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Transformation of a Monoterpene Ketone, (R)-(+)-Pulegone, a Potent Hepatotoxin, in Mucor piriformis

Madyastha, KM and Thulasiram, HV (1999) Transformation of a Monoterpene Ketone, (R)-(+)-Pulegone, a Potent Hepatotoxin, in Mucor piriformis. In: Journal of Agricultural and Food Chemistry, 47 (3). pp. 1203-1207.

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Biotransformation of a monoterpene ketone, (R)-(+)-pulegone (I), a potent hepatotoxin, was studied using a fungal strain, Mucor piriformis. Eight metabolites, namely, 5-hydroxypulegone (II), piperitenone (III), 6-hydroxypulegone (IV), 3-hydroxypulegone (V), 5-methyl-2-(1-hydroxy-1-methylethyl)-2-cyclohexene-1-one (VI), 3-hydroxyisopulegone (VII), 7-hydroxypiperitenone (VIII), and 7-hydroxypulegone (IX), have been isolated from the fermentation medium and identified. GC analysis of the metabolites indicated that II was the major metabolite formed. The organism initiates transformation either by hydroxylation at the C-5 position or by hydroxylation of the ring methylenes, the former being the major activity. On the basis of the identification of the metabolites, pathways for the biotransformation of (R)-(+)-pulegone have been proposed. The mode of transformation of (S)-(-)-pulegone by this organism was shown to be similar to that of its (R)-(+)-enantiomer. When isopulegone (X) was used as the substrate, the organism isomerized it to pulegone (I), which was then transformed to metabolites II-IX.

Item Type: Journal Article
Publication: Journal of Agricultural and Food Chemistry
Publisher: American Chemical Society
Additional Information: Copyright of this article belongs to American Chemical Society.
Keywords: Monoterpene ketone;Biotransformation;Fungal system;Hepatotoxin;Metabolites
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 12 Oct 2007
Last Modified: 19 Sep 2010 04:40
URI: http://eprints.iisc.ac.in/id/eprint/12238

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