80183-38-6Relevant articles and documents
Biosynthesis of menthofuran in Mentha x piperita: Stereoselective and mechanistic studies
Fuchs, Sabine,Zinn, Silvia,Beck, Thomas,Mosandl, Armin
, p. 4100 - 4105 (1999)
Mentha x piperita shoot tips and first leaf pair were fed with aqueous solutions of [2H2]- and [2H2]/[18O]-labeled pulegone. The essential oil was analyzed by solid phase microextraction and enantioselective multidimensional gas chromatography/mass spectrometry. After feeding experiments with labeled pulegone racemate, both labeled (S)-menthofuran and (R)-menthofuran were detectable simultaneously together with genuine (R)- menthofuran. It could be shown that both labeled pulegone enantiomers are converted by Mentha x piperita to the corresponding labeled menthofuran enantiomers, favoring the labeled analogue of the nongenuine (S)-pulegone. The oxygen in menthofuran is introduced by enzymatic oxidation of pulegone, as concluded from feeding experiments with mixed labeled [2H2]/[18O]pulegone.