DOCSLIB.ORG

Mass Spectrometry Fragmentation Pattern of Coloured Flavanol

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Mass Spectrometry Fragmentation Pattern of Coloured Flavanol Sánchez-Ilárduya et al. Flavanol-anthocyanin derivatives mass spectrometry 203 Mass spectrometry fragmentation pattern of coloured flavanol-anthocyanin and anthocyanin-flavanol derivatives in aged red wines of Rioja_190 203..214 M.B. SÁNCHEZ-ILÁRDUYA, C. SÁNCHEZ-FERNÁNDEZ, M. VILORIA-BERNAL, D.M. LÓPEZ-MÁRQUEZ, L.A. BERRUETA, B. GALLO and F. VICENTE Analytical Chemistry Department, Science and Technology Faculty, Basque Country University, PO Box 644, 48080 Bilbao, Spain Corresponding author: Dr Luis A. Berrueta, fax +34 94 601 3500, email [email protected] Abstract Background and Aims: During wine ageing, a great variety of reactions take place, resulting in an immense variety of products whose structure sometimes remains unknown. The aim of this work is the study of different fragmentation patterns of flavanol-anthocyanin derivatives formed along the wine ageing; these patterns are useful for elucidating the different structures of these compounds and other new related ones. Methods and Results: Several wines from the Protected Denomination of Origin Rioja have been studied by an analytical method that combines column chromatography and high-performance liquid chromatography with diode array and mass and tandem mass spectrometric detections. Thirty-five coloured flavanol-anthocyanin compounds formed by direct reaction or by acetaldehyde-mediated condensation have been identified. For direct reaction derivatives, two different fragmentation patterns (one of them not previously reported) have been observed depending on the position of flavanol in the coloured derivative. Several compounds have been identified in aged wines for the first time to the authors’ knowledge, like (+)-gallocatechin-cyanidin-3-glucoside and (+)-catechin- cyanidin-3-glucoside Conclusions: The developed analytical procedure has allowed the identification of some compounds for the first time, and two different fragmentation patterns have been observed depending on the position of flavanol in the pigment. Significance of the Study: The establishment of different fragmentation patterns allows the structural elucidation of unknown compounds. Keywords: anthocyanin-derived pigment, colour, flavanol, MS, wine Introduction In recent years, different anthocyanin-derived pigments Polyphenols play an important role in the nutritional, organo- have been identified; they can be classified in two groups: pyra- leptic and commercial properties of agrofoods. In wine, they noanthocyanins and pigments originated by reactions between have importance in the final quality because of their influence anthocyanins and flavanols. On one hand, pyranoanthocyanins on characteristics such as colour, astringency or bitterness are obtained by a cycloaddition reaction of some compounds (Monagas et al. 2005) and they can also help in the differentia- present in wine with the flavylium form of anthocyanins, giving tion among grape variety and, sometimes, among growing con- rise to the formation of a new pyranic ring. Pyranoanthocyanins ditions of fruit. can be formed with pyruvic acid, acetaldehyde, acetoacetic Wine phenolics belong to two main groups: non-flavonoid acid, vinylphenols, hydroxycinnamic acids and vinylflavanols compounds (namely, hydroxybenzoic and hydroxycinnamic (Hayasaka and Asenstorfer 2002, Pozo-Bayón et al. 2004). acids and their derivatives, stilbenes and phenolic alcohols) These anthocyanin-derived pigments cause hypsochromic shifts and flavonoid compounds (namely anthocyanins, flavanols, fla- in the visible absorption maxima of the initial anthocyanins, vonols, flavanonols and flavones). providing a brick-red hue to the wine. Anthocyanins are water-soluble pigments that are respon- On the other hand, reactions between anthocyanins and sible for flower and fruit colour. In red grapes, anthocyanins flavanols can proceed directly (Remy et al. 2000, Hayasaka and provide the red colour to the grape skin and also to the pulp in Kennedy 2003, Ribéreau-Gayon et al. 2006), be mediated by some variety. Anthocyanins and flavanols are the major pheno- acetaldehyde (Rivas-Gonzalo et al. 1995, Francia-Aricha et al. lics in red wines. Colour evolution during vinification and 1997, Es-Safi et al. 1999, Lee et al. 2004) or be mediated by ageing has been attributed to the progressive changes of phe- other aldehydes (Es-Safi et al. 2002, Pissarra et al. 2004). These nolic compounds extracted from the grapes. The original grape condensations cause bathochromic shifts in the visible absorp- anthocyanins, which are responsible for the