Caylobolide A, a Unique 36-Membered Macrolactone from a Bahamian Lyngbya majuscula

John B. MacMillan, Tadeusz F. Molinski

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

(matrix presented) A new 36-membered macrolactone, (25S,27S,29S,33S)-caylobolided 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 stereochemistry 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 μM).

Original languageEnglish (US)
Pages (from-to)1535-1538
Number of pages4
JournalOrganic Letters
Volume4
Issue number9
DOIs
StatePublished - May 2 2002

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triols
HCT116 Cells
Stereochemistry
stereochemistry
Cyanobacteria
Inhibitory Concentration 50
Colon
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Cytotoxicity
Tumors
Neoplasms
tumors
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Nuclear magnetic resonance
nuclear magnetic resonance
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In Vitro Techniques
caylobolide A

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Caylobolide A, a Unique 36-Membered Macrolactone from a Bahamian Lyngbya majuscula. / MacMillan, John B.; Molinski, Tadeusz F.

In: Organic Letters, Vol. 4, No. 9, 02.05.2002, p. 1535-1538.

Research output: Contribution to journalArticle

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