Isolation and identification of urinary metabolites of kakkalide in rats

Drug Metabolism and Disposition

Volumn 38, Issue 2, 2010, Pages 281-286

  Bai, Xue ^a   Xie, Yuanyuan ^a   Liu, Jia ^a   Qu, Jialin ^a   Kano, Yoshihiro ^a   Yuan, Dan ^a  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

5,7 DIHYDROXY 8,4' DIMETHOXYISOFLAVONE; BIOCHANIN A; BIOCHANIN A 6 O SULFATE; CHEMICAL COMPOUND; DAIDZEIN; DRUG METABOLITE; EQUOL; GENISTEIN; IRISOLIDONE; IRISOLIDONE 7 O GLUCURONIDE; ISOFLAVONOID; ISOTECTORIGENIN; KAKKALIDE; TECTORIGENIN; TECTORIGENIN 4' O SULFATE; TECTORIGENIN 7 O SULFATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG DISPOSITION; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG METABOLISM; INFRARED SPECTROSCOPY; MALE; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; RAT; SOLVENT EXTRACTION; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; FLAVONOIDS; FLOWERS; GLUCURONIDES; GLYCOSIDES; ISOFLAVONES; MAGNETIC RESONANCE SPECTROSCOPY; MALE; METABOLIC DETOXICATION, DRUG; METABOLIC NETWORKS AND PATHWAYS; MOLECULAR STRUCTURE; PUERARIA; RATS; RATS, WISTAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFURIC ACID ESTERS; TANDEM MASS SPECTROMETRY;

PUERARIA MONTANA VAR. LOBATA; RATTUS;

EID: 76149098187     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.109.028555     Document Type: Article

References (34)

