ACS Publications. Most Trusted. Most Cited. Most Read
Analysis of Proanthocyanidin Cleavage Products Following Acid-Catalysis in the Presence of Excess Phloroglucinol

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Agric. Food Chem. 2001, 49, 4, 1740-1746
    Article

    Analysis of Proanthocyanidin Cleavage Products Following Acid-Catalysis in the Presence of Excess Phloroglucinol
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Horticulture, Viticulture and Oenology, University of Adelaide, Waite Campus, PMB 1, Glen Osmond, South Australia 5064, Australia
    Other Access OptionsSupporting Information (1)

    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2001, 49, 4, 1740–1746
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jf001030o
    Published March 22, 2001
    Copyright © 2001 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!

    The analysis of proanthocyanidin cleavage products after acid-catalysis in the presence of excess phloroglucinol was investigated. In the developed analytical method, a solution of 0.1 N HCl in methanol, containing 50 g/L phloroglucinol and 10 g/L ascorbic acid was prepared. The proanthocyanidin of interest was reacted in this solution (5 g/L) at 50 °C for 20 min, and afterward combined with 5 volumes of 40 mM aqueous sodium acetate before analysis by reversed-phase HPLC using an aqueous acetic acid and methanol gradient. This procedure was used to investigate the composition of proanthocyanidins isolated from the seed and skin tissue of Vitis vinifera L. berries. The results compared favorably to results obtained when benzyl mercaptan was used as the trapping nucleophile, indicating that phloroglucinol is an effective reagent for this analysis.

    Keywords: Proanthocyanidin; tannin; flavan-3-ol; molar absorptivity; Vitis vinifera; grape; phloroglucinol; benzyl mercaptan; thiolysis; yield

    Copyright © 2001 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    *

     Corresponding author (fax:  61 08 8303 7116; e-mail:  [email protected]).

    †

     University of Adelaide.

    Supporting Information Available

    Click to copy section linkSection link copied!

    1H, 13C, and 2D NMR data of epicatechin-3-O-gallate-(4β→2)-phloroglucinol. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 650 publications.

