovskeho 1203, Hradec Kralove 50005, Czech Republic d Department of Environmental Toxicology, University of California, Meyer Hall, One Shields Avenue, Davis, CA 95616-8588, USA e Institute of Pharmacology, Faculty of Medicine and Dentistry, Palacky University, Hnevotinska 3, 775 15 Olomouc, Czech Republic h i g h l i g h t s • Food constituents may interact with drug metabolizing pathways. • AhR–CYP1A1 pathway is involved in drug metabolism and carcinogenesis. • We examined effects of 21 anthocyanins on AhR–CYP1A1 signaling. • Human hepatocytes and cell lines HepG2 and LS174T were used as the models. • Tested anthocyanins possess very low potential for food–drug interactions. a r t i c l e i n f o a b s t r a c t