In Vitro metabolism of Jaceosidin and characterization of cytochrome P450 and UDP-glucuronosyltransferase enzymes in human liver microsomes

Archives of Pharmacal Research

Volumn 33, Issue 12, 2010, Pages 1985-1996

  Song, Won Young ^a   Ji, Hye Young ^a   Baek, Nam In ^b   Jeong, Tae Sook ^c   Lee, Hye Suk ^a  

^a Wonkwang University   (South Korea)

^b Kyung Hee University   (South Korea)

^c Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

CYP1A2; Glucuronidation; Hydroxylation; Jaceosidin metabolism; O Demethylation; UGTs

Indexed keywords

6 O DESMETHYLJACEOSIDIN; 6 O DESMETHYLJACEOSIDIN GLUCURONIDE; ARTEMISIA PRINCEPS EXTRACT; CYTOCHROME P450; CYTOCHROME P450 1A2; DRUG METABOLITE; GLUCURONIDE; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A1; GLUCURONOSYLTRANSFERASE 1A10; GLUCURONOSYLTRANSFERASE 1A3; GLUCURONOSYLTRANSFERASE 1A7; GLUCURONOSYLTRANSFERASE 1A9; HYDROXYJACEOSIDIN; HYDROXYJACEOSIDIN GLUCURONIDE; JACEOSIDIN; JACEOSIDIN GLUCURONIDE; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; DRUG INHIBITION; DRUG METABOLISM; ENZYME ANALYSIS; GLUCURONIDATION; HUMAN; HUMAN CELL; IN VITRO STUDY; LIVER MICROSOME; MEDICINAL PLANT; PROTEIN EXPRESSION;

ARTEMISIA; CYTOCHROME P-450 CYP1A2; CYTOCHROME P-450 ENZYME SYSTEM; FLAVONOIDS; GLUCURONOSYLTRANSFERASE; HUMANS; MICROSOMES, LIVER; PLANT COMPONENTS, AERIAL; PLANT PREPARATIONS;

EID: 78751546669     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-010-1214-1     Document Type: Article

References (29)

