C5-Hydroxylation of liquiritigenin is catalyzed selectively by CYP1A2

References

• 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; Pharmaceutical Research and Manufacturers of America (PhRMA) Drug Metabolism/Clinical Pharmacology Technical Working Group; FDA Center for Drug Evaluation and Research (CDER). (2003). The conduct of in vitro and in vivo drug-drug interaction studies: a Pharmaceutical Research and Manufacturers of America (PhRMA) perspective. Drug Metab Dispos 31:815–832.
   PubMed Web of Science ®Google Scholar
• Cao Y, Wang Y, Ji C, Ye J. (2004). Determination of liquiritigenin and isoliquiritigenin in Glycyrrhiza uralensis and its medicinal preparations by capillary electrophoresis with electrochemical detection. J Chromatogr A 1042:203–209.
   PubMedGoogle Scholar
• Chauret N, Gauthier A, Martin J, Nicoll-Griffith DA. (1997). In vitro comparison of cytochrome P450-mediated metabolic activities in human, dog, cat, and horse. Drug Metab Dispos 25:1130–1136.
   PubMed Web of Science ®Google Scholar
• Guengerich FP. (1997). Comparisons of catalytic selectivity of cytochrome P450 subfamily enzymes from different species. Chem Biol Interact 106:161–182.
   PubMed Web of Science ®Google Scholar
• 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 54:4026–4035.
   PubMed Web of Science ®Google Scholar
• Hollman PC, Katan MB. (1997). Absorption, metabolism and health effects of dietary flavonoids in man. Biomed Pharmacother 51:305–310.
   PubMed Web of Science ®Google Scholar
• Kakegawa H, Matsumoto H, Satoh T. (1992). Inhibitory effects of some natural products on the activation of hyaluronidase and their anti-allergic actions. Chem Pharm Bull 40:1439–1442.
   PubMed Web of Science ®Google Scholar
• Kanazawa M, Satomi Y, Mizutani Y, Ukimura O, Kawauchi A, Sakai T, Baba M, Okuyama T, Nishino H, Miki T. (2003). Isoliquiritigenin inhibits the growth of prostate cancer. Eur Urol 43:580–586.
   PubMed Web of Science ®Google Scholar
• Kim SC, Byun SH, Yang CH, Kim CY, Kim JW, Kim SG. (2004). Cytoprotective effects of Glycyrrhizae radix extract and its active component liquiritigenin against cadmium-induced toxicity (effects on bad translocation and cytochrome c-mediated PARP cleavage). Toxicology 197:239–251.
   PubMed Web of Science ®Google Scholar
• Kobayashi S, Miyamoto T, Kimura I, Kimura M. (1995). Inhibitory effect of isoliquiritin, a compound in licorice root, on angiogenesis in vivo and tube formation in vitro. Biol Pharm Bull 18:1382–1386.
   PubMedGoogle Scholar
• 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 Dispos 25:1407–1415.
   PubMed Web of Science ®Google Scholar
• Kong LD, Zhang Y, Pan X, Tan RX, Cheng CH. (2000). Inhibition of xanthine oxidase by liquiritigenin and isoliquiritigenin isolated from Sinofranchetia chinensis. Cell Mol Life Sci 57:500–505.
   PubMed Web of Science ®Google Scholar
• Kupfer R, Swanson L, Chow S, Staub RE, Zhang YL, Cohen I, Christians U. (2008). Oxidative in vitro metabolism of liquiritigenin, a bioactive compound isolated from the Chinese herbal selective estrogen beta-receptor agonist MF101. Drug Metab Dispos 36:2261–2269.
   PubMed Web of Science ®Google Scholar
• Lee SE, Hwang HJ, Ha JS, Jeong HS, Kim JH. (2003). Screening of medicinal plant extracts for antioxidant activity. Life Sci 73:167–179.
   PubMed Web of Science ®Google Scholar
• 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 38:1551–1565.
