Pharmacokinetics and metabolism of the flavonoid scutellarin in humans after a single oral administration

Drug Metabolism and Disposition

Volumn 34, Issue 8, 2006, Pages 1345-1352

  Chen, Xiaoyan ^a   Cui, Liang ^b   Duan, Xiaotao ^b   Ma, Bin ^b   Zhong, Dafang ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AGLYCONE; BACTERIAL ENZYME; FLAVONOID SCUTELLARIN; GLUCURONIC ACID; SCUTELLAREIN; UNCLASSIFIED DRUG;

ADULT; ARTICLE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG METABOLISM; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; HYDROLYSIS; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; NORMAL HUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SPECIES DIFFERENCE; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY; URINALYSIS;

ADMINISTRATION, ORAL; ADULT; APIGENIN; CHROMATOGRAPHY, LIQUID; GLUCURONIC ACIDS; HUMANS; MALE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

BACTERIA (MICROORGANISMS);

EID: 33746093547     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.106.009779     Document Type: Article

References (39)

1. Abe KI, Inoue O, and Yumioka E (1990) Biliary excretion of metabolites of baicalin and baicalein in rats. Chem Pharm Bull 38:208-211.
2. Akao T, Kawabata K, Yanagisawa E, Ishihara K, Mizuhara Y, Wakui Y, Sakashita Y, and Kobashi K (2000) Baicalin, the predominant flavone glucuronide of scutellariae radix, is absorbed from the rat gastrointestinal tract as the aglycone and restored to its original form. J Pharm Pharmacol 52:1563-1568.
3. Boersma MG, van der Woude H, Bogaards J, Boeren S, Vervoort J, Cnubben NH, van Iersel ML, van Bladeren PJ, and Rietjens IM (2002) Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases. Chem Res Toxicol 15:662-670.
4. Bors W, Heller W, Michel C, and Saran M (1990) Flavonoids as antioxidants: determination of radical-scavenging efficiencies. Methods Enzymol 186:343-355.
5. Brown JE, Khodr H, Hider RC, and Rice-Evans CA (1998) Structural dependence of flavonoid interactions with Cu2+ ions: implications for their antioxidant properties. Biochem J 330:1173-1178.
6. Che QM, Huang XL, Li YM, Kun Z, Teruaki A, and Masao H (2001) Studies on metabolites of baicalin in human urine. 26:768-769.
7. Chen J, Lin H, and Hu M (2005) Absorption and metabolism of genistein and its five isoflavone analogs in the human intestinal Caco-2 model. Cancer Chemother Pharmacol 55:159-169.
8. Choudhury R, Chowrimootoo G, Srai K, Debnam E, and Rice-Evans CA (1999) Interactions of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation. Biochem Biophys Res Commun 265:410-415.
9. Donovan JL, Crespy V, Manach C, Morand C, Besson C, Scalbert A, and Rémémsy C (2001) Catechin is metabolized by both the small intestine and liver of rats. J Nutr 131:1753-1757.
10. Erlund I, Kosonen T, Alfthan G, Ma EJ, Perttunen K, Kenraali J, Parantainen J, and Aro A (2000) Pharmacokinetics of quercetin from quercetin aglycone and rutin in healthy volunteers. Eur J Clin Pharmacol 56:545-553.
11. Fang N, Yu S, and Badger TM (2002) Characterization of isoflavones and their conjugates in female rat urine using LC/MS/MS. J Agric Food Chem 50:2700-2707.
12. Gafner S, Bergeron C, Batcha LL, Reich J, Arnason JT, Burdette JE, Pezzuto JM, and Angerhofer CK (2003) Inhibition of [3H]-LSD binding to 5-HT7 receptors by flavonoids from Scutellaria lateriflora. J Nat Prod 66:535-537.
13. Goh D, Lee YH, and Ong ES (2005) Inhibitory effects of a chemically standardized extract from Scutellaria barbata in human colon cancer cell lines, LoVo. J Agric Food Chem 53:8197-8204.
14. Gradolatto A, Canivenc-Lavier MC, Basly JP, Siess MH, and Teyssier C (2004) Metabolism of apigenin by rat liver phase I and phase ii enzymes and by isolated perfused rat liver. Drug Metab Dispos 32:58-65.
15. Grayer RJ, Veitch NC, Kite GC, Paton AJ, and Garnock-Jones PJ (2002) Scutellarein 4′-methyl ether glycosides as taxonomic markers in Teucridium and Tripora (Lamiaceae, Ajugoideae). Phytochemistry 60:727-731.
