Antifungal Alkyl Amino Alcohols from the Tropical Marine Sponge Haliclona n. sp

Three new amino alcohols presumably deriving from l-alanine were isolated from the tropical marine sponge Haliclona n. sp. and characterized by 2D NMR, while a fourth amino alcohol was characterized as an acetamide derivative. Relative stereochemistry was deduced from the NMR characteristics of oxaz...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2001-12, Vol.64 (12), p.1568-1571
Hauptverfasser:	Clark, Richard J, Garson, Mary J, Hooper, John N. A
Format:	Artikel
Sprache:	eng
Schlagworte:	Alanine - analogs & derivatives Alanine - chemistry Alanine - isolation & purification Alanine - pharmacology Alkanes - chemistry Alkanes - isolation & purification Alkanes - pharmacology alkyl amino alcohols Amino Alcohols - chemistry Amino Alcohols - isolation & purification Amino Alcohols - pharmacology Animals Anti-Bacterial Agents Anti-Infective Agents - chemistry Anti-Infective Agents - isolation & purification Anti-Infective Agents - pharmacology Antifungal Agents - chemistry Antifungal Agents - isolation & purification Antifungal Agents - pharmacology Australia Bacillus subtilis - drug effects Biological and medical sciences Candida albicans - drug effects Chromatography, High Pressure Liquid Demospongiae Escherichia coli - drug effects General pharmacology Haliclona Marine Medical sciences Molecular Structure natural products Nuclear Magnetic Resonance, Biomolecular Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Porifera - chemistry Stereoisomerism Urochordata - drug effects
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Beschreibung
Zusammenfassung:	Three new amino alcohols presumably deriving from l-alanine were isolated from the tropical marine sponge Haliclona n. sp. and characterized by 2D NMR, while a fourth amino alcohol was characterized as an acetamide derivative. Relative stereochemistry was deduced from the NMR characteristics of oxazolidinone derivatives and absolute stereochemistry secured by preparation and analysis of an MPA ester. The amino alcohol fraction from Haliclona n. sp. acts as an antifungal agent and inhibits the development of larvae of the ascidian Herdmania curvata.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np010246x