Unique cholesteryl glucosides in Helicobacter pylori: composition and structural analysis.
A chloroform-methanol-extracted lipid of Helicobacter pylori was studied. Three kinds of glycolipids, accounting for about 25% (wt/wt) of the total lipid, were detected and identified to be cholesteryl glucosides. The structures of two of them were determined to be cholesteryl-alpha-D-glucopyranoside and cholesteryl-6-O-tetrade-canoyl-alpha-D-glucopyranoside, and the plausible structure of the third one was identified as cholesteryl-6-O-phosphatidyl-alpha-D-glucopyranoside. Cholesteryl glucosides are very rare in animals and bacteria. Furthermore, those in H. pylori had an alpha-glycosidic linkage, which is rather unusual for natural glycosides, and a phosphate-linked cholesteryl glycoside like the cholesteryl-6-O-phosphatidyl-alpha-D-glucopyranoside has not been reported previously. As the cholesterol glucosides were detected in strains obtained from diverse geographical locations, the presence of cholesteryl glucosides in H. pylori is a very unique and a characteristic feature of the species. These findings add a new facet to the physiology and biochemistry, especially the cholesterol and glucose metabolism, of H. pylori. Furthermore, the cholesteryl glucosides of H. pylori showed hemolytic activities.
Hirai
Y
Y
Department of Bacteriology, Okayama University Medical School, Japan.
Haque
M
M
Yoshida
T
T
Yokota
K
K
Yasuda
T
T
Oguma
K
K
D002784:Cholesterol / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry; D005227:Fatty Acids / Q000032:analysis; D005947:Glucose / Q000032:analysis; D005990:Glycerol / Q000032:analysis; D006017:Glycolipids / Q000032:analysis; D016480:Helicobacter pylori / Q000737:chemistry*; D006461:Hemolysis; D008081:Liposomes; D015394:Molecular Structure; D010743:Phospholipids / Q000032:analysis
D005227:Fatty Acids; D006017:Glycolipids; D008081:Liposomes; D010743:Phospholipids; C027578:cholesteryl glucoside; D002784:Cholesterol; D005947:Glucose; D005990:Glycerol