Structural studies on lipoteichoic acids from four Listeria strains

Abstract

The lipoteichoic acids were isolated from phenol extracts of four Listeria strains representing serotypes 4a, 4b, 6a, and 6 to compare the differences in structure of amphiphilic polysaccharides from various serotypes of Listeria spp. The lipoteichoic acids from the four strains examined had the same structure in both hydrophilic chains and lipid portions. On the basis of the results of nuclear magnetic resonance spectroscopy and Smith degradation, the hydrophilic chains were shown to be 1,3-linked poly(glycerol phosphate) in which some of the glycerol residues had a-galactosyl substituents. The lipid portions were released by treatment with 46% hydrogen fluoride or 98% acetic acid. They were determined to be 3(1)-(2'-O-a-D-galactopyranosyl-a-Dglucopyranosyl)-1(3),2-diacylglycerol and 3(1)-[6'-phosphatidyl-2' -O-(a-D-galactopyranosyl)-a-Dglucopyranosyl]-1(3),2-diacylglycerol. The degrees of glycosyl substitution and proportions of the two lipids varied to some extent among these four strains.The antigenic scheme of Listeria spp., based on the somatic (0) and flagellar (H) antigens, includes 17 recognized serotypes, which can be divided into 13 groups by the differences in their somatic antigens (31). Ullmann and Cameron (35) reported the immunochemical properties of the cell wall carbohydrates of several serotypes of Listeria monocytogenes and described the monosaccharide constituents which should serve as the major antigenic determinant. Fiedler et al. (7) reported the composition of the cell walls from various serotypes of Listeria spp. and suggested that the glycosidic substituents of the cell wall teichoic acids determine the 0 antigenic specificities. Recently, the structures of cell wall teichoic acid from eight serotypes of Listeria spp. were reported (12,18,34), and some immunological properties of these teichoic acids were examined (18, 19) in our laboratory. In these studies, it seemed that the 0 serofactors of Listeria spp. cannot be entirely accounted for by cell wall teichoic acids; for instance, the structures of the cell wall teichoic acids from strain 5214 (serotype 4a) and strain 1383 (serotype 6) are identical (12,34). Therefore, other cell surface substances such as lipoteichoic acids also have to be taken into consideration in listerial 0 antigenicity.Lipoteichoic acids are membrane-associated amphiphilic molecules found in many gram-positive bacteria. They can act as surface antigens and often function as basis for serological classification of bacteria (20,39,40). Extracts obtained from L. monocytogenes contain apparent amphiphilic polysaccharides. The monocytosis-producing agent from serotype 1 cells is present in a high-molecularweight fraction containing phosphorus, lipids, and sugars (13). A phenol-water extract from serotype 1 cells contained a complex of peptide, polysaccharide, and lipid which had the biological activity of lipopolysaccharide (16,23 amphiphilic polysaccharide which was strikingly similar to gram-negative bacterial lipopolysaccharides in both chemical composition an...

Analysis of surface proteins of Listeria in relation to species, serovar and pathogenicity

“…The analysis of peptidoglycan and lipoteichoic acids has shown a similar structure for all Listeria species (Uchikawa et al, 1986;Fiedler & Ruhland, 1987). The analysis of somatic (0) and flagellar (H) antigens, using highly absorbed antisera, allowed the determination of 16 serovars but not the identification of strains, since different species can have the same 0 and H composition (Seeliger & Jones, 1986).…”

Lipoteichoic Acids, Phosphate-Containing Polymers in the Envelope of Gram-Positive Bacteria

“…For example, Lactobacillus gasseri JCM 1131 carries a tetrahexosylglycerol with either two or three fatty acid chains (37). Some species, including lactobacilli, streptococci, and listeria, may produce two variants of LTA where the glycolipid anchor may be substituted with acyl or phosphatidyl (25,29,38). For example, in lactobacilli the structure of the glycolipid anchor may be Glc(␤1-6)Gal(␣1-2)Glc(␤1-3) DAG or Glc(␤1-6)Gal(␣1-2)6-O-acyl-6Glc(␣1-3) DAG (25).…”

Wall Teichoic Acids Restrict Access of Bacteriophage Endolysin Ply118, Ply511, and PlyP40 Cell Wall Binding Domains to the Listeria monocytogenes Peptidoglycan

“…LTAs usually show less structural diversity (54). In L. monocytogenes, LTA polymers consist of hydrophilic poly(glycerol phosphate) chains decorated with D-alanine and galactosyl residues (23,39,50).…”

“…LTAs usually show less structural diversity (54). In L. monocytogenes, LTA polymers consist of hydrophilic poly(glycerol phosphate) chains decorated with D-alanine and galactosyl residues (23,39,50).The CBD of Listeria phage endolysin PlyP35 specifically recognizes N-acetylglucosamine (GlcNAc) residues attached to the ribitol phosphate in WTA polymers of L. monocytogenes serovar 1/2 and 3 strains (11). In contrast, the CBDs of Listeria phage endolysins Ply118, Ply511, and PlyP40 (34, 43) investigated here are assumed to recognize a more common, serovar-independent motif in the peptidoglycan structure (43).…”