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Polyenylpyrroles and polyenylfurans from an Australian Isolate of the soil ascomycete Gymnoascus reessii.来自澳大利亚土壤子囊菌瑞斯裸囊菌一个分离株的聚烯基吡咯和聚烯基呋喃。
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海洋来源的链霉菌属中吡喃并吡咯酮、聚烯吡咯酮的结构与生物合成。

Structures and biosynthesis of the pyridinopyrones, polyenepyrones from a marine-derived Streptomyces species.

机构信息

Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, La Jolla, California 92093-0204, USA.

出版信息

J Nat Prod. 2011 Aug 26;74(8):1773-8. doi: 10.1021/np200323e. Epub 2011 Jul 13.

DOI:10.1021/np200323e
PMID:21751787
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3163021/
Abstract

Three polyenylpyrone metabolites, pyridinopyrones A to C (1-3), have been isolated from the culture broth of a marine-derived Streptomyces sp., strain CNQ-301. The structures of the pyridinopyrones were assigned on the basis of chemical modification and combined spectroscopic methods, focusing on interpretation of 1D and 2D NMR data. Pyridinopyrones B and C (2, 3), examined as an inseparable mixture of methyl positional isomers, were ultimately defined by hydrogenation and NMR analysis of a saturated derivative. The biosynthesis of these metabolites was defined by the incorporation of stable isotope-labeled precursors, revealing that the biosynthetic starter unit is nicotinic acid, while the polyene chain and pendant methyl groups are acetate- and methionine-derived, respectively.

摘要

从海洋来源的链霉菌 CNQ-301 的发酵液中分离到三种聚烯基吡啶酮代谢物,吡啶酮 A 到 C(1-3)。基于化学修饰和综合光谱方法,特别是对 1D 和 2D NMR 数据的解释,确定了吡啶酮的结构。作为甲基位置异构体混合物不可分离的混合物,吡啶酮 B 和 C(2、3)最终通过饱和衍生物的氢化和 NMR 分析来定义。这些代谢物的生物合成通过掺入稳定同位素标记的前体来定义,表明生物合成的起始单元是烟酸,而多烯链和侧挂甲基分别来自乙酸盐和蛋氨酸。