Hepatotoxicity of the herbal medicine germander: Metabolic activation of its furano diterpenoids by cytochrome P450 3A depletes cytoskeleton- associated protein thiols and forms plasma membrane blebs in rat hepatocytes

Hepatology

Volumn 24, Issue 1, 1996, Pages 212-218

  Lekehal, Mounia ^a   Pessayre, Dominique ^a   Lereau, Jean Marc ^a   Moulis, Claude ^b   Fourasté, Isabelle ^b   Fau, Daniel ^a  

^a BEAUJON HOSPITAL   (France)

^b UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTINE; CYTOCHROME P450 ISOENZYME; CYTOSKELETON PROTEIN; DEXAMETHASONE; DITERPENOID; FURAN DERIVATIVE; GLUTATHIONE; SULFUR AMINO ACID; TEUCHAMAEDRYN A; TEUCRIN A; THIOL; TROLEANDOMYCIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CELL MEMBRANE; CONTROLLED STUDY; DIET SUPPLEMENTATION; DRUG TOXICITY; FEMALE; HERBAL MEDICINE; LIVER CELL; LIVER TOXICITY; MALE; METABOLIC ACTIVATION; NONHUMAN; PRIORITY JOURNAL; RAT;

EID: 0029994146     PISSN: 02709139     EISSN: None     Source Type: Journal    
DOI: 10.1053/jhep.1996.v24.pm0008707265     Document Type: Article

References (33)