    1. James R. Campbell, Thibaut Scholasch, Andrew L. Waterhouse, James A. Kennedy. Napa Valley Cabernet Sauvignon Proanthocyanidin Changes During Fruit Ripening: A Multi-Appellation Survey. Journal of Agricultural and Food Chemistry 2024, 72 (24) , 13561-13570. https://doi.org/10.1021/acs.jafc.4c02146
    2. Müzeyyen Berkel Kasikci, Sophie Guilois-Dubois, Kevin Billet, Julien Jardin, Sylvain Guyot, Martine Morzel. Interactions between Salivary Proteins and Apple Polyphenols and the Fate of Complexes during Gastric Digestion. Journal of Agricultural and Food Chemistry 2024, 72 (16) , 9179-9189. https://doi.org/10.1021/acs.jafc.4c00468
    3. Yiliang Cheng, Pradeep M. Wimalasiri, Bin Tian, Aude A. Watrelot. Influence of Grape Flesh on the Retention and Composition of Polyphenols from Skins and Seeds. Journal of Agricultural and Food Chemistry 2024, 72 (16) , 9351-9364. https://doi.org/10.1021/acs.jafc.4c00612
    4. Jan-Peter Hensen, Maria Dörner, Lara Etzbach, Andreas Schieber, Fabian Weber. Seed Maturation Dynamics in Cabernet Sauvignon and Pinot Noir Grapes During Berry Ripening in Cool Climate Zones. ACS Food Science & Technology 2024, 4 (1) , 161-172. https://doi.org/10.1021/acsfoodscitech.3c00445
    5. Laura A. Orozco-Flores, Erika Salas, Beatriz Rocha-Gutiérrez, María Del R. Peralta-Pérez, Guillermo González-Sánchez, Lourdes Ballinas-Casarrubias. Determination of Polyphenolic Profile of Apple Pomace (Malus domestica Golden Delicious Variety) by HPLC–MS. ACS Omega 2024, 9 (1) , 196-203. https://doi.org/10.1021/acsomega.3c03218
    6. Pradeep M. Wimalasiri, Roland Harrison, Richard Hider, Ivan Donaldson, Belinda Kemp, Bin Tian. Development of Tannins and Methoxypyrazines in Grape Skins, Seeds, and Stems of Two Pinot Noir Clones during Ripening. Journal of Agricultural and Food Chemistry 2023, 71 (42) , 15754-15765. https://doi.org/10.1021/acs.jafc.3c04864
    7. Shu-Xi Jing, Daneel Ferreira, Pankaj Pandey, Larry L. Klein, Amar Gopal Chittiboyina, James B. McAlpine, David C. Lankin, Yvette Alania, Mariana Reis-Havlat, Ana K. Bedran-Russo, Shao-Nong Chen, Guido F. Pauli. Unprecedented Benzoquinone Motifs Reveal Post-Oligomerizational Modification of Proanthocyanidins. The Journal of Organic Chemistry 2023, 88 (19) , 13490-13503. https://doi.org/10.1021/acs.joc.3c00950
    8. Jan Steck, Florian Junker, Hendrik Eichhöfer, Mirko Bunzel. Chemically Different but Often Mistaken Phenolic Polymers of Food Plants: Proanthocyanidins and Lignin in Seeds. Journal of Agricultural and Food Chemistry 2022, 70 (37) , 11704-11714. https://doi.org/10.1021/acs.jafc.2c03782
    9. Shu-Xi Jing, Yvette Alania, Mariana Reis, James B. McAlpine, Shao-Nong Chen, Ana K. Bedran-Russo, Guido F. Pauli. Proanthocyanidin Tetramers and Pentamers from Cinnamomum verum Bark and Their Dentin Biomodification Bioactivities. Journal of Natural Products 2022, 85 (2) , 391-404. https://doi.org/10.1021/acs.jnatprod.1c00972
    10. Taiki Igari, Yukinori Chikada, Riku Hoshino, Eri Inoue, Fumie Watanabe-Saito, Masashi Hisamoto, Tohru Okuda. Abundant Existence of Bovine Serum Albumin Non-precipitable Tannins in Red Wines. ACS Food Science & Technology 2021, 1 (11) , 2062-2068. https://doi.org/10.1021/acsfoodscitech.1c00290
    11. Haibo Pan, Yi Wang, Xinlei Xu, Ziqi Qian, Huan Cheng, Xingqian Ye, Shiguo Chen. Simultaneous Extraction and Depolymerization of Condensed Tannins from Chinese Bayberry Leaves for Improved Bioavailability and Antioxidant Activity. Journal of Agricultural and Food Chemistry 2021, 69 (38) , 11292-11302. https://doi.org/10.1021/acs.jafc.1c03962
    12. James R. Campbell, Florian Grosnickel, James A. Kennedy, Andrew L. Waterhouse. Anthocyanin Addition Alters Tannin Extraction from Grape Skins in Model Solutions via Chemical Reactions. Journal of Agricultural and Food Chemistry 2021, 69 (27) , 7687-7697. https://doi.org/10.1021/acs.jafc.1c00112
    13. Bo Teng, Yoji Hayasaka, Paul A. Smith, Keren A. Bindon. Precipitation of Tannin–Anthocyanin Derivatives in Wine is Influenced by Acetaldehyde Concentration and Tannin Molecular Mass with Implications for the Development of Nonbleachable Pigments. Journal of Agricultural and Food Chemistry 2021, 69 (16) , 4804-4815. https://doi.org/10.1021/acs.jafc.1c00396
    14. Susana Río Segade, Ana Belén Bautista-Ortín, Maria Alessandra Paissoni, Simone Giacosa, Vincenzo Gerbi, Luca Rolle, Encarna Gómez-Plaza. Changes in Skin Flavanol Composition as a Response to Ozone-Induced Stress during Postharvest Dehydration of Red Wine Grapes with Different Phenolic Profiles. Journal of Agricultural and Food Chemistry 2020, 68 (47) , 13439-13449. https://doi.org/10.1021/acs.jafc.0c04081
