Metabolism of monoterpenes: demonstration that (+)-cis-isopulegone, not piperitenone, is the key intermediate in the conversion of (-)-isopiperitenone to (+)-pulegone in peppermint (Mentha piperita)

Archives of Biochemistry and Biophysics
R Croteau, K V Venkatachalam

Abstract

Piperitenone is commonly considered to be the key intermediate in the conversion of (-)-isopiperitenone to (+)-pulegone in peppermint; however, [3H]piperitenone gave rise only to the inert metabolite (+)-piperitone when incubated with peppermint leaf discs. Under identical conditions, (-)-[3H]isopiperitenone was efficiently incorporated into (+)-pulegone, (-)-menthone, and (+)-isomenthone in leaf discs, and yielded an additional metabolite identified as (+)-cis-isopulegone; piperitenone was poorly labeled. Moreover, (+)-cis-[3H]isopulegone was rapidly converted to (+)-pulegone, (-)-menthone, and (+)-isomenthone in leaf discs, and the reduction of (+)-[3H]pulegone to (-)-menthone and (+)-isomenthone was similarly documented. Each step of the pathway was demonstrated in a crude soluble preparation from peppermint leaf epidermis and each of the relevant enzymes was partially purified in order to compare relative rates of catalysis. The results of these studies indicate that the endocyclic double bond of (-)-isopiperitenone is reduced to yield (+)-cis-isopulegone, which is isomerized to (+)-pulegone as the immediate precursor of (-)-menthone and (+)-isomenthone, and they rule out piperitenone as an intermediate of the pathway.

References

Jan 1, 1961·Journal of Pharmaceutical Sciences·R H REITSEMAW CHORNEY
Aug 19, 1961·Biochimica Et Biophysica Acta·J BATTAILEW D LOOMIS
Aug 19, 1961·Biochimica Et Biophysica Acta·J BATTAILE, W D LOOMIS

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Citations

Jun 1, 1994·Journal of Chemical Ecology·J Gershenzon
Nov 18, 2005·Die Naturwissenschaften·Rodney B CroteauMark R Wildung
Jan 13, 2000·Plant Physiology·J GershenzonR B Croteau
Nov 19, 2003·Proceedings of the National Academy of Sciences of the United States of America·Soheil S Mahmoud, Rodney B Croteau
Jan 3, 2015·Natural Product Research·K B RameshkumarV George
Nov 7, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Matthew E BergmanMichael A Phillips
Oct 28, 1988·Journal of Chromatography·D M Satterwhite, R B Croteau

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