A typical bacterial ornithine-containing lipid Nalpha-(D)-[3-(hexadecanoyloxy)hexadecanoyl]-ornithine is a strong stimulant for macrophages and a useful adjuvant.
Nalpha-[3-(Hexadecanoyloxy)hexadecanoyl]-ornithine is a typical bacterial ornithine-containing lipid (OL). The configuration of the 3-hydroxy fatty acids in the OL was proved to be D by using HPLC with chiral column. For this analysis, Nalpha-(D or L)-[3-(hexadecanoyloxy)hexadecanoyl]-L-ornithine were synthesized and used as standards. The typical bacterial OL, as well as the synthesized one, exhibited strong interleukin-1- and prostaglandin E2-inducing activities, and further, it induced the production of high IgG anti-tetanus toxoid antibodies in mice. The typical OL is expected to be utilized as a nontoxic, potent adjuvant.
Kawai
Y
Y
Department of Biochemistry and Cell Biology, National Institute of Infectious Diseases, Tokyo, Japan.
Nakagawa
Y
Y
Matuyama
T
T
Akagawa
K
K
Itagawa
K
K
Fukase
K
K
Kusumoto
S
S
Nishijima
M
M
Yano
I
I
D000276:Adjuvants, Immunologic; D000818:Animals; D006090:Gram-Negative Bacteria / Q000737:chemistry* / Q000276:immunology; D007074:Immunoglobulin G / Q000097:blood; D007375:Interleukin-1 / Q000096:biosynthesis; D008055:Lipids / Q000737:chemistry / Q000276:immunology* / Q000302:isolation & purification; D008262:Macrophage Activation; D017737:Macrophages, Peritoneal / Q000276:immunology; D051379:Mice; D009952:Ornithine / Q000032:analysis*; D011458:Prostaglandins E / Q000096:biosynthesis; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013745:Tetanus Toxoid / Q000276:immunology
C120475:3-(hexadecanoyloxy)hexadecanoyl-ornithine; D000276:Adjuvants, Immunologic; D007074:Immunoglobulin G; D007375:Interleukin-1; D008055:Lipids; D011458:Prostaglandins E; D013745:Tetanus Toxoid; D009952:Ornithine