    15. Bin Zhou, Yvette Alania, Mariana Reis, Rasika S. Phansalkar, Joo-Won Nam, James B. McAlpine, Shao-Nong Chen, Ana K. Bedran-Russo, Guido F. Pauli. Tri- and Tetrameric Proanthocyanidins with Dentin Bioactivities from Pinus massoniana. The Journal of Organic Chemistry 2020, 85 (13) , 8462-8479. https://doi.org/10.1021/acs.joc.0c00783
    16. Federica Moccia, Sarai Agustin-Salazar, Anna-Lisa Berg, Brunella Setaro, Raffaella Micillo, Elio Pizzo, Fabian Weber, Nohemi Gamez-Meza, Andreas Schieber, Pierfrancesco Cerruti, Lucia Panzella, Alessandra Napolitano. Pecan (Carya illinoinensis (Wagenh.) K. Koch) Nut Shell as an Accessible Polyphenol Source for Active Packaging and Food Colorant Stabilization. ACS Sustainable Chemistry & Engineering 2020, 8 (17) , 6700-6712. https://doi.org/10.1021/acssuschemeng.0c00356
    17. Guillaume Billerach, Laurent Rouméas, Eric Dubreucq, Hélène Fulcrand. Furanolysis with Menthofuran: A New Depolymerization Method for Analyzing Condensed Tannins. Journal of Agricultural and Food Chemistry 2020, 68 (10) , 2917-2926. https://doi.org/10.1021/acs.jafc.9b00497
    18. J. W. Beaver, C. Medina-Plaza, K. Miller, N. Dokoozlian, R. Ponangi, T. Blair, D. Block, A. Oberholster. Effects of the Temperature and Ethanol on the Kinetics of Proanthocyanidin Adsorption in Model Wine Systems. Journal of Agricultural and Food Chemistry 2020, 68 (10) , 2891-2899. https://doi.org/10.1021/acs.jafc.9b02605
    19. Rasika S. Phansalkar, Joo-Won Nam, Ariene A. Leme-Kraus, Li-She Gan, Bin Zhou, James B. McAlpine, Shao-Nong Chen, Ana K. Bedran-Russo, Guido F. Pauli. Proanthocyanidin Dimers and Trimers from Vitis vinifera Provide Diverse Structural Motifs for the Evaluation of Dentin Biomodification. Journal of Natural Products 2019, 82 (9) , 2387-2399. https://doi.org/10.1021/acs.jnatprod.8b00953
    20. Huertas M. Díaz-Mula, Francisco A. Tomás-Barberán, Rocío García-Villalba. Pomegranate Fruit and Juice (cv. Mollar), Rich in Ellagitannins and Anthocyanins, Also Provide a Significant Content of a Wide Range of Proanthocyanidins. Journal of Agricultural and Food Chemistry 2019, 67 (33) , 9160-9167. https://doi.org/10.1021/acs.jafc.8b07155
    21. Bo Teng, Yoji Hayasaka, Paul A. Smith, Keren A. Bindon. Effect of Grape Seed and Skin Tannin Molecular Mass and Composition on the Rate of Reaction with Anthocyanin and Subsequent Formation of Polymeric Pigments in the Presence of Acetaldehyde. Journal of Agricultural and Food Chemistry 2019, 67 (32) , 8938-8949. https://doi.org/10.1021/acs.jafc.9b01498
    22. Raul C. Girardello, Monica L. Cooper, Rhonda J. Smith, Larry A. Lerno, Robert C. Bruce, Sean Eridon, Anita Oberholster. Impact of Grapevine Red Blotch Disease on Grape Composition of Vitis vinifera Cabernet Sauvignon, Merlot, and Chardonnay. Journal of Agricultural and Food Chemistry 2019, 67 (19) , 5496-5511. https://doi.org/10.1021/acs.jafc.9b01125
    23. Johann Martínez-Lüscher, Cassandra M. Plank, Luca Brillante, Monica L. Cooper, Rhonda J. Smith, Maher Al-Rwahnih, Runze Yu, Anita Oberholster, Raul Girardello, S. Kaan Kurtural. Grapevine Red Blotch Virus May Reduce Carbon Translocation Leading to Impaired Grape Berry Ripening. Journal of Agricultural and Food Chemistry 2019, 67 (9) , 2437-2448. https://doi.org/10.1021/acs.jafc.8b05555
    24. Lingjun Ma, Aude A. Watrelot, Bennett Addison, Andrew L. Waterhouse. Condensed Tannin Reacts with SO2 during Wine Aging, Yielding Flavan-3-ol Sulfonates. Journal of Agricultural and Food Chemistry 2018, 66 (35) , 9259-9268. https://doi.org/10.1021/acs.jafc.8b01996
    25. Wen Jiang, Xiaohua Zhou, Yang Yang, Zhiming Zhou. Integrated Utilization of Red Radish for the Efficient Production of High-Purity Procyanidin Dimers. Journal of Agricultural and Food Chemistry 2018, 66 (35) , 9291-9300. https://doi.org/10.1021/acs.jafc.8b02478
    26. Can Cui, Ailong Shi, Shuang Bai, Pengyu Yan, Qing Li, Kaishun Bi. Novel Antihypertensive Prodrug from Grape Seed Proanthocyanidin Extract via Acid-Mediated Depolymerization in the Presence of Captopril: Synthesis, Process Optimization, and Metabolism in Rats. Journal of Agricultural and Food Chemistry 2018, 66 (14) , 3700-3707. https://doi.org/10.1021/acs.jafc.8b00373
    27. Chi Gao, David G. Cunningham, Haiyan Liu, Christina Khoo, Liwei Gu. Development of a Thiolysis HPLC Method for the Analysis of Procyanidins in Cranberry Products. Journal of Agricultural and Food Chemistry 2018, 66 (9) , 2159-2167. https://doi.org/10.1021/acs.jafc.7b04625
    28. Constanza Mellado, Toribio Figueroa, Ricardo Báez, Rosario Castillo, Manuel Melendrez, Berta Schulz, Katherina Fernández. Development of Graphene Oxide Composite Aerogel with Proanthocyanidins with Hemostatic Properties As a Delivery System. ACS Applied Materials & Interfaces 2018, 10 (9) , 7717-7729. https://doi.org/10.1021/acsami.7b16084
