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Chemical Compound Review

SureCN113711     (6R)-3,6-dimethyl-4,5,6,7...

Synonyms: CPD-4981, CHEBI:6750, AC1L9CWQ, ZINC04098388, FT-0617128, ...
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Disease relevance of C09868


High impact information on C09868

  • Peppermint (Mentha x piperita L.) was independently transformed with a homologous sense version of the 1-deoxy-d-xylulose-5-phosphate reductoisomerase cDNA and with a homologous antisense version of the menthofuran synthase cDNA, both driven by the CaMV 35S promoter [3].
  • METHODS: Sera from each infant were analyzed for the toxic constituents of pennyroyal oil, including pulegone and its metabolite menthofuran [4].
  • Studies in vivo and in vitro with inhibitors and inducers of hepatic cytochromes P-450 demonstrated an association between hepatocellular damage caused by menthofuran and its metabolic activation and covalent binding to target organ proteins [5].
  • Reactive intermediates in the oxidation of menthofuran by cytochromes P-450 [5].
  • Diastereomeric mintlactones also are formed, and studies with H218O and 18O2 indicate that the gamma-ketoenal is a precursor to the mintlactones, as well as other reactive intermediates in the cytochrome P-450 mediated oxidation of menthofuran [5].

Associations of C09868 with other chemical compounds


Gene context of C09868

  • Menthofuran caused a time- and concentration-dependent loss of CYP2A6 activity [6].
  • The menthofuran metabolite formation/CYP2A6 inactivation partition ratio was determined to be 3.5 +/- 0.6 nmol/nmol of P450 [6].
  • Expressed human liver cytochrome (CYP) P-450s (1A2, 2A6, 2C9, 2C19, 2D6, 2E1, and 3A4) were tested for their ability to catalyze the oxidations of pulegone and menthofuran [7].
  • Administration of menthofuran also resulted in a decrease in the levels of liver microsomal cytochrome P-450, whereas cytochrome b5 and NAD(P)H-cytochrome c reductase activities were not affected [8].


  1. Metabolic fate of menthofuran in rats. Novel oxidative pathways. Madyastha, K.M., Raj, C.P. Drug Metab. Dispos. (1992) [Pubmed]
  2. Biotransformations of R-(+)-pulegone and menthofuran in vitro: chemical basis for toxicity. Madyastha, K.M., Raj, C.P. Biochem. Biophys. Res. Commun. (1990) [Pubmed]
  3. Metabolic engineering of essential oil yield and composition in mint by altering expression of deoxyxylulose phosphate reductoisomerase and menthofuran synthase. Mahmoud, S.S., Croteau, R.B. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  4. Multiple organ failure after ingestion of pennyroyal oil from herbal tea in two infants. Bakerink, J.A., Gospe, S.M., Dimand, R.J., Eldridge, M.W. Pediatrics (1996) [Pubmed]
  5. Reactive intermediates in the oxidation of menthofuran by cytochromes P-450. Thomassen, D., Knebel, N., Slattery, J.T., McClanahan, R.H., Nelson, S.D. Chem. Res. Toxicol. (1992) [Pubmed]
  6. (R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6. Khojasteh-Bakht, S.C., Koenigs, L.L., Peter, R.M., Trager, W.F., Nelson, S.D. Drug Metab. Dispos. (1998) [Pubmed]
  7. Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide. Khojasteh-Bakht, S.C., Chen, W., Koenigs, L.L., Peter, R.M., Nelson, S.D. Drug Metab. Dispos. (1999) [Pubmed]
  8. Effects of menthofuran, a monoterpene furan on rat liver microsomal enzymes, in vivo. Madyastha, K.M., Raj, C.P. Toxicology (1994) [Pubmed]
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