1. M. H. Bang D. H. Kim J. S. Yoo D. Y. Lee M. C. Song H. J. Yang T. S. Jeong K. T. Lee M. S. Choi H. G. Chung N. I. Baek 2005 Development of biologically active compounds from edible plant sources XIV. Isolation and identification of flavonoids from aerial parts of Sajabalssuk (Artemisia herba) J. Kor. Soc. Appl. Biol. Chem. 48 418 420 1:CAS:528:DC%2BD28XntlWhuw%3D%3D
2. M. Bourrié V. Meunier Y. Berger G. Fabre 1996 Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes J. Pharmacol. Exp. Ther. 277 321 332 8613937
3. B. Burchell 2003 Genetic variation of human UDP-glucuronosyltransferase implications in disease and drug glucuronidation Am. J. Pharmacogenomics 3 37 52 1:CAS:528:DC%2BD3sXisVOitLg%3D 10.2165/00129785-200303010-00006 12562215
4. Z. Cheng A. Radominska-Pandya T. R. Tephly 1998 Cloning and expression of human UDP-glucuronosyltransferase (UGT) 1A8 Arch. Biochem. Biophys. 356 301 305 1:CAS:528:DyaK1cXlsFCkurs%3D 10.1006/abbi.1998.0781 9705221
5. M. Clavin S. Gorzalczany A. Macho E. Munoz G. Ferraro C. Acevedo V. Martino 2007 Anti-inflammatory activity of flavonoids from Eupatorium arnottianum J. Ethnopharmacol. 112 585 589 1:CAS:528:DC%2BD2sXnsFylsrk%3D 10.1016/j.jep.2007.04.007 17570627
6. E. A. Dierks K. R. Stams H. K. Lim G. Cornelius H. Zhang S. E. Ball 2001 A method for the simultaneous evaluation of the activities of seven major human drug-metabolizing cytochrome P450s using an in vitro cocktail of probe substrates and fast gradient liquid chromatography tandem mass spectrometry Drug Metab. Dispos. 29 23 29 1:CAS:528:DC%2BD3MXpvFGq 11124225
7. V. A. Eagling J. F. Tjia D. J. Back 1998 Differential selectivity of cytochrome P450 inhibitors against probe substrates in human and rat liver microsomes Br. J. Clin. Pharmacol. 45 107 114 1:CAS:528:DyaK1cXhtFSkt7c%3D 10.1046/j.1365-2125.1998.00679.x 9491822
8. C. Guillemette 2003 Pharmacogenomics of human UDP-glucuronosyltransferase enzymes Pharmacogenomics J. 3 136 158 1:CAS:528:DC%2BD3sXks1Cnu7w%3D 10.1038/sj.tpj.6500171 12815363
9. J. Jakobsson L. Ekström N. Inotsume M. Garle M. Lorentzon C. Ohlsson H. K. Roh K. Carlstrom A. Rane 2006 Large differences in testosterone excretion in Korean and Swedish men are strongly associated with UDP- glucuronosyltransferase 2B17 polymorphism J. Clin. Endocrinol. Metab. 91 687 693 1:CAS:528:DC%2BD28XhsFKmsrw%3D 10.1210/jc.2005-1643 16332934
10. M. A. Jeong K. W. Lee D. Y. Yoon Y. J. Surh 2007 Jaceosidin, a pharmacologically active flavone derived from Artemisia argyi, inhibits phorbolester-induced upregulation of COX-2 and MMP-9 by blocking phosphorylation of ERK-1 and -2 in cultured human mammary epithelial cells Ann. N. Y. Acad. Sci. 1095 458 466 1:CAS:528:DC%2BD2sXks1Gku7w%3D 10.1196/annals.1397.049 17404058
11. T. K. Kiang M. H. Ensom T. K. Chang 2005 UDP-glucuronosyltransferase and clinical drug-drug interactions Pharmacol. Ther. 106 97 132 1:CAS:528: DC%2BD2MXisFGlsLk%3D 10.1016/j.pharmthera.2004.10.013 15781124
12. A. R. Kim Y. N. Zou T. H. Park K. H. Shim M. S. Kim N. D. Kim J. D. Kim S. J. Bae J. S. Choi H. Y. Chung 2004 Active components from Artemisia iwayomogi displaying ONOO(-) scavenging activity Phytother. Res. 18 1 7 10.1002/ptr.1358 14750192
13. M. J. Kim D. H. Kim K. W. Lee D. Y. Yoon Y. J. Surh 2007 Jaceosidin induces apoptosis in ras-transformed human breast epithelial cells through generation of reactive oxygen species Ann. N. Y. Acad. Sci. 1095 483 495 1:CAS:528:DC%2BD2sXks1Gku7s%3D 10.1196/annals.1397.052 17404061
14. M. J. Kim J. M. Han Y. Y. Jin N. I. Baek M. H. Bang H. G. Chung M. S. Choi K. T. Lee D. E. Sok T. S. Jeong 2008 In vitro antioxidant and anti-inflammatory activities of jaceosidin from Artemisia princeps Pampanini cv. Sajabal Arch. Pharm. Res. 31 429 437 1:CAS:528:DC%2BD1cXltlWntLs%3D 10.1007/s12272-001-1175-8 18449499
