Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021 - an insight into the biosynthesis of maleidrides.
Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021 - an insight into the biosynthesis of maleidrides.
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DOI：
10.1039/c5cc06988b
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发表时间：
2015-12-14
期刊：
影响因子：
--
通讯作者：
Simpson TJ
中科院分区：
文献类型：
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作者：
Szwalbe AJ;Williams K;O'Flynn DE;Bailey AM;Mulholland NP;Vincent JL;Willis CL;Cox RJ;Simpson TJ
通过马来酸单体的交替二聚作用生物合成了Bysochlamic酸和新型七氢环，即镁氢环A。丝状真菌Byssochlamys fulva菌株IMI 40021产生（+）-bysochlamic acid 1、其新的二氢类似物2和四种相关的次级代谢产物。Agnestadrides A，17和B，18构成一类新的七元环，含马来酸酐（因此称为heptadride）的天然产物。第一次从发酵产物中分离出了推测的用于九氢吡啶和七氢吡啶生物合成的马来酸酐前体5，并通过合成证实了其结构。酸5容易脱羧成酸酐6。通用术语马来酸酐被提议包括含有与脂环稠合的马来酸酐部分的生物合成相关的化合物，其大小和取代基不同。
Byssochlamic acid and the novel heptadride, agnestadride A are biosynthesised via alternative dimerisations of a maleic acid monomer. The filamentous fungus Byssochlamys fulva strain IMI 40021 produces (+)-byssochlamic acid 1, its novel dihydroanalogue 2 and four related secondary metabolites. Agnestadrides A, 17 and B, 18 constitute a novel class of seven-membered ring, maleic anhydride-containing (hence termed heptadride) natural products. The putative maleic anhydride precursor 5 for both nonadride and heptadride biosynthesis was isolated as a fermentation product for the first time and its structure confirmed by synthesis. Acid 5 undergoes facile decarboxylation to anhydride 6. The generic term maleidrides is proposed to encompass biosynthetically-related compounds containing maleic anhydride moieties fused to an alicyclic ring, varying in size and substituents.