Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 39, 2009 - Issue 5
137
Views
13
CrossRef citations to date
0
Altmetric
Research Article

Hydroxylation of tanshinone IIa in human liver microsomes is specifically catalysed by cytochrome P4502A6

, , , , &
Pages 382-390 | Received 01 Jan 2009, Accepted 12 Feb 2009, Published online: 01 May 2009

References

  • Benowitz NL, Jacob P III, Sachs DP. (1995). Deficient C-oxidation of nicotine. Clin Pharmacol Ther 57(5):590–594.
  • Benowitz NL, Swan GE, Jacob P III, Lessov-Schlaggar CN, Tyndale RF. (2006). CYP2A6 genotype and the metabolism and disposition kinetics of nicotine. Clin Pharmacol Ther 80:457–67.
  • Bjornsson TD, Callaghan JT, Einolf HJ, Fischer V, Gan L, Grimm S, Kao J, King SP, Miwa G, Ni L, Kumar G, McLeod J, Obach RS, Roberts S, Roe A, Shah A, Snikeris F, Sullivan JT, Tweedie D, Vega JM, Walsh J, Wrighton SA. (2003). The conduct of in vitro and in vivo drug–drug interaction studies: a Pharmaceutical Research and Manufacturers of America (PhRMA) perspective. Drug Metab Disposit 31:815–32.
  • Chang PN, Mao JC, Huang SH, Ning L, Wang ZJ, On T, Duan W, Zhu YZ. (2006). Analysis of cardioprotective effects using purified Salvia miltiorrhiza extract on isolated rat hearts. J Pharmacol Sci 101:245–9.
  • Ding M, Ye TX, Zhao GR, Yuan YJ, Guo ZX. (2005). Aqueous extract of Salvia miltiorrhiza attenuates increased endothelial permeability induced by tumor necrosis factor-alpha. Int Immunopharmacol 5:1641–51.
  • Evans WE, McLeod HL. (2003). Pharmacogenomics-drug disposition, drug targets, and side effects. N Engl J Med 348:538–49.
  • Gören AC, Topçu G, Oksüz S, Kökdil G, Voelter W, Ulubelen A. (2002). Diterpenoids from Salvia ceratophylla. Natural Prod Lett 16:47–52.
  • Harris JW, Rahman A, Kim BR, Guengerich FP, Collins JM. (1994). Metabolism of taxol by human hepatic microsomes and liver slices: participation of cytochrome P450 3A4 and an unknown P450 enzyme. Cancer Res 54:4026–35.
  • Hasler JA, Estabrook R, Murray M, Pikuleva I, Watreman M, Capdevila J, Holla V, Helvig C, Falck JR, Farrell G, Kaminsky LS, Spivack SD, Boitier E, Beaune P. (1999). Human cytochrome P450. Mol Aspect Med 20:1–137.
  • Itoh M, Nakajima M, Higashi E, Yoshida R, Nagata K, Yamazoe Y, Yokoi T. (2006). Induction of human CYP2A6 is mediated by the pregnane X receptor with peroxisome proliferator-activated receptor-gamma coactivator 1alpha. J Pharmacol Exp Ther 319:693–702.
  • Koenigs LL, Peter RM, Thompson SJ, Rettie AE, Trager WF. (1997). Mechanism-based inactivation of human liver cytochrome P450 2A6 by 8-methoxypsoralen. Drug Metab Disposit 25:1407–15.
  • Ko JS, Ryu SY, Kim YS, Chung MY, Kang JS, Rho MC, Lee HS Kim YK. (2002). Inhibitory activity of diacylglycerol acyltransferase by tanshinones from the root of Salvia miltiorrhiza. Arch Pharma Res 25:446–8.
  • Koskela S, Hakkola J, Hukkanen J, Pelkonen O, Sorri M, Saranen A, Anttila S, Fernandez-Salguero P, Gonzalez F, Raunio H. (1999). Expression of CYP2A genes in human liver and extrahepatic tissues. Biochem Pharmacol 57:1407–13.
  • Kuo YH, Lin YL, Don MJ, Chen RM, Ueng YF. (2006). Induction of cytochrome P450 dependent monooxygenase by extracts of the medicinal herb Salvia miltiorrhiza. J Pharm Pharmacol 58: 521–6.
