Caylobolide A, a unique 36-membered macrolactone from a Bahamian Lyngbya majuscula.

Abstract

[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).

• Authors: John B MacMillan, Tadeusz F Molinski
• Journal: Organic letters (Org Lett) Vol. 4 Issue 9 Pg. 1535-8 (May 02 2002) ISSN: 1523-7060 [Print] United States
• PMID: 11975622 (Publication Type: Journal Article, Research Support, U.S. Gov't, Non-P.H.S., Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Antifungal Agents
• Antineoplastic Agents
• Lactones
• caylobolide A

Topics

• Antifungal Agents (pharmacology)
• Antineoplastic Agents (chemistry, pharmacology)
• Bahamas
• Cyanobacteria (chemistry)
• Humans
• Lactones (chemistry, pharmacology)
• Magnetic Resonance Spectroscopy
• Microbial Sensitivity Tests
• Molecular Conformation
• Spectrometry, Mass, Fast Atom Bombardment
• Tumor Cells, Cultured