Caylobolide A, a unique 36-membered macrolactone from a Bahamian Lyngbya majuscula.
[structure: see text]. A new 36-membered macrolactone, (25S,27S,29S,33S)-caylobolide A, was isolated from the Bahamian cyanobacterium Lyngbya majuscula. The structure of caylobolide contains an unprecedented repeated unit-a contiguous pentad of 1,5 diols-and a 1,3,5-triol. The relative steroechemistry of the 1,3,5-triol was determined using Kishi's Universal NMR database, and absolute stereochemistry at C25,27,29 and C33 were determined by Mosher's analysis. Caylobolide A exhibited in vitro cytotoxicity against human colon tumor cells (IC50 HCT 116, 9.9 microM).
MacMillan
John B
JB
Department of Chemistry, University of California, Davis, California 95616, USA.
Molinski
Tadeusz F
TF
D000935:Antifungal Agents / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology; D001444:Bahamas; D000458:Cyanobacteria / Q000737:chemistry*; D006801:Humans; D007783:Lactones / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014407:Tumor Cells, Cultured
D000935:Antifungal Agents; D000970:Antineoplastic Agents; D007783:Lactones; C456999:caylobolide A