Antillatoxin B, a neurotoxic lipopeptide from the marine cyanobacterium Lyngbya majuscula.
Bioassay-guided fractionation of organic extracts from two Lyngbya majuscula collections led to the isolation of a new secondary metabolite, antillatoxin B, an unusual N-methyl homophenylalanine analogue of the potent neurotoxin antillatoxin. Its structure was deduced from 2D NMR and data comparisons with antillatoxin. Antillatoxin B exhibited significant sodium channel-activating (EC(50) = 1.77 microM) and ichthyotoxic (LC(50) = 1 microM) properties.
Nogle
L M
LM
College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, USA.
Okino
T
T
Gerwick
W H
WH
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D000458:Cyanobacteria / Q000737:chemistry*; D006054:Goldfish; D055666:Lipopeptides; D008074:Lipoproteins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008235:Lyngbya Toxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D009447:Neuroblastoma; D010456:Peptides, Cyclic; D015222:Sodium Channels / Q000187:drug effects; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D055666:Lipopeptides; D008074:Lipoproteins; D008235:Lyngbya Toxins; D010456:Peptides, Cyclic; D015222:Sodium Channels; C121886:antillatoxin; C435814:antillatoxin B