1. Bashir A, Hamburger M, Msonthi JD, and Hostettmann K (1991) Isoflavones and xanthones from Polygala virgata. Phytochemistry 31:309-311.
2. Bursztyka J, Perdu E, Tulliez J, Debrauwer L, Delous G, Canlet C, De Sousa G, Rahmani R, Benfenati E, and Cravedi JP (2008) Comparison of genistein metabolism in rats and humans using liver microsomes and hepatocytes. Food Chem Toxicol 46:939-948.
3. Chang X, Yuan Y, Xie YY, Hu JL, and Yuan D (2009) Flavonoid constituents in the flowers of Pueraria thomsonii Benth. Chinese J Med Chem 19:284-287.
4. Chen Y, Song W, Peng ZH, Ge BY, and Han FM (2008) Identification of metabolites of tectoridin in-vivo and in-vitro by liquid chromatography-tandem mass spectrometry. J Pharm Pharmacol 60:709-716.
5. Han YO, Han MJ, Park SH, and Kim DH (2003) Protective effects of kakkalide from Flos puerariae on ethanol-induced lethality and hepatic injury are dependent on its biotransformation by human intestinal microflora. J Pharmacol Sci 93:331-336.
6. Horie T, Sasagawa M, Torii F, Kawamura Y, and Yamashita K (1996) Studies of the selective O-alkylation and dealkylation of flavonoids. XX. A convenient method for synthesizing 5,6,7-trihydroxyisoflavones and 5,6-dihydroxy-7- methoxyisoflavones. Chem Pharm Bull 44:486-491.
7. Kang KA, Zhang R, Piao MJ, Ko DO, Wang ZH, Kim BJ, Park JW, Kim HS, Kim DH, and Hyun JW (2008) Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect. Bioorg Med Chem 16:1133-1141.
8. Kang SW, Kim MC, Kim CY, Jung SH, and Um BH (2008) The rapid identification of isoflavonoids from Belamcanda chinensis by LC-NMR and LC-MS. Chem Pharm Bull 56:1452-1454.
9. Kurihara T and Kikuchi M(1975) Studies on the constituents of flowers. V. On the components of flower of Pueraria thunbergiana benth (2). Isolation of a new isoflavone glycoside. Yakugaku Zasshi 95:1283-1285.
10. Lee HU, Bae EA, and Kim DH (2005a) Hepatoprotective effects of irisolidone on tert-butyl hyperoxide-induced liver injury. Biol Pharm Bull 28:531-533.
11. Lee HU, Bae EA, and Kim DH (2005b) Hepatoprotective effect of tectoridin and tectorigenin on tert-butyl hyperoxide-induced liver injury. J Pharmacol Sci 97:541-544.
12. Liu TH, Wang Y, Wang BX, and Wu LJ (2000) Studies on the metabolism of icariin by intestinal bacteria, part 1: the transformation of Icariin by Intestinal Flora. Chinese Traditional and Herbal Drugs 31:834-837.
13. Liska DJ (1998) The detoxification enzyme systems. Altern Med Rev 3:187-198.
14. Meyer MR, Peters FT, and Maurer HH (2009) Stereoselective differences in the cytochrome P450-dependent dealkylation and demethylenation of N-methyl-benzodioxolyl-butanamine (MBDB, Eden) enantiomers. Biochem Pharmacol. 77:1725-1734.
15. Min SW and Kim DH (2007) Kakkalide and irisolidone: HMG-CoA reductase inhibitors isolated from the flower of Pueraria thunbergiana. Biol Pharm Bull 30:1965-1968.
16. Moriyasu M, Igi Y, Ichimaru M, Iwasa K, Kobayakawa J, Sato-Nishimori F, Matsukawa Y, and Nagase C (2007) New isoflavones from Belamcandae Rhizoma. Nat Med (Tokyo) 61:329-333.
17. Niiho Y, Yamazaki T, Nakajima Y, Itoh H, Takeshita T, Kinjo J, and Nohara T (1989) Pharmacological studies on puerariae flos. I. The effects of puerariae flos on alcoholic metabolism and spontaneous movement in mice. Yakugaku Zasshi 109:424-431.
18. Park JS, Woo MS, Kim DH, Hyun JW, Kim WK, Lee JC, and Kim HS (2007) Anti-inflammatory mechanisms of isoflavone metabolites in lipopolysaccharide- stimulated microglial cells. J Pharmacol Exp Ther 320:1237-1245.
19. Simons AL, Renouf M, Hendrich S, and Murphy PA (2005)Metabolism of glycitein (7,4′-dihydroxy-6-methoxy-isoflavone) by human gut microflora. J Agric Food Chem 53:8519-8525.
20. Shin JE, Bae EA, Lee YC, Ma JY, and Kim DH (2006) Estrogenic effect of main components kakkalide and tectoridin of Puerariae Flos and their metabolites. Biol Pharm Bull 29:1202-1206.
21. Song LR, Hong X, Ding XL, and Zang ZY (2001) A Modern Dictionary of Chinese Traditional Medicine, 1st ed, People's Health Press, China.
22. Sun Y and Chen QH (1986) Isolation and identification of metabolites of physcion in rats and mice in vivo and in vitro. Yao Xue Xue Bao 21:748-752.
23. Talukdar AC, Jain N, De S, and Krishnamurty HG (2000) An isoflavone from Myristica malabarica. Phytochemistry 53:155-157.
24. Yamaki K, Kim DH, Ryu N, Kim YP, Shin KH, and Ohuchi K (2002) Effects of naturally occurring isoflavones on prostaglandin E2 production. Planta Med 68:97-100.
25. Yamazaki T, Nakajima Y, Niho Y, Hosono T, Kurashige T, Kinjo J, and Nohara T (1997) Pharmacological studies on Puerariae flos III: protective effects of kakkalide on ethanolinduced lethality and acute hepatic injury in mice. J Pharm Pharmacol 49:831-833.
26. Yasuda T, Kano Y, Saito K, and Ohsawa K (1994) Urinary and biliary metabolites of daidzin and daidzein in rats. Biol Pharm Bull 17:1369-1374.
27. Yasuda T and Ohsawa K (1998) Urinary metabolites of daidzin orally administered in rats. Biol Pharm Bull 21:953-957.
28. Yasuda T, Ueda J, and Ohsawa K (2001) Urinary metabolites of genistein administered orally to rats. Chem Pharm Bull 49:1495-1497.
29. Yin JT, Zhong Y, Sun JY, Liu L, and Wang B (2006) The studies on the chemical composition of Puerariae flos. Chinese Traditional and Herbal Drugs 37:350-352.
30. Yuan D, Xie YY, Bai X, Wu X, Yang JY, and Wu CF (2009) Inhibitory activity of isoflavones of Pueraria flowers on nitric oxide production from lipopolysaccharide-activated primary rat microglia. J Asian Nat Prod Res 11:471-481.
31. Zhang GF (2008) Studies on Chemical Quality Evaluation and the Antioxidant Activity of Flos Puerariae. Master's dissertation, Shenyang Pharmaceutical University, Shenyang, China.
32. Zhang GF, Wu X, Bai Xue, Yoshihiro K, Toshiaki M, and Yuan D (2009) Simultaneous determination of four isoflavone compounds in flowers of Pueraria lobata by HPLC. Journal of Shenyang Pharmaceutical University 26:40-44.
33. Zhang WD, Qi LW, Yang XL, Huang WZ, Li P, and Yang ZL (2008) Identification of the major metabolites of tectorigenin in rat bile by liquid chromatography combined with time-of-flight and ion trap tandem mass spectrometry. Rapid Commun Mass Spectrom 22:2677-2684.
34. Zhang WD, Yang XL, Lei-Xu, Cao J, Li P, and Yang ZL (2009) Identification of key metabolites of tectorigenin in rat urine by HPLC-MSn. Biomed Chromatogr 23:219-221.