    29. Yu Zhang Shiguo Chen Yu Fu Haihua Yang Xingqian Ye . Proanthocyanidins from Chinese Bayberry (Myrica rubra Sieb. et Zucc.) Leaves: Structure Elucidation and Bioactive Functions. 2018, 185-199. https://doi.org/10.1021/bk-2018-1286.ch010
    30. Johann Martínez-Lüscher, Christopher Cody Lee Chen, Luca Brillante, and Sahap Kaan Kurtural . Partial Solar Radiation Exclusion with Color Shade Nets Reduces the Degradation of Organic Acids and Flavonoids of Grape Berry (Vitis vinifera L.). Journal of Agricultural and Food Chemistry 2017, 65 (49) , 10693-10702. https://doi.org/10.1021/acs.jafc.7b04163
    31. Maxime Pérot, Roberta Lupi, Sylvain Guyot, Carine Delayre-Orthez, Pascale Gadonna-Widehem, Jean-Yves Thébaudin, Marie Bodinier, and Colette Larré . Polyphenol Interactions Mitigate the Immunogenicity and Allergenicity of Gliadins. Journal of Agricultural and Food Chemistry 2017, 65 (31) , 6442-6451. https://doi.org/10.1021/acs.jafc.6b05371
    32. Melanie Millet, Pascal Poupard, Jean-Michel Le Quéré, Remi Bauduin, and Sylvain Guyot . Haze in Apple-Based Beverages: Detailed Polyphenol, Polysaccharide, Protein, and Mineral Compositions. Journal of Agricultural and Food Chemistry 2017, 65 (31) , 6404-6414. https://doi.org/10.1021/acs.jafc.6b05819
    33. Sijing Li, Keren Bindon, Susan E. P. Bastian, Vladimir Jiranek, and Kerry L. Wilkinson . Use of Winemaking Supplements To Modify the Composition and Sensory Properties of Shiraz Wine. Journal of Agricultural and Food Chemistry 2017, 65 (7) , 1353-1364. https://doi.org/10.1021/acs.jafc.6b04505
    34. Joo-Won Nam, Rasika S. Phansalkar, David C. Lankin, James B. McAlpine, Ariene A. Leme-Kraus, Cristina M. P. Vidal, Li-She Gan, Ana Bedran-Russo, Shao-Nong Chen, and Guido F. Pauli . Absolute Configuration of Native Oligomeric Proanthocyanidins with Dentin Biomodification Potency. The Journal of Organic Chemistry 2017, 82 (3) , 1316-1329. https://doi.org/10.1021/acs.joc.6b02161
    35. Keren A. Bindon, Sijing Li, Stella Kassara, and Paul A. Smith . Retention of Proanthocyanidin in Wine-like Solution Is Conferred by a Dynamic Interaction between Soluble and Insoluble Grape Cell Wall Components. Journal of Agricultural and Food Chemistry 2016, 64 (44) , 8406-8419. https://doi.org/10.1021/acs.jafc.6b02900
    36. Runze Yu, Michael G. Cook, Ralph S. Yacco, Aude A. Watrelot, Gregory Gambetta, James A. Kennedy, and S. Kaan Kurtural . Effects of Leaf Removal and Applied Water on Flavonoid Accumulation in Grapevine (Vitis vinifera L. cv. Merlot) Berry in a Hot Climate. Journal of Agricultural and Food Chemistry 2016, 64 (43) , 8118-8127. https://doi.org/10.1021/acs.jafc.6b03748
    37. Susana Soares, Raúl Ferrer-Galego, Elsa Brandão, Mafalda Silva, Nuno Mateus, and Victor de Freitas . Contribution of Human Oral Cells to Astringency by Binding Salivary Protein/Tannin Complexes. Journal of Agricultural and Food Chemistry 2016, 64 (41) , 7823-7828. https://doi.org/10.1021/acs.jafc.6b02659
    38. Josh L. Hixson, Joe L. Jacobs, Eric N. Wilkes, and Paul A. Smith . Survey of the Variation in Grape Marc Condensed Tannin Composition and Concentration and Analysis of Key Compositional Factors. Journal of Agricultural and Food Chemistry 2016, 64 (38) , 7076-7086. https://doi.org/10.1021/acs.jafc.6b03126
    39. Olga Pascual, Elena González-Royo, Mariona Gil, Sergio Gómez-Alonso, Esteban García-Romero, Joan Miquel Canals, Isidro Hermosín-Gutíerrez, and Fernando Zamora . Influence of Grape Seeds and Stems on Wine Composition and Astringency. Journal of Agricultural and Food Chemistry 2016, 64 (34) , 6555-6566. https://doi.org/10.1021/acs.jafc.6b01806
    40. Qian Li, Xieyi Wang, Taotao Dai, Chengmei Liu, Ti Li, David Julian McClements, Jun Chen, and Jiyan Liu . Proanthocyanidins, Isolated from Choerospondias axillaris Fruit Peels, Exhibit Potent Antioxidant Activities in Vitro and a Novel Anti-angiogenic Property in Vitro and in Vivo. Journal of Agricultural and Food Chemistry 2016, 64 (18) , 3546-3556. https://doi.org/10.1021/acs.jafc.6b00236
    41. Ralph S. Yacco, Aude A. Watrelot, and James A. Kennedy . Red Wine Tannin Structure–Activity Relationships during Fermentation and Maceration. Journal of Agricultural and Food Chemistry 2016, 64 (4) , 860-869. https://doi.org/10.1021/acs.jafc.5b05058
    42. Josh L. Hixson, Keren A. Bindon, and Paul A. Smith . Evaluation of Direct Phloroglucinolysis and Colorimetric Depolymerization Assays and Their Applicability for Determining Condensed Tannins in Grape Marc. Journal of Agricultural and Food Chemistry 2015, 63 (45) , 9954-9962. https://doi.org/10.1021/acs.jafc.5b04207
    43. Erell Le Deun, Remmelt Van der Werf, Gildas Le Bail, Jean-Michel Le Quéré, and Sylvain Guyot . HPLC-DAD-MS Profiling of Polyphenols Responsible for the Yellow-Orange Color in Apple Juices of Different French Cider Apple Varieties. Journal of Agricultural and Food Chemistry 2015, 63 (35) , 7675-7684. https://doi.org/10.1021/acs.jafc.5b00988
