Fukinolic acid derivatives and triterpene glycosides from black cohosh inhibit CYP isozymes, but are not cytotoxic to Hep-G2 cells in vitro

Current Drug Safety

Volumn 5, Issue 2, 2010, Pages 118-124

  Huang, Yue ^a   Jiang, Bei ^b   Nuntanakorn, Paiboon ^b   KennellY , Edward J ^b   Shord, Stacy ^a   Lawal, Temitope O ^c   SonI , Kapil K ^a   Mahady, Gail B ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b CITY UNIVERSITY OF NEW YORK   (United States)

^c UNIVERSITY OF IBADAN   (Nigeria)

Author keywords

Black cohosh; Cytochrome P450; HepatotoxicitY.; Herb drug interactions; Menopause

Indexed keywords

2 PROPANOL; 23 EPI 26 DEOXYACTEIN; ACTEIN; ALCOHOL; CIMICIFUGA RACEMOSA EXTRACT; CIMICIFUGIC ACID A; CIMICIFUGIC ACID B; CIMIRACEMOSIDE A; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; FUKINOLIC ACID; GLYCOSIDE; RESVERATROL; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CELL GROWTH; CELL STRAIN HEPG2; CIMICIFUGA RACEMOSA; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIET SUPPLEMENTATION; DRUG INHIBITION; DRUG ISOLATION; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME ASSAY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LIVER CELL CARCINOMA; LIVER TOXICITY; PRIORITY JOURNAL;

EID: 77950813145     PISSN: 15748863     EISSN: None     Source Type: Journal    
DOI: 10.2174/157488610790936150     Document Type: Article

References (41)