initial red colour of tion maxima of the initial anthocyanins, providing a bluish-red young red wines, are involved in irreversible reactions towards hue to the wine. more stable pigments. These pigments are responsible for the Within the pigments formed by direct reaction, two different different hues of the more aged wines. mechanisms have been described depending on the position of doi: 10.1111/j.1755-0238.2012.00190.x © 2012 Australian Society of Viticulture and Oenology Inc. 204 Flavanol-anthocyanin derivatives mass spectrometry Australian Journal of Grape and Wine Research 18, 203–214, 2012 R OH R HO O OH OH + HO O OH R H OH OH OH OH HO O OH OH F+ OH OH R Flavanol oligomer Figure 1. Formation scheme of OH F-A+ pigments. A, anthocyanin; F, HO O flavanol; glc, glucoside. R OH R OH OH R1 HO O OH OH -H (Epi)catechin OH OH HO O -OH (Epi)gallocatechin R C4 OH 2 OH O-glc R1 R2 Anthocyanidin OH R1 OH Colourless F-AOH -OH -OH Delphinidin C8 OH HO O -OH -H Cyanidin R2 -OCH3 -OH Petunidin C6 O-glc -H2O -OCH3 -H Peonidin OH R -OCH3 -OCH3 Malvidin Hydrated anthocyanin AOH OH HO O OH OH R1 OH OH HO O R2 O-glc OH Red-coloured F-A+ the flavanol: F-A+ and A+-F formation. The F-A+ formation The formation of most of anthocyanin-derived pigments mechanism (Figure 1) begins with the acid cleavage of the occurs in the first months of ageing, as the oxidative conditions in interflavanic bond of a procyanidin (flavanol oligomer), giving a oak barrels favour their formation (Atanasova et al. 2002, Alcalde- carbocation F+ which reacts as an electrophile through the C4 Eon et al. 2006). Both anthocyanin-flavanol derived pigments, with the C6 or C8 of the hydrated form of the anthocyanin, that direct ones and ethyl-linked ones, show less stability during ageing acts as nucleophile. This mechanism leads to a colourless com- than pyranoanthocyanins. The pyranic ring in pyranoanthocya- pound (F-AOH) which easily dehydrates to the coloured flavy- nins provides a protection against the nucleophilic attack from lium form F-A+ (Macz-Pop et al. 2006). In the formation of A+-F water or bisulfite, increasing their stability (He et al. 2006). pigments (Figure 2), the anthocyanin in flavylium form A+ acts The aim of this work was the identification of the coloured as electrophile through the C4. The hydroxyl groups of C5 and flavanol-anthocyanin derivatives that provide bluish hues to C7 of flavanol have mesomeric effect and give nucleophilic aged wines. Wine colour, together with other sensorial charac- characteristics to the C6 and C8 of flavanol. A nucleophilic teristics, is a very important wine quality parameter. A study addition of the flavanol takes place onto the flavylium form of mass spectrometry (MS) fragmentation patterns of these of the anthocyanin, yielding a colourless compound with the compounds, present in aged red wines of the Protected Denomi- anthocyanin in flavene form. This flavene can be oxidized, nation of Origin (PDO) Rioja has been carried out in order resulting in a coloured flavylium A+-F pigment or in a colourless to establish different fragmentation patterns that ensure the compound A-F with a type-A bond (Salas et al. 2003). correct identification of these derivatives and allow the struc- Acetaldehyde-mediated condensation of anthocyanin- tural characterization of unknown compounds. flavanol begins with the protonation of the acetaldehyde, leading to the formation of a carbocation (Figure 3). This carbocation is added to a nuclephilic position (C8) of the phloroglucinol ring of a Materials and methods flavanol, followed by a dehydration which yields a new carboca- Reagents tion. This carbocation suffers a nucleophilic attack by an antho- Methanol and acetonitrile (Romil Chemical Ltd, Heidelberg, cyanin to give rise the final acetaldehyde-mediated anthocyanin- Germany) were of high-performance liquid chromatography flavanol condensation pigment (Pissarra et al. 2004). (HPLC) grade. Water was ultrapurified on a Milli-Q system © 2012 Australian Society of Viticulture and Oenology Inc. Sánchez-Ilárduya et al. Flavanol-anthocyanin derivatives mass spectrometry 205 Anthocyanin A+ R1 R1 OH OH HO O HO O R2 R2 R C4 O-glc O-glc OH OH R OH Figure 2. Formation scheme of OH HO O A+-F pigments. A, anthocyanin; F, OH flavanol; glc, glucoside. HO C8 O OH OH R C6 OH OH OH Colourless flavene A-F -H (Epi)catechin Flavanol -OH (Epi)gallocatechin R1 R2 Anthocyanidin -OH -OH Delphinidin R1 R 1 -OH -H Cyanidin OH OH -OCH3 -OH Petunidin HO O R HO O 2 R2 -OCH3 -H Peonidin R O-glc O-glc R -OCH3 -OCH3 Malvidin OH OH OH OH O O HO O OH OH OH OH OH OH Colourless A-type A-F Red-coloured flavilyum A+-F (Millipore, Bedford, Massachusetts, USA). Trifluoroacetic commercial cartridges (IST, Hengoed