Identification of quercetin 3-O-β-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin

Free Radical Biology and Medicine

Volumn 30, Issue 11, 2001, Pages 1274-1285

  Moon, Jae Hak ^a   Tsushida, Tojiro ^b   Nakahara, Kazuhiko ^c   Terao, Junji ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b NATIONAL FOOD RESEARCH INSTITUTE   (Japan)

^c JAPAN INTERNATIONAL RESEARCH CENTER FOR AGRICULTURAL SCIENCES   (Japan)

Author keywords

Free radicals; Quercetin 3 O D glucuronide; Quercetin 4 O D glucuronide; Quercetin conjugates; Quercetin metabolites; Radical scavenging activity

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; ACETIC ACID; ACETIC ACID ETHYL ESTER; ANTIOXIDANT; CARBON 13; COPPER ION; DRUG METABOLITE; LOW DENSITY LIPOPROTEIN; QUERCETIN; QUERCETIN 3 O BETA DEXTRO GLUCORONIDE; QUERCETIN 4 O BETA DEXTRO GLUCORONIDE; QUERCETIN MONOGLUCORONIDE; SCAVENGER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BLOOD ANALYSIS; BLOOD PH; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG CONJUGATION; DRUG EFFECT; DRUG IDENTIFICATION; DRUG RETENTION; DRUG STRUCTURE; DRUG SYNTHESIS; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; IN VIVO STUDY; MALE; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ADMINISTRATION, ORAL; ANIMALS; ANTIOXIDANTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COPPER; FREE RADICAL SCAVENGERS; FREE RADICALS; LIPID PEROXIDATION; LIPOPROTEINS, LDL; MALE; PICRATES; QUERCETIN; RATS; RATS, WISTAR;

EID: 0035370769     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(01)00522-6     Document Type: Article

References (38)

