Enantioselectivity in the Biotransformation of Mono- and Bicyclic Monoterpenoids with the Cultured Cells of Nicotiana tabacum

The biotransformation of the enantiomeric pairs of p-menthane and bicyclo[2.2.1] and [3.1.1]heptane derivatives with the cultured cells of Nicotiana tabacum was investigated. It was found that (i) the cultured cells discriminate the enantiomers of p-menthan-2-ol and bicyclo[2.2.1]heptan-2-ol and bicyclo[3.1.1]heptan-3-ol derivatives, and enantioselectively convert these alcohols to the corresponding ketones, (ii) the cells reduce the carbonyl group of p-menthan-2-one derivatives to a high extent, but not that of p-menthan-3-ones, and (iii) the cells discriminate the enantiomers of bicyclo[3.1.1]hept-2-en-4-one (verbenone) and enantioselectively reduce the C–C double bond of the (1S,5S)-enantiomer.