User menu

Accès à distance ? S'identifier sur le proxy UCLouvain

Structure, Organoleptic Properties, Quantification Methods, and Stability of Phenolic Compounds in Beer-A Review

Primary tabs

Callemien, Delphine [UCL] Collin, Sonia [UCL]

Beer composition changes through storage, altering the quality of the product. In the past decade, many papers have been devoted to the compounds responsible for aged-beer off-flavors, mainly trans-2-nonenal, methional, and dimethyltrisulfide. Due to their huge antioxidant activity, polyphenols have often been described as key compounds for limiting beer staling. Yet phenolic structures also evolve through storage. Low-molecular-weight phenols like 4-vinylsyringol can impart off-flavors in aged beer, whilst flavonoids strongly influence astringency, haze, and color. The instability of stilbenes, prenylchalcones, and derived flavanones could also modify their health potential through storage. After reviewing the structures and properties of all phenolic compounds found in beer, this paper will try to assess the impact of their degradation through aging. Extraction procedures for their quantification and treatments for their removal are also described.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2010
Language Anglais
Journal information "Food Reviews International" - Vol. 26, no. 1, p. 1-84 (2010)
Peer reviewed yes
Publisher Taylor & Francis Inc (Philadelphia)
issn 8755-9129
e-issn 1525-6103
Publication status Publié
Affiliation UCL - SST/ELI/ELIM - Applied Microbiology
Keywords beer ; storage ; aging ; flavor stability ; polyphenols
Links
  1. Dalgliesh C.E., Proceedings of the European Brewery Convention (Amsterdam), 623 (1977)
  2. McMurrough Ian, Hennigan Gerard P., Loughrey Malcolm J., Quantitative analysis of hop flavonols using high-performance liquid chromatography, 10.1021/jf00114a024
  3. Wackerbauer K., Brauwelt, 122, 618 (1982)
  4. Achilli Guido, Piero Cellerino Gian, Gamache Paul H., Vico Melzi d'Eril Gian, Identification and determination of phenolic constituents in natural beverages and plant extracts by means of a coulometric electrode array system, 10.1016/0021-9673(93)80033-5
  5. Bartolomé B., Peña-Neira A., Gómez-Cordovés C., Phenolics and related substances in alcohol-free beers, 10.1007/s002170050574
  6. Floridi Simona, Montanari Luigi, Marconi Ombretta, Fantozzi Paolo, Determination of Free Phenolic Acids in Wort and Beer by Coulometric Array Detection, 10.1021/jf0260040
  7. Alonso García A., Cancho Grande B., Simal Gándara J., Development of a rapid method based on solid-phase extraction and liquid chromatography with ultraviolet absorbance detection for the determination of polyphenols in alcohol-free beers, 10.1016/j.chroma.2004.07.092
  8. Gorinstein Shela, Caspi Abraham, Zemser Marina, Trakhtenberg Simon, Comparative contents of some phenolics in beer, red and white wines, 10.1016/s0271-5317(99)00145-1
  9. Hayes Patrick J., Smyth Malcolm R., McMurrough Ian, Comparison of electrochemical and ultraviolet detection methods in high-performance liquid chromatography for the determination of phenolic compounds commonly found in beers. Part 2. Analysis of beers, 10.1039/an9871201205
  10. Mcmurrough I., Roche G. P., Cleary K. G., PHENOLIC ACIDS IN BEERS AND WORTS, 10.1002/j.2050-0416.1984.tb04260.x
  11. Moll M., Beers & Coolers: definition, production, and composition. Collection Sciences of Techniques Agro-alimentaries, Apria, TEC&DOC Lavoiser (1991)
  12. Montanari Luigi, Perretti Giuseppe, Natella Fausta, Guidi Alessia, Fantozzi Paolo, Organic and Phenolic Acids in Beer, 10.1006/fstl.1999.0593
  13. Nardini M, Determination of free and bound phenolic acids in beer, 10.1016/s0308-8146(03)00257-7
  14. Wackerbauer K., Monatsschrift fuer Brauerei, 31, 52 (1978)
  15. Stewart D., Robertson G. W., Morrison I. M., Phenolic acids dimers in the cell walls of barley, 10.1002/bms.1200230205
  16. Kenyhercz Thomas M., Kissinger Peter T., A new approach to the phenolic components in beer. Application to the determination of sinapic, ferulic, and p-coumaric acids, 10.1021/jf60212a037
  17. McMurrough Ian, Madigan David, Donnelly Dan, Hurley June, Doyle Ann-Marie, Hennigan Gerard, McNulty Niall, Smyth Malcolm R., CONTROL OF FERULIC ACID AND 4-VINYL GUAIACOL IN BREWING, 10.1002/j.2050-0416.1996.tb00918.x
  18. Vanbeneden Nele, Delvaux Filip, Delvaux Freddy R., Determination of hydroxycinnamic acids and volatile phenols in wort and beer by isocratic high-performance liquid chromatography using electrochemical detection, 10.1016/j.chroma.2006.11.001
  19. Tressl R., Monatsschrift fuer Brauerei, 28, 195 (1975)
  20. Vanbeneden N., Proceedings of XIIth De Clerck Chair (Leuven) (2006)
  21. Coghe Stefan, Benoot Koen, Delvaux Filip, Vanderhaegen Bart, Delvaux Freddy R., Ferulic Acid Release and 4-Vinylguaiacol Formation during Brewing and Fermentation:  Indications for Feruloyl Esterase Activity inSaccharomyces cerevisiae, 10.1021/jf0346556
  22. Fiddler Walter., Parker William Ernest., Wasserman Aaron E., Doerr Robert C., Thermal decomposition of ferulic acid, 10.1021/jf60153a003
