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Polyphenols and Beer Quality

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Natural Products

Abstract

Beer phenols issued from malt and hop can contribute directly to several characteristics of beer, mainly flavor, astringency, haze, body, and fullness. Some phenolic structures can also impart very interesting health properties. Yet phenolic structures also evolve through storage. Low-molecular-weight phenols like 4-vinylsyringol can impart off-flavors in aged beer, while oxidized flavonoids strongly influence astringency, haze, and color. The instability of stilbenes, prenylchalcones, and derived flavanones could also modify their health potential.

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Abbreviations

AEDA:

Aroma extract dilution analysis

APCI:

Atmospheric-pressure chemical ionization

C:

Catechin

E:

Epicatechin

EGC and GC:

Epigallocatechin and gallocatechin

ESI:

Electrospray ionization

FD:

Dilution factor

HPLC or LC:

High-performance liquid chromatography

MS:

Mass spectroscopy

MS/MS:

Tandem mass spectroscopy

NP:

Normal phase

P1 to P10:

Procyanidins from monomers to decamers

PVP:

Polyvinylpyrrolidone

PVPP:

Polyvinylpolypyrrolidone

RP:

Reversed phase

UV:

Ultraviolet

References

  1. Lermusieau G, Liégeois C, Collin S (2001) Reducing power of hop cultivars and beer ageing. Food Chem 72:413–418

    Article  CAS  Google Scholar 

  2. Moll M, Fonknechten G, Carnielo M, Flayeux R (1984) Changes in polyphenols from raw materials to finished beer. Tech Q Master Brew Assoc Am 21:79–87

    CAS  Google Scholar 

  3. McMurrough I (1981) High-performance liquid chromatography of flavonoids in barley and hops. J Chromatogr A 218:683–693

    Article  CAS  Google Scholar 

  4. Callemien D, Jerkovic V, Rozenberg R, Collin S (2005) 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. J Agric Food Chem 53:424–429

    Article  CAS  Google Scholar 

  5. Jerumanis J (1985) Quantitative analysis of flavanoids in barley, hops and beer by high-performance liquid chromatography (HPLC). J Inst Brew 91:250–252

    Article  CAS  Google Scholar 

  6. Li HJ, Deinzer ML (2006) Structural identification and distribution of proanthocyanidins in 13 different hops. J Agric Food Chem 54:4048–4056

    Article  CAS  Google Scholar 

  7. Stevens JF, Miranda CL, Wolthers KR, Schimerlik M, Deinzer ML, Buhler DR (2002) Identification and in vitro biological activities of hop proanthocyanidins: inhibition of nNOS activity and scavenging of reactive nitrogen species. J Agric Food Chem 50:3435–3443

    Article  CAS  Google Scholar 

  8. Moll M (1991) Beers & coolers: definition, production, and composition. Collection sciences et techniques agro-alimentaires. Tec & Doc–Lavoisier et Apria, Paris

    Google Scholar 

  9. Friedrich W, Galensa R (2002) Identification of a new flavanol glucoside from barley (Hordeum vulgare L.) and malt. European Food Research and Technology 214:388–393

    Article  CAS  Google Scholar 

  10. Zimmermann BF, Galensa R (2007) One for all- all for one: proof of authenticity and tracing of foods with flavonoids - Analysis of proanthocyanidins in barley and malt. European Food Research and Technology 224:385–393

    Article  CAS  Google Scholar 

  11. Achilli G, Cellerino GP, Gamache PH, Deril GVM (1993) Identification and determination of phenolic constituents in natural beverages and plant-extracts by means of a coulometric electrode array system. J Chromatogr 632:111–117

    Article  CAS  Google Scholar 

  12. Bartolome B, Pena-Neira A, Gomez-Cordoves C (2000) Phenolics and related substances in alcohol-free beers. Eur Food Res Technol 210:419–423

    Article  CAS  Google Scholar 

  13. Gorinstein S, Caspi A, Zemser M, Trakhtenberg S (2000) Comparative contents of some phenolics in beer, red and white wines. Nutr Res 20:131–139