16. Havsteen BH (2002) The biochemistry and medical significance of the flavonoids. Pharmacol Ther 96:67-202.
17. Hollman PCH, Bijsman MNCP, van Gameren Y, Cnossen EP, de Vries JH, and Katan MB (1999) The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man. Free Radic Res 31:569-573.
18. Hong H and Liu GQ (2004) Protection against hydrogen peroxide-induced cytotoxicity in PC12 cells by scutellarin. Life Sci 74:2959-2973.
19. Huang JM, Weng WY, Huang XB, Ji YH, and Chen E (2005) Pharmacokinetics of scutellarin and its aglycone conjugated metabolites in rats. Eur J Drug Metab Pharmacokinet 30:165-170.
20. Jiang XH, Li SH, Lan K, Yang JY, and Zhou J (2003) Study on the pharmacokinetics of scutellarin in dogs. Yao Xue Xue Bao 38:371-373.
21. Kuhnle G, Spencer JPE, Chowrimootoo G, Schroeter H, Debnam ES, Srai S, Rice-Evans C, and Hahn U (2000) Resveratrol is absorbed in the small intestine as resveratrol glucuronide. Biochem Biophys Res Commun 272:212-217.
22. Le Marchand L (2002) Cancer preventive effects of flavonoids - a review. Biomed Pharmacother 56:296-301.
23. Liu H, Yang X, Tang R, Liu J, and Xu H (2005) Effect of scutellarin on nitric oxide production in early stages of neuron damage induced by hydrogen peroxide. Pharmacol Res 51:205-210.
24. Liu YM, Lin AH, Chen H, and Zeng FD (2003) Study on pharmacokinetics of scutellarin in rabbits. Yao Xue Xue Bao 38:775-778.
25. Morand C, Crespy V, Manach C, Besson C, Demigne C, and Remesy C (1998) Plasma metabolites of quercetin and their antioxidant properties. Am J Physiol 275:R212-R219.
26. Nestel P (2003) Isoflavones: their effects on cardiovascular risk and functions. Curr Opin Lipidol 14:3-8.
27. O'Leary KA, Day AJ, Needs PW, Mellon FA, O'Brien NM, and Williamson G (2003) Metabolism of quercetin-7- and quercetin-3-glucuronides by an in vitro hepatic model: the role of human beta-glucuronidase, sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 (MRP2) in flavonoid metabolism. Biochem Pharmacol 65:479-491.
28. Pouzet B (2002) SB-258741: a 5-HT7 receptor antagonist of potential clinical interest. CNS Drug Rev 8:90-100.
29. Prasain JK, Wang CC, and Barnes S (2004) Mass spectrometric methods for the determination of flavonoids in biological samples. Free Radic Biol Med 37:1324-1350.
30. Qiu MF, Jia W, Li SS, Xu ZH, Sun X, Wang XR, Zhang YY, and Xie GX (2005) A new silymarin preparation based on solid dispersion technique. Adv Ther 22:595-600.
31. Rice-Evans CA, Miller NJ, and Paganga G (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20:933-956.
32. Shen YL and Feng F (2006) Sensitive liquid chromatography-tandem mass spectrometry method for the determination of scutellarin in human plasma: application to a pharmacokinetic study. J Chromatogr B 830:1-5.
33. Spencer JP (2003) Metabolism of tea flavonoids in the gastrointestinal tract. J Nutr 133:3255S-3261S.
34. Walle T (2004) Absorption and metabolism of flavonoids. Free Radic Biol Med 36:829-837.
35. Walle T, Eaton EA, and Walle UK (1995) Quercetin, a potent and specific inhibitor of the human P-form phenosulfotransferase. Biochem Pharmacol 50:731-734.
36. Xing J, Chen X, and Zhong D (2005) Stability of baicalin in biological fluids in vitro. J Pharm Biomed Anal 39:593-600.
37. Yodogawa S, Arakawa T, Sugihara N, and Furuno K (2003) Glucurono- and sulfo-conjugation of kaempferol in rat liver subcellular preparations and cultured hepatocytes. Biol Pharm Bull 26:1120-1124.
38. Zhang J and Brodbelt JS (2004) Screening flavonoid metabolites of naringin and narirutin in urine after human consumption of grapefruit juice by LC-MS and LC-MS/MS. Analyst 129:1227-1233.
39. Zhang JL, Che QM, Li SZ, and Zhou TH (2003) Study on metabolism of scutellarin in rats by HPLC-MS and HPLC-NMR. J Asian Nat Prod Res 5:249-256.