Wehrli S L, Moore K S, Roder H, Durell S, Zasloff M
Division of Biochemical Development and Molecular Disease, Children's Hospital of Philadelphia, Pennsylvania.
Steroids. 1993 Aug;58(8):370-8. doi: 10.1016/0039-128x(93)90040-t.
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, 3 beta-N-1-[N(3-[4-aminobutyl])-1,3 diaminopropane]-7 alpha,24 zeta-dihydroxy-5 alpha-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.
鲨胺是一种最近从白斑角鲨（Squalus acanthias）中分离出来的新型氨基甾醇。这种水溶性类固醇对革兰氏阴性菌和革兰氏阳性菌均表现出强大的抗菌活性。此外，鲨胺具有杀真菌作用，并能诱导原生动物发生渗透性裂解。我们在此报告鲨胺（3β-N-1-[N(3-[4-氨基丁基])-1,3-二氨基丙烷]-7α,24ζ-二羟基-5α-胆甾烷24-硫酸盐）的结构测定，该结构是通过对快原子轰击光谱和一系列二维核磁共振（NMR）光谱的分析推导出来的。鲨胺是一种阳离子类固醇，其特征是阴离子胆汁盐中间体与多胺亚精胺缩合而成。这种分子是鲨鱼体内一种潜在的宿主防御剂，为一类新的脊椎动物抗菌分子提供了深入了解。