    Article  CAS  Google Scholar 

  14. Hayes PJ, Smyth MR, McMurrough I (1987) Comparison of electrochemical and ultraviolet detection methods in high-performance liquid-chromatography for the determination of Phenolic-compounds commonly found in beers. 2. Analysis of beers. Analyst 112:1205–1207

    Article  CAS  Google Scholar 

  15. Callemien D, Collin S (2007) Involvement of flavanoids in beer color instability during storage. J Agric Food Chem 55:9066–9073

    Article  CAS  Google Scholar 

  16. Callemien D, Collin S (2008) Use of RP-HPLC-ESI(−)-MS/MS to differentiate various proanthocyanidin isomers in lager beer extracts. J Am Soc Brew Chem 66:109–115

    CAS  Google Scholar 

  17. Callemien D, Guyot S, Collin S (2008) Use of thiolysis hyphenated to RP-HPLC-ESI(−)-MS/MS for the analysis of flavanoids of fresh lager beers. Food Chem 110:1012–1018

    Article  CAS  Google Scholar 

  18. Gerhauser C, Alt A, Heiss E, Gamal-Eldeen A, Klimo K, Knauft J, Neumann I, Scherf HR, Frank N, Bartsch H, Becker H (2002) Cancer chemopreventive activity of Xanthohumol, a natural product derived from hop. Mol Cancer Ther 1:959–969

    CAS  Google Scholar 

  19. Kirby W, Wheeler RE (1980) The extraction of beer polyphenols and their assay by H.P.L.C. J Inst Brew 86:15–17

    Article  CAS  Google Scholar 

  20. Madigan D, McMurrough I, Smyth MR (1994) Determination of proanthocyanidins and catechins in beer and barley by high-performance liquid chromatography with dual-electrode electrochemical detection. Analyst 119:863–868

    Article  CAS  Google Scholar 

  21. McMurrough I, Madigan D, Smyth MR (1996) Semipreparative chromatographic procedure for the isolation of dimeric and trimeric proanthocyanidins from barley. J Agric Food Chem 44:1731–1735

    Article  CAS  Google Scholar 

  22. Mulkay P, Touillaux R, Jerumanis J (1981) Proanthocyanidins of barley: separation and identification. J Chromatogr 208:419–423

    Article  CAS  Google Scholar 

  23. McMurrough I, Kelly R, Byrne J, O’Brien M (1992) Effect of the removal of sensitive proteins and proanthocyanidins on the colloidal stability of lager beer. J Am Soc Brew Chem 50:67–76

    CAS  Google Scholar 

  24. Gardner RJ, McGuinness JD (1977) Complex phenols in brewing – a critical survey. Tech Q Master Brew Assoc Am 14:250–261

    CAS  Google Scholar 

  25. Leemans C, Pellaud J, Melotte L, Dupire S (2003) Opportunities for lag phase prediction: a new tool to assess beer colloidal stability. In: Proceedings of the 29th European Brewery Convention (Dublin), pp 88/1–88/11, Fachverlag Hans Carl, Nürnberg, Germany

    Google Scholar 

  26. Asano K, Shinagawa K, Hashimoto N (1982) Characterization of haze-forming proteins of beer and their roles in chill haze formation. J Am Soc Brew Chem 40:147–154

    CAS  Google Scholar 

  27. Eastmond R, Gardner RJ (1974) Effect of various polyphenols on the rate of haze formation in beer. J Inst Brew 80:192–200

    Article  CAS  Google Scholar 

  28. O’Rourke T, Ianniello R, McMurrough I, Springle A (1998) The role of tannoids in the colloidal stabilization of beer. In: Proceedings of the 25th Convention – Institute of Brewing, Asia Pacific Section (Adelaide), pp 143–146, Commercial Printing Company

    Google Scholar 

  29. Kaneda H, Kano Y, Osawa T, Kawakishi S, Kamimura M (1990) Effect of free-radicals on haze formation in beer. J Agric Food Chem 38:1909–1912

