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Differential metabolism of diastereoisomeric diterpenes by Preussia minima, found as endophytic fungus in Cupressus lusitanica.
Ud Din, Zia; de Medeiros, L S; Abreu, L M; Pfenning, Ludwig H; Lopes Jymeni, D B; Rodrigues-Filho, E.
Afiliación
  • Ud Din Z; LaBioMMi - Departamento de Química, Universidade Federal de São Carlos, PO Box 676, 13565-905 São Carlos, SP, Brazil.
  • de Medeiros LS; Departamento de Química, Universidade Federal de São Paulo (UNIFESP), Rua São Nicolau, 210, CEP 09913-030 Diadema, SP, Brazil.
  • Abreu LM; Departamento de Fitopatologia, Universidade Federal de Viçosa, Campus Universitário, 36570-900 Viçosa, MG, Brazil.
  • Pfenning LH; Departamento de Fitopatologia, Universidade Federal de Lavras, PO Box 3037, 37200-000 Lavras, MG, Brazil.
  • Lopes Jymeni DB; LaBioMMi - Departamento de Química, Universidade Federal de São Carlos, PO Box 676, 13565-905 São Carlos, SP, Brazil.
  • Rodrigues-Filho E; LaBioMMi - Departamento de Química, Universidade Federal de São Carlos, PO Box 676, 13565-905 São Carlos, SP, Brazil. Electronic address: edinho@pq.cnpq.br.
Bioorg Chem ; 78: 436-443, 2018 08.
Article en En | MEDLINE | ID: mdl-29702360
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 7ß-hydroxy-ent-pimara-8(14)-15-dien-19-oic acid, and into the novel diterpenes 7-oxo-8 ß-hydroxy-ent-pimara-8(14)-15-dien-19-oic and 7-oxo-9ß-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, 7ß,11α-dihydroxyisopimara-8(14)-15-dien-18-oic acid, and 1ß,11α-dihydroxyisopimara-8(14)-15-dien-18-oic acid, along with the known 7ß-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-9ß-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.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ascomicetos / Cupressus / Diterpenos Idioma: En Revista: Bioorg Chem Año: 2018 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Estados Unidos
Texto completo
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Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ascomicetos / Cupressus / Diterpenos Idioma: En Revista: Bioorg Chem Año: 2018 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Estados Unidos