Sokodosides, steroid glycosides with an isopropyl side chain, from the marine sponge Erylus placenta.
Two novel steroid glycosides, sokodosides A and B (1 and 2, respectively), were isolated from the marine sponge Erylus placenta as growth-inhibitory principles against several strains of yeast and a cancer cell line. Sokodosides possess the novel carbon skeleton as characterized by the presence of a combination of isopropyl side chain and the 4,4-dimethyl steroid nucleus. Sokodoside B has another unique characteristic in the presence of delta(8,14,16) unsaturation. The structures of sokodosides were determined by analysis of spectral data and chemical degradation. The absolute stereochemistry of sokodoside A (1) was determined by the application of the modified Mosher analysis to the aglycon obtained by acid hydrolysis, whereas the absolute stereochemistry of the monosaccharide units in 1 and 2 was determined by chiral GC analyses of the acid hydrolysates.
Okada
Yumika
Y
Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.
Matsunaga
Shigeki
S
van Soest
Rob W M
RW
Fusetani
Nobuhiro
N
D000818:Animals; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D051379:Mice; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D020094:Mortierella / Q000187:drug effects / Q000254:growth & development; D011161:Porifera / Q000737:chemistry*; D012441:Saccharomyces cerevisiae / Q000187:drug effects / Q000254:growth & development; D012680:Sensitivity and Specificity; D012995:Solubility; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship
D006027:Glycosides; D013256:Steroids; C520520:sokodoside A; C520521:sokodoside B