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

被引：11
作者：
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 ]
机构：
[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
来源：
BIOORGANIC CHEMISTRY | 2018年 / 78卷
基金：
巴西圣保罗研究基金会;
关键词：
Diterpene; Biotransformation; Cupressus lusitanica; Preussia minima; Endophytic; Cytochrome P450; CYPRESS; PIMARANE; LEAVES; CANKER;
D O I：
10.1016/j.bioorg.2018.04.003
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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.
引用
收藏
页码：436 / 443
页数：8
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