1. Larrey D, Vial T, Pauwels A, Castot A, Biour M, David M, Michel H. Hepatitis after germander (Teucrium chamaedrys) administration: another instance of herbal medicine hepatotoxicity. Ann Intern Med 1992; 117:129-132.
2. Castot A, Larrey D. Hépatites observées au cours d'un traitement par un médicament ou une tisane contenant de la Germandrée petit-chêne. Bilan des 26 cas rapportés aux Centres Régionaux de Pharmacovigilance. Gastroenterol Clin Biol 1992;16:916-922.
3. Mostefa-Kara N, Pauwels A, Pines E, Biour M, Levy VG. Fatal hepatitis after herbal tea. Lancet 1992;340:674.
4. Ben Yahia M, Mavier P, Métreau JM, Zafrani ES, Fabre M, Gatineau-Saillant G, Dhumeaux D, et al. Hépatite chronique active et cirrhose induites par la germandrée petit-chêne. Trois cas. Gastroenterol Clin Biol 1993; 17:959-962.
5. Piozzi F, Rodriguez B, Savona G. Advances in the chemistry of the furano-diterpenoids from Teucrium species. Heterocycles 1987;25:807-841.
6. Loeper J, Descatoire V, Letteron P, Moulis C, Degott C, Dansette P, Fau D, et al. Hepatotoxicity of germander in mice. Gastroenterology 1994;106: 464-472.
7. Kouzi SA, McMurtry RJ, Nelson SD. Hepatotoxicity of germander (Teucrium chamaedrys L.) and one of its constituent neoclerodane diterpenes, teucrin A in the mouse. Chem Res Toxicol 1994;7:850-856.
8. p. Biochemistry 1985;24:2171-2178.
9. Hostetler KA, Wrighton SA, Molowa DT, Thomas PE, Levin W, Guzelian PS. Coinduction of multiple hepatic cytochrome P-450 proteins and their mRNAs in rats treated with imidazole antimycotic agents. Mol Pharmacol 1989;35:279-285.
10. Papanov GY, Malakov PY. Furanoid diterpenes in the bitter fraction of Teucrium chamaedrys. Zeitschrift Naturforschung 1980;35b:764-766.
11. Ulubelen A, Topcu G, Kaya Ü. Steroidal compounds from Teucrium chamaedrys subsp. chamaedrys. Phytochemistry 1994;36:171-173.
12. Greuter W, Burdet HM, Long G. Conservatoire et Jardin Botaniques, Ville de Genève Med-Checklist Trust of OPTIMA. Vol 3. Geneva: Éditions des Conservatoire et Jardin Botaniques de la Ville de Genève, 1984:366-380.
13. Popa DP, Reinbold AM. Bitter substances from Teucrium chamaedrys. Khimiya Prirodnykh Soedinenii 1972;8:67-69.
14. Rodriguez M-C, Barluenga J, Savona G, Piozzi F, Servettaz O, Rodriguez B. Isoteuflidin, a neo-clerodane diterpenoid from Teucrium Chamaedrys, and revised structures of teucrin F and G. Phytochemistry 1984;23:1465-1469.
15. Node M, Sai M, Fujita E. Isolation of the diterpenoid teuflin (6-epiteucvin) from Teucrium viscidum var. miquelianum. Phytochemistry 1981;20:757-760.
16. Fau D, Eugene D, Berson A, Letteron P, Fromenty B, Fisch C, Pessayre D. Toxicity of the antiandrogen flutamide in isolated rat hepatocytes. J Pharmacol Exp Ther 1994;269:954-962.
17. Fau D, Chanez M, Bois-Joyeux B, Delhomme B, Peret J. Effects of excess methionine ingestion on hepatic phosphate, adenine nucleotides and free amino acids in the rat. J Nutr 1982;112:833-840.
18. Berry MN, Friend DS. High-yield preparation of isolated rat liver parenchymal cells. J Biol Chem 1969;43:506-520.
19. Seglen FC. Preparation of isolated rat hepatocyte cells. Methods Cell Biol 1976;13:29-83.
20. Fau D, Berson A, Eugene D, Fromenty B, Fisch C, Pessayre D. Mechanism for the hepatotoxicity of the antiandrogen nilutamide. Evidence suggesting that redox cycling of this nitroaromatic drug leads to oxidative stress in isolated hepatocytes. J Pharmacol Exp Ther 1992;263:69-77.
21. Beliveau GA, Freedland RA. Metabolism of serine, glycine and threonine in isolated cat hepatocytes Felis domestica. Comp Biochem Physiol 1982; 71B:13-18.
22. Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with the Folin phenol reagent. J Biol Chem 1951;193:265-275.
23. Bergmeyer HU, Gawehn K, Grassl M. In: Bergmeyer HU, ed. Methods of enzymatic analysis. Vol. 1. Weinheim: Verlag Chemie, 1974:481-482.
24. Tietze F. Enzymic method for quantitative determination of nanogram amounts of total and oxidized glutathione: applications to mammalian blood and other tissues. Anal Biochem 1969;27:502-522.
25. Bump EA, Taylor YC, Brown JM. Role of glutathione in the hypoxic cell cytotoxicity of misonidasole. Cancer Res 1983;43:997-1002.
26. Mirabelli F, Salis A, Marinoni V, Finardi G, Bellomo G, Thor H, Orrenius S. Menadione-induced bleb formation in hepatocytes is associated with the oxidation of thiol groups in actin. Arch Biochem Biophys 1988;264: 261-269.
27. Gonzales FJ. Molecular genetics of the P-450 superfamily. Pharmacol Ther 1990;45:1-38.
28. Mitchell JR, Potter WZ, Hinson JA, Jollow DJ. Hepatic necrosis caused by furosemide. Nature 1974;251:508-511.
29. Labbe G, Descatoire V, Beaune P, Lettéron P, Larrey D, Pessayre D. Suicide inactivation of cytochrome P-450 by methoxsalen. Evidence for the covalent binding of a reactive intermediate to the protein moiety. J Pharmacol Exp Ther 1989;250:1034-1042.
30. 1 by human liver microsomes. Role of cytochrome P450 IIIA enzymes. Toxicol Appl Pharmacol 1991;108:436-447.
31. Thomassen D, Slattery JT, Nelson SD. Menthofuran-dependent and independent aspects of pulegone hepatotoxicity: roles of glutathione. J Pharmacol Exp Ther 1990;253:567-572.
32. Gores GJ, Herman B, Lemasters JJ. Plasma membrane bleb formation and rupture: a common cause of hepatocellular injury. HEPATOLOGY 1990; 11:690-698.
33. Pessayre D, Dolder A, Artigou JY, Wanscheer JC, Descatoire V, Degott C, Benhamou JP. Effect of fasting on metabolite-mediated hepatotoxicity in the rat. Gastroenterology 1979;77:264-271.