Metabolism of echinacoside, a good antioxidant, in rats: Isolation and identification of its biliary metabolites

Drug Metabolism and Disposition

Volumn 37, Issue 2, 2009, Pages 431-438

  Jia, Cunqin ^a   Shi, Haiming ^b   Jin, Wei ^a   Zhang, Ke ^a   Jiang, Yong ^a   Zhao, Mingbo ^a   Tu, Pengfei ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT; DRUG METABOLITE; ECHINACOSIDE;

ANIMAL EXPERIMENT; ARTICLE; BILE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG DETERMINATION; DRUG GLUCURONIDATION; DRUG ISOLATION; DRUG METABOLISM; DRUG STRUCTURE; LIVER PROTECTION; MALE; NEUROPROTECTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STEREOCHEMISTRY;

ANIMALS; ANTIOXIDANTS; BILIARY TRACT; BIOCHEMICAL PROCESSES; GLYCOSIDES; MALE; METABOLIC NETWORKS AND PATHWAYS; RATS; RATS, SPRAGUE-DAWLEY;

RATTUS;

EID: 59649109539     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.023697     Document Type: Article

References (32)

1. 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.
2. Bursztyka J, Perdu E, Tulliez J, Debrauwer L, Delous G, Canlet C, De Sousa G, Rahmani R, Benfenati E, and Cravedi JP (2008) Comparion of genistein metabolism in rats and humans using liver microsomes and hepatocytes. Food Chem Toxicol 46:939-948.
3. Cervellati R, Renzulli C, Guerra MC, and Speroni E (2002) Evaluation of antioxidant activity of some natural polyphenolic compounds using the Briggs-Rauscher reaction method. J Agric Food Chem 50:7504-7509.
4. Chen H, Jing FC, Li CL, Tu PF, Zheng QS, and Wang ZH (2007) Echinacoside prevents the striatal extracellular levels of monoamine neurotransmitters from diminution in 6-hydroxydo-pamine lesion rats. J Ethnopharmacol 114:285-289.
5. Chen X, Cui L, Duan X, Ma B, and Zhong D (2006) Pharmacokinetics and metabolism of the flavonoid scutellarin in humans after a single oral administration. Drug Metab Dispos 34:1345-1352.
6. Deng M, Zhao JY, Tu PF, Jiang Y, Li ZB, and Wang YH (2004) Echinacoside rescues the SHSY5Y neuronal cells from TNFα-induced apoptosis. Eur J Pharmacol 505:11-18.
7. Elgindi MR and Mabry TJ (2000) Phenylethanoid glycosides from Verbascum sinaiticum. Asian J Chem 12:127-130.
8. Geng X, Tian X, Tu P, and Pu X (2007) Neuroprotective effects of echinacoside in the mouse MPTP model of Parkinson's disease. Eur J Pharmacol 564:66-74.
9. Havsteen BH (2002) The biochemistry and medical significance of the flavonoids. Pharmacol Ther 96:67-202.
10. Houghton PJ and Hikino H (1989) Anti-hepatotoxic activity of extracts and constituents of Buddleja species. Planta Med 55:123-126.
11. Hu C and Kitts DD (2000) Studies on the antioxidant activity of Echinacea root extract. J Agric Food Chem 48:1466-1472.
12. Jia C, Shi H, Wu X, Li Y, Chen J, and Tu P (2006) Determination of echinacoside in rat serum by reversed-phase high-performance liquid chromatography with ultraviolet detection and its application to pharmacokinetics and bioavailability. J Chromatogr B Analyt Technol Biomed Life Sci 844:308-313.
13. Karhunen T, Tilgmann C, Ulmanen I, Julkunen I, and Panula P (1994) Distribution of catechol- o-methyltransferase enzyme in rat tissues. J Histochem Cytochem 42:1079-1090.
14. Kobayashi H, Karasawa H, Miyase T, and Fukushima S (1984) Studies on the constituents of Cistanchis herba. III. Isolation and structures of new phenylpropanoid glycosides, cistanosides A and B. Chem Pharm Bull 32:3009-3014.