  23. Tressl R., Proceedings of the Congress—European Brewery Convention, 15, 737 (1975)
  24. Clausen M., Saccharomyces cerevisiae. Gene, 142, 107 (1994)
  25. Meaden Philip G., Taylor Niina R., CLONING OF A YEAST GENE WHICH CAUSES PHENOLIC OFF-FLAVOURS IN BEER, 10.1002/j.2050-0416.1991.tb01075.x
  26. Chatonnet Pascal, Dubourdie Denis, Boidron Jean-noël, Pons Monique, The origin of ethylphenols in wines, 10.1002/jsfa.2740600205
  27. LINDSAY R. F., PRIEST F. G., Decarboxylation of Substituted Cinnamic Acids by Enterobacteria: the Influence on Beer Flavour, 10.1111/j.1365-2672.1975.tb00560.x
  28. Steinhaus Martin, Schieberle Peter, Comparison of the Most Odor-Active Compounds in Fresh and Dried Hop Cones (Humulus lupulusL. Variety Spalter Select) Based on GC−Olfactometry and Odor Dilution Techniques, 10.1021/jf990514l
  29. Kieninger H., Monatsschrift fuer Brauwissenschaft, 37, 9 (1984)
  30. Madigan D., Journal of the American Society of Brewing Chemists, 52, 152 (1994)
  31. Schieberle Peter, Primary odorants of pale lager beer : Differences to other beers and changes during storage, 10.1007/bf01190873
  32. Tressl Roland, Renner Roland, Apetz Martin, Fl�chtige phenolische Verbindungen in Bier, Rauchbier und Sherry, 10.1007/bf01274253
  33. Villarreal R., Journal of the American Society of Brewing Chemists, 44, 114 (1986)
  34. Wackerbauer K., Brauwelt, 122, 758 (1982)
  35. Tressl R., Monatsschrift fuer Brauerei, 27, 98 (1974)
  36. Fickert B., Schieberle P., Identification of the key odorants in barley malt (caramalt) using GC/MS techniques and odour dilution analyses, 10.1002/(sici)1521-3803(199812)42:06<371::aid-food371>3.0.co;2-v
  37. Kieninger H., Brauwissenschaft, 30, 357 (1977)
  38. McMurrough I., High-performance liquid chromatography of flavonoids in barley and hops, 10.1016/s0021-9673(00)82094-4
  39. Sagesser M., Journal of the American Society of Brewing Chemists, 54, 129 (1996)
  40. Vancraenenbroeck R., Proceedings of the Congress—European Brewery Convention, 360 (1965)
  41. Vancraenenbroeck R., Proceedings of the Congress - European Brewery Convention, 12, 29 (1970)
  42. Vancraenenbroeck R., Cerevisia (1976–1990), 5, 69 (1980)
  43. Callemien Delphine, Jerkovic Vesna, Rozenberg Raoul, Collin Sonia, Hop as an Interesting Source of Resveratrol for Brewers:  Optimization of the Extraction and Quantitative Study by Liquid Chromatography/Atmospheric Pressure Chemical Ionization Tandem Mass Spectrometry, 10.1021/jf040179n
  44. Vancraenenbroeck R., Cerevisia (1976–1990), 8, 13 (1983)
  45. Lermusieau Guillaume, Liégeois Catherine, Collin Sonia, Reducing power of hop cultivars and beer ageing, 10.1016/s0308-8146(00)00247-8
  46. Moll M., Technical Quarterly - Master Brewers Association of the Americas, 21, 79 (1984)
  47. Jerumanis J., QUANTITATIVE ANALYSIS OF FLAVANOIDS IN BARLEY, HOPS AND BEER BY HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY (HPLC), 10.1002/j.2050-0416.1985.tb04334.x
  48. Li Hui-Jing, Deinzer Max L., Structural Identification and Distribution of Proanthocyanidins in 13 Different Hops, 10.1021/jf060395r
  49. Stevens Jan F., Miranda Cristobal L., Wolthers Kirsten R., Schimerlik Michael, Deinzer Max L., Buhler Donald R., Identification and in Vitro Biological Activities of Hop Proanthocyanidins:  Inhibition of nNOS Activity and Scavenging of Reactive Nitrogen Species, 10.1021/jf0116202
  50. Friedrich Wolfgang, Galensa Rudolf, Identification of a new flavanol glucoside from barley ( Hordeum vulgare L.) and malt, 10.1007/s00217-002-0498-x
  51. Zimmermann Benno F., Galensa Rudolf, One for all—all for one: proof of authenticity and tracing of foods with flavonoids : Analysis of proanthocyanidins in barley and malt, 10.1007/s00217-006-0333-x
  52. Callemien Delphine, Collin Sonia, Involvement of Flavanoids in Beer Color Instability during Storage, 10.1021/jf0716230
  53. Callemien D., Journal of the American Society of Brewing Chemists, 66, 109 (2008)
  54. Callemien Delphine, Guyot Sylvain, Collin Sonia, Use of thiolysis hyphenated to RP-HPLC-ESI(-)-MS/MS for the analysis of flavanoids in fresh lager beers, 10.1016/j.foodchem.2008.02.081
  55. Gerhauser C., Molecular Cancer Therapeutics, 1, 959 (2002)
  56. Kirby W., Wheeler R. E., THE EXTRACTION OF BEER POLYPHENOLS AND THEIR ASSAY BY H.P.L.C., 10.1002/j.2050-0416.1980.tb03947.x
  57. Madigan David, McMurrough Ian, Smyth Malcolm R., Determination of proanthocyanidins and catechins in beer and barley by high-performance liquid chromatography with dual-electrode electrochemical detection, 10.1039/an9941900863
  58. McMurrough Ian, Madigan David, Smyth Malcolm R., Semipreparative Chromatographic Procedure for the Isolation of Dimeric and Trimeric Proanthocyanidins from Barley, 10.1021/jf960139m
  59. Mulkay P., Touillaux R., Jerumanis J., Proanthocyanidins of barley: separation and identification, 10.1016/s0021-9673(00)81958-5
  60. Delcour Jan A., Tuytens Geert M., STRUCTURE ELUCIDATION OF THREE DIMERIC PROANTHOCYANIDINS ISOLATED FROM A COMMERCIAL BELGIAN PILSNER BEER, 10.1002/j.2050-0416.1984.tb04256.x
