Metabolism of salvianolic acid a and antioxidant activities of its methylated metabolites

Drug Metabolism and Disposition

Volumn 42, Issue 2, 2014, Pages 274-281

  Xu, Hui ^a   Li, Yanli ^a   Che, Xin ^a   Tian, Hongcui ^a   Fan, Huaying ^a   Liu, Ke ^a  

^a YANTAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3 (3,4 DIHYDROXYPHENYL)LACTIC ACID; 3 O METHYL SALVIANOLIC ACID A; 3' O METHYL SALVIANOLIC ACID A; 3',3'' O DIMETHYL SALVIANOLIC ACID A; 3,3'' O DIMETHYL SALVIANOLIC ACID A; ALPHA TOCOPHEROL; BETA GLUCURONIDASE; BUTYLCRESOL; CAFFEIC ACID; CAFFEIC ACID DERIVATIVE; CATECHOL METHYLTRANSFERASE; CELL PROTEIN; DRUG METABOLITE; ENTACAPONE; SALVIANOLIC ACID A; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; BILE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DRUG EFFECT; DRUG METABOLISM; DRUG STRUCTURE; ENZYME INHIBITION; HYDROLYSIS; IN VITRO STUDY; IN VIVO STUDY; LIPID PEROXIDATION; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; METHYLATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; PRIORITY JOURNAL; RAT; STRUCTURE ANALYSIS;

ALKENES; ANIMALS; ANTIOXIDANTS; BILE; BIOTRANSFORMATION; CATECHOL O-METHYLTRANSFERASE; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; GLUCURONIDES; LIPID PEROXIDATION; MALE; METHYLATION; POLYPHENOLS; RATS; RATS, SPRAGUE-DAWLEY;

EID: 84891802087     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.113.053694     Document Type: Article

References (28)

