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Candidaspongiolides, distinctive analogues of tedanolide from sponges of the genus Candidaspongia.


ABSTRACT: Fractionation of cytotoxic extracts of specimens of a newly described sponge genus, Candidaspongia, has yielded the candidaspongiolides (3), a complex mixture of acyl esters of a macrolide related to tedanolide. The general structure of the candidaspongiolides was determined by analyses of various 2D NMR and MS data sets. The acyl ester components were identified by GC-MS analysis of the derived fatty acid methyl esters. The mixture could be selectively converted to the deacylated macrolide core (4) by enzymolysis with immobilized porcine lipase, with the structure of the candidaspongiolide core then secured by NMR and MS analysis. The candidaspongiolide mixture was potently cytotoxic, exhibiting a mean panel 50% growth inhibition (GI50) of 14 ng/mL in the National Cancer Institute's 60-cell-line in vitro antitumor screen.

SUBMITTER: Meragelman TL 

PROVIDER: S-EPMC2288652 | biostudies-other | 2007 Jul

REPOSITORIES: biostudies-other

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Candidaspongiolides, distinctive analogues of tedanolide from sponges of the genus Candidaspongia.

Meragelman Tamara L TL   Willis Richard H RH   Woldemichael Girma M GM   Heaton Andrew A   Murphy Peter T PT   Snader Kenneth M KM   Newman David J DJ   van Soest Rob R   Boyd Michael R MR   Cardellina John H JH   McKee Tawnya C TC  

Journal of natural products 20070612 7


Fractionation of cytotoxic extracts of specimens of a newly described sponge genus, Candidaspongia, has yielded the candidaspongiolides (3), a complex mixture of acyl esters of a macrolide related to tedanolide. The general structure of the candidaspongiolides was determined by analyses of various 2D NMR and MS data sets. The acyl ester components were identified by GC-MS analysis of the derived fatty acid methyl esters. The mixture could be selectively converted to the deacylated macrolide core  ...[more]

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