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

Article abstract of DOI:10.1246/bcsj.61.869

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-methan-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.