A typical bacterial ornithine-containing lipid Nalpha-(D)-[3-(hexadecanoyloxy)hexadecanoyl]-ornithine is a strong stimulant for macrophages and a useful adjuvant

FEMS Immunol Med Microbiol. 1999 Jan;23(1):67-73. doi: 10.1111/j.1574-695X.1999.tb01718.x.


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.

MeSH terms

  • Adjuvants, Immunologic*
  • Animals
  • Gram-Negative Bacteria / chemistry*
  • Gram-Negative Bacteria / immunology
  • Immunoglobulin G / blood
  • Interleukin-1 / biosynthesis
  • Lipids / chemistry
  • Lipids / immunology*
  • Lipids / isolation & purification
  • Macrophage Activation
  • Macrophages, Peritoneal / immunology
  • Mice
  • Ornithine / analysis*
  • Prostaglandins E / biosynthesis
  • Spectrometry, Mass, Fast Atom Bombardment
  • Tetanus Toxoid / immunology


  • 3-(hexadecanoyloxy)hexadecanoyl-ornithine
  • Adjuvants, Immunologic
  • Immunoglobulin G
  • Interleukin-1
  • Lipids
  • Prostaglandins E
  • Tetanus Toxoid
  • Ornithine