1. Guay MP, Dragomir A, Pilon D, Moride Y, Perreault S. Changes in pattern of use, clinical characteristics and persistence rate of hormone replacement therapy among postmenopausal women after the WHI publication. Pharmacoepidemiol Drug Saf 2007; 16: 17-27.
2. Houmard BS, Seifer DB. Predicting the Onset of Menopause. In: Seifer DB and Kennard EA Eds, Menopause: Endocrinology and Management, Totwa, New Jersey: Humana Press 1999; 1-19.
3. Doyle BJ, Mahady GB. Phytotherapies for menopause. Drugs of the Future 2007; 32: 897-905.
4. Locklear TD, Doyle BJ, Caceres A, Perez A, Mahady GB. Menopause a universal female experience: lessons from central america. Curr Rev Women's Health 2007; 4: 1-10.
5. Mahady GB. Black cohosh (Actaea racemosa): review of the clinical data for safety and efficacy in menopausal symptoms. Treat Endocrinol 2005; 4: 177-184
6. Kronenberg F, Fugh-Berman A. Complementary and alternative medicine for menopausal symptoms: a review of randomized, controlled trials. Ann Intern Med 2002; 137: 805-813
7. Low Dog T, Powell KL, Weisman SM. Critical evaluation of the safety of Cimicifuga racemosa in menopause symptom relief. Menopause 2003; 10: 299-313.
8. Mahady GB, Low Dog T, Barrett ML, et al. United States Pharmacopoeia review of the black cohosh case reports of hepatoxicity. Menopause 2008; 15: 628-638
9. Teschke R, Bahre R, Genthner A, Fuchs J, Schmidt-Taenzer W, Wolff A. Suspected black cohosh hepatotoxicity--challenges and pitfalls of causality assessment. Maturitas 2009; 63: 302-314
10. Borrelli F, Ernst E. Black cohosh (Cimicifuga racemosa) for menopausal symptoms: a systematic review of its efficacy. Pharmacol Res 2008; 58: 8-14.
11. Palacio C, Masri G, Mooradian AD. Black cohosh for the management of menopausal symptoms: a systematic review of clinical trials. Drugs Aging 2009; 26: 23-36.
12. Geller SE, Shulman LP, van Breemen RB, et al. Safety and efficacy of black cohosh and red clover for the management of vasomotor symptoms: a randomized controlled trial. Menopause 2009; 16: 1156-1166
13. Newton KM, Reed SD, LaCroix AZ, Grothaus LC, Ehrlich K, Guiltinan J. Treatment of vasomotor symptoms of menopause with black cohosh, multibotanicals, soy, hormone therapy, or placebo: a randomized trial. Ann Intern Med 2006; 145: 869-879
14. Prendy ML, De Angelis P, Chamberlain JL. Black cohosh Actaea racemosa: an annotated bibliography. Gen. Tech. Rep. SRS-97. Asheville, NC: U.S. Department of Agriculture Forest Service, Southern Research Station. 2006; 1-99.
15. Strandell, J, Neil A, Carlin G. An approach to the in vitro evaluation of potential for cytochrome P450 enzyme inhibition from herbals and other natural remedies. Phytomed 2004; 11: 98-104.
16. Venkatakrishnan K, Von Moltke LL, Greenblatt DJ. Human drug metabolism and the cytochromes P450: application and relevance of in vitro models. J Clin Pharmacol 2001; 41: 1149-1179
17. Gaube F, Wolfl S, Pusch L, Kroll TC, Hamburger M. Gene expression profiling reveals effects of Cimicifuga racemosa (L.) NUTT. (black cohosh) on the estrogen receptor positive human breast cancer cell line MCF-7. BMC Pharmacol 2007; 7: 11-21.
18. Gurley BJ, Gardner SF, Hubbard MA, et al. In vivo effects of goldenseal, kava kava, black cohosh, and valerian on human cytochrome P450 1A2, 2D6, 2E1, and 3A4/5 phenotypes. Clin Pharmacol Ther 2005; 77: 415-426
19. Gurley B, Hubbard MA, Williams DK, et al. Assessing the clinical significance of botanical supplementation on human cytochrome P450 3A activity: comparison of a milk thistle and black cohosh product to rifampin and clarithromycin. J Clin Pharmaco 2006; 46: 201-213
20. Gurley BJ, Swain A, Hubbard MA, et al. Clinical assessment of CYP2D6-mediated herb-drug interactions in humans: effects of milk thistle, black cohosh, goldenseal, kava kava, St. John's wort, and Echinacea. Mol Nutr Food Res 2008; 52: 755-763
21. Jiang B, Kronenberg F, Nuntanakorn P, Qiu MH, Kennelly EJ. Evaluation of the botanical authenticity and phytochemical profile of black cohosh products by high-performance liquid chromatography with selected ion monitoring liquid chromatography-mass spectrometry. J Agric Food Chem 2006; 54: 3242-3253
22. Chen SN, Li W, Fabricant DS, et al. Isolation, structure elucidation, and absolute configuration of 26-deoxyactein from Cimicifuga racemosa and clarification of nomenclature associated with 27-deoxyactein. J Nat Prod 2002; 65: 601-605
23. Nuntanakorn P, Jiang B, Einbond LS, et al. Polyphenolic constituents of Actaea racemosa. J Nat Prod 2006; 69: 314-318
24. Foster BC, Vandenhoek S, Hana J, et al. In vitro inhibition of human cytochrome P450-mediated metabolism of marker substrates by natural products. Phytomedicine 2003; 10: 334-342
25. Crespi CL, Miller VP, Penman BW. Microtiter plate assays for inhibition of human drug metabolizing cytochromes P450. Anal Biochem 1997; 248: 188-190
26. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63.
27. Yueh MF, Kawahara M, Raucy J. Cell-based high-throughput bioassays to assess induction and inhibition of CYP1A enzymes. Toxicol In Vitro 2005; 19: 275-287
28. Baldwin SJ, Bloomer JC, Smith GJ, Ayrton AD, Clarke SE, Chenery RJ. Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9. Xenobiotica 1995; 25: 261-267
29. Bourrié M, Meunier V, Berger Y, Fabre G. Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J Pharmacol Exp Ther 1996; 277: 321-332
30. Masubuchi Y, Hosokawa S, Horie T, et al. Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metab Dispos 1994; 22: 909-915
31. Yin H, Racha J, Li SY, Olejnik N, Satoh H, Moore D. Automated high throughput human CYP isoform activity assay using SPELC/ MS method: application in CYP inhibition evaluation. Xenobiotica 2000; 30: 141-154
32. Tsukamoto S, Aburatani M, Ohta T. Isolation of CYP3A4 Inhibitors from the black cohosh (Cimicifuga racemosa). Evid Based Complement Alternat Med 2005; 2: 223-226
33. Lüde S, Török M, Dieterle S, et al. Hepatic effects of Cimicifuga racemosa extract in vivo and in vitro. Cell Mol Life Sci 2007; 64: 2848-2857
34. Fabricant DS, Nikolic D, Lankin DC, et al. Cimipronidine, a cyclic guanidine alkaloid from Cimicifuga racemosa. J Nat Prod 2005; 68: 1266-1267
35. Burdette JE, Liu J, Chen SN, et al. Black cohosh acts as a mixed competitive ligand and partial agonist of the serotonin receptor. J Agric Food Chem 2003; 51: 5661-5670
36. Spina E, Santoro V, D'Arrigo C. Clinically relevant pharmacokinetic drug interactions with second-generation antidepressants: an update. Clin Ther 2008; 30: 1206-1227
37. Stedman C. Herbal hepatotoxicity. Semin Liver Dis 2002; 22: 195-206.
38. Chitturi S, Farrell GC. Herbal hepatotoxicity: an expanding but poorly defined problem. J Gastroenterol Hepatol 2000; 15: 1093-1099
39. Harris RZ, Benet LZ, Schwartz JB. Gender effects in pharmacokinetics and pharmacodynamics. Drugs 1995; 50: 222-239
40. Tanaka E. Gender-related differences in pharmacokinetics and their clinical significance. J Clin Pharm Ther 1999; 24: 339-346
41. Scandlyn MJ, Stuart EC, Rosengren RJ. Sex-specific differences in CYP450 isoforms in humans. Expert Opin Drug Metab Toxicol 2008; 4: 413-424