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Transformation of a monoterpene ketone, piperitenone, and related terpenoids using Mucor piriformis

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Abstract:

Biotransformation of piperitenone (I), 5,5-dimethyl-2-(1-methylethylidene)-cyclohexanone (II), and 2-(1-ethyl-1-propylidene)-5-methylcyclohexanone (III) was studied using a versatile fungal strain, Mucor piriformis. The organism initiates transformation of these compounds by hydroxylation at the allylic positions or at the tertiary carbon. Transformation of piperitenone (I) by this strain yielded 5-hydroxypiperitenone (Ic), 7-hydroxypiperitenone (Id), 7-hydroxypulegone (Ie), 10-hydroxypiperitenone (If), and 4-hydroxypiperitenone (Ig) as metabolites. It was possible to block some of the metabolic activities of the organism through structural modification of piperitenone (I). This was evidenced by the fact that biotransformation of 5,5-dimethyl-2-(1-methylethylidene)-cyclohexanone (II) yielded 5,5-dimethyl-2-(1-hydroxy-1-methylethyl)-2-cyclohexen-1-one (IIb) and 5,5-dimethyl-3-hydroxy-2-(1-methylethylidene)-cyclohexanone (IIa), whereas 2-(1-ethyl-1-propylidene)-5-methylcyclohexanone (III) yielded 6-(1-ethyl-1-propylidene)-5-methyl-2-cyclohexen-1-one (IIIb) and 6-(1-ethyl-1-propylidene)-5-hydroxy-5-methylcyclohexanone (IIIa) as metabolites. Based on the identification of the metabolites, pathways for the biotransformation of I, II, and III have been proposed. The mode of biotransformation of these compounds by M. piriformis also compared to their modes of metabolism in the rat system.Key words: piperitenone, monoterpene ketone, biotransformation, fungal system, metabolites.

La biotransformation du piperitenone (I), du 5,5-diméthyl-2-(1-méthyléthylidène)-cyclohexanone (II) et du 2-(1-éthyl-1-propylidène)-5-méthylcyclohexanone (III) a été étudiée à l'aide d'une souche de champignon versatile, Mucor piriformis. L'organisme amorce la transformation de ces composés par l'hydroxylation aux positions allyliques ou au niveau du carbone tertiaire. La transformation du piperitenone (I) par cette souche a produit le 5-hydroxypiperitenone (Ic), le 7-hydroxypiperitenone (Id), le 7-hydroxypulegone (Ie), le 10-hydroxypiperitenone (If) et le 4-hydroxypiperitenone (Ig) comme métabolites. Il est possible de bloquer certaines des activités métaboliques de l'organisme par la modification structurale du piperitenone (I). Ceci fut démontré par le fait que la biotransformation du 5,5-diméthyl-2-(1-méthyléthylidène)-cyclohexanone (II) a produit du 5,5-diméthyl-2-(1-hydroxy-1-méthyléthyl)-2-cyclohexen-1-one (IIb) et du 5,5-diméthyl-3-hydroxy-2-(1-méthyléthylidène)-cyclohexanone (IIa) alors que le 2-(1-éthyl-1-propylidène)-5-méthylcyclohexanone (III) a produit du 6-(1-éthyl-1-propylidène)-5-méthyl-2-cyclohexen-1-one (IIIb) et du 6-(1-éthyl-1-propylidène)-5-hydroxy-5-méthylcyclohexanone (IIIa) comme métabolites. Selon l'identification des métabolites, des voies de biotransformation des composés I, II et III ont été proposées. Le mode de biotransformation de ces composés par M. piriformis était comparable à ses modes de métabolisme dans le système du rat.Mots clés : piperitenone, cétone monoterpène, biotransformation, système fongique, métabolites.[Traduit par la Rédaction]

Document Type: Research Article

Publication date: June 1, 2005

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  • Published since 1954, this monthly journal contains new research in the field of microbiology including applied microbiology and biotechnology; microbial structure and function; fungi and other eucaryotic protists; infection and immunity; microbial ecology; physiology, metabolism and enzymology; and virology, genetics, and molecular biology. It also publishes review articles and notes on an occasional basis, contributed by recognized scientists worldwide.
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