Marinisporolides, polyene-polyol macrolides from a marine actinomycete of the new genus Marinispora.
Marinisporolides, polyene-polyol macrolides from a marine actinomycete of the new genus Marinispora.
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新型墨西哥菌的海洋放线菌的多烯 - 多聚酚多醇盐。
DOI：
10.1021/jo801944d
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发表时间：
2009-01-16
期刊：
影响因子：
--
通讯作者：
Fenical W
中科院分区：
文献类型：
--
作者：
Kwon HC;Kauffman CA;Jensen PR;Fenical W
从海洋放线菌CNQ-140的盐培养物中分离得到两个新的多烯大环内酯类化合物marinisporolides A和B（1，2）。marinisporolides是由共轭五烯和几对1，3-二羟基官能团组成的34元大环内酯。marinisporcine A（1）含有双环螺-双-四氢吡喃缩酮官能团，而marinisporcine B（2）是相应的半缩酮。这些新化合物的结构通过光谱和化学相结合的方法，包括广泛的2D NMR实验和相关的13 C NMR数据与Kishi的通用NMR数据库进行了指定。化学修饰，包括甲醇分解，丙酮化合物的形成，和应用修改的Mosher方法，提供了这些分子的完整立体结构。还分离出另外三种大环内酯，marinisporolides C-E（3-5），它们是marinisporcine A（1）的烯烃几何异构体，并确定了它们的结构。在室内光照下，marinisporolides A和B容易光异构化为C-E，表明它们最有可能是在培养或分离过程中通过光化学转化产生的。虽然多烯，marinisporolides A（1）和B（2）显示对白色念珠菌的抗真菌活性弱或没有。
Two new polyene macrolides, marinisporolides A and B (1, 2), were isolated from the saline culture of the marine actinomycete, strain CNQ-140, identified as a member of the new marine genus “Marinispora.” The marinisporolides are 34 membered macrolides composed of a conjugated pentaene and several pairs of 1,3-dihydroxyl functionalities. Marinisporolide A (1) contains a bicyclic spiro-bis-tetrahydropyran ketal functionality, while marinisporolide B (2) is the corresponding hemiketal. The structures of these new compounds were assigned by combined spectral and chemical methods including extensive 2D NMR experiments and correlations of 13C NMR data with Kishi’s Universal NMR Database. Chemical modifications, including methanolysis, acetonide formation, and application of the modified Mosher method, provided the full stereostructures of these molecules. Three additional macrolides, marinisporolides C–E (3–5), which are olefin geometric isomers of marinisporolide A (1), were also isolated and their structures defined. Under room light, marinisporolides A and B readily photoisomerize to C–E indicating that they are most likely produced by photochemical conversion during the cultivation or isolation procedures. Although polyenes, marinisporolides A (1) and B (2) showed weak to no antifungal activity against Candida albicans.
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影响因子：
1.4
作者：
Prieto-Davo, Alejandra;Fenical, William;Jensen, Paul R.
通讯作者：
Jensen, Paul R.
影响因子：
7.3
作者：
Macherla, VR;Mitchell, SS;Potts, BCM
通讯作者：
Potts, BCM
影响因子：
15
作者：
OHTANI, I;KUSUMI, T;KAKISAWA, H
通讯作者：
KAKISAWA, H
影响因子：
3.3
作者：
Kundim, BA;Itou, Y;Ojika, M
通讯作者：
Ojika, M
影响因子：
16.6
作者：
Feling, RH;Buchanan, GO;Fenical, W
通讯作者：
Fenical, W