Biogenetic Studies in Mentha × piperita. 2. Stereoselectivity in the Bioconversion of Pulegone into Menthone and Isomenthone

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• 作者：Sabine Fuchs ; Thomas Beck ; Martin Sandvoss ; and Armin Mosandl
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：1999
• 出版时间：August 1999
• 年：1999
• 卷：47
• 期：8
• 页码：3058 - 3062
• 全文大小：76K
• 年卷期：v.47,no.8(August 1999)
• ISSN：1520-5118

文摘

Mentha × piperita shoot tips and first leaf pairs were fed with aqueous solutions of differentdeuterium-labeled pulegone and various enantiomeric distributions. The essential oil was extractedby solid-phase microextraction and analyzed using enantioselective multidimensional gas chromatography/mass spectrometry. The genuine p-menthan-3-ones (-)-menthone and (+)-isomenthoneas well as their labeled analogues were analyzed simultaneously. Both enantiomers of labeledpulegone were converted into the corresponding labeled p-menthan-3-ones by Mentha × 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 × piperitamore rapidly rather than (R)-pulegone. From a comparison of labeled pulegone enantiomers thebioconversion preferrably led to 4S-configured diastereomers.Keywords: Bioconversion; deuterium-labeled pulegone; Mentha × piperita biosynthesis; enantioselective multidimensional gas chromatography/mass spectrometry (enantio-MDGC/MS)