  61. Eastmond R., THE SEPARATION AND IDENTIFICATION OF A DIMER OF CATECHIN OCCURRING IN BEER, 10.1002/j.2050-0416.1974.tb03602.x
  62. McMurrough I., Baert T., IDENTIFICATION OF PROANTHOCYANIDINS IN BEER AND THEIR DIRECT MEASUREMENT WITH A DUAL ELECTRODE ELECTROCHEMICAL DETECTOR, 10.1002/j.2050-0416.1994.tb00839.x
  63. Whittle Nigel, Eldridge Helen, Bartley John, Organ Gregory, Identification of the Polyphenols in Barley and Beer by HPLC/MS and HPLC/Electrochemical Detection, 10.1002/j.2050-0416.1999.tb00011.x
  64. Stevens Jan F., Taylor Alan W., Nickerson Gail B., Ivancic Monika, Henning John, Haunold Alfred, Deinzer Max L., Prenylflavonoid variation in Humulus lupulus: distribution and taxonomic significance of xanthogalenol and 4′-O-methylxanthohumol, 10.1016/s0031-9422(00)00005-4
  65. Stevens Jan F, Taylor Alan W, Deinzer Max L, Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography–tandem mass spectrometry, 10.1016/s0021-9673(98)01001-2
  66. De Keukeleire Jelle, Ooms Geert, Heyerick Arne, Roldan-Ruiz Isabel, Van Bockstaele Erik, De Keukeleire Denis, Formation and Accumulation of α-Acids, β-Acids, Desmethylxanthohumol, and Xanthohumol during Flowering of Hops (Humulus lupulusL.), 10.1021/jf034263z
  67. Walker C.J., Brauwelt, 143, 1709 (2003)
  68. Biendl M., Brauwelt International, 39 (2002)
  69. Biendl M., Brauwelt International, 182 (2004)
  70. Stevens Jan F., Taylor Alan W., Clawson Jeff E., Deinzer Max L., Fate of Xanthohumol and Related Prenylflavonoids from Hops to Beer, 10.1021/jf990101k
  71. Stevens Jan F, Page Jonathan E, Xanthohumol and related prenylflavonoids from hops and beer: to your good health!, 10.1016/j.phytochem.2004.04.025
  72. Callemien D., Proceedings of the Congress - European Brewery Convention (2003)
  73. Jerkovic V., Journal of the American Society of Brewing Chemists, 55, 8758 (2007)
  74. Jeandet P., Bessis R., Sbaghi M., Meunier P., Production of the Phytoalexin Resveratrol by Grapes as a Response to Botrytis Attack Under Natural Conditions, 10.1111/j.1439-0434.1995.tb00246.x
  75. Langcake P., Pryce R.J., The production of resveratrol by Vitis vinifera and other members of the Vitaceae as a response to infection or injury, 10.1016/0048-4059(76)90077-1
  76. Jerkovic Vesna, Collin Sonia, Fate of Resveratrol and Piceid through Different Hop Processings and Storage Times, 10.1021/jf072465f
  77. Jerkovic Vesna, Callemien Delphine, Collin Sonia, Determination of Stilbenes in Hop Pellets from Different Cultivars, 10.1021/jf050222m
  78. Jerkovic V., Proceedings of the 31th European Brewery Convention, 76, 1 (2007)
  79. Gerhäuser C., Alt A.P., Klimo K., Knauft J., Frank N., Becker H., Isolation and potential cancer chemopreventive activities of phenolic compounds of beer, 10.1023/a:1026082325529
  80. Stevens Jan F., Ivancic Monika, Hsu Victor L., Deinzer Max L., Prenylflavonoids from Humulus lupulus, 10.1016/s0031-9422(96)00744-3
  81. Tekel' Jozef, De Keukeleire Denis, Rong Haojing, Daeseleire Els, Van Peteghem Carlos, Determination of the Hop-Derived Phytoestrogen, 8-Prenylnaringenin, in Beer by Gas Chromatography/Mass Spectrometry, 10.1021/jf990645m
  82. Jerkovic Vesna, Nguyen Fanny, Timmermans Aurore, Collin Sonia, Comparison of Procedures for Resveratrol Analysis in Beer: Assessment of Stilbenoids Stability through Wort Fermentation and Beer Aging, 10.1002/j.2050-0416.2008.tb00319.x
  83. Singleton V.L., American Journal of Enology and Viticulture, 16, 144 (1965)
  84. Singleton Vernon L., Orthofer Rudolf, Lamuela-Raventós Rosa M., [14] Analysis of total phenols and other oxidation substrates and antioxidants by means of folin-ciocalteu reagent, Oxidants and Antioxidants Part A (1999) ISBN:9780121822002 p.152-178, 10.1016/s0076-6879(99)99017-1
  85. Georgé Stephane, Brat Pierre, Alter Pascaline, Amiot Marie J., Rapid Determination of Polyphenols and Vitamin C in Plant-Derived Products, 10.1021/jf048396b
  86. Bishop L. R., , ANALYSIS COMMITTEE OF THE EUROPEAN BREWERY CONVENTION THE MEASUREMENT OF TOTAL POLYPHENOLS IN WORTS AND BEERS, 10.1002/j.2050-0416.1972.tb03426.x
  87. Fernandez M.Tereza, Mira M.Lurdes, Florêncio M.Helena, Jennings Keith R., Iron and copper chelation by flavonoids: an electrospray mass spectrometry study, 10.1016/s0162-0134(02)00511-1
  88. Mira Lurdes, Tereza Fernandez M., Santos Marta, Rocha Rui, Helena Florêncio M., Jennings Keith R., Interactions of Flavonoids with Iron and Copper Ions: A Mechanism for their Antioxidant Activity, 10.1080/1071576021000016463
  89. Jerumanis J., Bulletin de l'Association Royale des Anciens Etudiants en Brasserie de l'Universite de Louvain, 65, 169 (1969)
  90. Jerumanis J., Bulletin de l'Association Royale des Anciens Etudiants en Brasserie de l'Universite de Louvain, 64, 223 (1968)
  91. Jerumanis J., Bulletin de l'Association Royale des Anciens Etudiants en Brasserie de l'Universite de Louvain, 69, 1 (1973)
  92. De Clerck J., Bulletin de l'Association Royale des Anciens Etudiants en Brasserie de l'Universite de Louvain, 63, 137 (1967)
  93. McMurrough Ian, McDowell June, Chromatographic separation and automated analysis of flavanols, 10.1016/0003-2697(78)90819-9
