Harzianone Biosynthesis by the Biocontrol Fungus Trichoderma

Harzianone Biosynthesis by the Biocontrol Fungus Trichoderma
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DOI:
10.1002/cbic.201700462
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发表时间:
2017-12-05
期刊:
影响因子:
3.2
通讯作者:
Dickschat, Jeroen S.
Dickschat, Jeroen S.
中科院分区:
生物学3区
文献类型:
--
作者:
Barra, Lena;Dickschat, Jeroen S.

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通过使用闭环汽提装置(CLSA)分析由木霉属的七种真菌菌株产生的挥发性萜烯,揭示了共同产生哈茨酮(harzianone),哈茨酮是由稠合四环4,7,5,6-元环系统组成的生物活性的、结构独特的二萜类化合物。萜烯环化机理通过使用选择性C-13-和H-2-标记的合成甲羟戊酸内酯同位素体的喂养实验进行研究,随后通过(CNMR)-C-13光谱和GC/MS分析掺入模式。哈茨酮的结构进一步得到体内产生的完全C-13-标记的二萜的C-13,(CCOSY)-C-13实验的支持。
Analysis of the volatile terpenes produced by seven fungal strains of the genus Trichoderma by use of a closed-loop stripping apparatus (CLSA) revealed a common production of harzianone, a bioactive, structurally unique diterpenoid consisting of a fused tetracyclic 4,7,5,6-membered ring system. The terpene cyclization mechanism was studied by feeding experiments using selectively C-13- and H-2-labeled synthetic mevalonolactone isotopologues, followed by analysis of the incorporation patterns by (CNMR)-C-13 spectroscopy and GC/MS. The structure of harzianone was further supported from a C-13,(CCOSY)-C-13 experiment of the in-vivo-generated fully C-13-labeled diterpene.