    44. Silvia Pérez-Magariño, Leticia Martínez-Lapuente, Marta Bueno-Herrera, Miriam Ortega-Heras, Zenaida Guadalupe, and Belén Ayestarán . Use of Commercial Dry Yeast Products Rich in Mannoproteins for White and Rosé Sparkling Wine Elaboration. Journal of Agricultural and Food Chemistry 2015, 63 (23) , 5670-5681. https://doi.org/10.1021/acs.jafc.5b01336
    45. Alena L. Jin, Jocelyn A. Ozga, James A. Kennedy, Jayma L. Koerner-Smith, Gabor Botar, and Dennis M. Reinecke . Developmental Profile of Anthocyanin, Flavonol, and Proanthocyanidin Type, Content, and Localization in Saskatoon Fruits (Amelanchier alnifolia Nutt.). Journal of Agricultural and Food Chemistry 2015, 63 (5) , 1601-1614. https://doi.org/10.1021/jf504722x
    46. Ana Belén Bautista-Ortín, Yolanda Ruiz-García, Fátima Marín, Noelia Molero, Rafael Apolinar-Valiente, and Encarna Gómez-Plaza . Remarkable Proanthocyanidin Adsorption Properties of Monastrell Pomace Cell Wall Material Highlight Its Potential Use as an Alternative Fining Agent in Red Wine Production. Journal of Agricultural and Food Chemistry 2015, 63 (2) , 620-633. https://doi.org/10.1021/jf503659y
    47. Keren Bindon, Stella Kassara, Yoji Hayasaka, Alex Schulkin, and Paul Smith . Properties of Wine Polymeric Pigments Formed from Anthocyanin and Tannins Differing in Size Distribution and Subunit Composition. Journal of Agricultural and Food Chemistry 2014, 62 (47) , 11582-11593. https://doi.org/10.1021/jf503922h
    48. Van-Long Truong, Min-Ji Bak, Mira Jun, Ah-Ng Tony Kong, Chi-Tang Ho, and Woo-Sik Jeong . Antioxidant Defense and Hepatoprotection by Procyanidins from Almond (Prunus amygdalus) Skins. Journal of Agricultural and Food Chemistry 2014, 62 (34) , 8668-8678. https://doi.org/10.1021/jf5027247
    49. Jacqui M. McRae, Nigel Kirby, Haydyn D. T. Mertens, Stella Kassara, and Paul A. Smith . Measuring the Molecular Dimensions of Wine Tannins: Comparison of Small-Angle X-ray Scattering, Gel-Permeation Chromatography and Mean Degree of Polymerization. Journal of Agricultural and Food Chemistry 2014, 62 (29) , 7216-7224. https://doi.org/10.1021/jf405308m
    50. Marta Malec, Jean-Michel Le Quéré, Hélène Sotin, Krzysztof Kolodziejczyk, Rémi Bauduin, and Sylvain Guyot . Polyphenol Profiling of a Red-Fleshed Apple Cultivar and Evaluation of the Color Extractability and Stability in the Juice. Journal of Agricultural and Food Chemistry 2014, 62 (29) , 6944-6954. https://doi.org/10.1021/jf500336v
    51. Tuba Esatbeyoglu, Andreas Juadjur, Victor Wray, and Peter Winterhalter . Semisynthetic Preparation and Isolation of Dimeric Procyanidins B1–B8 from Roasted Hazelnut Skins (Corylus avellana L.) on a Large Scale Using Countercurrent Chromatography. Journal of Agricultural and Food Chemistry 2014, 62 (29) , 7101-7110. https://doi.org/10.1021/jf501312a
    52. Matthew R. Revelette, Jennifer A. Barak, and James A. Kennedy . High-Performance Liquid Chromatography Determination of Red Wine Tannin Stickiness. Journal of Agricultural and Food Chemistry 2014, 62 (28) , 6626-6631. https://doi.org/10.1021/jf501666z
    53. Bartosz Fotschki, Joanna Milala, Adam Jurgoński, Elżbieta Karlińska, Zenon Zduńczyk, and Jerzy Juśkiewicz . Strawberry Ellagitannins Thwarted the Positive Effects of Dietary Fructooligosaccharides in Rat Cecum. Journal of Agricultural and Food Chemistry 2014, 62 (25) , 5871-5880. https://doi.org/10.1021/jf405612a
    54. Keren A. Bindon, Stella Kassara, Wieslawa U. Cynkar, Ella M. C. Robinson, Neil Scrimgeour, and Paul A. Smith . Comparison of Extraction Protocols To Determine Differences in Wine-Extractable Tannin and Anthocyanin in Vitis vinifera L. cv. Shiraz and Cabernet Sauvignon Grapes. Journal of Agricultural and Food Chemistry 2014, 62 (20) , 4558-4570. https://doi.org/10.1021/jf5002777
    55. Priscilla R. V. Campana, Christina M. Coleman, Mauro M. Teixeira, Daneel Ferreira, and Fernão C. Braga . TNF-α Inhibition Elicited by Mansoins A and B, Heterotrimeric Flavonoids Isolated from Mansoa hirsuta. Journal of Natural Products 2014, 77 (4) , 824-830. https://doi.org/10.1021/np400929g
    56. Keren A. Bindon, S. Hadi Madani, Phillip Pendleton, Paul A. Smith, and James A. Kennedy . Factors Affecting Skin Tannin Extractability in Ripening Grapes. Journal of Agricultural and Food Chemistry 2014, 62 (5) , 1130-1141. https://doi.org/10.1021/jf4050606
    57. Jacqui M. McRae, Stella Kassara, James A. Kennedy, Elizabeth J. Waters, and Paul A. Smith . Effect of Wine pH and Bottle Closure on Tannins. Journal of Agricultural and Food Chemistry 2013, 61 (47) , 11618-11627. https://doi.org/10.1021/jf403704f
