In vitro biological properties of flavonoid conjugates found in vivo

Free Radical Research

Volumn 39, Issue 5, 2005, Pages 457-469

  Williamson, Gary ^a   Barron, D ^a   Shimoi, K ^b   Terao, J ^c  

^a NESTLÉ RESEARCH CENTER   (Switzerland)

^b UNIVERSITY OF SHIZUOKA   (Japan)

^c UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Biological property; Conjugates; Genistein; Glucuronide; Quercetin; Sulfate

Indexed keywords

4' O METHYLEPICATECHIN; BAICALIN; CATECHIN; CHRYSIN 7 O BETA DEXTRO GLUCURONIDE; CHRYSIN 7 O SULFATE; DAIDZEIN; DAIDZEIN 4' O BETA DEXTRO GLUCURONIDE; DAIDZEIN 4',7 DI O BETA DEXTRO DIGLUCURONIDE; DAIDZEIN 7 O BETA DEXTRO GLUCURONIDE; DAIDZEIN 7 O SULFATE; DRUG METABOLITE; EPICATECHIN; EPICATECHIN 3' O BETA DEXTRO GLUCURONIDE; FLAVONOID; GLUCOSIDE; HESPERETIN; ISOFLAVONE; ISORHAMNETIN 3 O BETA DEXTRO GLUCURONIDE; KAEMPFEROL 3 O BETA DEXTRO GLUCURONIDE; MORIN; MYRICETIN; MYRICETIN 3 O BETA DEXTRO GLUCURONIDE; QUERCETIN; QUERCETIN 3 O BETA DEXTRO GLUCURONIDE; QUERCETIN 3' O SULFATE; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; APOPTOSIS; CELL PROLIFERATION; DRUG ABSORPTION; DRUG ACTIVITY; DRUG BIOAVAILABILITY; DRUG CONJUGATION; DRUG ISOLATION; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SYNTHESIS; HUMAN; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PARTITION COEFFICIENT; REVIEW;

BIOLOGICAL AVAILABILITY; FLAVONOIDS; HUMANS;

EID: 19044388959     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.1080/10715760500053610     Document Type: Review

References (105)

