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Wehrli SL, Moore KS, Roder H, Durell S, Zasloff M
Structure of the Novel Steroidal Antibiotic Squalamine Determined by 2-Dimensional Nmr-Spectroscopy
Steroids (1993) 58:370-378.
Abstract
Squalamine is a novel aminosterol recently isolated from the dogfish shark, Squalus acanthias. This water-soluble steroid exhibits potent antibacterial activity against both gram- negative and gram-positive bacteria. In addition, squalamine is fungicidal and induces osmotic lysis of protozoa. We report here the structural determination of squalamine, 3beta-N-1- [N(3-[4-aminobutyl])-1,3 diaminopropane]-7alpha,24zeta- dihydroxy-5alpha-cholestane 24-sulfate, which was deduced from the analysis of fast atom bombardment spectra and a series of two-dimensional nuclear magnetic resonance (NMR) spectra. Squalamine is a cationic steroid characterized by a condensation of an anionic bile salt intermediate with the polyamine, spermidine. This molecule is a potential host- defense agent in the shark, and provides insight into a new class of vertebrate antimicrobial molecules.
Note
Publication Date: 1993-08-01.
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