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Chemical Compound Review

Pulegone     5-methyl-2-propan-2-ylidene- cyclohexan-1-one

Synonyms: Pulegon, pulegones, Pulegone, d-, PULEGONE, (D), SureCN58181, ...
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Disease relevance of Pulegon

  • Administration of menthofuran, a known oxidative and hepatotoxic metabolite of pulegone, only marginally affected glutathione levels in plasma and liver, and toxicity was not augmented by buthionine sulfoximine [1].
  • At the two highest doses, pulegone induced atonia, decreased blood creatinine content, lowered terminal body weight and caused histopathological changes in the liver and in the white matter of cerebellum [2].
  • Only pulegone showed antimicrobial activity, particularly against all the Salmonella species [3].

High impact information on Pulegon


Chemical compound and disease context of Pulegon


Biological context of Pulegon

  • [figure: see text] A series of epimeric 8-aryl menthyl derivatives 5a-d and 6a-l, prepared from the same chiral source (R)-pulegone, were employed as chiral auxiliaries in the asymmetric radical cyclization reactions of beta-keto esters mediated by Mn(OAc)3 [9].

Anatomical context of Pulegon


Associations of Pulegon with other chemical compounds

  • Partial characterization of biliary metabolites of pulegone by tandem mass spectrometry. Detection of glucuronide, glutathione, and glutathionyl glucuronide conjugates [13].
  • It could be shown that both labeled pulegone enantiomers are converted by Mentha x piperita to the corresponding labeled menthofuran enantiomers, favoring the labeled analogue of the nongenuine (S)-pulegone [14].

Gene context of Pulegon

  • 1. (R)-(+)-Pulegone is a monoterpene that is oxidized by cytochromes P-450 to reactive metabolites that initiate events in the pathogenesis of hepatotoxicity in mice, rats and humans [15].
  • Pulegone was given orally by gavage to groups of 28 SPF Wistar rats at dosage levels of 0 or 160 mg/kg body weight per day for 28 days [16].

Analytical, diagnostic and therapeutic context of Pulegon


  1. Menthofuran-dependent and independent aspects of pulegone hepatotoxicity: roles of glutathione. Thomassen, D., Slattery, J.T., Nelson, S.D. J. Pharmacol. Exp. Ther. (1990) [Pubmed]
  2. Short term toxicity study in rats dosed with pulegone and menthol. Thorup, I., Würtzen, G., Carstensen, J., Olsen, P. Toxicol. Lett. (1983) [Pubmed]
  3. Antimicrobial activity of the essential oil of Calamintha nepeta and its constituent pulegone against bacteria and fungi. Flamini, G., Cioni, P.L., Puleio, R., Morelli, I., Panizzi, L. Phytotherapy research : PTR. (1999) [Pubmed]
  4. Synthesis of a highly hindered hydrindanone via alpha-carbonyl radical cyclization: enantiospecific formal syntheses of (-)-pinguisenol and (-)-alpha-pinguisene. Sha, C.K., Liao, H.W., Cheng, P.C., Yen, S.C. J. Org. Chem. (2003) [Pubmed]
  5. Metabolic activation of (R)-(+)-pulegone to a reactive enonal that covalently binds to mouse liver proteins. McClanahan, R.H., Thomassen, D., Slattery, J.T., Nelson, S.D. Chem. Res. Toxicol. (1989) [Pubmed]
  6. Inhibitory effects of the essential oil of Mentha pulegium on the isolated rat myometrium. Soares, P.M., Assreuy, A.M., Souza, E.P., Lima, R.F., Silva, T.O., Fontenele, S.R., Criddle, D.N. Planta Med. (2005) [Pubmed]
  7. Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites. Chen, L.J., Lebetkin, E.H., Burka, L.T. Drug Metab. Dispos. (2003) [Pubmed]
  8. Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae). Tak, J.H., Kim, H.K., Lee, S.H., Ahn, Y.J. Pest Manag. Sci. (2006) [Pubmed]
  9. Chiral auxiliaries for asymmetric radical cyclization reactions: application to the enantioselective synthesis of (+)-triptocallol. Yang, D., Xu, M., Bian, M.Y. Org. Lett. (2001) [Pubmed]
  10. In vivo and in vitro destruction of rat liver cytochrome P-450 by a monoterpene ketone, pulegone. Madyastha, P., Moorthy, B., Vaidyanathan, C.S., Madyastha, K.M. Biochem. Biophys. Res. Commun. (1985) [Pubmed]
  11. Antihistaminic activity of pulegone on the guinea-pig ileum. Ortiz de Urbina, A.V., Martin, M.L., Montero, M.J., Carron, R., Sevilla, M.A., San Roman, L. J. Pharm. Pharmacol. (1990) [Pubmed]
  12. Effects of drug metabolism modifiers on pulegone-induced hepatotoxicity in mice. Mizutani, T., Nomura, H., Nakanishi, K., Fujita, S. Res. Commun. Chem. Pathol. Pharmacol. (1987) [Pubmed]
  13. Partial characterization of biliary metabolites of pulegone by tandem mass spectrometry. Detection of glucuronide, glutathione, and glutathionyl glucuronide conjugates. Thomassen, D., Pearson, P.G., Slattery, J.T., Nelson, S.D. Drug Metab. Dispos. (1991) [Pubmed]
  14. Biosynthesis of menthofuran in Mentha x piperita: stereoselective and mechanistic studies. Fuchs, S., Zinn, S., Beck, T., Mosandl, A. J. Agric. Food Chem. (1999) [Pubmed]
  15. Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone. Nelson, S.D., McClanahan, R.H., Thomassen, D., Gordon, W.P., Knebel, N. Xenobiotica (1992) [Pubmed]
  16. Lack of histological cerebellar changes in Wistar rats given pulegone for 28 days. Comparison of immersion and perfusion tissue fixation. Mølck, A.M., Poulsen, M., Tindgard Lauridsen, S., Olsen, P. Toxicol. Lett. (1998) [Pubmed]
  17. Metabolism of (R)-(+)-pulegone in F344 rats. Chen, L.J., Lebetkin, E.H., Burka, L.T. Drug Metab. Dispos. (2001) [Pubmed]
  18. Analysis of pulegone and its enanthiomeric distribution in mint-flavoured food products. Siano, F., Catalfamo, M., Cautela, D., Servillo, L., Castaldo, D. Food additives and contaminants. (2005) [Pubmed]
  19. Hepatotoxicity of pulegone in rats: its effects on microsomal enzymes, in vivo. Moorthy, B., Madyastha, P., Madyastha, K.M. Toxicology (1989) [Pubmed]
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