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Biocatalytic transformation represents a green approach to the asymmetric hydrogenation of activated alkenes. This paper details catabolic events after the addition of (−)-carvone or (+)-carvone to submerged cultures of Penicillium citrinum and Fusarium oxysporium. These microorganisms were shown to biotransform the isomers of carvone, leading to the formation of a diastereoisomeric excess of derivatives of carvone and reduced carveols, and also to isomerize both dihydrocarvone, and their derivatives dihydrocarveols. [ABSTRACT FROM AUTHOR]

Abstract: The biotransformation of (4R)-(−)-carvone by Mentha pulegium (pennyroyal) leaves and its endophytic bacteria was performed in order to search for novel biocatalysts with enoate reductase activity. The obtained results clearly indicated that endophytes play an important role in the biotransformation of (4R)-(−)-carvone with pennyroyal plant tissues. The best activity was associated to the endophytic bacteria Pseudomonas proteolytica FM18Mci1 and Bacillus sp. FM18civ1. Enoate reductase activity for the reduction of (4R)-(−)-carvone and (4S)-(+)-carvone as model substrates was evaluated for each strain. Finally, both isolated strains were evaluated for the kinetic resolution of racemic carvone. The two bacteria gave (1R, 4R) or (1R, 4S)-dihydrocarvone as major products. P. proteolytica FM18Mci1 had preference for the 4S-(−)-carvone, reaching a conversion 95% in 24 h. In contrast, Bacillus sp. FM18civ1 had preference for (4R)-(−)-carvone. The results obtained in the kinetic resolution of carvone indicated that the Bacillus strain could be useful for resolving a racemic mixture of carvone.Graphical Abstract: [ABSTRACT FROM AUTHOR]