  94. Delcour Jan A., Varebeke Didier Janssens de, A NEW COLOURIMETRIC ASSAY FOR FLAVANOIDS IN PILSNER BEERS, 10.1002/j.2050-0416.1985.tb04303.x
  95. Sarkar Subodh K., Howarth Ronald E., Specificity of the vanillin test for flavanols, 10.1021/jf60204a041
  96. Sun Baoshan, Ricardo-da-Silva Jorge M., Spranger Isabel, Critical Factors of Vanillin Assay for Catechins and Proanthocyanidins, 10.1021/jf980366j
  97. Porter Lawrence J., Hrstich Liana N., Chan Bock G., The conversion of procyanidins and prodelphinidins to cyanidin and delphinidin, 10.1016/s0031-9422(00)94533-3
  98. Harris G., Ricketts R. W., STUDIES ON NON-BIOLOGICAL HAZES OF BEERS VIII. RAPID ESTIMATION OF ANTHOCYANOGENS IN BEER, 10.1002/j.2050-0416.1959.tb01465.x
  99. McFarlane W. D., DETERMINATION OF ANTHOCYANOGENS, 10.1002/j.2050-0416.1961.tb01831.x
  100. McFarlane W. D., Vader Marra J., DETERMINATION OF ANTHOCYANOGENS II. FURTHER STUDIES ON THE ANALYSIS OF BEER, 10.1002/j.2050-0416.1962.tb01861.x
  101. Chapon L., Proceedings of the European Brewery Convention, Fachverlag Hans Carl, Nürnberg, Germany, 5, 423 (1975)
  102. McMurrough I., Journal of the American Society of Brewing Chemists, 55, 38 (1997)
  103. Chapon L., Brewers’ Guardian, 123, 50 (1994)
  104. McMurrough Ian, Hennigan Gerard P., Loughrey Malcolm J., CONTENTS OF SIMPLE, POLYMERIC AND COMPLEXED FLAVANOLS IN WORTS AND BEERS AND THEIR RELATIONSHIP TO HAZE FORMATION, 10.1002/j.2050-0416.1983.tb04137.x
  105. Schriner R.L., The systematic identification of organic compounds (1998)
  106. Counet Christine, Collin Sonia, Effect of the Number of Flavanol Units on the Antioxidant Activity of Procyanidin Fractions Isolated from Chocolate, 10.1021/jf030349g
  107. Jerumanis J., Proceedings of the Congress - European Brewery Convention, 17, 309 (1979)
  108. Zhao Haifeng, Dong Jianjun, Lu Jian, Chen Jian, Li Yin, Shan Lianju, Lin Yan, Fan Wei, Gu Guoxian, Effects of Extraction Solvent Mixtures on Antioxidant Activity Evaluation and Their Extraction Capacity and Selectivity for Free Phenolic Compounds in Barley (HordeumvulgareL.), 10.1021/jf061087w
  109. Noël Sophie, Metais Nadine, Bonte Sabine, Bodart Etienne, Peladan Fabrice, Dupire Stéphane, Collin Sonia, The use of Oxygen 18 in appraising the impact of oxidation process during beer storage, 10.1002/j.2050-0416.1999.tb00519.x
  110. Owades J. L., Rubin George, Brenner M. W., Food Tannins Measurement, Determination of Food Tannins by Ultraviolet Spectrophotometry, 10.1021/jf60083a008
  111. Owades J.L., Proceedings of the American Society of Brewing Chemists, 66 (1958)
  112. Callemien Delphine, Dasnoy Sébastien, Collin Sonia, Identification of a Stale-Beer-like Odorant in Extracts of Naturally Aged Beer, 10.1021/jf051772n
  113. Milligan S, Kalita J, Pocock V, Heyerick A, De Cooman L, Rong H, De Keukeleire D, Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin, 10.1530/rep.0.1230235
  114. Kantz K., American Journal of Enology and Viticulture, 41, 223 (1990)
  115. Prior Ronald L., Gu Liwei, Occurrence and biological significance of proanthocyanidins in the American diet, 10.1016/j.phytochem.2005.03.025
  116. Zhu Qin Yan, Holt Roberta R., Lazarus Sheryl A., Ensunsa Jodi L., Hammerstone John F., Schmitz Harold H., Keen Carl L., Stability of the Flavan-3-ols Epicatechin and Catechin and Related Dimeric Procyanidins Derived from Cocoa, 10.1021/jf011228o
  117. Guyot Sylvain, Vercauteren Joseph, Cheynier Véronique, Structural determination of colourless and yellow dimers resulting from (+)-catechin coupling catalysed by grape polyphenoloxidase, 10.1016/0031-9422(96)00127-6
  118. Trela Brent C., Waterhouse Andrew L., Resveratrol:  Isomeric Molar Absorptivities and Stability, 10.1021/jf9504576
  119. Fritsch H., Proceedings of the Congress - European Brewery Convention (2003)
  120. Luan Tiangang, Li Gongke, Zhang Zhanxia, Gas-phase postderivatization following solid-phase microextraction for rapid determination of trans-resveratrol in wine by gas chromatography-mass spectrometry, 10.1016/s0003-2670(00)01103-x
  121. Yanagida Akio, Kanda Tomomasa, Shoji Toshihiko, Ohnishi-Kameyama Mayumi, Nagata Tadahiro, Fractionation of apple procyanidins by size-exclusion chromatography, 10.1016/s0021-9673(99)00684-6
  122. YANAGIDA Akio, SHOJI Toshihiko, KANDA Tomomasa, Characterization of Polymerized Polyphenols by Size-exclusion HPLC, 10.1271/bbb.66.1972
  123. Yanagida Akio, Shoji Toshihiko, Shibusawa Yoichi, Separation of proanthocyanidins by degree of polymerization by means of size-exclusion chromatography and related techniques, 10.1016/s0165-022x(03)00068-x
  124. Pinelo Manuel, Arnous Anis, Meyer Anne S., Upgrading of grape skins: Significance of plant cell-wall structural components and extraction techniques for phenol release, 10.1016/j.tifs.2006.05.003
  125. Andres-Lacueva C., LC-GC Europe, 13, 902 (2000)
  126. Pinelo Manuel, Rubilar Monica, Jerez María, Sineiro Jorge, Núñez María José, Effect of Solvent, Temperature, and Solvent-to-Solid Ratio on the Total Phenolic Content and Antiradical Activity of Extracts from Different Components of Grape Pomace, 10.1021/jf0488110
