(+)-7S-Hydroxyxestospongin A from the marine sponge Xestospongia sp. and absolute configuration of (+)-xestospongin D.
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.
Moon
Surk-Sik
SS
Department of Chemistry, College of Letters and Science, School of Veterinary Medicine, One Shields Avenue, University of California, Davis, California 95616, USA.
MacMillan
John B
JB
Olmstead
Marilyn M
MM
Ta
Tram Anh
TA
Pessah
Isaac N
IN
Molinski
Tadeusz F
TF
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001315:Australia; D002175:Candida / Q000187:drug effects*; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D047028:Macrocyclic Compounds; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010080:Oxazoles / Q000737:chemistry / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D011807:Quinolizines / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism
C452827:7-hydroxyxestospongin A; D000470:Alkaloids; D000935:Antifungal Agents; D047028:Macrocyclic Compounds; D010080:Oxazoles; D011807:Quinolizines; C455173:araguspongine C; C108644:xestospongin A; C108642:xestospongin D; C078550:demethylxestospongine B