Biogenetic studies in Mentha x piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone.
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.
Fuchs
S
S
Institut für Lebensmittelchemie, Johann Wolfgang Goethe-Universität Frankfurt, Germany.
Beck
T
T
Sandvoss
M
M
Mosandl
A
A
D001711:Biotransformation; D000081005:Cyclohexane Monoterpenes; D007536:Isomerism; D019686:Lamiaceae / Q000378:metabolism*; D019684:Magnoliopsida / Q000378:metabolism; D008610:Menthol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D039821:Monoterpenes; D013729:Terpenes / Q000737:chemistry / Q000378:metabolism*
D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D013729:Terpenes; D008610:Menthol; C039648:pulegone; C019466:menthone