Biotransformation of (+)-carvone and (−)-carvone using human skin fungi: A green method of obtaining fragrances and flavours

Abstract

The synthesis of optically pure compounds is increasingly in demand among the pharmaceutical, fine chemical and agro-food industries, while the importance of chirality in the activity and biological properties of many compounds has previously been established. The aim of the present study was therefore to evaluate the biotransformation capacities of (+)-carvone and (−)-carvone using the fungi Scolecobasidium sp, three lines of Cladosporium sp, Phoma sp, Aureobasidium sp and Epicoccum sp, all obtained from human skin. The seven fungi evaluated were capable of hydrogenating the activated alkene, followed by the reduction of ketone to chiral alcohol, with conversions between 9.5 and 100%, and with diastereomer excess (d.e.) of over 89% of dihydrocarveol when (+)-carvone was used as a substrate. These results demonstrate that the filamentous fungi of human skin are potential biocatalytic tools for obtaining chiral alcohols.