Aminosterols from the dogfish shark Squalus acanthias
| Autor: | Sharkansky I, Noecker La, Kinney Wa, Jones, Zasloff M, Rao Mn, Feibush B, Sarkahian A, Shinnar Ae, Chao Tl, Snyder B, Zhang X |
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| Rok vydání: | 2000 |
| Předmět: |
Magnetic Resonance Spectroscopy
Stereochemistry Pharmaceutical Science Spermine Microbial Sensitivity Tests Biology Spectrometry Mass Fast Atom Bombardment Analytical Chemistry chemistry.chemical_compound Sulfation Squalus acanthias Drug Discovery Animals Chromatography High Pressure Liquid Pharmacology Bacteria Organic Chemistry Anti-Bacterial Agents Spermidine Sterols Complementary and alternative medicine chemistry Liver Squalamine Dogfish Molecular Medicine Cholestane Two-dimensional nuclear magnetic resonance spectroscopy Conjugate |
| Zdroj: | Journal of natural products. 63(5) |
| ISSN: | 0163-3864 |
| Popis: | Seven new aminosterols related to squalamine (8) were isolated from the liver of the dogfish shark Squalus acanthias. Their structures (1-7) were determined using spectroscopic methods, including 2D NMR and HRFABMS. These aminosterols possess a relatively invariant cholestane skeleton with a trans AB ring junction, a spermidine or spermine attached equatorially at C3, and a steroidal side-chain that may be sulfated. The structure of the lone spermine conjugate, 7 (MSI-1436), was confirmed by its synthesis from (5alpha,7alpha, 24R)-7-hydroxy-3-ketocholestan-24-yl sulfate. Some members of this family of aminosterols exhibit a broad spectrum of antimicrobial activity comparable to squalamine. |
| Databáze: | OpenAIRE |
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