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Multi-step bioconversion of annonalide by Fusarium oxysporum f. sp. tracheiphilum and theoretical investigation of the decarboxylase pathway

2019; Elsevier BV; Volume: 1204; Linguagem: Inglês

10.1016/j.molstruc.2019.127514

1872-8014

Akenaton Onassis Cardoso Viana Gomes, Maria Vieira de Brito, Ricardo de Araújo Marques, Leandro B. Lima, Igor Marques Cavalcante, Tellin D.N. Vieira, Fátima Miranda Nunes, Mary Anne Sousa Lima, Daniel E. A. Uchôa, Cristiano S. Lima, Gisele da Silva, José R. Candido-Júnior, Pedro de Lima‐Neto, Marcos Carlos de Mattos, Francisco Lucas Santos de Oliveira, Geancarlo Zanatta, Maria da Conceição Ferreira de Oliveira,

Phytochemical compounds biological activities

Microorganisms can produce a great variety of enzymes in short growing time, and their enzyme complexes have been used in multi-step bioconversions of natural products. Whole cells from different fungal strains were capable of biotransforming diterpenes through a variety of reactions, most of them involving enzymes that promote carbon oxidations. In this paper, we report the first biotransformation of the cytotoxic pimarane-type diterpene annonalide (1) into nor-annonalide (2) by growing cells of the filamentous fungus Fusarium oxysporum f. sp. tracheiphilum (UFCM 0089). Lipase, decarboxylase and alcohol dehydrogenase (ADH) enzymes mediated this unprecedented bioconversion. Theoretical studies (DFT analysis, molecular docking and molecular dynamics) were performed as an attempt to propose a plausive pathway involved on the formation of product 2, and binding interactions of intermediate 1a into the catalytic site of pyruvate decarboxylase enzyme were identified.