Marinisporolides, Polyene-Polyol Macrolides from a Marine Actinomycete of the New Genus Marinispora

Title
Marinisporolides, Polyene-Polyol Macrolides from a Marine Actinomycete of the New Genus Marinispora
Authors
권학철Christopher KauffmanPaul R. JensenWilliam Fenical
Keywords
Marine Actinomycete; Novel Compound; Marinisporolide; Marine natural products
Issue Date
2009-02
Publisher
Journal of organic chemistry
Citation
VOL 74, NO 2, 675-684
Abstract
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.
URI
http://pubs.kist.re.kr/handle/201004/35663
ISSN
0022-3263
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KIST Publication > Article
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