15. Koo KA, Sung SH, Park JH, Kim SH, Lee KY, and Kim YC (2005) In vitro neuroprotective activities of phenylethanoid glycosides from Callicarpa dichotoma. Planta Med 71:778-780.
16. LeiL, SongZH, TuPF,LiYZ, WuLJ, andChenFK (2001) Metabolicregulationofphenylethanoid glycosides from Herba cistanches in dogs' gastrointestine. Yao Xue Xue Bao 36:432-435.
17. Li J, Zheng RL, Liu ZM, and Jia ZJ (1992) Scavenging effects of phenylpropanoid glycosides on superoxide and its antioxidation effect. Acta Pharmacol Sin 13:427-430.
18. Matthias A, Blanchfield JT, Penman KG, Toth I, Lang CS, De Voss JJ, and Lehmann RP (2004) Permeability studies of alkylamides and caffeic acid conjugates from echinacea using a Caco-2 cell monolayer model. J Clin Pharm Ther 29:7-13.
19. Morand C, Crespy V, Manach C, Besson C, Demigne C, and Rémésy C (1998) Plasma metabolites of quercetin and their antioxidant properties. Am J Physiol 275:R212-R219.
20. Moridani MY, Scobie H, and O'Brien PJ (2002) Metabolism of caffeic acid by isolated rat hepatocytes and subcellular fractions. Toxicol Lett 133:141-151.
21. Mutlib AE and Shockcor JP (2003) Application of LC/MS, LC/NMR, NMR and stable isotopes in identifying and characterizing metabolites, in Drug Metabolizing Enzymes (Lee JS and Fisher MB eds) pp 39-50, FontisMedia SA, Lausanne, Switzerland, and Marcel Dekker, Inc., New York.
22. 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 β-glucuronidase, sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 in flavonoid metabolism. Biochem Pharmacol 65:479-491.
23. Perry NB, Burgess EJ, and Glennie VL (2001) Echinacea standardization: analytical methods for phenolic compounds and typical levels in medicinal species. J Agric Food Chem 49:1702-1706.
24. Rüfer CE, Glatt H, and Kulling SE (2006) Structure elucidation of hydroxylated metabolites of the isoflavan equol by gas chromatography-mass spectrometry and high performance liquid chromatography-mass spectrometry. Drug Metab Dispos 34:51-60.
25. Tu PF, Wang B, Deyama T, Zhang ZG, and Lou ZC (1997) Analysis of phenylethanoid glycoside of Herba cistanchis by RP-HPLC. Acta Pharmacol Sin 32:294-300.
26. Warashina T, Miyase T, and Ueno A (1992) Phenylethnoid and lignan glycosides from Verbas- cum thapsus. Phytochemistry 31:961-965.
27. Wu Y, Li L, Wen T, and Li YQ (2007) Protective effects of echinacoside on carbon tetrachloride- induced hepatotoxicity in rats. Toxicology 232:50-56.
28. Xiong Q, Tezuka Y, Kaneko T, Li H, Tran LQ, Hase K, Namba T, and Kadota S (2000) Inhibition of nitric oxide by phenylethanoids in activated macrophages. Eur J Pharmacol 400:137-144.
29. Xiong Q, Kadota S, Tani T, and Namba T (1996) Antioxidative effects of phenylethanoids from Cistanche deserticola. Biol Pharm Bull 19:1580-1585.
30. Xu F, Zhang Y, Xiao S, Lu X, Yang D, Yang X, Li C, Shang M, Tu P, and Cai S (2006) Absorption and metabolism of Astragali radix decoction: in silico, in vitro, and a case study in vivo. Drug Metab Dispos 34:913-924.
31. Zeng Y, Qiu F, Liu Y, Qu G, and Yao X (2007) Isolation and identification of phase 1 metabolites of demethoxycurcumin in rats. Drug Metab Dispos 35:1564-1573.
32. Zhang Y, Akao T, Nakamura N, Hattori M, Yang XW, Duan CL, and Liu JX (2004) Magnesium lithospermate B is excreted rapidly into rat bile mostly as methylated metabolites, which are potent antioxidants. Drug Metab Dispos 32:752-757.