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

John B. MacMillan; Tadeusz F. Molinski

doi:10.1021/ol025759p

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

John B. MacMillan, Tadeusz F. Molinski

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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 language	English (US)
Pages (from-to)	1535-1538
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	9
DOIs	https://doi.org/10.1021/ol025759p
State	Published - May 2 2002

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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).",

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AU - Molinski, Tadeusz F.

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AB - (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).

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

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