Disease relevance of C09868

• Menthofuran (II) was administered orally (200 mg/kg of the body weight/day) to rats for 3 days [1].
• Biotransformations of R-(+)-pulegone and menthofuran in vitro: chemical basis for toxicity [2].

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

• On the basis of both in vivo and in vitro studies, a possible mechanism for the formation of p-cresol from menthofuran has been proposed [1].

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].

References