    58. Kathithileni M. Kalili, Jochen Vestner, Maria A. Stander, and André de Villiers . Toward Unraveling Grape Tannin Composition: Application of Online Hydrophilic Interaction Chromatography × Reversed-Phase Liquid Chromatography–Time-of-Flight Mass Spectrometry for Grape Seed Analysis. Analytical Chemistry 2013, 85 (19) , 9107-9115. https://doi.org/10.1021/ac401896r
    59. Fabrizio Torchio, Susana Río Segade, Simone Giacosa, Vincenzo Gerbi, and Luca Rolle . Effect of Growing Zone and Vintage on the Prediction of Extractable Flavanols in Winegrape Seeds by a FT-NIR Method. Journal of Agricultural and Food Chemistry 2013, 61 (38) , 9076-9088. https://doi.org/10.1021/jf401955m
    60. Luca Rolle, Simone Giacosa, Fabrizio Torchio, Daniele Perenzoni, Susana Río Segade, Vincenzo Gerbi, and Fulvio Mattivi . Use of Instrumental Acoustic Parameters of Winegrape Seeds as Possible Predictors of Extractable Phenolic Compounds. Journal of Agricultural and Food Chemistry 2013, 61 (37) , 8752-8764. https://doi.org/10.1021/jf4024382
    61. L. Federico Casassa, Richard C. Larsen, Christopher W. Beaver, Maria S. Mireles, Markus Keller, William R. Riley, Russell Smithyman, and James F. Harbertson . Impact of Extended Maceration and Regulated Deficit Irrigation (RDI) in Cabernet Sauvignon Wines: Characterization of Proanthocyanidin Distribution, Anthocyanin Extraction, and Chromatic Properties. Journal of Agricultural and Food Chemistry 2013, 61 (26) , 6446-6457. https://doi.org/10.1021/jf400733u
    62. M. Gil, M. Esteruelas, E. González, N. Kontoudakis, J. Jiménez, F. Fort, J. M. Canals, I. Hermosín-Gutiérrez, and F. Zamora . Effect of Two Different Treatments for Reducing Grape Yield in Vitis vinifera cv Syrah on Wine Composition and Quality: Berry Thinning versus Cluster Thinning. Journal of Agricultural and Food Chemistry 2013, 61 (20) , 4968-4978. https://doi.org/10.1021/jf400722z
    63. Raúl F. Guerrero, Paul Smith, and Keren A. Bindon . Application of Insoluble Fibers in the Fining of Wine Phenolics. Journal of Agricultural and Food Chemistry 2013, 61 (18) , 4424-4432. https://doi.org/10.1021/jf400172f
    64. Jennifer A. Barak and James A. Kennedy . HPLC Retention Thermodynamics of Grape and Wine Tannins. Journal of Agricultural and Food Chemistry 2013, 61 (18) , 4270-4277. https://doi.org/10.1021/jf400366z
    65. Yolanda Ruiz-García, Rocío Gil-Muñoz, Jose María López-Roca, Adrián Martínez-Cutillas, Inmaculada Romero-Cascales, and Encarna Gómez-Plaza . Increasing the Phenolic Compound Content of Grapes by Preharvest Application of Abcisic Acid and a Combination of Methyl Jasmonate and Benzothiadiazole. Journal of Agricultural and Food Chemistry 2013, 61 (16) , 3978-3983. https://doi.org/10.1021/jf400631m
    66. Hédi Hammouda, Jamila Kalthoum Chérif, Malika Trabelsi-Ayadi, Alain Baron, and Sylvain Guyot . Detailed Polyphenol and Tannin Composition and Its Variability in Tunisian Dates (Phoenix dactylifera L.) at Different Maturity Stages. Journal of Agricultural and Food Chemistry 2013, 61 (13) , 3252-3263. https://doi.org/10.1021/jf304614j
    67. Alexandre G. Pugliese, Francisco A. Tomas-Barberan, Pilar Truchado, and Maria I. Genovese . Flavonoids, Proanthocyanidins, Vitamin C, and Antioxidant Activity of Theobroma grandiflorum (Cupuassu) Pulp and Seeds. Journal of Agricultural and Food Chemistry 2013, 61 (11) , 2720-2728. https://doi.org/10.1021/jf304349u
    68. Aneta Wojdyło, Jan Oszmiański, and Paweł Bielicki . Polyphenolic Composition, Antioxidant Activity, and Polyphenol Oxidase (PPO) Activity of Quince (Cydonia oblonga Miller) Varieties. Journal of Agricultural and Food Chemistry 2013, 61 (11) , 2762-2772. https://doi.org/10.1021/jf304969b
    69. Nadine Wollmann and Thomas Hofmann . Compositional and Sensory Characterization of Red Wine Polymers. Journal of Agricultural and Food Chemistry 2013, 61 (9) , 2045-2061. https://doi.org/10.1021/jf3052576
    70. Jacqui M. McRae, Alex Schulkin, Stella Kassara, Helen E. Holt, and Paul A. Smith . Sensory Properties of Wine Tannin Fractions: Implications for In-Mouth Sensory Properties. Journal of Agricultural and Food Chemistry 2013, 61 (3) , 719-727. https://doi.org/10.1021/jf304239n
    71. Natalia Quijada-Morín, Jorge Regueiro, Jesús Simal-Gándara, Esperanza Tomás, Julián C. Rivas-Gonzalo, and M. Teresa Escribano-Bailón . Relationship between the Sensory-Determined Astringency and the Flavanolic Composition of Red Wines. Journal of Agricultural and Food Chemistry 2012, 60 (50) , 12355-12361. https://doi.org/10.1021/jf3044346
    72. Jacqui M. McRae, Robert G. Dambergs, Stella Kassara, Mango Parker, David W. Jeffery, Markus J. Herderich, and Paul A. Smith . Phenolic Compositions of 50 and 30 Year Sequences of Australian Red Wines: The Impact of Wine Age. Journal of Agricultural and Food Chemistry 2012, 60 (40) , 10093-10102. https://doi.org/10.1021/jf301571q