    Article  CAS  Google Scholar 

  30. Chapon L (1994) The mechanics of beer stabilisation. Brewers’ Guardian 123:50

    Google Scholar 

  31. Callemien D, Collin S (2010) Structure, organoleptic properties, quantification methods, and stability of phenolic compounds in beer – a review. Food Rev Int 26:1–84

    Article  CAS  Google Scholar 

  32. Leiper KA, Stewart GG, McKeown IP (2003) Beer polypeptides and silica gel - Part I. Polypeptides involved in haze formation. J Inst Brew 109:57–72

    Article  CAS  Google Scholar 

  33. Siebert KJ, Carrasco A, Lynn PY (1996) Formation of protein-polyphenol haze in beverages. J Agric Food Chem 44:1997–2005

    Article  CAS  Google Scholar 

  34. Siebert KJ (1999) Effects of protein-polyphenol interactions on beverage haze. Stabilization and analysis. J Agric Food Chem 47:353–362

    Article  CAS  Google Scholar 

  35. De Clerck J (1969) The use of proteolytic enzymes for the stabilization of beer. Tech Q Master Brew Assoc Am 6:136–140

    Google Scholar 

  36. Siebert KJ, Lynn PY (1997) Mechanisms of adsorbent action in beverage stabilization. J Agric Food Chem 45:4275–4280

    Article  CAS  Google Scholar 

  37. Siebert KJ, Lynn PY (1997) Mechanisms of beer colloidal stabilization. J Am Soc Brew Chem 55:73–78

    CAS  Google Scholar 

  38. Siebert KJ, Lynn PY (1998) Comparison of polyphenol interactions with polyvinylpolypyrrolidone and haze-active protein. J Am Soc Brew Chem 56:24–31

    CAS  Google Scholar 

  39. Leiper KA, Stewart GG, McKeown IP, Nock T, Thompson MJ (2005) Optimising beer stabilisation by the selective removal of tannoids and sensitive proteins. J Inst Brew 111:118–127

    Article  CAS  Google Scholar 

  40. Erdal K, Outtrup H, Ahrenst-Larsen B (1985) Barley and hop proanthocyanidins and the colloidal stability of beer. In: Proceedings of the 20th European Brewery Convention (Helsinki). IRL Press, Oxford, pp 459–466

    Google Scholar 

  41. Counet C (2004) Détermination des structures chimiques des polyphénols du chocolat et étude de leurs principales propriétés fonctionnelles. Thesis, UCL, Belgium

    Google Scholar 

  42. Dadic M, Belleau G (1973) Polyphenols and beer flavors. Proc Am Soc Brew Chem 4:107–114

    Google Scholar 

  43. Siebert KJ (2004) pH and colloidal stability. In: Proceedings of XIth De Clerck Chair. Louvain-la-Neuve, Belgium

    Google Scholar 

  44. Francois N, Guyot-Declerck C, Hug B, Callemien D, Govaerts B, Collin S (2006) Beer astringency assessed by time-intensity and quantitative descriptive analysis: influence of pH and accelerated aging. Food Qual Prefer 17:445–452

    Article  Google Scholar 

  45. Vanderhaegen B, Neven H, Coghe S, Verstrepen KJ, Verachter H, Derdelinckx G (2003) Evolution of chemical and sensory properties during aging of top-fermented beer. J Agric Food Chem 51:6782–6790

    Article  CAS  Google Scholar 

  46. Guyot S, Vercauteren J, Cheynier V (1996) Structural determination of colourless and yellow dimers resulting from (+)-catechin coupling catalysed by grape polyphenoloxidase. Phytochemistry 42:1279–1288

    Article  CAS  Google Scholar 

  47. Young DA, Young E, Roux DG, Brandt EV, Ferreira D (1987) Synthesis of condensed tannins.19. Phenol oxidative coupling of (+)-catechin and (+)-mesquitol - conformation of bis-(+)-catechins. J Chem Soc Perkin Trans 1:2345–2351

