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Chemical structure and biological activity of a lipid A component from Helicobacter pylori strain 206

Department of Chemistry, Graduate School of Science, Osaka University, Osaka, Japan, ysuda{at}chem.sci.osaka-u.ac.jp, Department of Bacteriology and Laboratory of Host Defenses, Institute for Advanced Medical Sciences (IAMS), Hyogo College of Medicine, Hyogo, Japan

Yong-Min Kim

Department of Internal Medicine IV, Hyogo College of Medicine, Hyogo, Japan

Tomohiko Ogawa

Department of Oral Microbiology, Asahi University School of Dentistry, Gifu, Japan

Norio Yasui

Department of Chemistry, Graduate School of Science, Osaka University, Osaka, Japan

Yushi Hasegawa

Department of Chemistry, Graduate School of Science, Osaka University, Osaka, Japan

Wataru Kashihara

Department of Internal Medicine IV, Hyogo College of Medicine, Hyogo, Japan

Takashi Shimoyama

Department of Internal Medicine IV, Hyogo College of Medicine, Hyogo, Japan

Kazue Aoyama

Department of Bacteriology and Laboratory of Host Defenses, Institute for Advanced Medical Sciences (IAMS), Hyogo College of Medicine, Hyogo, Japan

Kumiko Nagata

Department of Bacteriology and Laboratory of Host Defenses, Institute for Advanced Medical Sciences (IAMS), Hyogo College of Medicine, Hyogo, Japan

Toshihide Tamura

Department of Bacteriology and Laboratory of Host Defenses, Institute for Advanced Medical Sciences (IAMS), Hyogo College of Medicine, Hyogo, Japan

Shoichi Kusumoto

Department of Chemistry, Graduate School of Science, Osaka University, Osaka, Japan

The chemical structure of a lipid A, which was obtained as a minor component from lipopolysaccharide of Helicobacter pylori strain 206-1, was determined to be a glucosamine ß-(1-6) disaccharide 1-(2-aminoethyl)phosphate acylated by (R)-3-hydroxyoctadecanoic acid, (R)-3-hydroxyhexadecanoic acid, and (R)-3-(octadecanoyloxy)octadecanoic acid at the 2-, 3- and 2'positions, respectively. Compared with the other major lipid A from the same strain, which was previously reported [Suda Y, Ogawa T, Kashihara W et al. Chemical structure of lipid A from Helicobacter pylori strain 206-1 lipopolysaccharide. J Biochem 1997; 121: 1129—1133], the structure was very similar with one exception. An (R)-3-hydroxyhexadecanoic acid was present at the 3-position of the novel lipid A component. The structure is apparently identical to one of the proposals by Moran et al. [Moran AP, Lindner B, Walsh EJ. Structural characterization of the lipid A component of Helicobacter pylori rough- and smooth-form lipopolysaccharides. J Bacteriol 1997; 179: 6453—6463], who concluded the same structure as the so-called major lipid A from the H. pylori strain NCTC 11637 but without isolating a homogenous component. The endotoxic properties and pro-inflammatory cytokine-inducing activities of this novel tetra-acyl type lipid A were lower than those of previously reported major tri-acyl type lipid A.

Journal of Endotoxin Research, Vol. 7, No. 2, 95-104 (2001)
DOI: 10.1177/09680519010070020301


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