  127. Thurston P. A., Tubb R. S., SCREENING YEAST STRAINS FOR THEIR ABILITY TO PRODUCE PHENOLIC OFF-FLAVOURS: A SIMPLE METHOD FOR DETERMINING PHENOLS IN WORT AND BEER, 10.1002/j.2050-0416.1981.tb04012.x
  128. Fritsch Helge T., Schieberle Peter, Identification Based on Quantitative Measurements and Aroma Recombination of the Character Impact Odorants in a Bavarian Pilsner-type Beer, 10.1021/jf051167k
  129. Coghe Stefan, Martens Els, D'Hollander Hélène, Dirinck Patrick J., Delvaux Freddy R., Sensory and Instrumental Flavour Analysis of Wort Brewed with Dark Specialty Malts, 10.1002/j.2050-0416.2004.tb00188.x
  130. Hayes Patrick J., Smyth Malcolm R., McMurrough Ian, Comparison of electrochemical and ultraviolet detection methods in high-performance liquid chromatography for the determination of phenolic compounds commonly found in beers. Part 1. Optimisation of operating parameters, 10.1039/an9871201197
  131. Li Hui-Jing, Deinzer Max L., Tandem Mass Spectrometry for Sequencing Proanthocyanidins, 10.1021/ac061823v
  132. Derdelinckx G., Proceedings of the Congress—European Brewery Convention, 21, 577 (1987)
  133. Gu Liwei, Kelm Mark A., Hammerstone John F., Beecher Gary, Holden Joanne, Haytowitz David, Prior Ronald L., Screening of Foods Containing Proanthocyanidins and Their Structural Characterization Using LC-MS/MS and Thiolytic Degradation, 10.1021/jf034815d
  134. Milligan S. R., Identification of a Potent Phytoestrogen in Hops (Humulus lupulus L.) and Beer, 10.1210/jc.84.6.2249
  135. Milligan S. R., The Endocrine Activities of 8-Prenylnaringenin and Related Hop (Humulus lupulus L.) Flavonoids, 10.1210/jc.85.12.4912
  136. Miranda Cristobal L., Stevens Jan F., Ivanov Vadim, McCall Mark, Frei Balz, Deinzer Max L., Buhler Donald R., Antioxidant and Prooxidant Actions of Prenylated and Nonprenylated Chalcones and Flavanones in Vitro, 10.1021/jf0002995
  137. Buckee G.K., Mundy A.P., DETERMINATION OF VICINAL DIKETONES IN BEER BY GAS CHROMATOGRAPHY (HEADSPACE TECHNIQUE)-COLLABORATIVE TRIAL, 10.1002/j.2050-0416.1994.tb00820.x
  138. Guyot Sylvain, Doco Thierry, Souquet Jean-Marc, Moutounet Michel, Drilleau Jean-François, Characterization of highly polymerized procyanidins in cider apple (Malus sylvestris var. kermerrien) skin and pulp, 10.1016/s0031-9422(96)00480-3
  139. Kelm Mark A., Johnson J. Chris, Robbins Rebecca J., Hammerstone John F., Schmitz Harold H., High-Performance Liquid Chromatography Separation and Purification of Cacao (Theobroma cacaoL.) Procyanidins According to Degree of Polymerization Using a Diol Stationary Phase, 10.1021/jf0525941
  140. Gu Liwei, Kelm Mark, Hammerstone John F., Beecher Gary, Cunningham David, Vannozzi Sarah, Prior Ronald L., Fractionation of Polymeric Procyanidins from Lowbush Blueberry and Quantification of Procyanidins in Selected Foods with an Optimized Normal-Phase HPLC−MS Fluorescent Detection Method, 10.1021/jf020214v
  141. Guyot Sylvain, Marnet Nathalie, Sanoner Philippe, Drilleau Jean-Francois, Direct thiolysis on crude apple materials for high-performance liquid chromatography characterization and quantification of polyphenols in cider apple tissues and juices, Methods in Enzymology (2001) ISBN:9780121822361 p.57-70, 10.1016/s0076-6879(01)35231-x
  142. Kennedy James A., Jones Graham P., Analysis of Proanthocyanidin Cleavage Products Following Acid-Catalysis in the Presence of Excess Phloroglucinol, 10.1021/jf001030o
  143. Matthews Sara, Mila Isabelle, Scalbert Augustin, Pollet Brigitte, Lapierre Catherine, Hervé du Penhoat Catherine L. M., Rolando Christian, Donnelly Dervilla M. X., Method for Estimation of Proanthocyanidins Based on Their Acid Depolymerization in the Presence of Nucleophiles, 10.1021/jf9607573
  144. Kennedy James A, Taylor Alan W, Analysis of proanthocyanidins by high-performance gel permeation chromatography, 10.1016/s0021-9673(03)00420-5
  145. Taylor Alan W., Barofsky Elizabeth, Kennedy James A., Deinzer Max L., Hop (Humulus lupulusL.) Proanthocyanidins Characterized by Mass Spectrometry, Acid Catalysis, and Gel Permeation Chromatography, 10.1021/jf0340409
  146. Gu Liwei, Kelm Mark A., Hammerstone John F., Zhang Ze, Beecher Gary, Holden Joanne, Haytowitz David, Prior Ronald L., Liquid chromatographic/electrospray ionization mass spectrometric studies of proanthocyanidins in foods, 10.1002/jms.541
  147. Stevens J.F., Journal of the American Society of Brewing Chemists, 56, 136 (1998)
  148. Ohnishi-Kameyama Mayumi, Yanagida Akio, Kanda Tomomasa, Nagata Tadahiro, Identification of Catechin Oligomers from Apple (Malus pumila cv. Fuji) in Matrix-assisted Laser Desorption/Ionization Time-of-flight Mass Spectrometry and Fast-atom Bombardment Mass Spectrometry, 10.1002/(sici)1097-0231(19970115)11:1<31::aid-rcm784>3.0.co;2-t
  149. Ramirez-Coronel Maria Ascencion, Marnet Nathalie, Kolli V. S. Kumar, Roussos Sevastianos, Guyot Sylvain, Augur Christopher, Characterization and Estimation of Proanthocyanidins and Other Phenolics in Coffee Pulp (Coffea arabica) by Thiolysis−High-Performance Liquid Chromatography, 10.1021/jf035208t
