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 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.
Clark
R J
RJ
Department of Chemistry, The University of Queensland, Brisbane QLD 4072, Australia.
Garson
M J
MJ
Hooper
J N
JN
D000409:Alanine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000473:Alkanes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000605:Amino Alcohols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001315:Australia; D001412:Bacillus subtilis / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D004926:Escherichia coli / Q000187:drug effects; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism; D014561:Urochordata / Q000187:drug effects
D000473:Alkanes; D000605:Amino Alcohols; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000409:Alanine