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Simplexolides A-E and plakorfuran A, six butyrate derived polyketides from the marine sponge Plakortis simplex.


ABSTRACT: Six new polyketides, simplexolides A-E (1-5) and a furan ester, plakorfuran A (6), together with four known furanylidenic methyl esters (7-10) were isolated from the marine sponge Plakortis simplex. Compounds 1-5 feature a tetrahydrofuran ring opened seco-plakortone skeleton. These new structures, including relative configurations, were determined on the basis of extensive analysis of spectroscopic data. The absolute configurations of 1-6 were established by the modified Mosher's method, and the CD exciton chirality method. However, configurations of the remote stereocenters at C-8 in compounds 1-5 were not determined. Antifungal, cytotoxicity, antileismanial, and antimalarial activities of these poly-ketides were evaluated.

SUBMITTER: Liu XF 

PROVIDER: S-EPMC5114024 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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Simplexolides A-E and plakorfuran A, six butyrate derived polyketides from the marine sponge <i>Plakortis simplex</i>.

Liu Xiang-Fang XF   Shen Yang Y   Yang Fan F   Hamann Mark T MT   Jiao Wei-Hua WH   Zhang Hong-Jun HJ   Chen Wan-Sheng WS   Lin Hou-Wen HW  

Tetrahedron 20120414 24


Six new polyketides, simplexolides A-E (<b>1-5</b>) and a furan ester, plakorfuran A (<b>6</b>), together with four known furanylidenic methyl esters (<b>7-10</b>) were isolated from the marine sponge <i>Plakortis simplex</i>. Compounds <b>1-5</b> feature a tetrahydrofuran ring opened <i>seco-plakortone</i> skeleton. These new structures, including relative configurations, were determined on the basis of extensive analysis of spectroscopic data. The absolute configurations of <b>1-6</b> were est  ...[more]

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