Mid, Glam, UK, 150 mL acid (TFA) provided by Merck (Darmstadt, Germany) was of capacity) were filled with 40 g of C18-modified silica (IST, par- spectroscopic grade. NaH2PO4 and Na2HPO4 (Fluka, Steinheim, ticle size 60 mm). Both top and bottom of solid phase were Germany) were of analysis grade. All solvents used were covered with 20 mm polyethylene frits (IST). The cartridges were previously filtered through 0.45-mm nylon membranes (Lida, activated with 120 mL of methanol, washed with 2 ¥ 120 mL of Kenosha, Wisconsin, USA). Malvidin-3-glucoside (Extrasyn- ultrapurified water and preconditioned with 120 mL of phos- thèse, Lyon, France) was used as standard. phate buffer (1 mol/L, pH = 7.0). Two hundred millilitres of red wine were de-alcoholized in a Büchi (Büchi Labortechnik AG, Fractionation of wine by column chromatography (CC) Flawil, Switzerland) R200 rotary evaporator at 25°C during 30 min.
Load more

Recommended publications
  • 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.
    [Show full text]
  • A Combined Experimental and Computational Study of Chrysanthemin As a Pigment for Dye-Sensitized Solar Cells
    molecules Article A Combined Experimental and Computational Study of Chrysanthemin as a Pigment for Dye-Sensitized Solar Cells Atoumane Ndiaye 1,2 , Alle Dioum 1, Corneliu I. Oprea 2 , Anca Dumbrava 3,* , Jeanina Lungu 2, Adrian Georgescu 2, Florin Moscalu 2, Mihai A. Gîr¸tu 2,* , Aboubaker Chedikh Beye 1 and Issakha Youm 1,* 1 Department of Physics, Cheikh Anta Diop University of Dakar, 5005 Dakar-Fann, Senegal; [email protected] (A.N.); [email protected] (A.D.); [email protected] (A.C.B.) 2 Department of Physics, Ovidius University of Constanta, 900527 Constanta, Romania; [email protected] (C.I.O.); [email protected] (J.L.); [email protected] (A.G.); fl[email protected] (F.M.) 3 Department of Chemistry and Chemical Engineering, Ovidius University of Constanta, 900527 Constanta, Romania * Correspondence: [email protected] (A.D.); [email protected] (M.A.G.); [email protected] (I.Y.) Abstract: The theoretical study of chrysanthemin (cyanidin 3-glucoside) as a pigment for TiO2-based dye-sensitized solar cells (DSSCs) was performed with the GAUSSSIAN 09 simulation. The electronic spectra of neutral and anionic chrysanthemin molecules were calculated by density functional theory with B3LYP functional and DGDZVP basis set. A better energy level alignment was found for partially deprotonated molecules of chrysanthemin, with the excited photoelectron having enough energy in order to be transferred to the conduction band of TiO2 semiconductor in DSSCs. In addition, we used the raw aqueous extracts of roselle (Hibiscus sabdariffa) calyces as the source of chrysanthemin Citation: Ndiaye, A.; Dioum, A.; and the extracts with various pH values were tested in DSSCs.
    [Show full text]
  • 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].
    [Show full text]
  • Determination of Major Anthocyanin
    02_benmeziane_05b-tomazic 13/10/16 13:03 Page125 DETERMINATION OF MAJOR ANTHOCYANIN PIGMENTS AND FLAVONOLS IN RED GRAPE SKIN OF SOME TABLE GRAPE VARIETIES ( VITIS VINIFERA SP.) BY HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY–PHOTODIODE ARRAY DETECTION (HPLC-DAD) Farida BENMEZIANE 1* , Yves CADOT 2, Rachid DJAMAI 3 and Lynda DJERMOUN 4 1: Department of Agronomy, University of El-Tarf, PB 73, El-Tarf 36000, Algeria 2: Institut de Recherche en Horticulture et Semences UMR1345 (INRA / Agrocampus-Ouest / Université d’Angers), 42 rue Georges Morel BP 60057, 49071 Beaucouzé Cedex, France 3: Department of Biology, University of Badji-Mokhtar, Annaba, PB 12, Annaba 23000, Algeria 4: University A. Mira of Bejaia, Faculty of Sciences of Nature and Life, Department of Food Science, 3BS Laboratory, Bejaia 06000, Algeria Abstract Aim : The aim of this study was the investigation of the anthocyanin and flavonol content in grape skin extracts. Five prevalent anthocyanin-types and four flavonol-types were determined in the skin of three red table grape varieties widely cultivated in El- Tarf (Algeria). Methods and results : The identification of the compounds was performed by HPLC-DAD based on C-18 reversed phase column separation. Results from HPLC analysis showed that malvidin and petunidin-3- O-glucoside were the major anthocyanin glucoside, whereas quercetin-3- O-glucoside was the major flavonol among the four identified. Conclusion : The content of anthocyanins and flavonols in the grape skin of three grapevine ( Vitis vinifera ) varieties exhibits notable differences among the cultivars studied, confirming their importance in the varietal characterization. The highest concentrations of total anthocyanins and flavonols corresponded to the Gros noir variety.