1. Manach C, Donovan JL. Pharmacokinetics and metabolism of dietary flavonoids in humans. Free Radic Res 2004;38:771-785.
2. Williamson G, Manach C. Bioavailability and bioefficacy studies of polyphenols in humans. II. Review of 93 intervention studies. Am J Clin Nutr 2005;80s.
3. Frances B, Gout R, Monsarrat B, Cros J, Zajac JM. Further evidence that morphine-6 beta-glucuronide is a more potent opioid agonist than morphine. J Pharmacol Exp Ther 1992;262:25-31.
4. Frances B, Gout R, Campistron G, Panconi E, Cros J. Morphine-6-glucuronide is more mu-selective and potent in analgesic tests than morphine. Prog Clin Biol Res 1990;328:477-480.
5. Skopp G, Potsch L, Ganssmann B, Aderjan R, Mattern R. A preliminary study on the distribution of morphine and its glucuronides in the subcompartments of blood. J Anal Toxicol 1998;22:261-264.
6. Sesink AL, O'Leary KA, Hollman PC. Quercetin glucuronides but not glucosides are present in human plasma after consumption of quercetin-3-glucoside or quercetin-4′-glucoside. J Nutr 2001;131:1938-1941.
7. Day AJ, Mellon FA, Barron D, Sarrrazin G, Morgan MRA, Williamson G. Human Metabolism of dietary flavonoids: Identification of plasma metabolites of quercetin. Free Radic Res 2001;212:941-952.
8. Ullmann U, Haller J, Decourt JP, Girault N, Girault J, Richard-Caudron AS, Pineau B, Weber P. A single ascending dose study of epigallocatechin gallate in healthy volunteers. J Int Med Res 2003;31:88-101.
9. Shimoi K, Okada H, Furugori M, Goda T, Takase S, Suzuki M, Hara Y, Yamamoto H, Kinae N. Intestinal absorption of luteolin and luteolin 7-O-β-glucoside in rats and humans. FEBS lett 1998; 438:220-224.
10. Talavera S, Felgines C, Texier O, Besson C, Manach C, Lamaison JL, Remesy C. Anthocyanins are efficiently absorbed from the small intestine in rats. J Nutr 2004;134:2275-2279.
11. Price KR, Colquhoun IJ, Barnes KA, Rhodes MJC. Composition and content of flavonol glycosides in green beans and their fate during processing. J Agric Food Chem 1998;46:4898-4903.
12. Day AJ, Bao Y, Morgan MRA, Williamson G. Conjugation position of quercetin glucuronides and effect on biological activity. Free Rad Biol Med 2000;29:1234-1243.
13. Kuo HM, Ho HJ, Chao PDL, Chung JG. Quercetin glucuronides inhibited 2-aminofluorene acetylation in human acute myeloid HL-60 leukemia cells. Phytomedicine 2002;9:625-631.
14. Rimbach G, Weinberg PD, Pascual-Teresa S, Alonso MG, Ewins BA, Turner R, Minihane AM, Botting N, Fairley B, Matsugo S, Uchida Y, Cassidy A. Sulfation of genistein alters its antioxidant properties and its effect on platelet aggregation and monocyte and endothelial function. Biochim Biophys Acta 2004;1670:229-237.
15. Zhang Y, Song TT, Cunnick JE, Murphy PA, Hendrich S. Daidzein and genistein glucuronides in vitro are weakly estrogenic and activate human natural killer cells at nutritionally relevant concentrations. J Nutr 1999;129:399-405.
16. Kinjo J, Tsuchihashi R, Morito K, Hirose T, Aomori T, Nagao T, Okabe H, Nohara T, Masamune Y. Interactions of phytoestrogens with estrogen receptors alpha and beta (III). Estrogenic activities of soy isoflavone aglycones and their metabolites isolated from human urine. Biol Pharm Bull 2004;27:185-188.
17. Abd El Mohsen MM, Kuhnle G, Rechner AR, Schroeter H, Rose S, Jenner P, Rice-Evans CA. Uptake and metabolism of epicatechin and its access to the brain after oral ingestion. Free Rad Biol Med 2002;33:1693-1702.
18. Spencer JP, Schroeter H, Crossthwaithe AJ, Kuhnle G, Williams RJ, Rice-Evans C. Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts. Free Radic Biol Med 2001;31:1139-1146.
19. Lu H, Meng XF, Li C, Sang SM, Patten C, Sheng SQ, Hong JG, Bai NS, Winnik B, Ho CT, Yang CS. Glucuronides of tea catechins: Enzymology of biosynthesis and biological activities. Drug Metab Dispos 2003;31:452-461.
