Biotransformation of labdane and halimane diterpenoids by two filamentous fungi strains

Autor(es)

Monteiro, Afif F. ^[1] ; Seidl, Claudia ^[2] ; Severino, Vanessa G. P. ^[3] ; Cardoso, Carmen Luia ^[2] ; Castro-Gamboa, Ian ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Paulista UNESP, Dept Quim Organ, Inst Quim, Nucle Bioensaios Biossintese & Ecofisiol Prod Nat, Francisco Degni 55, BR-14800900 Araraquara - Brazil

^[2] Univ Sao Paulo, Fac Filos Ciencias & Letras Ribeirao Preto, Grp Cromatog Bioafinidade & Prod Nat, Dept Quim, BR-14040901 Ribeirao Preto, SP - Brazil

^[3] Univ Fed Goias, Inst Quim, Campus Samambaia, BR-74690900 Goiania, Go - Brazil

• Tipo de documento: Artigo Científico
• Fonte: ROYAL SOCIETY OPEN SCIENCE; v. 4, n. 11 NOV 2017.
• Citações Web of Science: 5

Resumo

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 alpha-hydroxy (7) derivative, while M. verrucaria yielded 7 alpha-(7) and 3 beta-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. (AU)

• Processo FAPESP: 14/11640-3 - Métodos LC-MS/2D para triagem de ligantes para a avaliação de atividade inibitória de enzimas e identificação dos compostos ativos em extratos brutos
• Beneficiário: Cláudia Seidl
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado
• Processo FAPESP: 13/07600-3 - CIBFar - Centro de Inovação em Biodiversidade e Fármacos
• Beneficiário: Glaucius Oliva
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs