Content of individual phenolic acids in worts and beers and their possible contribution to the antiradical activity of beer

Journal of the Institute of Brewing

Volumn 115, Issue 3, 2009, Pages 243-252

  Szwajgier, Dominik ^a  

^a UNIVERSITY OF LIFE SCIENCES IN LUBLIN   (Poland)

Author keywords

Antioxidant; Beer; Ferulic acid; Phenolic acids; Synergy; Wort

Indexed keywords

HORDEUM;

EID: 70450162460     PISSN: 00469750     EISSN: None     Source Type: Journal    
DOI: 10.1002/j.2050-0416.2009.tb00376.x     Document Type: Article

References (62)

1. Andreason, M. F., Kroon, P., Williamson, G. and Garcia-Conesa, M. T., Esterase activity able to hydrolyze dietary antioxidant hydroxycinnamates is distributed along the intestine of mammals. J. Agric. Food Chem., 2001, 49, 5679-5684.
2. Atwood, C. S., Perry G., Zeng, H., Kato, Y., Jones, W. D., Ling, K. Q., Huang, X., Moir, R. D., Wang, D., Sayre L. M., Smith, M. A., Chen, S. G. and Bush, A. I., Copper mediates dityrosine cross-linking of Alzheimer's amyloid-β. Biochemistry, 2004, 43, 560-568.
3. Auld, S. D., Kornecook, T. J., Bastianetto, S. and Quirion, R., Alzheimer's disease and the basal forebrain cholinergic system: relations to β-amyloid peptides, cognition, and treatment strategies. Prog. Neurobiol., 2002, 68, 209 245.
4. Bakalbassis, E. G., Chatzopoulou A., Melissas V. S., Tsimidou M., Tsolaki M. and Vafiadis A., Ab initio and density functional theory studies for the explanation of the antioxidant activity of certain phenolic acids. Lipids, 2001, 36, 181-191.
5. Bartolome, B., Pena-Neira, A. and Gomes-Cordoves, C., Phenolics and related substances in alcohol-free beers. Eur. Food Res. Technol. 2000, 210, 419-423.
6. Becker, E. M., Ntouma, G. and Skibsted, L. H., Synergism and antagonism between quercetin and other chain-breaking antioxidants in lipid systems of increasing structural organization. Food Chem., 2007, 103(4), 1288-1296.
7. Behl, C., Vitamin E protects neurons against oxidative cell death in vitro more efficiently than 17-β estradiol and induces the activity of the transcription factor NF-κB. J. Neural Transm., 2000, 107, 393-407.
8. Bourne, L., Paganga, G., Baxter, D., Hughes, P. and Rice-Evans, C., Absorption of ferulic acid from low-alcohol beer. Free Radic. Res., 2000, 32 (3), 273-280.
9. Bourne, L. C. and Rice-Evans, C., Bioavailability of ferulic acid. Biochem. Biophys. Res. Commun., 1998, 253, 222-227.
10. Brand-Williams, W., Cuvelier, M. E. and Berset, C., Use of free radical method to evaluate antioxidant activity. Lebensm. Wiss. u. Technol., 1995, 28, 25-30.
11. Chen, J. H. and Ho, C.-T., Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. J. Agric. Food Chem., 1997, 45, 2374-2378.
12. Chepda, T., Cadau, M., Lassabliere, F., Reynaud, E., Perier, C., Frey, J. and Chamson, A., Synergy between ascorbate and α-tocopherol on fibroblasts in culture. Life Sci., 2001, 69(14), 1587-1596.
13. Choudhury, R., Srai, K., Debnam, E. and Rice-Evans, C. A., Urinary excretion of hydroxycinnamates and flavonoids after oral and intravenous administration. Free Radical. Biol. Med., 1999, 27, 278-286.
14. Clifford, M. N., Copeland, E. L., Bloxsidge, J. P. and Mitchell, L. A., Hippuric acid as a major excretion product associated with black tea consumption. Xenobiotica, 2000, 50, 317-326.
15. Couteau, D., McCartney, A. L., Gibson, G. R., Williamson, G. and Faulds, C. B., Isolation and characterization of human colonic bacteria able to hydrolyze chlorogenic acid. J. Appl. Microbiol., 2001, 90(6), 873-881.
16. Cuvelier, M. E., Richard, H. and Berset, C., Comparison of the antioxidative activity of some acid-phenols: structure-activity relationship. Biosci. Biotech. Biochem., 1992, 56, 324-325.
17. Dai, F., Chen, W-F. and Zhou, B., Antioxidant synergism of green tea polyphenols with α-tocopherol and L-ascorbic acid in SDS micelles. Biochimie, 2008, 90(10), 1499-1505.
18. Deprez, S., Brezillon, C., Raport, S., Philippe, C., Mila, I., Lapierre, C. and Scalbert, A., Polymeric proanthocyanidins are catabolized by human colonic microflora into low-molecular-weight phenolic acids. J. Nutr., 2000, 130(11), 2733-2738.
19. Floridi, S., Montanari, L., Marconi, O. and Fantozzi, P., Determination of free phenolic acids in wort and beer by coulometric array detection. J. Agric. Food Chem., 2003, 51, 1548-1554.