    [Show full text]
  • Could Purple Tomatoes Help Us Be Healthier?
    Caroline Wood Could purple tomatoes Key words genetic engineering cancer help us be healthier? superfoods ne of the greatest global health challenges just three crops – rice, wheat and maize – provide an BMI (body mass we face is the obesity epidemic. In 2014, estimated 60% of the world’s energy intake. Yet as index) is mass (in Othe World Health Organisation (WHO) our dietary repertoire has shrunk, levels of obesity kg) / height (in m) estimated that worldwide 39% of adults over 18 and its associated diseases have rapidly climbed. squared years were overweight (with a BMI of 25+) and 13% In fact, a lack of fruit and vegetables is ranked as were obese (with a BMI of 30+). This has led to a the second highest risk factor for cancer in men, dramatic surge in the levels of non-communicable and the fifth highest in women in the UK Figure( 2). diseases such as type II diabetes, cardiovascular This is thought to be because plants produce many heart disease (CVD) and certain cancers. We’ve all products as part of their natural metabolism that heard that certain ‘superfoods’ contain compounds are beneficial for our health. that can help combat these diseases, but these are often expensive and not accessible to everyone. If only everyday foods could be engineered to have these enhanced health effects… but thanks to genetic engineering, scientists have started to do just that, giving us purple tomatoes! Our changing diet Andrew Davis, John Innes Centre When humans lived as hunter-gatherers, we would have consumed a much wider range of fruit and vegetables, whereas today our diets are heavily Figure 1 A comparison between what our hunter-gatherer ancestors may have ! based on cereal crops (Figure 1).
    [Show full text]
  • 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.
    [Show full text]
  • 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.
    [Show full text]
  • 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.
    [Show full text]
  • 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.
    [Show full text]
  • 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.
    [Show full text]
  • 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
    [Show full text]
  • Naturally Occurring Anthocyanin, Structure, Functions And
    iochemis t B try n & la P P h f y o s l i Journal of o a l n o r g Pervaiz et al., J Plant Biochem Physiol 2017, 5:2 u y o J DOI: 10.4172/2329-9029.1000187 ISSN: 2329-9029 Plant Biochemistry & Physiology Review Article Open Access Naturally Occurring Anthocyanin, Structure, Functions and Biosynthetic Pathway in Fruit Plants Tariq Pervaiz1,2, Jiu Songtao1, Faezeh Faghihi3, Muhammad Salman Haider1 and Jinggui Fang1* 1Key Laboratory of Genetics and Fruit Development, College of Horticulture, Nanjing Agricultural University, Nanjing 210095, PR China 2Department of Agriculture and Food Technology, Karakoram International University Gilgit, Pakistan 3Cellular and Molecular Research Center, Iran University of Medical Sciences, Tehran, Iran *Corresponding author: Jinggui Fang, Key Laboratory of Genetics and Fruit Development, College of Horticulture, Nanjing Agricultural University, Nanjing, PR China, E-mail: [email protected] Received Date: April 25, 2017; Accepted Date: April 29, 2017; Published Date: May 06, 2017 Copyright: © 2017 Pervaiz T, 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 Anthocyanins are naturally occurring compounds, member of the flavonoid groups of photochemical, involved in defense against the damaging effects of UV irradiation in plants and protect from many oxidants. The anthocyanins, group of pigments are relatively small and diverse flavonoid family in nature, and responsible for the attractive colors, red and purple to blue in many plants. Presence of pigments in flowers and fruits seems to provide attraction for pollination and aiding seed distribution, it also provides antiviral and antimicrobial activities, however their occurrence in the vacuoles remains ambiguous.
    [Show full text]