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The structure of lipid A from lipopolysaccharide (LPS) of Rhodomicrobium vannielii ATCC 17100 ( Rv ) a phototrophic, budding bacterium was re-investigated using high-resolution mass spectrometry, NMR, and chemical degradation protocols. It was found that the (Glc p N)-disaccharide lipid A backbone was substituted by a Gal p A residue that was connected to C-1 of proximal Glc p N. Some of this Gal p A residue was β-eliminated by alkaline de-acylation, which indicated the possibility of the presence of another so far unidentified substituent at C-4 in non-stoichiometric amounts. One Man p residue substituted C-4' of distal Glc p N. The lipid A backbone was acylated by 16:0(3-OH) at C-2 of proximal Glc p N, and by 16:0(3-OH), i 17:0(3-OH), or 18:0(3-OH) at C-2' of distal Glc p N. Two acyloxy-acyl moieties that were mainly formed by 14:0(3- O -14:0) and 16:0(3- O -22:1) occupied the distal Glc p N of lipid A. Genes that were possibly involved in the modification of Rv lipid A were compared with bacterial genes of known function. The biological activity was tested at the model of human mononuclear cells (MNC), showing that Rv lipid A alone does not significantly stimulate MNC. At low concentrations of toxic Escherichia coli O111:B4 LPS, pre-incubation with Rv lipid A resulted in a substantial reduction of activity, but, when higher concentrations of E. coli LPS were used, the stimulatory effect was increased.

The Lipid A from the Lipopolysaccharide of the Phototrophic Bacterium Rhodomicrobium vannielii ATCC 17100 Revisited