  • Lewis DF, Ioannides C, Parke DV, Schulte-Hermann R. (2000). Quantitative structure–activity relationships in a series of endogenous and synthetic steroids exhibiting induction of CYP3A activity and hepatomegaly associated with increased DNA synthesis. J Steroid Biochem Mol Biol 74:179–85.
  • Lin JH, Lu AYH. (2001). Interindividual variability in inhibition and induction of cytochrome P450 enzymes. Ann Rev Pharmacol Toxicol 41:535–67.
  • Li P, Wang GJ, Li J, Hao HP, Zheng CN. (2006). Identification of tanshinone IIA metabolites in rat liver microsomes by liquid chromatography-tandem mass spectrometry. J Chromatogr A 1104:366–9.
  • Li W, Liu Y, He YQ, Zhang JW, Gao Y, Ge GB, Liu HX, Huo H, Liu HT, Wang LM, Sun J, Wang Q, Yang L. (2008). Characterization of triptolide hydroxylation by cytochrome P450 in human and rat liver microsomes. Xenobiotica 38:1551–65.
  • Liu HX, Liu Y, Zhang JW, Li W, Liu HT, Yang L. (2008). UDP-glucuronosyltransferase 1A6 is the major isozyme responsible for protocatechuic aldehyde glucuronidation in human liver microsomes. Drug Metab Disposit 36:1562–9.
  • Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. (1951). Protein measurement with the Folin phenol reagent. J Biol Chem 193:265–75.
  • Omura T, Sato R. (1964). The carbon monoxide-binding pigment of liver microsomes. J Biol Chem 239:2370–85.
  • Ortiz de Montellano PR, Mathews JM. (1981). Autocatalytic alkylation of the cytochrome P-450 prosthetic haem group by 1-aminobenzotriazole. Isolation of an NN-bridged benzyne-protoporphyrin IX adduct. Biochem J 195:761–4.
  • Qiu F, Zhang R, Sun J, Jiye A, Hao H, Peng Y, Ai H, Wang G. (2008). Inhibitory effects of seven components of danshen extract on catalytic activity of cytochrome P450 enzyme in human liver microsomes. Drug Metab Disposit 36:1308–14.
  • Rae JM, Soukhova NV, Flockhart DA, Desta Z. (2002). Triethylenethiophosphoramide is a specific inhibitor of cytochrome P450 2B6: implications for cyclophosphamide metabolism. Drug Metab Disposit 30:525–30.
  • Sugiyama A, Zhu BM, Takahara A, Satoh Y, Hashimoto K. (2002). Cardiac effects of Salvia miltiorrhiza/Dalbergia odorifera mixture, an intravenously applicable Chinese medicine widely used for patients with ischemic heart disease in China. Circ J 66:182–4.
  • Ueng YF, Kuo YH, Peng HC, Chen TL, Jan WC, Guengerich FP, Lin YL. (2003). Diterpene quinone tanshinone IIA selectively inhibits mouse and human cytochrome P4501A2. Xenobiotica 33:603–13.
  • Ueng YF, Kuo YH, Wang SY, Lin YL, Chen CF. (2004). Induction of CYP1A by a diterpene quinone tanshinone IIA isolated from a medicinal herb Salvia miltiorrhiza in C57BL/6J but not in DBA/2J mice. Life Sci 74:885–96.
  • Wang X, Wei Y, Yuan S, Liu G, Lu Y, Zhang J, Wang WD. (2005). Potential anticancer activity of tanshinone IIA against human breast cancer. Int J Cancer 116:799–807.
  • Zhao BL, Jiang W, Zhao Y, Hou JW, Xin WJ. (1996). Scavenging effects of salvia miltiorrhiza on free radicals and its protection for myocardial mitochondrial membranes from ischemia reperfusion injury. Biochem Mol Biol Int 38:1171–82.
  • Zhang JW, Liu Y, Zhao JY, Wang LM, Ge GB, Gao Y, Li W, Liu HT, Liu HX, Zhang YY, Sun J, Yang L. (2008). Metabolic profiling and cytochrome P450 reaction phenotyping of medroxyprogesterone acetate. Drug Metab Disposit 36:2292–8.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.