Differential metabolism of diastereoisomeric diterpenes by Preussia minima, found as endophytic fungus in Cupressus lusitanica

Differential metabolism of diastereoisomeric diterpenes by Preussia minima, found as endophytic fungus in Cupressus lusitanica

Autor Din, Zia Ud Google Scholar
Medeiros, L. S. de Autor UNIFESP Google Scholar
Abreu, L. M. Google Scholar
Pfenning, Ludwig H. Google Scholar
Jymeni, D. B. L. Google Scholar
Rodrigues-Filho, E. Google Scholar
Resumo The plant diastereoisomeric diterpenes ent-pimara-8(14)-15-dien-19-oic acid, obtained from Viguiera arenaria, and isopimara-8(14)-15-dien-18-oic acid, isolated from Cupressus lusitanica, were distinctly functionalized by the enzymes produced in whole cell cultures of the fungus Preussia minima, isolated from surface sterilized stems of C. lusitanica. The ent-pimaradienoic acid was transformed into the known 7 beta-hydroxy-ent-pimara-8(14)-15-dien-19-oic acid, and into the novel diterpenes 7-oxo-8 beta-hydroxy-ent-pimara-8(14)-15-dien-19-oic and 7-oxo-9 beta-hydroxy-ent-pimara-8(14)-15-dien-19-oic acids. Isopimara-8(14)-15-dien-18-oic acid was converted into novel diterpenes 11 alpha-hydroxyisopimara-8(14)-15-dien-18-oic acid, 7 beta, 11 alpha-dihydroxyisopimara-8(14)-15-dien-18-oic acid, and 1 beta, 11 alpha-dihydroxyisopimara-8(14)-15-dien-18-oic acid, along with the known 7 beta-hydroxyisopimara-8(14)-15-dien-18-oic acid. All compounds were isolated and fully characterized by 1D and 2D NMR, especially C-13 NMR. The diterpene bioproduct-7-oxo-9 beta-hydroxy-ent-pimara-8(14)-15-dien-19-oicacid is an isomer of sphaeropsidin C, a phytotoxin that affects cypress trees produced by Shaeropsis sapinea, one of the main phytopathogen of Cupressus. The differential metabolism of the diterpene isomers used as substrates for biotransformation was interpreted with the help of computational molecular docking calculations, considering as target enzymes those of cytochrome P450 group.
Assunto Diterpene
Biotransformation
Cupressus lusitanica
Preussia minima
Endophytic
Cytochrome P450
Cobertura San Diego
Idioma Inglês
Financiador Brazilian institution FAPESP - Fundacao de Amparo a Pesquisa do Estado de Sao Paulo
Brazilian institution CNPq - Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (Sisbiota Brasil)
Brazilian institution CAPES - Coordenacao de Aperfeicoamento
Número do financiamento FAPESP: 2016/09690-8
CNPq: 563063/2010-6
Data 2018
Publicado em Bioorganic Chemistry. San Diego, v. 78, p. 436-443, 2018.
ISSN 0045-2068 (Sherpa/Romeo, fator de impacto)
Editor Academic Press Inc Elsevier Science
Extensão 436-443
Fonte http://dx.doi.org/10.1016/j.bioorg.2018.04.003
Direito de acesso Acesso restrito
Tipo Artigo
Web of Science WOS:000433242100046
URI http://repositorio.unifesp.br/11600/45817

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