Biosynthesis of \beta-substituted furan skeleton in the lower furanoterpenoids: A model study

Gaikwad, NW and Madyastha, KM (2002) Biosynthesis of \beta-substituted furan skeleton in the lower furanoterpenoids: A model study. In: Biochemical and Biophysical Research Communications, 290 (1). pp. 589-594.

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Abstract

Furanoterpenes are widely distributed in the plant kingdom. In this study we have carried out enzymatic synthesis of simple furan compounds from the molecules containing an alpha-isopropylidene ketone unit and the role of cytochrome P450 in this biotransformation has been conclusively established. Eight model compounds (acyclic, monocyclic, and bicyclic, 1-8), having an alpha-isopropylidene ketone unit, were synthesized and incubated with PB-induced rat liver microsomes in the presence of NADPH and O-2. GC-MS and NMR analyses of the product(s) indicated the formation of corresponding furano derivatives (11-18). Cytochrome P450 inhibitors, metyrapone, SKF-525, and carbon monoxide, inhibited the formation of furan (8) to 76, 62, and 97%, respectively. Incubation of dehydrofukinone (7), a aturally occurring terpene, with purified cytochrome P450, NADPH-cytochrome P450 reductase, and dilaurylphosphatidylcholine in the presence of NADPH and O-2 resulted in the formation of 10 and furanodehydrofukinone (19). Based on these observations, we propose one of the probable biosynthetic routes for lower furanoterpenoids in higher plants.

Item Type:	Journal Article
Publication:	Biochemical and Biophysical Research Communications
Publisher:	Academic Press
Additional Information:	Copyright of this article belongs to Elsevier Science.
Keywords:	Monoterpene Ketone;Rat;Cytochrome P-450; Metabolites; Reductase;Epoxide.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	09 Mar 2009 10:37
Last Modified:	19 Sep 2010 05:00
URI:	http://eprints.iisc.ac.in/id/eprint/18195

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