(+)-7S-hydroxyxestospongin A from the marine sponge Xestospongia sp. and absolute configuration of (+)-xestospongin D

Surk Sik Moon, John B. MacMillan, Marilyn M. Olmstead, Tram Anh Ta, Isaac N Pessah, Tadeusz F. Molinski

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23 Scopus citations

Abstract

The structure of the title compound, (+)-7S-hydroxyxestospongin A was solved by single-crystal X-ray diffraction analysis and the absolute stereochemistry obtained by analysis of the derived R and S Mosher's esters. The absolute configuration of xestospongin D was determined for the first time by analysis of anomalous scattering from the X-ray crystal diffraction data set. Xestospongins A, C, and D, araguspongine C, and demethylxestospongin B exhibited modest antifungal activity (MIC 30-100 g/mL) against various fluconazole-resistant Candida spp., but 7S-hydroxyxestospongin A was inactive.

Original languageEnglish (US)
Pages (from-to)249-254
Number of pages6
JournalJournal of Natural Products
Volume65
Issue number3
DOIs
StatePublished - 2002

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ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

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