  150. Jerkovic V., Proceedings of the Congress—European Brewery Convention (2005)
  151. Meilgaard M.C., Technical Quarterly - Master Brewers Association of the Americas, 12, 5 (1975)
  152. Narziss L., Monatsschrift fuer Brauwissenschaft, 43, 96 (1990)
  153. Drost B.W., Journal of American Society of Brewing Chemists, 48, 131 (1990)
  154. Lermusieau G., Journal of the American Society of Brewing Chemists, 57, 29 (1999)
  155. Noël Sophie, Liégeois Catherine, Lermusieau Guillaume, Bodart Etienne, Badot Camille, Collin Sonia, Release of Deuterated Nonenal during Beer Aging from Labeled Precursors Synthesized in the Boiling Kettle, 10.1021/jf990211r
  156. Gijs Laurence, Perpète Philippe, Timmermans Aurore, Collin Sonia, 3-Methylthiopropionaldehyde as Precursor of Dimethyl Trisulfide in Aged Beers, 10.1021/jf0007380
  157. Burns Colin S., Heyerick Arne, De Keukeleire Denis, Forbes Malcolm D. E., Mechanism for Formation of the Lightstruck Flavor in Beer Revealed by Time-Resolved Electron Paramagnetic Resonance, 10.1002/1521-3765(20011105)7:21<4553::aid-chem4553>3.0.co;2-0
  158. Chevance Fabienne, Guyot-Declerck Christine, Dupont Jérôme, Collin Sonia, Investigation of the β-Damascenone Level in Fresh and Aged Commercial Beers, 10.1021/jf020085i
  159. Gijs Laurence, Chevance Fabienne, Jerkovic Vesna, Collin Sonia, How Low pH Can Intensify β-Damascenone and Dimethyl Trisulfide Production through Beer Aging, 10.1021/jf020563p
  160. Theddy V., Birra e Malto, 9 (1997)
  161. Schieberle P., FRESHNESS AND SHELF LIFE OF FOODS ACS symposium series, 70 (2003)
  162. Vesely Petr, Lusk Lance, Basarova Gabriela, Seabrooks John, Ryder David, Analysis of Aldehydes in Beer Using Solid-Phase Microextraction with On-Fiber Derivatization and Gas Chromatography/Mass Spectrometry, 10.1021/jf034410t
  163. Harayama Koichi, Hayase Fumitaka, Kato Hiromichi, Contribution to Stale Flavor of 2-Furfuryl Ethyl Ether and Its Formation Mechanism in Beer, 10.1271/bbb.59.1144
  164. Vanderhaegen Bart, Neven Hedwig, Daenen Luk, Verstrepen Kevin J., Verachtert Hubert, Derdelinckx Guy, Furfuryl Ethyl Ether:  Important Aging Flavor and a New Marker for the Storage Conditions of Beer, 10.1021/jf035412g
  165. Vanderhaegen Bart, Neven Hedwig, Verstrepen Kevin J., Delvaux Freddy R., Verachtert Hubert, Derdelinckx Guy, Influence of the Brewing Process on Furfuryl Ethyl Ether Formation during Beer Aging, 10.1021/jf0490854
  166. Lejeune I., Proceedings of the 31th European Brewery Convention (2007)
  167. Moir Michael, THE 1990 LAURENCE BISHOP SILVER MEDAL LECTURE* THE DESIDERATUM FOR FLAVOUR CONTROL, 10.1002/j.2050-0416.1992.tb01107.x
  168. Bamforth C.W., Journal of the American Society of Brewing Chemists, 43, 197 (1985)
  169. Andersen Mogens L., Skibsted Leif H., Electron Spin Resonance Spin Trapping Identification of Radicals Formed during Aerobic Forced Aging of Beer, 10.1021/jf9708608
  170. Kaneda Hirotaka., Kano Yukinobu., Koshino Shouhei., Ohya-Nishiguchi Hiroaki., Behavior and role of iron ions in beer deterioration, 10.1021/jf00023a013
  171. Liégeois C., Proceedings of IXth De Clerck Chair (Louvain-la-Neuve, Belgium) (2000)
  172. Uchida M., Journal of the American Society of Brewing Chemists, 54, 205 (1996)
  173. Uchida M., Journal of the American Society of Brewing Chemists, 54, 198 (1996)
  174. Vanderhaegen Bart, Neven Hedwig, Coghe Stefan, Verstrepen Kevin J., Verachtert Hubert, Derdelinckx Guy, Evolution of Chemical and Sensory Properties during Aging of Top-Fermented Beer, 10.1021/jf034631z
  175. McMurrough I., Journal of the American Society of Brewing Chemists, 54, 141 (1996)
  176. Delcour Jan A., Dondeyne Pieter, Trousdale Eugene K., Singleton Vernon L., THE REACTIONS BETWEEN POLYPHENOLS AND ALDEHYDES AND THE INFLUENCE OF ACETALDEHYDE ON HAZE FORMATION IN BEER, 10.1002/j.2050-0416.1982.tb04100.x
  177. Cilliers Johannes J. L., Singleton Vernon L., Autoxidative phenolic ring opening under alkaline conditions as a model for natural polyphenols in food, 10.1021/jf00099a003
  178. Forster A., Brauwelt International, 426 (2004)
  179. Liégeois Catherine, Meurens Nicolas, Badot Camille, Collin Sonia, Release of Deuterated (E)-2-Nonenal during Beer Aging from Labeled Precursors Synthesized before Boiling, 10.1021/jf020617v
  180. Noël S., Proceedings of the Congress - European Brewery Convention, 25, 483 (1995)
  181. Collin S., Proceedings of the Congress—European Brewery Convention, 26, 535 (1997)
  182. Guinard Jean-Xavier, Pangborn Rose Marie, Lewis Michael J., Preliminary studies on acidity-astringency interactions in model solutions and wines, 10.1002/jsfa.2740370815
  183. Siebert Karl J, Chassy Alexander W, An alternate mechanism for the astringent sensation of acids, 10.1016/s0950-3293(02)00221-5
  184. Courregelongue Sandrine, Schlich Pascal, Noble Ann.C, Using repeated ingestion to determine the effect of sweetness, viscosity and oiliness on temporal perception of soymilk astringency, 10.1016/s0950-3293(98)00055-x