20. Gerhäuser, C., Beer constituents as potential cancer chemopreventive agents. Eur. J. Cancer, 2005, 41(13), 1941-1954.
21. Ghiselli, A., Natella, F., Guidi, A., Montanari, L., Fantozzi, P. and Scaccini, C., Beer increases plasma antioxidant capacity in humans. J. Nutr. Biochem., 2000, 11, 76-80.
22. Giacobini, E., Cholinesterase inhibitors: new roles and therapeutic alternatives. Pharmacol. Res., 2004, 50, 433-440.
23. Gorinstein, S., Caspi, A., Zemser, M. and Trakhtenberg, S., Comparative contents of some phenolics in beer, red and white wines. Nutr. Res., 2000, 20, 131-139.
24. Goupy, P., Hugues, M., Boivin, P. and Amiot, M. J., Antioxidant composition and activity of barley (Hordeum vulgare) and malt extracts and of isolated phenolic compounds. J. Sci. Food Agric., 1999, 79, 1625-1634.
25. Graversen, H. B., Becker, E. M., Miquel, E., Skibsted, L. H. and Andersen, M. L., Antioxidant synergism between fruit juice and α-tocopherol. A comparison between high phenolic black chokeberry (Aronia melanocarpa) and high ascorbic blackcurrant (Ribes nigrum). Eur. Food Res. Technol., 2008, 226(4), 737-743.
26. Gross, M., Pfeiffer, M., Martini, M., Campbell, D., Slavin, J. and Potter, J., The quantitation of metabolites of quercetin flavonols in human urine. Cancer Epidemiol. Biomarkers Prev., 1996, 5, 711-720.
27. Gustavson, A. R., Cholinesterase inhibitors in non-Alzheimer dementias. J. Am. Med. Dir. Assoc., 2003, S165-S169. Supplement 120.
28. Harvey, A., The pharmacology of galanthamine and its analogues. Pharmac. Ther., 1995, 68(1), 113-128.
29. Hollman, P. C. and Katan, M. B., Bioavailability and health effects of dietary flavonols in man. Arch. Toxicol., 1998, 20, 237-248.
30. Inns, E. L., Buggey, L. A., Booer, C., Nursten, H. E. and Ames, J., Effect of heat treatment on the antioxidant activity, color, and free phenolic acid profile of malt. J. Agric. Food Chem., 2007, 55, 6539-6546.
31. Irwandi, J., Che Man, Y. B., Kitts, D. D., Bakar, J. and Jinap, S., Synergies between plant antioxidant blends in preventing peroxidation reactions in model and food oil systems. J. Am. Oil Chem. Soc., 2000, 77(9), 945-951.
32. Kim, K.-H., Tsao, R., Yang, R. and Cui, S. W., Phenolic acid profiles and antioxidant activities of wheat bran extracts and the effect of hydrolysis conditions. Food Chem., 2006, 95, 466-473.
33. Liu, Q. and Yao, H., Antioxidant activities of barley seeds extracts. Food Chem., 2007, 12, 732-737.
34. Maillard, M.-N. and Berset, C., Evolution of antioxidant activity during kilning: role of insoluble bound phenolic acids of barley and malt. J. Agric. Food Chem., 1995, 43, 1789-1793.
35. Maillard, M. N., Soum, M. H., Boivin, P. and Berset, C., Antioxidant activity of barley and malt: relationship with phenolic content. Lebensm.-Wiss. u Technol., 1996, 29(3), 238-244.
36. Meyer, A. S., Donovan, J. L., Pearson, D. A., Waterhouse, A. L. and Frankel, E., Fruit hydroxycinnamic acids inhibit human low-density lipoprotein oxidation in vitro. J. Agric. Food Chem., 1998, 46, 1783-1787.
37. Miller, N. J., Rice-Evans, C., Davies, M. J., Gopinathan, V. and Milner, A., A novel method for measuring antioxidant capacity and its application to monitoring the antioxidant status in premature neonates. Clin. Sci., 1993, 84, 407-412.
38. Montanari, L., Perretti, G., Natella, F., Guidi, A. and Fantozzi, P., Organic and phenolic acids in beer. Lebensm.-Wiss. u Technol., 1999, 32, 535-539.
39. Moon, J. H. and Terao, J., Antioxidant activity of caffeic acid and dihydrocaffeic acid in lard and human low-density lipoprotein. J. Agric. Food Chem., 1998, 46, 5062-5065.
40. Nardini, M., Cirillo, E., Natella, F., Mencarelli, D., Comisso, A. and Scaccini, C., Detection of bound phenolic acids: prevention by ascorbic acid and ethylenediaminetetraacetic acid of degradation of phenolic acids during alkaline hydrolysis. Food Chem., 2002, 79, 190-124.
41. Nardini, M., Cirillo, E., Natella, F. and Scaccini, C., Absorption of phenolic acids in humans after coffee consumption. J. Agric. Food Chem., 2002, 50, 5735-5741.
42. Nardini, M., D'Aquino, M., Tomassi, G., Gentili, V., Di Felice, M. and Scaccini, C., Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives. Free Radic. Biol. Med., 1995, 19, 541-552.
