Protein Information

Name cytochrome P450 (protein family or complex)
Synonyms cytochrome P450; cytochrome P 450; CYP450; CYP 450

Compound Information

Name carvone
CAS 2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one

Reference List

PubMed Abstract RScore(About this table)
8820855 Lupien S, Karp F, Ponnamperuma K, Wildung M, Croteau R: Cytochrome P450 limonene hydroxylases of Mentha species. Drug Metabol Drug Interact. 1995;12(3-4):245-60.

In peppermint, C3-allylic hydroxylation leads to (-)-trans-isopiperitenol that ultimately is converted to (-)-menthol, whereas in spearmint, C6-allylic hydroxylation leads to (-)-trans-carveol that is oxidized to (-)-carvone.
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2541521 Moorthy B, Madyastha P, Madyastha KM: Hepatotoxicity of pulegone in rats: its effects on microsomal enzymes, in vivo. Toxicology. 1989 May 15;55(3):327-37.

Oral administration of pulegone (400 mg/kg) to rats once daily for five days caused significant decreases in the levels of liver microsomal cytochrome P-450 and heme.
Menthone or carvone (600 mg/kg), compounds related to pulegone, when administered orally did not cause any decrease in cytochrome P-450 levels.
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10864450 Haudenschild C, Schalk M, Karp F, Croteau R: Functional expression of regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha spp.) in Escherichia coli and saccharomyces cerevisiae. Arch Biochem Biophys. 2000 Jul 1;379(1):127-36.

In spearmint (M. spicata), C6-allylic hydroxylation leads to (-)-trans-carveol and thence (-)-carvone, whereas in peppermint (M. x piperita), C3-allylic hydroxylation leads to (-)-trans-isopiperitenol and ultimately (-)-menthol. cDNAs encoding the C6-hydroxylase and C3-hydroxylase from spearmint and peppermint, respectively, were isolated by a combination of reverse genetic and homology-based cloning methods (S.
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15516593 Warren R, Hsiao WW, Kudo H, Myhre M, Dosanjh M, Petrescu A, Kobayashi H, Shimizu S, Miyauchi K, Masai E, Yang G, Stott JM, Schein JE, Shin H, Khattra J, Smailus D, Butterfield YS, Siddiqui A, Holt R, Marra MA, Jones SJ, Mohn WW, Brinkman FS, Fukuda M, Davies J, Eltis LD: Functional characterization of a catabolic plasmid from polychlorinated- biphenyl-degrading Rhodococcus sp. strain RHA1. J Bacteriol. 2004 Nov;186(22):7783-95.

Consistent with this prediction, RHA1 grew on limonene, carveol, or carvone as the sole carbon source.
The plasmid carries three cytochrome P450-encoding (CYP) genes, a finding consistent with the high number of CYP genes found in other actinomycetes.
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11090685 van der Werf MJ, Keijzer PM, van der Schaft PH: Xanthobacter sp. J Biotechnol. 2001 Nov 30;84(2):133-43.


Cytochrome P-450 was shown to be induced concomitantly with limonene bioconversion activity following growth of Xanthobacter sp.
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3994727 Madyastha P, Moorthy B, Vaidyanathan CS, Madyastha KM: In vivo and in vitro destruction of rat liver cytochrome P-450 by a monoterpene ketone, pulegone. Biochem Biophys Res Commun. 1985 Apr 30;128(2):921-7.

In contrast, menthone or carvone upon incubation with PB-induced microsomes resulted in the conversion (25-40%) of cyt.
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15618705 Shimada T, Shindo M, Miyazawa M: Species differences in the metabolism of (+)- and (-)-limonenes and their metabolites, carveols and carvones, by cytochrome P450 enzymes in liver microsomes of mice, rats, guinea pigs, rabbits, dogs, monkeys, and humans. Drug Metab Pharmacokinet. 2002;17(6):507-15.

Reconstituted monooxygenase systems containing purified rabbit CYP1A2 and 2B4 and NADPH-P450 reductase were found to catalyze (+)-limonene to (+)-carveol, (+)-carvone, and (+)-perillyl alcohol, being more active with CYP2B4.
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15734920 Ringer KL, Davis EM, Croteau R: Monoterpene metabolism. Plant Physiol. 2005 Mar;137(3):863-72. Epub 2005 Feb 25.

The essential oils of peppermint (Mentha x piperita) and spearmint (Mentha spicata) are distinguished by the oxygenation position on the p-menthane ring of the constitutive monoterpenes that is conferred by two regiospecific cytochrome P450 limonene-3- and limonene-6-hydroxylases.
Following hydroxylation of limonene, an apparently similar dehydrogenase oxidizes (-)-trans-isopiperitenol to (-)-isopiperitenone in peppermint and (-)-trans-carveol to (-)-carvone in spearmint.
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