  185. Gawel R., Iland P.G., Francis I.L., Characterizing the astringency of red wine: a case study, 10.1016/s0950-3293(00)00033-1
  186. Corrigan Thomas Carol J., Lawless Harry T., Astringent Subqualities in Acids, 10.1093/chemse/20.6.593
  187. Dadic M., Proceedings of the American Society of Brewing Chemists, 4, 107 (1973)
  188. Valentová Helena, Skrovánková Soňa, Panovská Zdenka, Pokorný Jan, Time–intensity studies of astringent taste, 10.1016/s0308-8146(01)00330-2
  189. Noble A. C., Astringency and Bitterness of Flavonoid Phenols, ACS Symposium Series (2002) ISBN:0841237344 p.192-201, 10.1021/bk-2002-0825.ch015
  190. Peleg Hanna, Gacon Karine, Schlich Pascal, Noble Ann C, Bitterness and astringency of flavan-3-ol monomers, dimers and trimers, 10.1002/(sici)1097-0010(199906)79:8<1123::aid-jsfa336>3.0.co;2-d
  191. François Nancy, Guyot-Declerck Christine, Hug Bénédicte, Callemien Delphine, Govaerts Bernadette, Collin Sonia, Beer astringency assessed by time–intensity and quantitative descriptive analysis: Influence of pH and accelerated aging, 10.1016/j.foodqual.2005.05.008
  192. Pangborn R. M., Lewis M. J., Tanno L. S., SENSORY QUANTIFICATION OF BITTERNESS AND FLAVOUR OF BEER DURING STORAGE*, 10.1002/j.2050-0416.1977.tb03803.x
  193. Delcour J. A., American Journal of Enology and Viticulture, 35, 134 (1984)
  194. Kielhorn S, Thorngate III J.H, Oral sensations associated with the flavan-3-ols (+)-catechin and (−)-epicatechin, 10.1016/s0950-3293(98)00049-4
  195. Robichaud Jane L, Noble Ann C, Astringency and bitterness of selected phenolics in wine, 10.1002/jsfa.2740530307
  196. Thorngate J H, Noble A C, Sensory evaluation of bitterness and astringency of 3R(−)-epicatechin and 3S(+)-catechin, 10.1002/jsfa.2740670416
  197. Buggey L.A., The Brewer International, 4, 21 (2001)
  198. Andersen Mogens L., Outtrup Henrik, Skibsted Leif H., Potential Antioxidants in Beer Assessed by ESR Spin Trapping, 10.1021/jf000354+
  199. Andersen Mogens L., Skibsted Leif H., Modification of the Levels of Polyphenols in Wort and Beer by Addition of Hexamethylenetetramine or Sulfite during Mashing, 10.1021/jf0105945
  200. Liégeois Catherine, Lermusieau Guillaume, Collin Sonia, Measuring Antioxidant Efficiency of Wort, Malt, and Hops against the 2,2‘-Azobis(2-amidinopropane) Dihydrochloride-Induced Oxidation of an Aqueous Dispersion of Linoleic Acid, 10.1021/jf9911242
  201. Lotito Silvina B., Actis-Goretta Lucas, Renart M.Lourdes, Caligiuri Marina, Rein Dietrich, Schmitz Harold H., Steinberg Francene M., Keen Carl L., Fraga Cesar G., Influence of Oligomer Chain Length on the Antioxidant Activity of Procyanidins, 10.1006/bbrc.2000.3571
  202. Plumb Geoffrey W., De Pascual-Teresa Sonia, Santos-Buelga Celestino, Cheynier Veronique, Williamson Gary, Antioxidant properties of catechins and proanthocyanidins: Effect of polymerisation, galloylation and glycosylation, 10.1080/10715769800300391
  203. Santos-Buelga Celestino, Scalbert Augustin, Proanthocyanidins and tannin-like compounds - nature, occurrence, dietary intake and effects on nutrition and health, 10.1002/(sici)1097-0010(20000515)80:7<1094::aid-jsfa569>3.0.co;2-1
  204. Wang J.N., Acta Pharmacologica Sinica, 21, 633 (2000)
  205. Siebert Karl J., Troukhanova Nataliia V., Lynn Penelope Y., Nature of Polyphenol−Protein Interactions, 10.1021/jf9502459
  206. Asano K., Journal of the American Society of Brewing Chemists, 40, 147 (1982)
  207. Leiper Kenneth A., Stewart Graham G., McKeown Ian P., Beer Polypeptides and Silica Gel Part I. Polypeptides Involved in Haze Formation, 10.1002/j.2050-0416.2003.tb00594.x
  208. McMurrough I., Journal of the American Society of Brewing Chemists, 50, 67 (1992)
  209. Mulkay P., Cerevisia (1976–1990), 8, 29 (1983)
  210. ASANO Katsuhiko, OHTSU Keiji, SHINAGAWA Kyoko, HASHIMOTO Naoki, Turbidity formed in beer at low temperatures. Affinity of proanthocyanidins and their oxidation products for haze-forming proteins of beer and the formation of chill haze., 10.1271/bbb1961.48.1139
  211. Eastmond R., Gardner R. J., EFFECT OF VARIOUS POLYPHENOLS ON THE RATE OF HAZE FORMATION IN BEER, 10.1002/j.2050-0416.1974.tb03603.x
  212. Siebert Karl J., Carrasco Aurea, Lynn Penelope Y., Formation of Protein−Polyphenol Haze in Beverages, 10.1021/jf950716r
  213. Siebert Karl J., Effects of Protein−Polyphenol Interactions on Beverage Haze, Stabilization, and Analysis, 10.1021/jf980703o
  214. De Clerck J., Technical Quarterly—Master Brewers Association of the Americas, 6, 136 (1969)
  215. Siebert Karl J., Lynn Penelope Y., Mechanisms of Adsorbent Action in Beverage Stabilization, 10.1021/jf970430h
  216. Siebert K.J., Journal of the American Society of Brewing Chemists, 55, 73 (1997)
  217. Siebert K.J., Journal of the American Society of Brewing Chemists, 56, 24 (1998)
  218. Leiper Kenneth A., Stewart Graham G., McKeown Ian P., Nock Tony, Thompson Matthew J., Optimising Beer Stabilisation by the Selective Removal of Tannoids and Sensitive Proteins, 10.1002/j.2050-0416.2005.tb00657.x
  219. Erdal K., Proceedings of the Congress—European Brewery Convention, 20, 459 (1985)
