Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi.

Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi.
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Agnestin A 和 B 生物合成途径的表征揭示了真菌中大黄酚的还原途径。

DOI:
10.1039/c8sc03778g
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发表时间:
2019
期刊:
影响因子:
8.4
通讯作者:
Szwalbe AJ
Szwalbe AJ
中科院分区:
化学1区
文献类型:
--
作者:
Szwalbe AJ

文献摘要

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从多变拟青霉(Paecilomycesvariotii)中分离出两种新的二羟基氧杂蒽酮代谢产物--镁蛋白A和B,以及一些相关的二苯甲酮和氧杂蒽酮,包括单网苯酮。通过NMR分析和X射线晶体学鉴定了结构。agnestin(agn)的生物合成基因簇被确定和有针对性的基因破坏的PKS,Baeyer-Villiger单加氧酶,和其他氧化还原酶基因揭示了真菌吨酮生物合成的新细节。特别是,鉴定还原酶负责在体内蒽醌到蒽的转化证实了先前假定的蒽醌,例如大黄素到大黄酚的芳香脱氧的必要步骤。
Two new dihydroxy-xanthone metabolites, agnestins A and B, were isolated from Paecilomyces variotii along with a number of related benzophenones and xanthones including monodictyphenone. The structures were elucidated by NMR analyses and X-ray crystallography. The agnestin (agn) biosynthetic gene cluster was identified and targeted gene disruptions of the PKS, Baeyer–Villiger monooxygenase, and other oxido-reductase genes revealed new details of fungal xanthone biosynthesis. In particular, identification of a reductase responsible for in vivo anthraquinone to anthrol conversion confirms a previously postulated essential step in aromatic deoxygenation of anthraquinones, e.g. emodin to chrysophanol.