Biotransformation of labdane and halimane diterpenoids by two filamentous fungi strains.

Autor:	Monteiro AF; Núcleo de Bioensaios, Biossíntese e Ecofisiologia de Produtos Naturais (NuBBE), Universidade Estadual Paulista (UNESP), Instituto de Química, Departamento de Química Orgânica, Francisco Degni 55, Araraquara, 14800-900, Brazil., Seidl C; Departamento de Química, Grupo de Cromatografia de Bioafinidade e Produtos Naturais, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, 14040-901, São Paulo, Brazil., Severino VGP; Universidade Federal de Goiás (UFG), Instituto de Química, Campus Samambaia, Goiânia, 74690-900, Brazil., Cardoso CL; Departamento de Química, Grupo de Cromatografia de Bioafinidade e Produtos Naturais, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, 14040-901, São Paulo, Brazil., Castro-Gamboa I; Núcleo de Bioensaios, Biossíntese e Ecofisiologia de Produtos Naturais (NuBBE), Universidade Estadual Paulista (UNESP), Instituto de Química, Departamento de Química Orgânica, Francisco Degni 55, Araraquara, 14800-900, Brazil.
Jazyk:	angličtina
Zdroj:	Royal Society open science [R Soc Open Sci] 2017 Nov 08; Vol. 4 (11), pp. 170854. Date of Electronic Publication: 2017 Nov 08 (Print Publication: 2017).
DOI:	10.1098/rsos.170854
Abstrakt:	Biotransformation of natural products by filamentous fungi is a powerful and effective approach to achieve derivatives with valuable new chemical and biological properties. Although diterpenoid substrates usually exhibit good susceptibility towards fungi enzymes, there have been no studies concerning the microbiological transformation of halimane-type diterpenoids up to now. In this work, we investigated the capability of Fusarium oxysporum (a fungus isolated from the rhizosphere of Senna spectabilis ) and Myrothecium verrucaria (an endophyte) to transform halimane ( 1 ) and labdane ( 2 ) acids isolated from Hymenaea stigonocarpa (Fabaceae). Feeding experiments resulted in the production of six derivatives, including hydroxy, oxo, formyl and carboxy analogues. Incubation of 1 with F. oxysporum afforded 2-oxo-derivative ( 3 ), while bioconversion with M. verrucaria provided 18,19-dihydroxy ( 4 ), 18-formyl ( 5 ) and 18-carboxy ( 6 ) bioproducts. Transformation of substrate 2 mediated by F. oxysporum produced a 7 α -hydroxy ( 7 ) derivative, while M. verrucaria yielded 7 α - ( 7 ) and 3 β -hydroxy ( 8 ) metabolites. Unlike F. oxysporum , which showed a preference to transform ring B, M. verrucaria exhibited the ability to hydroxylate both rings A and B from substrate 2 . Additionally, compounds 1 - 8 were evaluated for inhibitory activity against Hr-AChE and Hu-BChE enzymes through ICER-IT-MS/MS assay. Competing Interests: The authors declare no competing interests.
Databáze:	MEDLINE
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