New fungi for whole-cell biotransformation of carvone enantiomers. Novel p-menthane-2,8,9-triols production

• Published in: Applied catalysis. A, General General, 2013-11, Vol.468, p.88-94
• Main Authors: Nunes, Fátima M., dos Santos, Gabriel F., Saraiva, Natália N., Trapp, Marília A., de Mattos, Marcos C., Oliveira, Maria da Conceição F., Rodrigues-Filho, Edson
• Format: Article
• Language: English
• Subjects: Biotransformation; Carvone; Catalysis; Chemistry; Enantiomers; Exact sciences and technology; Fungi; General and physical chemistry; Lasiodiplodia theobromae; Microorganisms; Mucor circinelloides; Nuclear magnetic resonance; p-Menthane-2,8,9-triol; Reduction; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Trichoderma harzianum
• ISSN: 0926-860X; 1873-3875
• DOI: 10.1016/j.apcata.2013.08.034

•Carvone enantiomers were biotransformed by three fungi species.•p-Menthane-2,8,9-triols were produced by L. theobromae and M. circinelloides.•Neodihydrocarveol was the only biotransformation product using T. harzianum.•p-Menthane-2,8,9-triols were produced for the first time by biotransformation. The microbial biotransformation of carvone enantiomers by Lasiodiplodia theobromae, Trichoderma harzianum and Mucor circinelloides was investigated. Biotransformation experiments were conducted using growing or resting fungi cells and the products were analyzed by GC–MS or LC–MS. The isolated compounds were identified by NMR. (S)-Carvone yielded only the enone reduction product dihydrocarvone by M. circinelloides, while (R)-carvone yielded p-menthane-2,8,9-triols when biotransformed by L. theobromae and M. circinelloides. These p-menthanetriols are being reported for the first time as biotransformation products. Neodihydrocarveol was the only product from the biotransformation of (R)-carvone by T. harzianum. These biotransformations can find practical applications, especially in the case of the dihydrocarveol production.