20. Koga T, Meydani M. Effect of plasma metabolites of (+)-catechin and quercetin on monocyte adhesion to human aortic endothelial cells. Am J Clin Nutr 2001;73:941-948.
21. Proteggente AR, Basu-Modak S, Kuhnle G, Gordon MJ, Youdim K, Tyrrell R, Rice-Evans CA. Hesperetin glucuronide, a photoprotective agent arising from flavonoid metabolism in human skin fibroblasts. Photochem Photobiol 2003;78:256-261.
22. Youdim KA, Dobbie MS, Kuhnle G, Proteggente AR, Abbott NJ, Rice-Evans C. Interaction between flavonoids and the blood-brain barrier: In vitro studies. J Neurochem 2003;85:180-192.
23. Chan FL, Choi HL, Chen ZY, Chan PS, Huang Y. Induction of apoptosis in prostate cancer cell lines by a flavonoid, baicalin. Cancer Lett 2000;160:219-228.
24. Ueda S, Nakamura H, Masutani H, Sasada T, Takabayashi A, Yamaoka Y, Yodoi J. Baicalin induces apoptosis via mitochondrial pathway as prooxidant. Mol Immunol 2002;38:781-791.
25. Liu ZL, Tanaka S, Horigome H, Hirano T, Oka K. Induction of apoptosis in human lung fibroblasts and peripheral lymphocytes in vitro by Shosaiko-to derived phenolic metabolites. Biol Pharm Bull 2002;25:37-41.
26. Fang SH, Hou YC, Chang WC, Hsiu SL, Chao PDL, Chiang BL. Morin sulfates/glucuronides exert anti-inflammatory activity on activated macrophages and decreased the incidence of septic shock. Life Sci 2003;74:743-756.
27. Hiermann A, Schramm HW, Laufer S. Anti-inflammatory activity of myricetin 3-O-β-D-glucuronide and related compounds. Inflamm Res 1998;47:421-427.
28. Plumb GW, Pascual-Teresa S, Santos-Buelga C, Cheynier V, Williamson G. Antioxidant properties of catechins and proanthocyanidins: Effect of polymerisation, galloylation and glycosylation. Free Radic Res 1998;29:351-358.
29. Day AJ, Williamson G. Biomarkers for exposure to dietary flavonoids: A review of the current evidence for identification of quercetin glycosides in plasma. Br J Nutr 2001;86:S105-S110.
30. Setchell KD, Brown NM, Desai P, Zimmer-Nechemias L, Wolfe BE, Brashear WT, Kirschner AS, Cassidy A, Heubi JE. Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements. J Nutr 2001;131:1362S-1375S.
31. Donovan JL, Bell JR, Kasim-Karakas S, German JB, Walzem RL, Hansen RJ, Waterhouse AL. Catechin is present as metabolites in human plasma after consumption of red wine. J Nutr 1999;129:1-7.
32. O'Leary KA, Day AJ, Needs PW, Mellon FA, O'Brien NM, Williamson G. Metabolism of quercetin-7-and quercetin-3-glucuronides by an in vitro hepatic model: The role of human beta-glucuronidase, sulfotransferase, catechol-O-methyl-transferase and multi-resistant protein 2 (MRP2) in flavonoid metabolism. Biochem Pharmacol 2003;65:479-491.
33. O'Leary KA, Day AJ, Needs PW, Sly WS, O'Brien NM, Williamson G. Flavonoid glucuronides are substrates for human liver beta-glucuronidase. FEBS Lett 2001;503:103-106.
34. Shimoi K, Saka N, Kaji K, Nozawa R, Kinae N. Metabolic fate of luteolin and its functional activity at focal site. Biofactors 2000;12:181-186.
35. Shimoi K, Saka N, Nozawa R, Sato M, Amano I, Nakayama T, Kinae N. Deglucuronidation of a flavonoid, luteolin monoglucuronide, during inflammation. Drug Metab Dispos 2001;29:1521-1524.
36. Mochizuki M, Kajiya K, Terao J, Kaji K, Kumazawa S, Nakayama T, Shimoi K. Effect of quercetin conjugates on vascular permeability and expression of adhesion molecules. Biofactors 2004; 22:201-204.
37. Harborne JB, Mabry TJ, Mabry H. The flavonoids. London: Chapman & Hall; 1975.
38. Harborne JB, Mabry TJ. The flavonoids: Advances in research. London: Chapman & Hall; 1982.
39. Harborne JB. The flavonoids. Advances in research since 1980. New-York: Chapman & Hall; 1988.
