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光动力活性鲁贝菌素的生物合成及由玉蜀黍赤霉产孢枝霉产生的新蒽醌衍生物的结构解析

Biosynthesis of photodynamically active rubellins and structure elucidation of new anthraquinone derivatives produced by Ramularia collo-cygni.

作者信息

Miethbauer Sebastian, Haase Susann, Schmidtke Kai-Uwe, Günther Wolfgang, Heiser Ingrid, Liebermann Bernd

机构信息

Friedrich-Schiller-Universität Jena, Institut für Pharmazie, Neugasse 23, D-07743 Jena, Germany.

出版信息

Phytochemistry. 2006 Jun;67(12):1206-13. doi: 10.1016/j.phytochem.2006.05.003. Epub 2006 Jun 15.

DOI:10.1016/j.phytochem.2006.05.003
PMID:16780904
Abstract

Here we present the first isolation of the anthrachinone derivative rubellin A out of mycelium and culture filtrate of Ramularia collo-cygni. Furthermore, two compounds, rubellin E and 14-dehydro rubellin D were isolated and their structures elucidated. In comparison to the other rubellins, rubellin A shows increased photodynamic oxygen activation. By incorporating both [1-(13)C]-acetate and [2-(13)C]-acetate into the rubellins, we showed that such anthraquinone derivatives were biosynthesised via the polyketide pathway. The labelling pattern after being fed [U-(13)C(6)]-glucose proved the existence of fungal folding mode of the poly-beta-keto chain. The ability to produce rubellins is not limited to R. collo-cygni in the anamorph genus Ramularia.

摘要

在此,我们首次从柱隔孢属真菌(Ramularia collo-cygni)的菌丝体和培养滤液中分离出蒽醌衍生物红菌素A。此外,还分离出了两种化合物,红菌素E和14-脱氢红菌素D,并阐明了它们的结构。与其他红菌素相比,红菌素A表现出更强的光动力氧激活作用。通过将[1-(13)C]-乙酸盐和[2-(13)C]-乙酸盐掺入红菌素中,我们发现此类蒽醌衍生物是通过聚酮途径生物合成的。用[U-(13)C(6)]-葡萄糖喂养后的标记模式证明了聚-β-酮链的真菌折叠模式的存在。产生红菌素的能力并不局限于无性型柱隔孢属真菌中的柱隔孢菌。

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