   PubMed Web of Science ®Google Scholar
• Liu HX, Hu Y, He YQ, Liu Y, Li W, Yang L. (2009). Ultra-performance liquid chromatographic-electrospray mass spectrometric determination (UPLC-ESI-MS) of O-demethylated metabolite of paeonol in vitro: assay development, human liver microsome activities and species differences. Talanta 79:1433–1440.
   PubMedGoogle Scholar
• Liu HX, Hu Y, Liu Y, He YQ, Li W, Yang L. (2009). CYP1A2 is the major isoform responsible for paeonol O-demethylation in human liver microsomes. Xenobiotica 39:672–679.
   PubMed Web of Science ®Google Scholar
• Liu HX, Hu Y, Liu Y, He YQ, Li W, Yang L. (2009). Hydroxylation of tanshinone IIa in human liver microsomes is specifically catalysed by cytochrome P4502A6. Xenobiotica 39:382–390.
   PubMed Web of Science ®Google Scholar
• 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 Dispos 36:1562–1569.
   PubMed Web of Science ®Google Scholar
• Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. (1951). Protein measurement with the Folin phenol reagent. J Biol Chem 193:265–275.
   PubMed Web of Science ®Google Scholar
• Mori H, Niwa K, Zheng Q, Yamada Y, Sakata K, Yoshimi N. (2001). Cell proliferation in cancer prevention; effects of preventive agents on estrogen-related endometrial carcinogenesis model and on an in vitro model in human colorectal cells. Mutat Res 480-481:201–207.
   PubMed Web of Science ®Google Scholar
• Nikolic D, van Breemen RB. (2004). New metabolic pathways for flavanones catalyzed by rat liver microsomes. Drug Metab Dispos 32:387–397.
   PubMed Web of Science ®Google Scholar
• Niwa K, Hashimoto M, Morishita S, Yokoyama Y, Mori H, Tamaya T. (1999). Preventive effects of Glycyrrhizae radix extract on estrogen-related endometrial carcinogenesis in mice. Jpn J Cancer Res 90:726–732.
   PubMedGoogle Scholar
• Omura T, Sato R. (1964). The carbon monoxide-binding pigment of liver microsomes. J Biol Chem 239:2370–2378.
   PubMed Web of Science ®Google Scholar
• 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 195:761–764.
   PubMed Web of Science ®Google Scholar
• Pan X, Kong LD, Zhang Y, Cheng CH, Tan RX. (2000). In vitro inhibition of rat monoamine oxidase by liquiritigenin and isoliquiritigenin isolated from Sinofranchetia chinensis. Acta Pharmacol Sin 21:949–953.
   PubMed Web of Science ®Google Scholar
• Rae JM, Soukhova NV, Flockhart DA, Desta Z. (2002). Triethylenethiophosphoramide is a specific inhibitor of cytochrome P450 2B6: implications for cyclophosphamide metabolism. Drug Metab Dispos 30:525–530.
   PubMed Web of Science ®Google Scholar
• Shibata S. (2000). A drug over the millennia: pharmacognosy, chemistry, and pharmacology of licorice. Yakugaku Zasshi 120:849–862.
   PubMed Web of Science ®Google Scholar
• Shinkyo R, Sakaki T, Ohta M, Inouye K. (2003). Metabolic pathways of dioxin by CYP1A1: species difference between rat and human CYP1A subfamily in the metabolism of dioxins. Arch Biochem Biophys 409:180–187.
   PubMed Web of Science ®Google Scholar
• Wang ZY, Nixon DW. (2001). Licorice and cancer. Nutr Cancer 39:1–11.
   PubMed Web of Science ®Google Scholar
• Zhang L, Zuo Z, Lin G. (2007a). Intestinal and hepatic glucuronidation of flavonoids. Mol Pharm 4:833–845.
   PubMed Web of Science ®Google Scholar
• Zhang JW, Liu Y, Cheng J, Li W, Ma H, Liu HT, Sun J, Wang LM, He YQ, Wang Y, Wang ZT, Yang L. (2007b). Inhibition of human liver cytochrome P450 by star fruit juice. J Pharm Pharm Sci 10:496–503.
   PubMed Web of Science ®Google Scholar