40. Harborne JB. The flavonoids. Advances in research since 1986. London: Chapman & Hall; 1994.
41. Harborne JB, Baxter H. Handbook of natural flavonoids. Chichester: Wiley; 1999.
42. Ryan JJ. Flavonol glycosides of the cultivated strawberry. J Food Sci 1971;36:867-870.
43. Ryan JJ, Coffin DE. Flavonol glucuronides from red raspberry, Rubus idaeus (Rosaceae). Phytochemistry 1971;10:1675-1677.
44. Wöldecke M, Herrmann K. Flavonols and flavones from vegetables IV. Flavonols and flavones of lettuce and endive. Z Lebensm Unter For 1974;156:153-157.
45. Fraisse D, Carnat A, Lamaison JL. Polyphenolic composition of blueberry leaf. Ann Pharm Fr 1996;54:280-283.
46. Yang H, Protiva P, Cui B, Ma C, Baggett S, Hequet V, Mori S, Weinstein IB, Kennelly EJ. New bioactive polyphenols from Theobroma grandiflorum ("Cupuaçu"). J Nat Prod 2003; 66:1501-1504.
47. Merfort I, Wendisch D. Flavonoid glucuronides from the flowers of Arnica montana. Planta Med 1988;54:247-250.
48. Albrecht M, Nahrstedt A, Wray V. Isolation, structure elucidation, and HPLC-analysis of flavonol glycosides from the leaves of Populus tremuloides and P. tremula. Planta Med 1989;55:611.
49. Barakat HA, Hussein SAM, Marzouk MS, Merfort I, Linscheid M, Nawwar MAM. Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry 1997;46:935-941.
50. Souleman AMA. Sulfated flavonols of the flowers of Tamarix amplexicaulis. Nat Prod Sci 1998;4:215-220.
51. Skibinski A, Merfort I, Willuhn G. Thirty-seven flavonoids from flowers of Arnica longifolia. Phytochemistry 1994; 37: 1635-1636.
52. Kombal R, Glasl H. Flavan-3-ols and flavonoids from Potentilla anserina. Planta Med 1995;61:484-485.
53. Sohn UD, Wang WK, Ham IH, Min YS, Bae KL, Yim SH, Park SY. Process for preparing quercetin-3-O-β-D-glucuronide (QGC) isolated from Rumex aquaticus. Patent WO 2003-KR1038 20030527 [WO 2003099307 A1 20031204]. 12-4-2003.
54. Harborne JB. Flavonoid sulfates. New class of sulfur compounds in higher plants. Phytochemistry 1975;14: 1147-1155.
55. Barron D, Varin L, Ibrahim RK, Harborne JB, Williams CA. Sulphated flavonoids. An update. Phytochemistry 1988;27:2375-2395.
56. Barron D, Cren-Olivé C, Needs P. Chemical synthesis of flavonoid conjugates. In: Santos-Buelga T, Williamson G, editors. Chemical synthesis of flavonoid conjugates. Cambridge: The Royal Society of Chemistry; 2003. p 187-213.
57. Fairley B, Botting NP, Cassidy A. The synthesis of daidzein sulfates. Tetrahedron 2003;59:5407-5410.
58. Gunnarsson GT, Desai UR. Interaction of designed sulfated flavonoids with antithrombin: Lessons on the design of organic activators. J Med Chem 2002;45:4460-4470.
59. Vaidyanathan JB, Walle T. Glucuronidation and sulfation of the tea flavonoid (-)-epicatechin by the human and rat enzymes. Drug Metab Dispos 2002;30:897-903.
60. Koizumi M, Akao T, Katoda S, Kikuchi T, Okuda T, Kobashi K. Enzymatic sulfation of polyphenols related to tannins by arylsulfotransferase. Chem Pharm Bull 1991; 39:2638-2643.
61. Koizumi M, Akao T, Imamura L, Dohi K, Yoshida T, Okuda T, Kobashi K. Enzymic sulfation of isoamyl gallate and (-)-epigallocatechin gallate by bacterial aryl sulfotransferase. Chem Pharm Bull 1992;40:1864-1867.
62. Ibrahim AR. Sulfation of naringenin by Cunninghamella elegans. Phytochemistry 2000;53:209-212.
63. Bors W, Heller W, Michel C, Saran M. Flavonoids as antioxidants: Determination of radical-scavenging efficiencies. Methods Enzymol 1990;186:343-355.
64. Rice-Evans CA, Miller NJ, Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 1996;20:933-956.
65. DuPont MS, Day AJ, Bennett RN, Mellon FA, Kroon PA. Absorption of kaempferol from endive, a source of kaempferol-3-glucuronide, in humans. Eur J Clin Nutr 2004;58:947-954.