    Article  Google Scholar 

  48. Santos-Buelga C, Scalbert A (2000) Proanthocyanidins and tannin-like compounds – nature, occurrence, dietary intake and effects on nutrition and health. J Sci Food Agric 80:1094–1117

    Article  CAS  Google Scholar 

  49. Oszmianski J, Cheynier V, Moutounet M (1996) Iron-catalyzed oxidation of (+)-catechin in model systems. J Agric Food Chem 44:1712–1715

    Article  CAS  Google Scholar 

  50. Prior RL, Gu LW (2005) Occurrence and biological significance of proanthocyanidins in the American diet. Phytochemistry 66:2264–2280

    Article  CAS  Google Scholar 

  51. Schewe T, Kuhn H, Sies H (2002) Flavonoids of cocoa inhibit recombinant human 5-lipoxygenase. J Nutr 132:1825–1829

    CAS  Google Scholar 

  52. Schramm DD, Wang JF, Holt RR, Ensunsa JL, Gonsalves JL, Lazarus SA, Schmitz HH, German JB, Keen CL (2001) Chocolate procyanidins decrease the leukotriene-prostacyclin ratio in humans and human aortic endothelial cells. Am J Clin Nutr 73:36–40

    CAS  Google Scholar 

  53. Sanbongi C, Suzuki N, Sakane T (1997) Polyphenols in chocolate, which have antioxidant activity, modulate immune functions in humans in vitro. Cell Immunol 177:129–136

    Article  CAS  Google Scholar 

  54. Stevens JF, Taylor AW, Nickerson GB, Ivancic M, Henning J, Haunold A, Deinzer ML (2000) Prenylflavonoid variation in humulus lupulus: distribution and taxonomic significance of xanthogalenol and 4’-O-methylxanthohumol. Phytochemistry 53:759–775

    Article  CAS  Google Scholar 

  55. Stevens JF, Taylor AW, Deinzer ML (1999) Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry. J Chromatogr A 832:97–107

    Article  CAS  Google Scholar 

  56. De Keukeleire J, Ooms G, Heyerick A, Roldan-Ruiz I, Van Bockstaele E, De Keukeleire D (2003) Formation and accumulation of alpha-acids, beta-acids, desmethylxanthohumol, and xanthohumol during flowering of hops (Humulus lupulus L.). J. Agric. Food Chem 51:4436–4441

    Article  CAS  Google Scholar 

  57. Walker CJ, Lence CF, Biendl M (2003) Studies on xanthohumol levels in stout/porter beer. Brauwelt 143:1709–1712

    CAS  Google Scholar 

  58. Biendl M, Mitter W, Peters U, Methner FJ (2002) Use of a xanthohumol-rich hop product in beer production. Brauwelt Int I:39–42

    Google Scholar 

  59. Biendl M, Methner FJ, Stettner G, Walker C (2004) Brewing trials with a xanthohumol-enriched hop product. Brauwelt Int III:182–184

    Google Scholar 

  60. Stevens JF, Taylor AW, Clawson JE, Deinzer ML (1999) Fate of xanthohumol and related prenylflavonoids from hops to beer. J Agric Food Chem 47:2421–2428

    Article  CAS  Google Scholar 

  61. Stevens JF, Page JE (2004) Xanthohumol and related prenylflavonoids from hops and beer: to your good health! Phytochemistry 65:1317–1330

    Article  CAS  Google Scholar 

  62. Gerhauser C, Alt A, Klimo K, Knauft J, Frank N, Becker H (2002) Isolation and potential cancer chemopreventive activities of phenolic compounds of beer. Phytochem Rev 1:369–377

    Article  Google Scholar 

  63. De Keukeleire D, Milligan SR, Kalita J, Pocock V, De Cooman L, Heyerick A, Rong H, Roelens F (2001) Prenylated hop flavonoids are key agents in relation to health-beneficial properties of beer. In: Proceedings of 28th European Brewery Convention (Budapest), Fachverlag Hans Carl, Nürnberg, Germany