1. Hertog M.G.L., Holmann P.C.H., Katan M.N., Kromhout D. Intake of potentially anticarcinogenic flavonoids and their determinants in adults in The Netherlands. Nutr. Cancer. 20:1993;21-29.
2. Hayek T., Fuhrman B., Vaya J., Rosenblat M., Belinky P., Coleman R., Elis A., Aviram M. Reduced progression of atherosclerosis in apolipoprotein E-deficient mice following consumption of red wine or its polyphenols quercetin or catechin, is associated with reduced susceptibility of LDL to oxidation and aggregation. Arterioscler. Thromb. Vasc. Biol. 17:1997;2744-2752.
3. Steinberg D., Parthasarathy S., Carew T.E., Khoo J.C., Witztum J.L.N. Beyond cholesterol-modification of low-density lipoprotein that increase its atherogenesity. N. Engl. J. Med. 320:1989;915-924.
4. Negre-Salvayre A., Salvayre R. Quercetin prevents the cytotoxicity of oxidized LDL on lymphoid cell lines. Free Radic. Biol. Med. 12:1992;101-106.
5. DeWhalley C.V., Rankin S.M., Hoult J.R., Jessup W., Leake D. Flavonoids inhibit the oxidative modification of low density lipoproteins by macrophages. Biochem. Pharmacol. 39:1990;1743-1750.
6. 2+-mediated oxidative modification of low-density lipoprotein. Biol. Pharm. Bull. 18:1995;1-4.
7. Yamamoto N., Moon J.H., Tsushida T., Nagao A., Terao J. Inhibitory effect of quercetin metabolites and their related derivatives on copper ion-induced lipid peroxidation in human low-density lipoprotein. Arch. Biochem. Biophys. 372:1999;347-354.
8. DaSilva E.L., Tsushida T., Terao J. Inhibition of Mammalian 15-lipoxygenase-dependent lipid peroxidation in low-density lipoprotein by quercetin and quercetin monoglucosides. Arch. Biochem. Biophys. 349:1998;313-320.
9. Hollman P.C.H., Vries J.H.M., Leeuwen S.D., Mengelers M.J.B., Katan M.B. Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers. Am. J. Clin. Nutr. 62:1995;1276-1282.
10. Hollman P.C.H., Trijp J.M.P., Buysman M.N.C.P., Gaag M.S., Mengelers J.B., De Vries J.H.M., Katan M.B. Relative bioabailability of the antioxidant flavonoid quercetin from various foods in man. FEBS Lett. 418:1997;152-156.
11. Manach C., Morand C., Crespy V., Demigné C.M., Texier O., Régérat F., Rémésy C. Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Lett. 426:1998;331-336.
12. Moon J.H., Nakata R., Oshima S., Inakuma T., Terao J. Accumulation of quercetin conjugates in blood plasma after the short-term ingestion of onion by women. Am. J. Physiol. 279:2000;R461-R467.
13. Manach C., Texier O., Régérat F., Agullo G., Demigné C., Rémésy C. Dietary quercetin is recovered in rat plasma as conjugated derivatives of isorhamnetin and quercetin. Nutr. Biochem. 7:1996;375-380.
14. DaSilva E.L., Piskula M.K., Yamamoto N., Moon J.H., Terao J. Quercetin metabolites inhibit copper ion-induced lipid peroxidation in rat plasma. FEBS Lett. 430:1998;405-408.
15. Tamura G., Gold C., Ferr-Luzi A., Ames B.N. Fecalase a model for activation of dietary glycosides to mutagens by intestinal flora . Proc. Natl. Acad. Sci. USA. 77:1981;4961.
16. Day A.J., Dupont M.S., Ridley S., Rhodes M., Rhodes M.J.C., Morgan M.R.A., Williamson G. Deglycosidation of flavonoid and isoflavonoid glycosides by human small intestine and liver β-glucosidase activity. FEBS Lett. 436:1998;71-75.
17. Hosokawa N., Hosokawa Y., Sakai T., Yoshida M., Murai N., Nishino H., Kawai K., Aoike A. Inhibitory effect of quercetin on the synthesis of a possibly cell-cycle-related 17-kDa protein, in human colon cancer cells. Int. J. Cancer. 45:1990;1119-1124.
18. Yoshida M., Yamamoto M., Nikaido T. Quercetin arrests human leukemic T-cells in late G1 phase of the cell cycle. Cancer Res. 52:1992;6676-6681.
19. Yoshida M., Sakai T., Hosokawa N., Murai N., Matsumoto K., Fujioka A., Nishino H., Aoike A. The effect of quercetin on cell cycle progression and growth of human gastric cancer cells. FEBS Lett. 260:1990;10-13.
20. Koenigs W., Knorr E. Veber einige derivate des traubenzuckers und der galactose. Ber. 34:1901;957.
21. Flowers H.M. Studies on the Koenigs-Knorr reaction. Part I. Synthesis of 6-O-α-D-glucopyranosyl-D-galactose and 3-O-α-D-glucopyranosyl-D-galactose. Carbohydr. Res. 18:1971;211-218.
22. Tsushida T., Suzuki M. Isolation of flavonoid-glycosides in onion and identification by chemical synthesis of the glycosides (flavonoid in fruits and vegetables part I). Jpn. Food Sci. Technol. 42:1995;100-108.
23. Blois M.S. Antioxidant determinations by the use of a stable free radical. Nature. 181:1958;1199-1200.
24. Moon J.H., Terao J. Antioxidant activity of caffeic acid and dihydrocaffeic acid in lard and human low-density lipoprotein. J. Agric. Food Chem. 46:1998;5062-5065.
25. DaSilva E.L., Piskula M., Terao J. Enhancement of antioxidative ability of rat plasma by oral administration of (-)-epicatechin. Free Radic. Biol. Med. 24:1998;1209-1216.
26. Arai H., Terao J., Abdalla D.S.P., Suzuki T., Takama K. Coulometric detection in high-performance liquid chromatographic analysis of cholesteryl ester hydropheroxides. Free Radic. Biol. Med. 20:1996;365-371.
27. Bors W., Heller W., Michel C., Saran N. Flavonoids as antioxidants determination of radical-scavenging efficiencies . Methods Enzymol. 186:1990;343-355.
28. Cao G., Sofic E., Prior R.L. Antioxidant and pro-oxidant behavior of flavonoids structure-activity relationships . Free Radic. Biol. Med. 22:1997;749-760.
29. Van Acker S.A.B.E., Van Den Berg D.-J., Tromp M.N., Griffioen D.H., Van Bennekom W.P., Van Der Vijgh W.J., Bast A. Structural aspects of antioxidant activity of flavonoids. Free Radic. Biol. Med. 20:1996;331-342.
30. Rice-Evans C.A., Miller N.J., Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20:1996;933-956.
31. Piskula M.K., Terao J. Accumulation of (-)-epicatechin metabolites in rat plasma after oral administration and distribution of conjugation enzymes in rat tissues. J. Nutr. 128:1998;1172-1178.
32. Radominska-Pandya A., Little J.M., Pandya J.T., Tephly T., King C.D., Barone G.W., Barone Raufman J.-P. UDP-glucuronosyltransferases in human intestinal mucosa. Biochim. Biophys. Acta. 1394:1998;199-208.
33. Noteborn H.P.J.M., Jansen E., Benito S., Mengelers M.J.B. Oral absorption and metabolism of quercetin and sugar-conjugated derivatives in specific transport systems. Cancer Lett. 114:1997;175-177.
34. Walgren R.A., Walle I.T., Walle T. Transport of quercetin and its glucosides across human intestinal epithelial Caco-2 cells. Biochem. Pharmacol. 55:1998;1721-1727.
35. Gee J.M., DuPont M.S., Day A.J., Plumb G.W., Williamson G., Johnson I.T. Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway. J. Nutr. 130:2000;2765-2771.
36. Walgren R.A., Lin J.-T., Kinne R.K.-H., Walle T. Cellular uptake of dietary flavonoid quercetin 4′-β-glucoside by sodium-dependent glucose transporter SGLT1. J. Pharmacol. Exp. Ther. 294:2000;837-843.
37. Crespy V., Morand C., Manach C., Besson C., Demigne C., Remesy C. Part of quercetin absorbed in the small intestine is conjugated and further secreted in the intestinal lumen. Am. J. Physiol. 277:1999;G120-G126.
38. Murota K., Shimizu S., Chujo H., Moon J.H., Terao J. Efficiency of absorption and metabolic conversion of quercetin and its glucosides in human intestinal cell line Caco-2. Arch. Biochem. Biophys. 384:2000;391-397.