66. Walle T, Otake Y, Brubaker JA, Walle UK, Halushka PV. Disposition and metabolism of the flavonoid chrysin in normal volunteers. Br J Clin Pharmacol 2001;51:143-146.
67. Clarke DB, Lloyd AS, Botting NP, Oldfield MF, Needs PW, Wiseman H. Measurement of intact sulfate and glucuronide phytoestrogen conjugates in human urine using isotope dilution liquid chromatography-tandem mass spectrometry with [13C(3)]isoflavone internal standards. Anal Biochem 2002;309:158-172.
68. Natsume M, Osakabe N, Oyama M, Sasaki M, Baba S, Nakamura Y, Osawa T, Terao J. Structures of (-)-epicatechin glucuronide identified from plasma and urine after oral ingestion of (-)-epicatechin: Differences between human and rat. Free Radic Biol Med 2003;34:840-849.
69. Milbury PE, Cao G, Prior RL, Blumberg J. Bioavailablility of elderberry anthocyanins. Mech Ageing Dev 2002;123: 997-1006.
70. Wu XL, Cao GH, Prior RL. Absorption and metabolism of anthocyanins in elderly women after consumption of elderberry or blueberry. J Nutr 2002;132:1865-1871.
71. Bub A, Watzl B, Heeb D, Rechkemmer G, Briviba K. Malvidin-3-glucoside bioavailability in humans after ingestion of red wine, dealcoholized red wine and red grape juice. Eur J Nutr 2001;40:113-120.
72. Matsumoto H, Inaba H, Kishi M, Tominaga S, Hirayama M, Tsuda T. Orally administered delphinidin 3-rutinoside and cyanidin 3-rutinoside are directly absorbed in rats and humans and appear in the blood as the intact forms. J Agric Food Chem 2001;49:1546-1551.
73. Rechner AR, Kuhnle G, Hu HL, Roedig-Penman A, van den Braak MH, Moore KP, Rice-Evans CA. The metabolism of dietary polyphenols and the relevance to circulating levels of conjugated metabolites. Free Radic Res 2002;36: 1229-1241.
74. Cooper DA, Webb DR, Peters JC. Evaluation of the potential for olestra to affect the availability of dietary phytochemicals. J Nutr 1997;127:1699S-1709S.
75. Shirai M, Jae HM, Tsushida T, Terao J. Inhibitory effect of a quercetin metabolite, quercetin 3-O-β-D-glucuronide, on lipid peroxidation in liposomal membranes. J Agric Food Chem 2001;49:5602-5608.
76. Murota K, Shimizu S, Chujo H, Moon JH, Terao J. Efficiency of absorption and metabolic conversion of quercetin and its glucosides in human intestinal cell line Caco-2. Arch Biochem Biophys 2000;384:391-397.
77. Foti M, Piattelli M, Baratta MT, Ruberto G. Flavonoids, coumarins and cinnamic acids as antioxidants in a micellar system. Structure-activity Relationship. J Agric Food Chem 1996;44:497-501.
78. Kandil FE, El-Sayed NH, Micheal HN, Ishak MS, Mabry TJ. Flavonoids from Psidium guaijava. Asian J Chem 1997;9:871-872.
79. Williams CA, Harborne JB, Eagles J. Variations in lipophilic and polar flavonoids in the genus Tanacetum. Phytochemistry 1999;52:1301-1306.
80. Saleh NA, Bohm B. Flavonoids of Lasthenia conjugens and Lasthenia fremontii. Phytochemistry 1971;10:611-614.
81. Fang N, Yu S, Mabry TJ. Flavonoids from Gutierrezia wrightii. J Nat Prod 1986;49:739-741.
82. Ishimatsu M, Tanaka T, Nonaka GI, Nishioka I. Alnusnins A and B from the leaves of Alnus sieboldiana. Phytochemistry 1989;28:3179-3184.
83. Jerga C, Merfort I, Willuhn G. Flavonoid glycosides and other hydrophilic compounds from flowers of Heterotheca inuloides. Planta Med 1990;56:413-415.
84. Rubio B, Villaescusa L, Diaz AM, Fernandez L, Martin T. Flavonol glycosides from Scolymus hispanicus and Jasonia glutinosa. Planta Med 1995;61:583.
85. Bisio A, Romussi G, Ciarallo G, De Tommassi N. Flavonoids and triterpenoids from Salvia blepharophylla. Pharmazie 1997;52:330-331.
86. Bonnländer B, Winterhalter P. 9-Hydroxypiperitone β-D-glucopyranoside and other polar constituents from dill (Anethum graveolens L.) herb. J Agric Food Chem 2000;48:4821-4825.