    Google Scholar 

  64. Gerhauser C (2005) Beer constituents as potential cancer chemopreventive agents. Eur J Cancer 41:1941–1954

    Article  CAS  Google Scholar 

  65. Milligan SR, Kalita JC, Heyerick A, Rong H, De Cooman L, De Keukeleire D (1999) Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer. J Clin Endocrinol Metab 84:2249–2252

    Article  CAS  Google Scholar 

  66. Milligan SR, Kalita JC, Pocock V, Van de Kauter V, Stevens JF, Deinzer ML, Rong H, De Keukeleire D (2000) The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids. J Clin Endocrinol Metab 85:4912–4915

    Article  CAS  Google Scholar 

  67. McMurrough I, Henningan GP, Loughrey ML (1982) Quantitative analysis of hop flavonols using high-performance liquid chromatography. J Agric Food Chem 30:1102–1106

    Article  CAS  Google Scholar 

  68. Vancraenenbroeck R, De Brackeleire C, Willems Y, Devreux A (1983) Quantitative determination of flavonols in beer. Cerevisia (1976–1990) 8:13–19

    Google Scholar 

  69. Prior RL, Lazarus SA, Cao G, Muccitelli H, Hammerstone JF (2001) Identification of procyanidins and anthocyanins in blueberries and cranberries (vaccinium spp.) using high-performance liquid chromatography/mass spectrometry. J Agric Food Chem 49:1270–1276

    Article  CAS  Google Scholar 

  70. Garcia AA, Grande BC, Gandara JS (2004) 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. J Chromatogr A 1054:175–180

    Google Scholar 

  71. Floridi S, Montanari L, Marconi O, Fantozzi P (2003) Determination of free phenolic acids in wort and beer by coulometric array detection. J Agric Food Chem 51:1548–1554

    Article  CAS  Google Scholar 

  72. McMurrough I, Roche GP, Cleary KC (1984) Phenolics acids in beers and worts. J Inst Brew 90:181–187

    Article  CAS  Google Scholar 

  73. Montanari L, Perretti G, Natella F, Guidi A, Fantozzi P (1999) Organic and phenolic acids in beer. LWT - Food Sci Technol 32:535–539

    Article  CAS  Google Scholar 

  74. Nardini M, Ghiselli A (2004) Determination of free and bound phenolic acids in beer. Food Chem 84:137–143

    Article  CAS  Google Scholar 

  75. Stewart D, Robertson GW, Morrison IH (1994) Phenolic-acids dimers in the cell-walls of barley. Biol Mass Spectrom 23:71–74

    Article  CAS  Google Scholar 

  76. Kenyhercz TM, Kissinger PT (1977) A new approach to the phenolic components in beer. Application to the determination of sinapic, ferulic, and p-coumaric acids. J Agric Food Chem 25:959–961

    Article  CAS  Google Scholar 

  77. McMurrough I, Madigan D, Donnelly D, Hurley J, Doyle AM, Hennigan G, McNulty N, Smyth MR (1996) Control of ferulic acid and 4-vinyl guaiacol in brewing. J Inst Brew 102:327–332

    Article  CAS  Google Scholar 

  78. Vanbeneden N, Delvaux F, Delvaux FR (2006) Determination of hydroxycinnamic acids and volatile phenols in wort and beer by isocratic high-performance liquid chromatography using electrochemical detection. J Chromatogr A 1136:237–242

    Article  CAS  Google Scholar 

  79. Tressl R, Renner R (1975) Gas chromatographic-mass spectrometric study of some lactones in beer. Monatsschrift fuer Brauerei 28:195–197

    CAS  Google Scholar 

  80. Vanbeneden N, Delvaux F, Delvaux FR (2006) Release of phenolic flavour precursors during mashing. In: Proceedings of XIIth De Clerck Chair, Leuven

