Structure of the ascarosides from Ascaris suum.
Six glycosides have been identified from the nematode Ascaris suum. The glycon part of all six glycosides is alpha L-3,6-dideoxymannose, previously known as ascarylose. The major components (4 and 5) and the minor components (8 and 9) have been shown by NMR and electrospray MS to involve a mixture of two homologous aglycons: the 2, omega-1 diols of hentriacontane and tritriacontane. Compounds 4 and 5 are glycosylated on only one of the hydroxy groups, while 8 and 9 are glycosylated on both. These compounds resemble ascarosides B and C previously isolated from Parascaris equorum. However, these aglycons are reported to be based on the 2,6-diol of hentriacontane. Compounds 6 and 7 are based on 2-hydroxy-nonacosane and 2-hydroxy-28-methylnonacosane glycosylated at C-2 with the same sugar. Although 6 and 7 are related to ascaroside A, previously isolated from P. equorum, these earlier reports suggest the chain in ascaroside A to be unbranched.
Bartley
J P
JP
School of Chemistry, Queensland University of Technology, Brisbane, Australia.
Bennett
E A
EA
Darben
P A
PA
D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry* / Q000302:isolation & purification; D017165:Ascaris suum / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D008969:Molecular Sequence Data
D000969:Antinematodal Agents; D006027:Glycosides