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

Show simple item record Din, Zia ud Medeiros, L.S. de Abreu, L.M. Pfenning, Ludwig H. Jymeni, D.B. Lopes Rodrigues-Filho, E. 2018-05-03T14:13:39Z 2018-05-03T14:13:39Z 2018-04-11
dc.identifier.issn 00452068
dc.description.abstract 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 7β-hydroxy-ent-pimara-8(14)-15-dien-19-oic acid, and into the novel diterpenes 7-oxo-8 β-hydroxy-ent-pimara-8(14)-15-dien-19-oic and 7-oxo-9β-hydroxy-ent-pimara-8(14)-15-dien-19-oic acids. Isopimara-8(14)-15-dien-18-oic acid was converted into novel diterpenes 11α-hydroxyisopimara-8(14)-15-dien-18-oic acid, 7β,11α-dihydroxyisopimara-8(14)-15-dien-18-oic acid, and 1β,11α-dihydroxyisopimara-8(14)-15-dien-18-oic acid, along with the known 7β-hydroxyisopimara-8(14)-15-dien-18-oic acid. All compounds were isolated and fully characterized by 1D and 2D NMR, especially 13C NMR. The diterpene bioproduct 7-oxo-9β-hydroxy-ent-pimara-8(14)-15-dien-19-oic acid 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. en
dc.format pdf pt-BR
dc.language.iso eng pt-BR
dc.publisher Bioorganic Chemistry pt-BR
dc.relation.ispartofseries v. 78, p. 436-443, August 2018 pt-BR
dc.rights Elsevier Inc. pt-BR
dc.subject Diterpene pt-BR
dc.subject Biotransformation pt-BR
dc.subject Cupressus lusitanica pt-BR
dc.subject Preussia minima pt-BR
dc.subject Endophytic pt-BR
dc.subject Cytochrome P450 pt-BR
dc.title Differential metabolism of diastereoisomeric diterpenes by Preussia minima, found as endophytic fungus in Cupressus lusitanica en
dc.type Artigo pt-BR

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