Chemical structure and biological activity of a lipid A component from Helicobacter pylori strain 206.
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 beta-(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 homogeneous 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.
Suda
Y
Y
Department of Chemistry, Graduate School of Science, Osaka University, Osaka, Japan. ysuda@chem.sci.osaka-u.ac.jp
Kim
Y M
YM
Ogawa
T
T
Yasui
N
N
Hasegawa
Y
Y
Kashihara
W
W
Shimoyama
T
T
Aoyama
K
K
Nagata
K
K
Tamura
T
T
Kusumoto
S
S
D000818:Animals; D002478:Cells, Cultured; D016207:Cytokines / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D005688:Galactosamine / Q000633:toxicity; D016480:Helicobacter pylori / Q000737:chemistry*; D006801:Humans; D007928:Lethal Dose 50; D008033:Limulus Test; D008050:Lipid A / Q000737:chemistry* / Q000502:physiology*; D008213:Lymphocyte Activation; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D008810:Mice, Inbred C57BL; D015394:Molecular Structure; D009000:Monocytes / Q000187:drug effects / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization
D016207:Cytokines; D008050:Lipid A; D005688:Galactosamine