87. Jürgenliemk G, Nahrstedt A. Polyphenolic compounds from Hypericum perforatum. Planta Med 2002;68:88-91.
88. Peng ZF, Strack D, Baumert A, Subramaniam R, Goh NK, Chia TF, Tan SN, Chia ES. Antioxidant flavonoids from leaves of Polygonum hydropiper L. Phytochemistry 2003;62:219-228.
89. Cano A, Arnao MB, Williamson G, Garcia-Conesa MT. Superoxide scavenging by polyphenols: Effect of conjugation and dimerization. Redox Rep 2002;7:379-383.
90. O'Leary KA, De Pascual-Teresa S, Needs PW, Bao YP, O'Brien NM, Williamson G. Effect of flavonoids and vitamin E on cyclo-oxygenase (COX-2) transcription. Mutat Res 2004;551:245-254.
91. Janisch KM, Williamson G, Needs P, Plumb GW. Properties of quercetin conjugates: Modulation of LDL oxidation and binding to human serum albumin. Free Radic Res 2004;38:877-884.
92. Moon JH, Tsushida T, Nakahara K, Terao J. Identification of quercetin 3-O-β-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin. Free Radic Biol Med 2001;30:1274-1285.
93. Terao J, Yamaguchi S, Shirai M, Miyoshi M, Moon JH, Oshima S, Inakuma T, Tsushida T, Kato Y. Protection by quercetin and quercetin 3-O-β-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein. Free Radic Res 2001; 35:925-931.
94. Shirai M, Yamanishi R, Moon JH, Murota K, Terao J. Effect of quercetin and its conjugated metabolite on the hydrogen peroxide-induced intracellular production of reactive oxygen species in mouse fibroblasts. Biosci Biotechnol Biochem 2002;66:1015-1021.
95. Yoshizumi M, Tsuchiya K, Suzaki Y, Kirima K, Kyaw M, Moon JH, Terao J, Tamaki T. Quercetin glucuronide prevents VSMC hypertrophy by angiotensin II via the inhibition of JNK and AP-1 signaling pathway. Biochem Biophys Res Commun 2002;293:1458-1465.
96. Tamaki T, Tsuchiya K, Yoshizumi M. Quercetin glucuronide prevents Angiotensin II-induced vascular smooth muscle cell hypertrophy. J Hypertens 2002;20:S31.
97. Pascual-Teresa S, Johnston KL, DuPont MS, O'Leary KA, Needs PW, Morgan LM, Clifford MN, Bao Y, Williamson G. Quercetin metabolites downregulate cyclooxygenase-2 transcription in human lymphocytes ex vivo but not in vivo. J Nutr 2004;134:552-557.
98. da Silva EL, Piskula MK, Yamamoto N, Moon JH, Terao J. Quercetin metabolites inhibit copper ion-induced lipid peroxidation in rat plasma. FEBS Lett 1998; 430:405-408.
99. Morand C, Crespy V, Manach C, Besson C, Demigne C, Remesy C. Plasma metabolites of quercetin and their antioxidant properties. Am J Physiol Regul Integr Comp Physiol 1998;44:R212-R219.
100. Saito A, Sugisawa A, Umegaki K, Sunagawa H. Protective effects of quercetin and its metabolites on H202-induced chromosomal damage to WIL2-NS cells. Biosci Biotechnol Biochem 2004;68:271-276.
101. Spencer JPE, Rice-Evans C, Williams RJ. Modulation of pro-survival Akt/protein kinase B and ERK1/2 signaling cascades by quercetin and its in vivo metabolites underlie their action on neuronal viability. J Biol Chem 2003; 278:34783-34793.
102. Spencer JPE, Kuhnle GGC, Williams RJ, Rice-Evans C. Intracellular metabolism and bioactivity of quercetin and its in vivo metabolites. Biochem J 2003;372:173-181.
103. Liu W, Liang NC. Inhibitory effect of disodium quercetin-7, 4′-disulfate on aggregation of pig platelets induced by thrombin and its mechanism. Acta Pharmacol Sin 2000;21:737-741.
104. Long LH, Clement MV, Halliwell B. Artifacts in cell culture: Rapid generation of hydrogen peroxide on addition of (-)-epigallocatechin, (-)-epigallocatechin gallate, (+)-catechin, and quercetin to commonly used cell culture media. Biochem Biophys Res Commun 2000;273:50-53.
105. Wee LM, Long LH, Whiteman M, Halliwell B. Factors affecting the ascorbate- and phenolic-dependent generation of hydrogen peroxide in Dulbecco's Modified Eagles Medium. Free Radic Res 2003; 37:1123-1130.