    Google Scholar 

  81. Coghe S, Benoot K, Delvaux F, Vanderhaegen B, Delvaux FR (2004) Ferulic acid release and 4-vinylguaiacol formation during brewing and fermentation: indications for feruloyl esterase activity in Saccharomyces cerevisiae. J Agric Food Chem 52:602–608

    Article  CAS  Google Scholar 

  82. Meilgaard MC (1975) Flavor chemistry of beer. II: Flavor and threshold of 239 aroma volatiles. Tech Q Master Brew Assoc Am 12:5–13

    Google Scholar 

  83. Fiddler W, Parker WE, Wasserman AE, Doerr RC (1967) Thermal decomposition of ferulic acid. J Agric Food Chem 15:757–761

    Article  CAS  Google Scholar 

  84. Tressl R, Kossa T, Renner R (1975) Gas-chromatographic-mass spectrometric studies of volatile substances of hops, wort, and beer and their genesis. II. Formation of phenols and oxygen-containing heterocyclic compounds in beer. In: Proceedings of the 15th European Brewery Convention (Nice). Elsevier, Scientific Pub, pp 737–756

    Google Scholar 

  85. Clausen M, Lamb CJ, Megnet R, Doerner PW (1994) PAD1 encodes phenylacrylic acid decarboxylase which confers resistance to cinnamic acid in Saccharomyces cerevisiae. Gene 142:107–112

    Article  CAS  Google Scholar 

  86. Meaden PG, Taylor NR (1991) Cloning of a yeast gene which causes phenolic off-flavors in beer. J Inst Brew 97:353–357

    Article  CAS  Google Scholar 

  87. Chatonnet P, Dubourdieu D, Boidron JN, Pons M (1992) The origin of ethylphenols in wines. J Sci Food Agric 60:165–178

    Article  CAS  Google Scholar 

  88. Lindsay RF, Priest FG (1975) Decarboxylation of substituted cinnamic acids by enterobacteria: the influence on beer flavour. J Appl Bacteriol 39:181–187

    Article  CAS  Google Scholar 

  89. Steinhaus M, Schieberle P (2000) Comparison of the most odor-active compounds in fresh and dried hop cones (Humulus lupulus L. variety spalter select) based on GC-olfactometry and odor dilution techniques. J Agric Food Chem 48:1776–1783

    Article  CAS  Google Scholar 

  90. Wackerbauer K, Kramer P, Siepert J (1982) Phenolic aromatic substances in beer. Phenolic carboxylic acid and phenols in the raw material and beer preparation. Brauwelt 122:618–20, 622, 624, 626.

    Google Scholar 

  91. Wackerbauer K, Kossa T, Tressl R (1978) Phenol formation by yeasts. Monatsschrift fuer Brauerei 31:52–55

    CAS  Google Scholar 

  92. Kieninger H, Narziss L, Miedaner H, Hecht S (1984) Changes of quality-determining compounds in the preparation of Bavarian wheat beers. Monatsschrift fuer Brauwissenschaft 37(9–18):55

    Google Scholar 

  93. Madigan D, McMurrough I (1994) Rapid determination of 4-vinyl guaiacol and ferulic acid in beers and worts by high-performance liquid chromatography. J Am Soc Brew Chem 52:152–155

    CAS  Google Scholar 

  94. Schieberle P (1991) Primary odorants of pale lager beer – differences to other beers and changes during storage. Zeitschrift fur Lebensmittel-Untersuchung und-Forschung 193:558–565

    Article  CAS  Google Scholar 

  95. Tressl R, Renner R, Apetz M (1976) Volatile phenolic components in beer, smoked beer and sherry. Zeitschrift fuer Lebensmittel-Untersuchung und -Forschung 162:115–122

    Article  CAS  Google Scholar 

  96. Villarreal R, Sierra JA, Cardenas L (1986) A rapid and sensitive method for the determination of 4-vinyl guaiacol in beer by electron-capture gas–liquid chromatography. J Am Soc Brew Chem 44:114–117

