The Lipid A from Rhodopseudomonas palustris Strain BisA53 LPS Possesses a Unique Structure and Low Immunostimulant Properties

Chemistry. 2017 Mar 13;23(15):3637-3647. doi: 10.1002/chem.201604379. Epub 2016 Dec 22.

Abstract

The search for novel lipid A analogues from any biological source that can act as antagonists, displaying inhibitory activity towards the production of pro-inflammatory cytokines, or as immunomodulators in mammals, is a very topical issue. To this aim, the structure and immunological properties of the lipopolysaccharide lipid A from the purple nonsulfur bacterium Rhodopseudomonas palustris strain BisA53 have been determined. This lipid A displays a unique structural feature, with a non-phosphorylated skeleton made up of the tetrasaccharide Manp-α-(1→4)-GlcpN3N-β-1→6-GlcpN3N-α-(1→1)-α-GalpA, and four primary amide-linked 14:0(3-OH) and, as secondary O-acyl substituents, a 16:0 and the very long-chain fatty acid 26:0(25-OAc), appended on the GlcpN3N units. This lipid A architecture is definitely rare, so far identified only in the genus Bradyrhizobium. Immunological tests on both murine bone-marrow-derived and human monocyte-derived macrophages revealed an extremely low immunostimulant capability of this LPS lipid A.

Keywords: NMR spectroscopy; fatty acids; glycolipids; innate immunity; lipopolysaccharides.

MeSH terms

  • Adjuvants, Immunologic / chemistry*
  • Adjuvants, Immunologic / pharmacology*
  • Animals
  • Cells, Cultured
  • Humans
  • Immunity, Innate / drug effects
  • Lipid A / chemistry*
  • Lipid A / pharmacology*
  • Macrophages / drug effects
  • Macrophages / immunology
  • Magnetic Resonance Spectroscopy
  • Mice, Inbred C57BL
  • Rhodopseudomonas / chemistry*
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Adjuvants, Immunologic
  • Lipid A