The structure of hemibrevetoxin-B: a new type of toxin in the Gulf of Mexico red tide organism

• Published in: Journal of the American Chemical Society Vol. 111; no. 16; pp. 6476 - 6477
• Main Authors: Prasad, A. V. Krishna, Shimizu, Yuzuru
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.08.1989
• Subjects: Analytical, structural and metabolic biochemistry; Aromatic and heterocyclic compounds; Biological and medical sciences; Fundamental and applied biological sciences. Psychology; Heterocyclic compounds, pigments; Other biological molecules; Neurotoxin
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja00198a098

Brevetoxins, represented by brevetoxin-A, and brevetoxin-B, are polycyclic ethers isolated form the red tide organism, Gymnodinium breve , which forms blooms in the Gulf of Mexico. These potent neurotoxins are responsible for massive fish kills and human intoxication known as neurotoxic shellfish poisoning (NSP). Because of their unprecedented structural feature, the unique mode of action on sodium channels, and unusual biosynthetic pathway, these compounds have been a subject of continuing studies in our laboratory and others. During the course of the studies, we have isolated a new series of compounds having molecular size about half that of brevetoxins. In this communication, we wish to report the structure of hemibrevetoxin-B, the first in the series.