    73. Keren A. Bindon, Antony Bacic, and James A. Kennedy . Tissue-Specific and Developmental Modifications of Grape Cell Walls Influence the Adsorption of Proanthocyanidins. Journal of Agricultural and Food Chemistry 2012, 60 (36) , 9249-9260. https://doi.org/10.1021/jf301552t
    74. Maria Nikolantonaki and Andrew L. Waterhouse . A Method To Quantify Quinone Reaction Rates with Wine Relevant Nucleophiles: A Key to the Understanding of Oxidative Loss of Varietal Thiols. Journal of Agricultural and Food Chemistry 2012, 60 (34) , 8484-8491. https://doi.org/10.1021/jf302017j
    75. Mariona Gil, Nikolaos Kontoudakis, Elena González, Mireia Esteruelas, Francesca Fort, Joan Miquel Canals, and Fernando Zamora . Influence of Grape Maturity and Maceration Length on Color, Polyphenolic Composition, and Polysaccharide Content of Cabernet Sauvignon and Tempranillo Wines. Journal of Agricultural and Food Chemistry 2012, 60 (32) , 7988-8001. https://doi.org/10.1021/jf302064n
    76. Shangwu Jin, Eerdunbayaer, Airi Doi, Teruo Kuroda, Guixia Zhang, Tsutomu Hatano, and Guilin Chen . Polyphenolic Constituents of Cynomorium songaricum Rupr. and Antibacterial Effect of Polymeric Proanthocyanidin on Methicillin-Resistant Staphylococcus aureus. Journal of Agricultural and Food Chemistry 2012, 60 (29) , 7297-7305. https://doi.org/10.1021/jf301621e
    77. Jun-Song Xiao, Bi-Jun Xie, Yan-Ping Cao, Hua Wu, Zhi-Da Sun, and Di Xiao . Characterization of Oligomeric Procyanidins and Identification of Quercetin Glucuronide from Lotus (Nelumbo nucifera Gaertn.) Seedpod. Journal of Agricultural and Food Chemistry 2012, 60 (11) , 2825-2829. https://doi.org/10.1021/jf205331e
    78. Yolanda Ruiz-García, Inmaculada Romero-Cascales, Rocio Gil-Muñoz, Jose Ignacio Fernández-Fernández, Jose María López-Roca, and Encarna Gómez-Plaza . Improving Grape Phenolic Content and Wine Chromatic Characteristics through the Use of Two Different Elicitors: Methyl Jasmonate versus Benzothiadiazole. Journal of Agricultural and Food Chemistry 2012, 60 (5) , 1283-1290. https://doi.org/10.1021/jf204028d
    79. Rachel L. Hanlin, Mark A. Kelm, Kerry L. Wilkinson, and Mark O. Downey . Detailed Characterization of Proanthocyanidins in Skin, Seeds, and Wine of Shiraz and Cabernet Sauvignon Wine Grapes (Vitis vinifera). Journal of Agricultural and Food Chemistry 2011, 59 (24) , 13265-13276. https://doi.org/10.1021/jf203466u
    80. Stella Kassara and James A. Kennedy . Relationship between Red Wine Grade and Phenolics. 2. Tannin Composition and Size. Journal of Agricultural and Food Chemistry 2011, 59 (15) , 8409-8412. https://doi.org/10.1021/jf201054p
    81. Naiara Busse-Valverde, Encarna Gómez-Plaza, Jose M. López-Roca, Rocio Gil-Muñoz, and Ana B. Bautista-Ortín . The Extraction of Anthocyanins and Proanthocyanidins from Grapes to Wine during Fermentative Maceration Is Affected by the Enological Technique. Journal of Agricultural and Food Chemistry 2011, 59 (10) , 5450-5455. https://doi.org/10.1021/jf2002188
    82. Keren A. Bindon and James A. Kennedy . Ripening-Induced Changes in Grape Skin Proanthocyanidins Modify Their Interaction with Cell Walls. Journal of Agricultural and Food Chemistry 2011, 59 (6) , 2696-2707. https://doi.org/10.1021/jf1047207
    83. Nikolaos Kontoudakis, Elena González, Mariona Gil, Mireia Esteruelas, Francesca Fort, Joan Miquel Canals, and Fernando Zamora . Influence of Wine pH on Changes in Color and Polyphenol Composition Induced by Micro-oxygenation. Journal of Agricultural and Food Chemistry 2011, 59 (5) , 1974-1984. https://doi.org/10.1021/jf103038g
    84. Haihua Yang, Xingqian Ye, Donghong Liu, Jianchu Chen, Jinjie Zhang, Yan Shen, and Dong Yu . Characterization of Unusual Proanthocyanidins in Leaves of Bayberry (Myrica rubra Sieb. et Zucc.). Journal of Agricultural and Food Chemistry 2011, 59 (5) , 1622-1629. https://doi.org/10.1021/jf103918v
    85. Tuba Esatbeyoglu, Beate Jaschok-Kentner, Victor Wray, and Peter Winterhalter . Structure Elucidation of Procyanidin Oligomers by Low-Temperature 1H NMR Spectroscopy. Journal of Agricultural and Food Chemistry 2011, 59 (1) , 62-69. https://doi.org/10.1021/jf1032334
    86. Jacqui M. McRae, Robert J. Falconer, and James A. Kennedy . Thermodynamics of Grape and Wine Tannin Interaction with Polyproline: Implications for Red Wine Astringency. Journal of Agricultural and Food Chemistry 2010, 58 (23) , 12510-12518. https://doi.org/10.1021/jf1030967
    87. Eleni D. Pliakoni, George D. Nanos, and Maria I. Gil . Two-Season Study of the Influence of Regulated Deficit Irrigation and Reflective Mulch on Individual and Total Phenolic Compounds of Nectarines at Harvest and during Storage. Journal of Agricultural and Food Chemistry 2010, 58 (22) , 11783-11789. https://doi.org/10.1021/jf102387m
