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Biologically active glycosides from asteroidea, XVII. Glycosphingolipids from the starfishAcanthaster planci, 3. Isolation and structure of two new ceramide lactosides

✍ Scribed by Kawano, Yasuhiro ;Higuchi, Ryuichi ;Isobe, Ryuichi ;Komori, Tetsuya

Publisher: John Wiley and Sons
Year: 1988
Tongue: English
Weight: 374 KB
Volume: 1988
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198819881213

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✦ Synopsis

Two new ccramidc lactosides. acanthalactoside A (1) and B (2) were isolatcd from the watcr-solublc lipid fraction of tlic chlordorrn:iiicthanol extract of h e starfish .Ir+u~trhrr,str~r pluwi. O n the h;isir or chemical and spcctral cvidencc. the structures of I and 2 wcrc ct1nractcri7.cd as 1 -U-~Pu-giilactopyranosyl-( 1 -+4)-p-~~, -p l u w p y ranosyl]-substituted (2S.3S.4R )-2-[(?R )-2-hydroxytet r;~cosanc~yl;iminn]-1.3.4-hexadecanetriol I1 J and (ZS.3.5.4R.13E)-2 -[ ( 2 K 1-2-hydrvxyhciadccanoylamin~]-13-docosene-l,3,4-triol (2). rcs pcct ivcl y . Rcvcrscd-phasc column chronia1ograph y was usdul 10 obtain tlic plycosphingolipid mixture from the walcrwtuhlc lipid fraction containing also othcr malcrial such as stcroici saponins. Rcrcrscd-phase H PLC was also effectual to isolalc ihrsc ccraniide diherosidcs rcmiling vcry close rcscmblancc in striictiire. Ncgativc FA B mass spectrometry was successfully used Cor tlic dvtcrmiiiatic~n :ind confirmation of the cerarnidc dihexosidcs.

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