    CAS  Google Scholar 

  97. Wackerbauer K, Kramer P (1982) Bavarian wheat beer – an alternative. Production and composition. Brauwelt 122:758–60–762

    CAS  Google Scholar 

  98. Narziss L, Miedaner H, Nitzsche F (1990) The formation of 4-vinylguaiacol during the manufacture of Bavarian wheat beers (Weizenbier). Monatsschrift fuer Brauwissenschaft 43:96–100

    CAS  Google Scholar 

  99. Tressl R, Kossa T, Renner R (1974) Formation of aroma compounds in malt, wort, and beer. Monatsschrift fuer Brauerei 27:98–102

    CAS  Google Scholar 

  100. Schieberle P, Komarek D (2003) Changes in key aroma compounds during natural beer aging. In: Freshness and shelf life of foods, ACS symposium series. ACS, Washington DC, pp 70–79

    Google Scholar 

  101. Moir M (1992) The 1990 Laurence Bishop silver medal lecture – The desideratum for flavor control. J Inst Brew 98:215–220

    Article  CAS  Google Scholar 

  102. Callemien D, Dasnoy S, Collin S (2006) Identification of a stale-beer-like odorant in extracts of naturally aged beer. J Agric Food Chem 54:1409–1413

    Article  CAS  Google Scholar 

  103. Gijs L, Chevance F, Jerkovic V, Collin S (2002) How low pH can intensify beta-damascenone and dimethyl trisulfide production through beer aging. J Agric Food Chem 50:5612–5616

    Article  CAS  Google Scholar 

  104. Asano K, Ohtsu K, Shinagawa K, Hashimoto N (1984) 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. Agric Biol Chem 48:1139–1146

    Article  CAS  Google Scholar 

  105. Es-Safi NE, Le Guerneve C, Fulcrand H, Cheynier V, Moutounet M (1999) New polyphenolic compounds with xanthylium skeletons formed through reaction between (+)-catechin and glyoxylic acid. J Agric Food Chem 47:5211–5217

    Article  CAS  Google Scholar 

  106. Es-Safi NE, Fulcrand H, Cheynier V, Moutounet M (1999) Studies on the acetaldehyde-induced condensation of (−)-epicatechin and malvidin 3-O-glucoside in a model solution system. J Agric Food Chem 47:2096–2102

    Article  CAS  Google Scholar 

  107. Es-Safi NE, Cheynier V, Moutounet M (2000) Study of the reactions between (+)-catechin and furfural derivatives in the presence or absence of anthocyanins and their implication in food color change. J Agric Food Chem 48:5946–5954

    Article  CAS  Google Scholar 

  108. Es-Safi NE, Le Guerneve C, Fulcrand H, Cheynier V, Moutounet M (2000) Xanthylium salts formation involved in wine colour changes. Int J Food Sci Technol 35:63–74

    Article  CAS  Google Scholar 

  109. Callemien D, Counet C, Cawet Q, Collin S (2003) Hop as a determinant nutrition key for health? In: Proceedings of the 29th European Brewery Convention (Dublin). Fachverlag Hans Carl, Nürnberg, p 137

    Google Scholar 

  110. Jerkovic V, Collin S (2007) Occurrence of resveratrol and piceid in American and European hop cones. J Agric Food Chem 55:8754–8758

    Article  CAS  Google Scholar 

  111. Jerkovic V, Collin S (2008) Fate of resveratrol and piceid through different hop processings and storage times. J Agric Food Chem 56:584–590

    Article  CAS  Google Scholar 

  112. Jerkovic V, Callemien D, Collin S (2005) Determination of stilbenes in hop pellets from different cultivars. J Agric Food Chem 53:4202–4206

    Article  CAS  Google Scholar 

  113. Jerkovic V, Collin S (2007) Resveratrol analogues in hop, malt, and adjuncts. In: Proceedings of the 31st European Brewery Convention, 76:1–6, Fachverlag Hans Carl, Nürnberg, Germany

