Structure of biologically active and inactive cerebrosides prepared from Schizophyllum commune.
A cerebroside fraction prepared from the mycelia of Schizophyllum commune was further fractionated into five components (I-V) by reverse-phase high-performance liquid chromatography. Fruiting-inducing activity was found in I-IV but not in V. By gas-liquid chromatography-mass spectrometry and nuclear magnetic resonance analyses it was shown that these fractions contained: I, a mixture of N-2'-hydroxypentadecanoyl-1-O-glucosyl-nonadecasphingadienine++ + and N-2'-hydroxyhexadecanoyl-1-O-glucosyl-sphingadienine; II, (4E,8E)-N-D-2'-hydroxyhexadecanoyl-1-O-beta-D-glucopyr anosyl-9-methyl-4,8- sphingadienine (Kawai and Ikeda. 1983. Biochim. Biophys. Acta. 754: 243-248); III, N-2'-hydroxyheptadecanoyl-1-O-glucosyl-nonadecasphingadienine++ +; IV, N-2'-hydroxyoctadecanoyl-1-O-glucosyl-nonadecasphinadienine; V, (4E,8E)-N-2'-hydroxytetracosanoyl-1-O-beta-glucopyrano syl-9-methyl-4,8- sphingadienine. The only structural difference observed between biologically active and inactive cerebrosides was the chain length of acyl moiety; the cerebroside having an acyl chain of 24 carbon atoms was inactive.
D000363:Agaricales / Q000032:analysis*; D000818:Animals; D002417:Cattle; D002554:Cerebrosides / Q000302:isolation & purification* / Q000502:physiology; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D008401:Gas Chromatography-Mass Spectrometry; D005776:Gaucher Disease / Q000378:metabolism; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D012567:Schizophyllum / Q000032:analysis*; D013154:Spleen / Q000032:analysis; D013329:Structure-Activity Relationship
D002554:Cerebrosides