43. Nardini, M. and Ghiselli, A., determination of free and bound phenolic acids in beer. Food Chem., 2004, 84, 137-143.
44. Nardini, M., Natella, F., Gentili, V., Di Felice, M. and Scaccini, C., Effect of caffeic acid dietary supplementation on the antioxidant defense system in rat: an in vivo study. Arch. Biochem. Biophys., 1997, 342(1), 157-160.
45. Nardini, M., Natella, F., Scaccini, C. and Ghiselli, A., Phenolic acids from beer are absorbed and extensively metabolized in humans. J. Nutr. Biochem., 2006, 17, 14-22.
46. Natella, F., Nardini, M., DiFelice, M. and Scaccini, C., Benzoic and cinnamic acid derivatives as antioxidants: structure-activity relation. J. Agric. Food Chem., 1999, 47, 1453-1459.
47. Olthof, M. R., Hollman, P. C., Bujisman, M. N., Van Amelsvoort, J. M. and Katan, M. B., Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolised in humans. J. Nutr., 2003, 133(6), 1806-1814.
48. Pascoe, H. M. and Ames, J. M., Critical stages of the brewing process for changes in antioxidant activity and levels of phenolic compounds in ale. J. Am. Soc. Brew. Chem., 2003, 61, 203-209.
49. Peyrat-Maillard, M. N., Cuvelier, M. E. and Berset, C., Antioxidant activity of phenolic compounds in 2,2′-azobis (2-amidino-propane) dihydrochloride (AAPH)-induced oxidation: Synergistic and antagonistic effects. J. Am. Oil Chem. Soc., 2003, 80(10), 1007-1012.
50. Plumb, G. W., Garcia-Conesa, M. T., Kroon, P. A., Rhodes, M., Ridley, S. and Williamson, G., Metabolism of chlorogenic acid by human plasma, liver, intestine and gut microflora. J. Sci. Food Agric., 1999, 79, 390-392.
51. Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M. and Rice-Evans, C., Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med., 1999, 26, 1231-1237.
52. Rechner, A. R., Kuhnle, G., Bremner, P. and Hubbard, G. P., The metabolic fate of dietary polyphenols in humans. Free Radic. Biol. Med., 2002, 33(2), 220-235.
53. Rechner, A. R., Pannala, A. S. and Rice-Evans, C. A., Caffeic acid derivatives in artichoke extract are metabolized to phenolic acids in vivo. Free Radic. Res., 2001, 35, 195-202.
54. Rechner, A. R., Spencer, J. P. E., Kuhnle, G., Hahn, U. and Rice-Evans, C. A., Novel biomarkers of the bioavailability and metabolism of caffeic acid derivatives in humans. Free Radic. Biol. Med., 2001, 30, 1213-1222.
55. Rondini, L., Peyrat-Maillard, M. N., Marsset-Baglieri, A. and Berset, C., Sulfated ferulic acid is the main in vivo metabolite found after short-term ingestion of free ferulic acid in rats. J. Agric. Food Chem., 2002, 50, 3037-3041.
56. Rossetto, M., Vanzani, P., Mattivi, F., Lunelli, M., Scarpa, M. and Rigo, A., Synergistic antioxidant effect of catechin and malvidin-3-glucoside on free radical-initiated peroxidation of linoleic acid in micelles. Arch. Biochem. Biophys., 2002, 408(2), 239-245.
57. Rottkamp, C. A., Raina, A. K., Zhu, X., Gaier, E., Bush, A., Atwood, C. S., Chevion, M., Perry, G. and Smith, M. A., Redox-active iron mediates amyloid-β toxicity. Free Radic. Biol. Med., 2001, 30(4), 447-450.
58. Scalbert, A. and Williamson, G., Dietary intake and bioavailability of polyphenols. J. Nutr., 2000, 130, 2073S-2085S.
59. Shinall, H., Song, E. S. and Hersh, L. B., Susceptibility of amyloid β peptide degrading enzymes to oxidative damage: A potential Alzheimer's disease spiral. Biochemistry, 2005, 44, 15345-15350.
60. Tanaka, T., Kojima, T., Kawamori, T., Wang, A., Suzui, M., Okamoto, K. and Mori, H., Inhibition of 4-nitroquinoline-1-oxide-induced rat tongue carcinogenesis by the naturally occurring plant phenolics caffeic, ellagic, chlorogenic and ferulic acids. In: Chemopreventions by Plant Phenolics. Oxford University Press: Oxford, 1993, pp. 1321-1325.
61. Vanbeneden, N., Delvaux, F. and Delvaux, F. R., Determination of hydroxycinnamic acids and volatile phenols in wort and beer by isocratic high-performance liquid chromatography using electrochemical detection. J. Chromatog. A, 2006, 1136, 237-242.
62. Wang, W. and Goodman, M. T., Antioxidant property of dietary phenolic agents in a human LDL-oxidation ex vivo model: interaction of protein binding activity. Nutr. Res., 1999, 19(2), 191-202.