Transformation of menthane monoterpenes by Mentha piperita cell culture

(+)-Isopiperitenone (100 mg l^sup -1^) was converted into (4S,6R)-6-hydroxy- and (4S,8R)-8,9-epoxyisopiperitenone, aside from the already known (+)-7-hydroxyisopiperitenone, by suspension cell culture of Mentha piperita. As (-)-isopiperitenone was hydroxylated similarly, this implies that the hydrox...

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Bibliographic Details
Published in:Biotechnology letters 2002-10, Vol.24 (19), p.1553-1556
Main Authors: KIM, Gwon-Soo, PARK, Si-Hyung, CHANG, Yung-Jin, LIM, Yoong-Ho, KIM, Soo-Un
Format: Article
Language:English
Subjects:
Biological and medical sciences
Biotechnology
Carbonyl compounds
Cell culture
Eukaryotic cell cultures
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
Miscellaneous
Monoterpenes
Plant cells and fungal cells
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Summary:(+)-Isopiperitenone (100 mg l^sup -1^) was converted into (4S,6R)-6-hydroxy- and (4S,8R)-8,9-epoxyisopiperitenone, aside from the already known (+)-7-hydroxyisopiperitenone, by suspension cell culture of Mentha piperita. As (-)-isopiperitenone was hydroxylated similarly, this implies that the hydroxylating enzyme(s) have a broad substrate stereospecificity in regards to the stereochemistry at C4. (-)-(4R)-Carvone was reduced by the Mentha cells both at carbonyl and C1-C6 double bond to give (1R,2S,4R)-neodihydrocarveol and (1R,2R,4R)-dihydrocarveol with the former being the major product. (+)-(4S)-Carvone had a similar reduction pattern, producing (1S,2R,4S)-neodihydrocarveol and (1S,4S)-dihydrocarvone. Formation of these compounds indicates that the peppermint cell culture cannot only hydroxylate the allylic position but also reduce the α,β-unsaturated carbonyl system.[PUBLICATION ABSTRACT]
ISSN:0141-5492
1573-6776
DOI:10.1023/A:1020323304171