1. Axelrod J and Tomchick R (1958) Enzymatic O-methylation of epinephrine and other catechols. J Biol Chem 233:702-705.
2. Baba S, Osakabe N, Natsume M, and Terao J (2004) Orally administered rosmarinic acid is present as the conjugated and/or methylated forms in plasma, and is degraded and metabolized to conjugated forms of caffeic acid, ferulic acid and m-coumaric acid. Life Sci 75: 165-178. (Pubitemid 38553873)
3. Chai YY, Wang F, Li YL, Liu K, and Xu H (2012) Antioxidant activities of stilbenoids from Rheum emodi Wall. Evid Based Complement Alternat Med 2012:603678.
4. Cheng TO (2006) Danshen: a versatile Chinese herbal drug for the treatment of coronary heart disease. Int J Cardiol 113:437-438. (Pubitemid 44708326)
5. Fagali N and Catalá A (2012) The antioxidant behaviour of melatonin and structural analogues during lipid peroxidation depends not only on their functional groups but also on the assay system. Biochem Biophys Res Commun 423:873-877.
6. Fan HY, Fu FH, Yang MY, Xu H, Zhang AH, and Liu K (2010) Antiplatelet and antithrombotic activities of salvianolic acid A. Thromb Res 126:e17-e22.
7. Fan HY, Yang L, Fu FH, Xu H, Meng QG, Zhu HB, Teng LR, Yang MY, Zhang LM, and Zhang ZL, et al. (2012) Cardioprotective effects of salvianolic acid a on myocardial ischemia-reperfusion injury in vivo and in vitro. Evid Based Complement Alternat Med 2012:508938.
8. Han DE, Zheng Y, Chen XJ, He J, Zhao D, Yang SY, Zhang CF, and Yang ZL (2012) Identification and characterization of human UDP-glucuronosyltransferases responsible for the in vitro glucuronidation of salvianolic acid A. Drug Metab Pharmacokinet 27:579-585.
9. Ho JH and Hong CY (2011) Salvianolic acids: small compounds with multiple mechanisms for cardiovascular protection. J Biomed Sci 18:30-34.
10. Hou YY, Peng JM, and Chao RB (2007) Pharmacokinetic study of salvianolic acid A in rat after intravenous administration of Danshen injection. Biomed Chromatogr 21:598-601.
11. Huang YS and Zhang JT (1992) [Antioxidative effect of three water-soluble components isolated from Salvia miltiorrhiza in vitro]. Yao Xue Xue Bao 27:96-100.
12. Ji XY, Tan BKH, and Zhu YZ (2000) Salvia miltiorrhiza and ischemic diseases. Acta Pharmacol Sin 21:1089-1094.
13. Lian-Niang L, Rui T, and Wei-Ming C (1984) Salvianolic acid A, a new depside from roots of Salvia miltiorrhiza. Planta Med 50:227-228. (Pubitemid 14025689)
14. Liu GT, Zhang TM, Wang BE, and Wang YW (1992) Protective action of seven natural phenolic compounds against peroxidative damage to biomembranes. Biochem Pharmacol 43:147-152.
15. Lu YR and Foo LY (2002) Polyphenolics of Salvia - a review. Phytochemistry 59:117-140.
16. Lv YH, Zhang X, Liang X, Liu XR, Dai WX, Yan SK, and Zhang WD (2010) Characterization of the constituents in rat biological fluids after oral administration of Fufang Danshen tablets by ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry. J Pharm Biomed Anal 52:155-159.
17. Pan HJ, Li DY, Fang F, Chen D, Qi LL, Zhang RQ, Xu TD, and Sun H (2011) Salvianolic acid A demonstrates cardioprotective effects in rat hearts and cardiomyocytes after ischemia/reperfusion injury. J Cardiovasc Pharmacol 58:535-542.
18. Pei LX, Bao YW, Wang HD, Yang F, Xu B, Wang SB, Yang XY, and Du GH (2008) A sensitive method for determination of salvianolic acid A in rat plasma using liquid chromatography/tandem mass spectrometry. Biomed Chromatogr 22:786-794.
19. Shen Y, Wang XY, Xu LH, Liu XW, and Chao RB (2009) Characterization of metabolites in rat plasma after intravenous administration of salvianolic acid A by liquid chromatography/timeof- flight mass spectrometry and liquid chromatography/ion trap mass spectrometry. Rapid Commun Mass Spectrom 23:1810-1816.
20. Sun YS, Zhu HF, Wang JH, Liu ZB, and Bi JJ (2009) Isolation and purification of salvianolic acid A and salvianolic acid B from Salvia miltiorrhiza by high-speed counter-current chromatography and comparison of their antioxidant activity. J Chromatogr B Analyt Technol Biomed Life Sci 877:733-737.
21. Wang JN, Chen YJ, Hano Y, Nomura T, and Tan RX (2000) Antioxidant activity of polyphenols from seeds of Vitis amurensis in vitro. Acta Pharmacol Sin 21:633-636. (Pubitemid 30482935)
22. Wang SB, Tian S, Yang F, Yang HG, Yang XY, and Du GH (2009) Cardioprotective effect of salvianolic acid A on isoproterenol-induced myocardial infarction in rats. Eur J Pharmacol 615:125-132.
23. Wang XH, Morris-Natschke SL, and Lee KH (2007) New developments in the chemistry and biology of the bioactive constituents of Tanshen. Med Res Rev 27:133-148. (Pubitemid 44975189)
24. Wang XJ, Wang ZB, and Xu JX (2005) Effect of salvianic acid A on lipid peroxidation and membrane permeability in mitochondria. J Ethnopharmacol 97:441-445.
25. Wasser S, Ho JM, Ang HK, and Tan CE (1998) Salvia miltiorrhiza reduces experimentallyinduced hepatic fibrosis in rats. J Hepatol 29:760-771.
26. Xu M, Guo H, Han J, Sun SF, Liu AH, Wang BR, Ma XC, Liu P, Qiao X, and Zhang ZC, et al. (2007) Structural characterization of metabolites of salvianolic acid B from Salvia miltiorrhiza in normal and antibiotic-treated rats by liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 858:184-198. (Pubitemid 47513610)
27. 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. (Pubitemid 38821877)
28. Zhou LM, Zuo Z, and Chow MSS (2005) Danshen: an overview of its chemistry, pharmacology, pharmacokinetics, and clinical use. J Clin Pharmacol 45:1345-1359. (Pubitemid 41643896)