Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 22, 1992 - Issue 9-10
65
Views
27
CrossRef citations to date
0
Altmetric
Research Article

Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone

, , , &
Pages 1157-1164 | Received 05 Oct 1990, Accepted 24 Apr 1992, Published online: 22 Sep 2008

References

  • Feely T.M., Hargreaves M.K. Circular dichroism studies. The pulegone epoxides. Journal of the Chemical Society (C) 1970; 1745–1750
  • Gleason M.N., Gosselin R.E., Hodge H.C., Smith R.P. Therapeutics Index. Clinical Toxicology of Commercial Products, 3rd edn. Williams & Wilkins, Baltimore 1969; 109
  • Gold J., Cates W. Herbal abortifacients. Journal of the American Medical Association 1980; 243: 1365–1366
  • Gordon W.P., Forte A.J., McMurtry R.J., Gal J., Nelson S.D. Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse. Toxicology and Applied Pharmacology 1982; 65: 413–424
  • Gordon W.P., Huitric A.C., Seth C.L., McClanahan R.H., Nelson S.D. The metabolism of the abortifacient terpene, (R)-(+)-pulegone, to a proximate toxin, menthofuran. Drug Metabolism and Disposition 1987; 15: 589–594
  • Grundschober F. Literature review of pulegone. Perfumer Flavorist 1979; 4: 15–17
  • Gunby P. Plant known for centuries still causes problems today. Journal of the American Medical Association 1979; 241: 2246–2247
  • Hall R.A., Oser B.L. Recent progress in the consideration of flavoring ingredients under the food additives amendment III Gras substances. Food Technology 1965; 19: 253–271
  • Hirsch J.A., Szur A.J. The hydrolysis of α,α'-dimethoxydihydrofurans. Journal of Heterocyclic Chemistry 1972; 9: 523–529
  • Jones J.P., Korzekwa K.R., Rettie A.E., Trager W.F. Isotopically sensitive branching and its effect on the observed intramolecular isotope effects in cytochrome P-450 catalyzed reactions: A new method for the estimation of intrinsic isotope effects. Journal of the American Chemical Society 1986; 108: 7074–7078
  • Madyastha K.M., Moorthy B. Pulegone mediated hepatotoxicity: Evidence for covalent binding of (R)-(+)-[14C] pulegone to microsomal proteins, in vitro. Chemico-Biological Interactions 1989; 72: 325–333
  • McClanahan R.H., Huitric A.C., Pearson P.G., Desper J.C., Nelson S.D. Evidence for a cytochrome P-450 catalyzed allylic rearrangement with double bond topomerization. Journal of the American Chemical Society 1988; 110: 1979–1981
  • McClanahan R.H., Thomassen D., Slattery J.T., Nelson S.D. Metabolic activation of (R)-(+)-pulegone to a reactive enonal that covalently binds to mouse liver proteins. Chemical Research in Toxicology 1989; 2: 349–355
  • Miwa C.T., Lu A. Y. H. Kinetic isotope effects and ‘metabolic switching’ in cytochrome P-450-catalyzed reactions. BioAssays 1987; 7: 215–219
  • Mizutani T., Nomura H., Nakanishi K., Fujita S. Effects of drug metabolism modifiers on pulegone-induced hepatotoxicity in mice. Research Communications in Chemical Pathology and Pharmacology 1987; 58: 75–83
  • Moorthy B., Madyastha P., Madyastha K.M. Metabolism of a monoterpene ketone, (R)-(+)-pulegone, a hepatotoxin in rat. Xenobiotica 1989; 19: 217–224
  • Nakanishi O., Fujitani M., Ichimoto I., Ueda H. An improved process for the synthesis of piperitenone from mesityloxide and methyl vinyl ketone. Agricultural and Biological Chemistry 1980; 44: 1667–1671
  • Nelson S.D., Gordon W.P. Mammalian drug metabolism. Journal of Natural Products 1983; 46: 71–78
  • Ruzo L.O., Casida J.E., Holden I. Direct N.M.R. detection of an epoxyfuran intermediate in peracid oxidation of the fungicide methfuroxam. Journal of the Chemical Society, Chemical Communications 1985; 1642–1643
  • Sullivan J.B., Rumack B.H., Thomas H., Peterson R.G., Brysch P. Pennyroyal oil poisoning and hepatotoxicity. Journal of the American Medical Association 1979; 242: 2873–2874
  • Takahashi K., Someya T., Muraki S., Yoshida T. A new keto-alcohol, (−)-mintlactone, (+)-isomintlactone and minor components in peppermint oil. Agricultural and Biological Chemistry, 44: 1535–1543
  • Thomassen D., Slattery J.T., Nelson S.D. Contribution of menthofuran to the hepatotoxicity of pulegone: Assessment based on matched area under the curve and on matched time course. Journal of Pharmacology and Experimental Therapeutics 1988; 224: 825–829
  • Vallance W.B. Pennyroyal oil poisoning: a fatal case. Lancet 1955; ii: 850–851
  • Watt J.M., Breyer-Brandwijk M.G. The Medicinal and Poisonous Plants of Southern and Eastern Africa, 2nd edn. E. & S. Livingstone, London 1962; 523

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.