Isolation, structure determination, and biological activity of lyngbyabellin A from the marine cyanobacterium Lyngbya majuscula

Hendrik Luesch, Wesley Y. Yoshida, Richard E. Moore, Valerie J. Paul, Susan L Mooberry

Research output: Contribution to journalArticle

137 Citations (Scopus)

Abstract

Lyngbyabellin A (1), a significantly cytotoxic compound with unusual structural features, was isolated from a Guamanian strain of the marine cyanobacterium Lyngbya majuscula. This novel peptolide is structurally related to dolabellin (2) in that both depsipeptides bear a dichlorinated β- hydroxy acid and two functionalized thiazole carboxylic acid units. Its gross structure has been elucidated by spectral analysis, including 2D NMR techniques. The absolute stereochemistry of 1 was determined by chiral HPLC analysis of hydrolysis products and by characterization of the degradation products methyl 7,7-dichloro-3-hydroxy-2,2-dimethyloctanoate (3) and the corresponding acid 4. The total structure was further supported by molecular modeling studies. The isolation of 1 from L. majuscula once more supports the proposal that many compounds originally isolated from the sea hare Dolabella auricularia are of cyanobacterial origin. Lyngbyabellin A (1) was shown to be a potent disrupter of the cellular microfilament network.

Original languageEnglish (US)
Pages (from-to)611-615
Number of pages5
JournalJournal of Natural Products
Volume63
Issue number5
DOIs
StatePublished - May 2000
Externally publishedYes

Fingerprint

Moorea producens
Cyanobacteria
Bioactivity
bioactive properties
depsipeptides
Depsipeptides
thiazoles
Hares
Thiazoles
Hydroxy Acids
Stereochemistry
Molecular modeling
acids
stereochemistry
carboxylic acids
Carboxylic Acids
microfilaments
Actin Cytoskeleton
Oceans and Seas
Spectrum analysis

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Isolation, structure determination, and biological activity of lyngbyabellin A from the marine cyanobacterium Lyngbya majuscula. / Luesch, Hendrik; Yoshida, Wesley Y.; Moore, Richard E.; Paul, Valerie J.; Mooberry, Susan L.

In: Journal of Natural Products, Vol. 63, No. 5, 05.2000, p. 611-615.

Research output: Contribution to journalArticle

Luesch, Hendrik ; Yoshida, Wesley Y. ; Moore, Richard E. ; Paul, Valerie J. ; Mooberry, Susan L. / Isolation, structure determination, and biological activity of lyngbyabellin A from the marine cyanobacterium Lyngbya majuscula. In: Journal of Natural Products. 2000 ; Vol. 63, No. 5. pp. 611-615.
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