State-of-art methodology of marine natural products chemistry: structure determination with extremely small sample amounts.
Structure elucidation studies on natural products are reviewed emphasizing extremely small sample amounts. Previous studies on insect pheromones, periplanones, and bean-originating kairomones, glycinoeclepins, are described briefly. Recent examples are selected from marine natural products such as ciguatoxin, dolastatin-3, and aurisides. A more detailed description is given of a sperm-activating and attracting factor (SAAF), which may be the smallest sample amount used in the structure elucidation of novel non-peptidic natural products. SAAF was isolated from the eggs of the ascidian, Ciona intestinalis, and its structure was deduced with only approximately 4 microg (6 nmol) of sample. Based upon the proposed structure, two epimers were synthesized from chenodeoxycholic acid in 17 steps, leading to the identification of SAAF as a novel sterol sulfate.
Murata
M
M
Department of Chemistry, Graduate School of Science, Osaka University, Toyonka, Osaka 560-0043, Japan.
Oishi
T
T
Yoshida
M
M
D000818:Animals; D001685:Biological Factors / Q000737:chemistry* / Q000302:isolation & purification; D005260:Female; D008297:Male; D008386:Marine Biology / Q000379:methods*; D008387:Marine Toxins / Q000737:chemistry; D015394:Molecular Structure; D013084:Sperm-Ovum Interactions / Q000502:physiology; D014561:Urochordata / Q000502:physiology
D001685:Biological Factors; D008387:Marine Toxins