Isolation and structure of the cytotoxin lyngbyabellin B and absolute configuration of lyngbyapeptin A from the marine cyanobacterium Lyngbya majuscula.
An analogue of the potent microfilament-disrupter lyngbyabellin A (1) has been isolated as a minor metabolite from the marine cyanobacterium Lyngbya majuscula collected at Apra Harbor, Guam. It possesses slightly weaker cytotoxicity than 1 and has been named lyngbyabellin B (2). Primarily NMR spectroscopy was used to determine its structure. The absolute configuration of 2 has been ascertained by chiral HPLC analysis of degradation products and by comparison with lyngbyabellin A (1). The known modified tetrapeptide lyngbyapeptin A (3) has also been found in the same extract, and its absolute stereochemistry could be determined for the first time.
Luesch
H
H
Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822, USA.
Yoshida
W Y
WY
Moore
R E
RE
Paul
V J
VJ
D001427:Bacterial Toxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000458:Cyanobacteria / Q000737:chemistry*; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047630:Depsipeptides; D020128:Inhibitory Concentration 50; D008235:Lyngbya Toxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013844:Thiazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D001427:Bacterial Toxins; D003603:Cytotoxins; D047630:Depsipeptides; D008235:Lyngbya Toxins; D010456:Peptides, Cyclic; D013844:Thiazoles; C410925:lyngbyabellin A; C416586:lyngbyabellin B