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Enantioselective monoterpene alcohol acetylation in Origanum, Mentha and Salvia species

Author:
Larkov, Olga, Zaks, Alon, Bar, Einat, Lewinshon, Efraim, Dudai, Nativ, Mayer, Alfred M., Ravid, Uzi
Source:
Phytochemistry 2008 v.69 no.14 pp. 2565-2571
ISSN:
0031-9422
Subject:
Origanum, Origanum majorana, Origanum vulgare, Origanum onites, Mentha, Mentha piperita nothosubsp. citrata, Salvia, monoterpenoids, alcohols, volatile organic compounds, acetylation, acetates, acyltransferases, enzyme activity, enzyme substrates, substrate specificity
Abstract:
Selected plants within the Origanum, Mentha and Salvia genera, that contain significant amounts of chiral volatile alcohols and their related acetates, exhibit remarkable enantioselectivity of alcohol acetyl transferase (AAT) activity and particularly can discriminate between linalool enantiomers. Origanum dayi AAT produced almost enantiomerically pure (R)-linalyl acetate by enzymatic acetylation of racemic linalool, whereas the closely related O. majorana AAT produced a mixture of (R)- and (S)-linalyl acetate with a ratio of 6:4. Vmax of O. dayi acetylation activity was 30-fold higher for (R)-linalool, whereas in O. majorana no such differences were found.
Agid:
744223