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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Din, Zia Ud [1] ; de Medeiros, L. S. [2] ; Abreu, L. M. [3] ; Pfenning, Ludwig H. [4] ; Lopes Jymeni, D. B. [1] ; Rodrigues-Filho, E. [1]
Total Authors: 6
Affiliation:
[1] Univ Fed Sao Carlos, LaBioMMi Dept Quim, POB 676, BR-13565905 Sao Carlos, SP - Brazil
[2] Univ Fed Sao Paulo UNIFESP, Dept Quim, Rua Sao Nicolau 210, BR-09913030 Diadema, SP - Brazil
[3] Univ Fed Vicosa, Dept Fitopatol, Campus Univ, BR-36570900 Vicosa, MG - Brazil
[4] Univ Fed Lavras, Dept Fitopatol, POB 3037, BR-37200000 Lavras, MG - Brazil
Total Affiliations: 4
Document type: Journal article
Source: BIOORGANIC CHEMISTRY; v. 78, p. 436-443, AUG 2018.
Web of Science Citations: 2
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 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. (AU)

FAPESP's process: 16/09690-8 - Prospecting terpenoid producers endophytic microorganisms
Grantee:Edson Rodrigues Filho
Support type: Regular Research Grants