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sporolides
Sporolides A and B are novel polycyclic macrolides from the obligate marine bacterium ''Salinispora tropica'' (which is found in ocean sediment) that are composed of a chlorinated cyclopenta()indene ring and a cyclohexenone moiety.〔McGlinchey, R. P.; Nett, M.; Moore, B. J. Am. Chem. Soc. 2008, 130, 2406-2407.〕 They are only the second class of compounds isolated from ''Salinispora'', and their unique carbon skeleton provides a clear indication of the tremendous potential of marine actinomycetes as a source of novel secondary metabolites.〔Buchanan, G. O.; Williams, P. G.; Feling, R. H.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Org. Lett. 2005, 7, pp. 2731-2734.〕 The structures and absolute stereochemistries of both metabolites were elucidated using a combination of NMR spectroscopy and X-ray crystallography, and are considered unique for two reasons:
- both compounds appear to be polyketides and therefore derived from acetate units,
- the number of oxidized carbons is amazing, with 23 of 24 carbons either oxygenated or sp2 - hybridized.
The complex aromatic structure of the sporolides is hypothesized to be derived from an unstable nine-membered ring enediyne precursor, which undergoes Bergman cyclization to generate a p-benzyne intermediate. A nucleophilic attack by chloride accounts for the 1:1 mixtures and for the single chlorine in enediyne-derived natural products. This mechanism has been recently demonstrated in laboratory experiments,〔Perrin, C. L.; Rodgers, B. L.; O' Connor, J. M.; J. Am. Chem. Soc. 2007, 129, (15), 4795-4799.〕 and can account for the biosynthesis of sporolides.
==Biosynthesis==
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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