    88. Naiara Busse-Valverde, Encarna Gómez-Plaza, Jose M. López-Roca, Rocio Gil-Muñoz, Jose I. Fernández-Fernández, and Ana B. Bautista-Ortín . Effect of Different Enological Practices on Skin and Seed Proanthocyanidins in Three Varietal Wines. Journal of Agricultural and Food Chemistry 2010, 58 (21) , 11333-11339. https://doi.org/10.1021/jf102265c
    89. Keren A. Bindon, Paul A. Smith, Helen Holt, and James A. Kennedy. Interaction between Grape-Derived Proanthocyanidins and Cell Wall Material. 2. Implications for Vinification. Journal of Agricultural and Food Chemistry 2010, 58 (19) , 10736-10746. https://doi.org/10.1021/jf1022274
    90. Tuba Esatbeyoglu, Victor Wray and Peter Winterhalter . Dimeric Procyanidins: Screening for B1 to B8 and Semisynthetic Preparation of B3, B4, B6, and B8 from a Polymeric Procyanidin Fraction of White Willow Bark (Salix alba). Journal of Agricultural and Food Chemistry 2010, 58 (13) , 7820-7830. https://doi.org/10.1021/jf101023e
    91. Bathilde Auger, Nathalie Marnet, Véronique Gautier, Alessandra Maia-Grondard, Françoise Leprince, Michel Renard, Sylvain Guyot, Nathalie Nesi and Jean-Marc Routaboul . A Detailed Survey of Seed Coat Flavonoids in Developing Seeds of Brassica napus L.. Journal of Agricultural and Food Chemistry 2010, 58 (10) , 6246-6256. https://doi.org/10.1021/jf903619v
    92. Tuba Esatbeyoglu and Peter Winterhalter. Preparation of Dimeric Procyanidins B1, B2, B5, and B7 from a Polymeric Procyanidin Fraction of Black Chokeberry (Aronia melanocarpa). Journal of Agricultural and Food Chemistry 2010, 58 (8) , 5147-5153. https://doi.org/10.1021/jf904354n
    93. Begoña Buendía, María I. Gil, Juan A. Tudela, Anne L. Gady, Juan J. Medina, Carmen Soria, Jose M. López and Francisco A. Tomás-Barberán . HPLC-MS Analysis of Proanthocyanidin Oligomers and Other Phenolics in 15 Strawberry Cultivars. Journal of Agricultural and Food Chemistry 2010, 58 (7) , 3916-3926. https://doi.org/10.1021/jf9030597
    94. Elías Obreque-Slier, Álvaro Peña-Neira, Remigio López-Solís, Fernando Zamora-Marín, Jorge M. Ricardo-da Silva and Olga Laureano . Comparative Study of the Phenolic Composition of Seeds and Skins from Carménère and Cabernet Sauvignon Grape Varieties (Vitis vinifera L.) during Ripening. Journal of Agricultural and Food Chemistry 2010, 58 (6) , 3591-3599. https://doi.org/10.1021/jf904314u
    95. Keren A. Bindon, Paul A. Smith and James A. Kennedy. Interaction between Grape-Derived Proanthocyanidins and Cell Wall Material. 1. Effect on Proanthocyanidin Composition and Molecular Mass. Journal of Agricultural and Food Chemistry 2010, 58 (4) , 2520-2528. https://doi.org/10.1021/jf9037453
    96. Alberto Hernández-Jiménez, Encarna Gómez-Plaza, Adrián Martínez-Cutillas and James A. Kennedy . Grape Skin and Seed Proanthocyanidins from Monastrell × Syrah Grapes. Journal of Agricultural and Food Chemistry 2009, 57 (22) , 10798-10803. https://doi.org/10.1021/jf903465p
    97. Jan Oszmiański, Aneta Wojdyl̷o and Joanna Kolniak. Effect of Enzymatic Mash Treatment and Storage on Phenolic Composition, Antioxidant Activity, and Turbidity of Cloudy Apple Juice. Journal of Agricultural and Food Chemistry 2009, 57 (15) , 7078-7085. https://doi.org/10.1021/jf900806u
    98. Fiorella K. Cerpa-Calderón and James A. Kennedy. Berry Integrity and Extraction of Skin and Seed Proanthocyanidins during Red Wine Fermentation. Journal of Agricultural and Food Chemistry 2008, 56 (19) , 9006-9014. https://doi.org/10.1021/jf801384v
    99. Nils Köhler, Victor Wray and Peter Winterhalter . New Approach for the Synthesis and Isolation of Dimeric Procyanidins. Journal of Agricultural and Food Chemistry 2008, 56 (13) , 5374-5385. https://doi.org/10.1021/jf7036505
    100. Clotilde Verries, Jean-Luc Guiraud, Jean-Marc Souquet, Sandrine Vialet, Nancy Terrier and Didier Ollé. Validation of an Extraction Method on Whole Pericarp of Grape Berry (Vitis vinifera L. cv. Shiraz) to Study Biochemical and Molecular Aspects of Flavan-3-ol Synthesis during Berry Development. Journal of Agricultural and Food Chemistry 2008, 56 (14) , 5896-5904. https://doi.org/10.1021/jf800028k
    Load more citations
    Download PDF
    Go to Journal of Agricultural and Food Chemistry
    Get e-Alerts
    Get e-Alerts

    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2001, 49, 4, 1740–1746
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jf001030o
    Published March 22, 2001
    Copyright © 2001 American Chemical Society
    Request reuse permissions

    Article Views

    6678

    Altmetric

    -

    Citations

    650
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.