A novel cytokine-inducing glycolipid isolated from the lipoteichoic acid fraction of Enterococcus hirae ATCC 9790: a fundamental structure of the hydrophilic part.
Previously, we showed that quantitatively minor several glycolipids totaling only less than 5% of the lipoteichoic acid (LTA) fraction from Enterococcus hirae ATCC 9790 possessed cytokine-inducing activity, whereas the major component (over 90%) did not [Suda et al. (1995) FEMS Immun Med Microbiol 12:97-112]. The major inactive component was shown to have the chemical structure as was proposed for the LTA by Fischer [Hashimoto et al. (1997) J Biochem 121:779-86], suggesting that so-called LTA is not a cytokine-inducing component in the Gram-positive bacteria. In the present paper, the structure of the hydrophilic part of one of the cytokine-inducing glycolipid tentatively named GL4 is elucidated. GL4 was first subjected to hydrolysis with aqueous HF to give a polysaccharide and a mixture of low molecular weight products. The polysaccharide was composed mainly of highly branching mannan as concluded from NMR and MS analyses of its acetolysis products. The low molecular weight products consisted of phosphate and glycerol, suggesting the presence of a poly(glycerophosphate) structure in the original GL4. From these observations, the hydrophilic part of GL4 was shown to consist of mannose-rich polysaccharide and poly(glycerophosphate), the latter being bound to the former by a phosphodiester linkage.
Hashimoto
M
M
Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Japan.
Imamura
Y
Y
Yasuoka
J
J
Kotani
S
S
Kusumoto
S
S
Suda
Y
Y
D002240:Carbohydrate Sequence; D016983:Enterococcus / Q000737:chemistry*; D006017:Glycolipids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015850:Interleukin-6 / Q000097:blood / Q000378:metabolism*; D008070:Lipopolysaccharides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D013682:Teichoic Acids / Q000737:chemistry*
D006017:Glycolipids; D015850:Interleukin-6; D008070:Lipopolysaccharides; D013682:Teichoic Acids; C009900:lipoteichoic acid