15. H. G. Lee K. A. Yu W. K. Oh T. W. Baeg H. C. Oh J. S. Ahn W. C. Jang J. W. Kim J. S. Lim Y. K. Choe D. Y. Yoon 2005 Inhibitory effect of jaceosidin isolated from Artemisiaargyi on the function of E6 and E7 oncoproteins of HPV 16 J. Ethnopharmacol. 98 339 343 1:CAS:528:DC%2BD2MXivFKrsL4%3D 10.1016/j.jep.2005.01.054 15814270
16. S. H. Lee E. A. Bae E. K. Park Y. W. Shin N. I. Baek E. J. Han H. G. Chung D. H. Kim 2007 Inhibitory effect of eupatilin and jaceosidin isolated from Artemisia princeps in IgE-induced hypersensitivity Int. Immunopharmacol. 7 1678 1684 1:CAS:528:DC%2BD2sXht12nsrfM 10.1016/j.intimp.2007.08.028 17996677
17. W. Lv X. Sheng T. Chen Q. Xu X. Xie 2008 Jaceosidin induces apoptosis in human ovary cancer cells through mitochondrial pathway J. Biomed. Biotechnol. 2008 394802 18769496
18. S. W. Min N. J. Kim N. I. Baek D. H. Kim 2009 Inhibitory effect of eupatilin and jaceosidin isolated from Artemisia princeps on carrageenan-induced inflammation in mice J. Ethnopharmacol. 125 497 500 1:CAS:528: DC%2BD1MXhtFajs73L 10.1016/j.jep.2009.06.001 19505561
19. Miners, J. O. and McKinnon, R. A., CYP1A. In Metabolic Drug Interactions edited by R. H. Levy, K. E. Thummel, W. F. Trager, P. D. Hansten, and M. Eichelbaum. Lippincott Williams & Wilkins, Philadelpia, pp. 61-73, (2000).
20. J. O. Miners R. A. McKinnon P. I. Mackenzie 2002 Genetic polymorphisms of UDP-glucuronosyltransferases and their functional significance Toxicology 181-182 453 456 10.1016/S0300-483X(02)00449-3 12505351
21. J. O. Miners K. M. Knight J. B. Houston P. I. Mackenzie 2006 In vitro-in vivo correlation for drugs and other compounds eliminated by glucuronidation in humans: pitfalls and promises Biochem. Pharmacol. 71 1531 1539 1:CAS:528:DC%2BD28XktVOqtLo%3D 10.1016/j.bcp.2005.12.019 16455060
22. J. O. Miners P. I. Mackenzie K. M. Knight 2010 The prediction of drug-glucuronidation parameters in humans: UDP-glucuronosyltransferase enzyme-selective substrate and inhibitor probes for reaction phenotyping and in vitro-in vivo extrapolation of drug clearance and drug-drug interaction potential Drug Metab. Rev. 42 189 201 10.3109/03602530903210716 19795925
23. V. Moscatelli O. Hnatyszyn C. Acevedo J. Megias M. J. Alcaraz G. Ferraro 2006 Flavonoids from Artemisia copa with anti-inflammatory activity Planta Med. 72 72 74 1:CAS:528:DC%2BD28XisVajur0%3D 10.1055/s-2005-873177 16450301
24. T. Nakasugi M. Nakashima K. Komai 2000 Antimutagens in gaiyou (Artemisia argyi levl. et vant.) J. Agric. Food Chem. 48 3256 3266 1:CAS:528: DC%2BD3cXkvVWgt78%3D 10.1021/jf9906679 10956099
25. A. Parkinson F. Kazmi D. B. Buckley P. Yerino B. W. Ogilvie B. L. Paris 2010 System-dependent outcomes during the evaluation of drug candidates as inhibitors of Cytochrome P450 (CYP) and uridine diphosphate glucuronosyltransferase (UGT) enzymes: human hepatocytes versus liver microsomes versus recombinant enzymes Drug Metab. Pharmacokinet. 25 16 27 1:CAS:528:DC%2BC3cXlsVSmurw%3D 10.2133/dmpk.25.16 20208386
26. G. R. Schinella R. M. Giner M. C. Recio P. Mordujovich de Buschiazzo J. L. Ríos S. Máñez 1998 Anti-inflammatory effects of South American Tanacetum vulgare J. Pharm. Pharmacol. 50 1069 1074 1:CAS:528:DyaK1cXmvVWjsbs%3D 9811170
27. H. Schweikl J. A. Taylor S. Kitareewan P. Linko D. Nagorney J. A. Goldstein 1993 Expression of CYP1A1 and CYP1A2 genes in human liver Pharmacogenetics 3 239 249 1:CAS:528:DyaK2cXhsF2ktrs%3D 10.1097/00008571- 199310000-00003 8287062
28. W. Y. Song N. J. Kim S. Y. Kim H. S. Lee 2009 Liquid chromatography- tandem mass spectrometry for the determination of jaceosidin in rat plasma J. Pharm. Biomed. Anal. 49 381 386 1:CAS:528:DC%2BD1MXhs1als7k%3D 10.1016/j.jpba.2008.10.021 19070985
29. C. P. Strassburg K. Oldhafer M. P. Manns R. H. Tukey 1997 Differential expression of the UGT1A locus in human liver, biliary and gastric tissue: Identification of UGT1A7 and UGT1A10 transcripts in extrahepatic tissues Mol. Pharmacol. 52 212 220 1:CAS:528:DyaK2sXlvVeis70%3D 9271343