Biogenetic studies in Mentha x piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone. |
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Authors: | S Fuchs T Beck M Sandvoss A Mosandl |
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Affiliation: | Institut für Lebensmittelchemie, Johann Wolfgang Goethe-Universit?t Frankfurt, Germany. |
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Abstract: | Mentha x piperita shoot tips and first leaf pairs were fed with aqueous solutions of different deuterium-labeled pulegone and various enantiomeric distributions. The essential oil was extracted by solid-phase microextraction and analyzed using enantioselective multidimensional gas chromatography/mass spectrometry. The genuine p-menthan-3-ones (-)-menthone and (+)-isomenthone as well as their labeled analogues were analyzed simultaneously. Both enantiomers of labeled pulegone were converted into the corresponding labeled p-menthan-3-ones by Mentha x piperita, indicating an unspecific reduction process. The generation of 4S- and 4R-configured p-menthan-3-ones differed in their stereoselectivities. Labeled (S)-pulegone was reduced by Mentha x piperita more rapidly rather than (R)-pulegone. From a comparison of labeled pulegone enantiomers the bioconversion preferrably led to 4S-configured diastereomers. |
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