    Google Scholar 

  114. Jerkovic V, Nguyen F, Timmermans A, Collin S (2008) Comparison of procedures for resveratrol analysis in beer. Assessment of stilbene stability through wort fermentation and beer aging. J Inst Brew 114:143–149

    Article  CAS  Google Scholar 

  115. Delmas D, Jannin B, Latruffe N (2005) Resveratrol: preventing properties against vascular alterations and ageing. Mol Nutr Food Res 49:377–395

    Article  CAS  Google Scholar 

  116. Fauconneau B, WaffoTeguo P, Huguet F, Barrier L, Decendit A, Merillon JM (1997) Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests. Life Sci 61:2103–2110

    Article  CAS  Google Scholar 

  117. Orallo F (2006) Comparative studies of the antioxidant effects of cis- and trans-resveratrol. Curr Med Chem 13:87–98

    Article  CAS  Google Scholar 

  118. Hollman PCH (1997) Bioavailability of flavonoids. Eur J Clin Nutr 51:S66–S69

    Google Scholar 

  119. Aggarwal BB, Bhardwaj A, Aggarwal RS, Seeram NP, Shishodia S, Takada Y (2004) Role of resveratrol in prevention and therapy of cancer: preclinical and clinical studies. Anticancer Research 24(5A):2783–2840

    CAS  Google Scholar 

  120. Baur JA, Sinclair DA (2006) Therapeutic potential of resveratrol: the in vivo evidence. Nat Rev Drug Discov 5:493–506

    Article  CAS  Google Scholar 

  121. Jang DS, Kang BS, Ryu SY, Chang IM, Min KR, Kim Y (1999) Inhibitory effects of resveratrol analogs on unopsonized zymosan-induced oxygen radical production. Biochem Pharmacol 57:705–712

    Article  CAS  Google Scholar 

  122. De la Lastra CA, Villegas I (2005) Resveratrol as an anti-inflammatory and anti-aging agent: mechanisms and clinical implications. Mol Nutr Food Res 49:405–430

    Article  CAS  Google Scholar 

  123. Basly JP, Marre-Fournier F, Le Bail JC, Habrioux G, Chulia AJ (2000) Estrogenic/antiestrogenic and scavenging properties of (E)- and (Z)-resveratrol. Life Sci 66:769–777

    Article  CAS  Google Scholar 

  124. McMurrough I, Baert T (1994) Identification of proanthocyanidins in beer and their direct measurement with a dual electrode electrochemical detector. J Inst Brew 100:409–416

    Article  CAS  Google Scholar 

  125. Delcour JA, Tuytens GM (1984) Structure elucidation of three dimeric proanthocyanidins isolated from a commercial Belgian pilsner beer. J Inst Brew 90:153–161

    Article  CAS  Google Scholar 

  126. Eastmond R (1974) Separation and identification of a dimer of catechin occurring in beer. J Inst Brew 80:188–192

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Unité de Brasserie et des Industries Alimentaires, Earth and Life Institute, Université catholique de Louvain, Croix du Sud, 2/box L7.05.07, 1348, Louvain-la-Neuve, Belgium

    Dr. Sonia Collin, Dr. Vesna Jerkovic, M. Bröhan & D. Callemien

Authors
  1. Dr. Sonia Collin
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  2. Dr. Vesna Jerkovic
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  3. M. Bröhan
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  4. D. Callemien
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Correspondence to Sonia Collin .

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Editors and Affiliations

  1. Botany Department, M.L. Sukhadia University, Durga Nursery Road, Udaipur, 313001, Rajasthan, India

    Kishan Gopal Ramawat

  2. Institute of Vine and Wine Sciences, Biological-Active Plant Substances Study, University of Bordeaux, 210 Chemin de Leysotte CS 50008, Villenave d'Ornon, 33882, France

    Jean-Michel Mérillon

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Collin, S., Jerkovic, V., Bröhan, M., Callemien, D. (2013). Polyphenols and Beer Quality. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_78

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