(+)-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

Research output: Contribution to journalArticle

23 Citations (Scopus)

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

Fingerprint

Xestospongia
Porifera
X-Ray Diffraction
crystals
Dilatation and Curettage
Stereochemistry
fluconazole
Fluconazole
Candida
stereochemistry
X-ray diffraction
X ray diffraction analysis
Esters
X-radiation
Diffraction
esters
Single crystals
Scattering
X rays
Crystals

ASJC Scopus subject areas

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

Cite this

(+)-7S-hydroxyxestospongin A from the marine sponge Xestospongia sp. and absolute configuration of (+)-xestospongin D. / Moon, Surk Sik; MacMillan, John B.; Olmstead, Marilyn M.; Ta, Tram Anh; Pessah, Isaac N; Molinski, Tadeusz F.

In: Journal of Natural Products, Vol. 65, No. 3, 2002, p. 249-254.

Research output: Contribution to journalArticle

Moon, Surk Sik ; MacMillan, John B. ; Olmstead, Marilyn M. ; Ta, Tram Anh ; Pessah, Isaac N ; Molinski, Tadeusz F. / (+)-7S-hydroxyxestospongin A from the marine sponge Xestospongia sp. and absolute configuration of (+)-xestospongin D. In: Journal of Natural Products. 2002 ; Vol. 65, No. 3. pp. 249-254.
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