Isolation of Smenopyrone, a Bis-γ-Pyrone Polypropionate from the Caribbean Sponge Smenospongia aurea
Isolation of Smenopyrone, a Bis-γ-Pyrone Polypropionate from the Caribbean Sponge Smenospongia aurea
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DOI：
10.3390/md16080285
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发表时间：
2018-08-01
期刊：
影响因子：
5.4
通讯作者：
Costantino, Valeria
中科院分区：
文献类型：
--
作者：
Esposito, Germana;Teta, Roberta;Costantino, Valeria
加勒比海海绵的有机提取物已被证明含有一系列新的氯化次级代谢产物，这些代谢产物来自混合的PKS-NRPS生物遗传途径，如Smenamides。在本文中，我们报告了一种生物遗传学上不同的化合物，称为斯梅诺吡喃酮，这是一种含有两个γ-吡喃酮环的聚丙酸酯。通过光谱分析（NMR、MS、ECD）确定了Smenopyrone的结构，包括其相对和绝对立体化学，并通过与来自研究的模型化合物的比较来支持。吡喃酮聚丙酸酯在海绵中是前所未有的，但在海洋软体动物中很常见，其中它们的生物合成被假设为共生细菌，至少在一个案例中得到了证实。由于吡喃酮类化合物最近被认为是细菌的信号分子，我们推测斯美诺吡喃酮可以介导细菌之间的界间化学通讯。金藻及其共生菌。
The organic extract of the Caribbean sponge Smenospongia aurea has been shown to contain an array of novel chlorinated secondary metabolites derived from a mixed PKS-NRPS biogenetic route such as the smenamides. In this paper, we report the presence of a biogenetically different compound known as smenopyrone, which is a polypropionate containing two gamma-pyrone rings. The structure of smenopyrone including its relative and absolute stereochemistry was determined by spectroscopic analysis (NMR, MS, ECD) and supported by a comparison with model compounds from research studies. Pyrone polypropionates are unprecedented in marine sponges but are commonly found in marine mollusks where their biosynthesis by symbiotic bacteria has been hypothesized and at least in one case demonstrated. Since pyrones have recently been recognized as bacterial signaling molecules, we speculate that smenopyrone could mediate inter-kingdom chemical communication between S. aurea and its symbiotic bacteria.