  220. Gardner R.J., Technical Quarterly—Master Brewers Association of the Americas, 14, 250 (1977)
  221. Leemans C., Proceedings of the Congress—European Brewery Convention (2003)
  222. O'Rourke T., Proceedings of the Convention—Institute of Brewing (Asia Pacific Section), 25, 143 (1998)
  223. Kaneda Hirotaka, Kano Yukinobu, Osawa Toshihiko, Kawakishi Shunro, Kamimura Minoru, Effect of free radicals on haze formation in beer, 10.1021/jf00100a006
  224. Young Desmond A., Young Esm�, Roux David G., Brandt E. Vincent, Ferreira Daneel, Synthesis of condensed tannins. Part 19. Phenol oxidative coupling of (+)-catechin and (+)-mesquitol. Conformation of bis-(+)-catechins, 10.1039/p19870002345
  225. Oszmianski Jan, Cheynier Véronique, Moutounet Michel, Iron-Catalyzed Oxidation of (+)-Catechin in Model Systems, 10.1021/jf9507710
  226. Es-Safı Nour-Eddine, Le Guernevé, Christine, Fulcrand Hélène, Cheynier Véronique, Moutounet Michel, New Polyphenolic Compounds with Xanthylium Skeletons Formed through Reaction between (+)-Catechin and Glyoxylic Acid, 10.1021/jf990424g
  227. Es-Safi Nour-Eddine, Fulcrand Hélène, Cheynier Véronique, Moutounet Michel, Studies on the Acetaldehyde-Induced Condensation of (−)-Epicatechin and Malvidin 3-O-Glucoside in a Model Solution System, 10.1021/jf9806309
  228. Es-Safi Nour-Eddine, Cheynier Véronique, Moutounet Michel, Study of the Reactions between (+)-Catechin and Furfural Derivatives in the Presence or Absence of Anthocyanins and Their Implication in Food Color Change, 10.1021/jf000394d
  229. Es-Safi Nour-Eddine, Guernevé Christine, Fulcrand Hélène, Cheynier Véronique, Moutounet Michel, Xanthylium salts formation involved in wine colour changes, 10.1046/j.1365-2621.2000.00339.x
  230. Fulcrand Hélène, Cheynier Véronique, Oszmianski Jan, Moutounet Michel, An oxidized tartaric acid residue as a new bridge potentially competing with acetaldehyde in flavan-3-OL condensation, 10.1016/s0031-9422(97)00276-8
  231. He Jingren, Santos-Buelga Celestino, Silva Artur M. S., Mateus Nuno, de Freitas Victor, Isolation and Structural Characterization of New Anthocyanin-Derived Yellow Pigments in Aged Red Wines, 10.1021/jf062325q
  232. Renaud S., de Lorgeril M., Wine, alcohol, platelets, and the French paradox for coronary heart disease, 10.1016/0140-6736(92)91277-f
  233. Frémont Lucie, Biological effects of resveratrol, 10.1016/s0024-3205(99)00410-5
  234. Rimm E. B, Klatsky A., Grobbee D., Stampfer M. J, Review of moderate alcohol consumption and reduced risk of coronary heart disease: is the effect due to beer, wine, or spirits?, 10.1136/bmj.312.7033.731
  235. Prior Ronald L., Lazarus Sheryl A., Cao Guohua, Muccitelli Helen, Hammerstone John F., Identification of Procyanidins and Anthocyanins in Blueberries and Cranberries (Vaccinium Spp.) Using High-Performance Liquid Chromatography/Mass Spectrometry, 10.1021/jf001211q
  236. Delmas Dominique, Jannin Brigitte, Latruffe Norbert, Resveratrol: Preventing properties against vascular alterations and ageing, 10.1002/mnfr.200400098
  237. Fauconneau Bernard, Waffo-Teguo Pierre, Huguet François, Barrier Laurence, Decendit Alain, Merillon Jean-Michel, Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests, 10.1016/s0024-3205(97)00883-7
  238. Orallo F., Comparative Studies of the Antioxidant Effects of Cis- and Trans- Resveratrol, 10.2174/092986706775197962
  239. Hollman P. C. H., European Journal of Clinical Nutrition, 51, S66 (1997)
  240. De Keukeleire D., Proceedings of 28th European Brewery Convention (Budapest), Fachverlag Hans Carl, Nürnberg, Germany, 566 (2001)
  241. Gerhäuser Clarissa, Beer constituents as potential cancer chemopreventive agents, 10.1016/j.ejca.2005.04.012
  242. Aggarwal B. B., Anticancer Research, 24, 2783 (2004)
  243. Baur Joseph A., Sinclair David A., Therapeutic potential of resveratrol: the in vivo evidence, 10.1038/nrd2060
  244. Jang Dae-Sig, Kang Bo-Seong, Ryu Shi Yong, Chang IL-Moo, Min Kyung Rak, Kim Youngsoo, Inhibitory effects of resveratrol analogs on unopsonized zymosan-induced oxygen radical production, 10.1016/s0006-2952(98)00350-5
  245. Schewe T., Journal of Nutrition, 132, 1825 (2002)
  246. Schramm D.D., American Journal of Clinical Nutrition, 73, 36 (2001)
  247. Sanbongi Chiaki, Suzuki Noboru, Sakane Tsuyoshi, Polyphenols in Chocolate, Which Have Antioxidant Activity, Modulate Immune Functions in Humansin Vitro, 10.1006/cimm.1997.1109
  248. Alarcón de la Lastra Catalina, Villegas Isabel, Resveratrol as an anti-inflammatory and anti-aging agent: Mechanisms and clinical implications, 10.1002/mnfr.200500022
  249. Basly Jean-Philippe, Marre-Fournier Françoise, Le Bail Jean-Christophe, Habrioux Gérard, Chulia Albert José, Estrogenic/antiestrogenic and scavenging properties of (E)- and (Z)-resveratrol, 10.1016/s0024-3205(99)00650-5
Bibliographic reference Callemien, Delphine ; Collin, Sonia. Structure, Organoleptic Properties, Quantification Methods, and Stability of Phenolic Compounds in Beer-A Review. In: Food Reviews International, Vol. 26, no. 1, p. 1-84 (2010)
Permanent URL http://hdl.handle.net/2078.1/34238