Structure of an Amino Acid-Decorated Exopolysaccharide Secreted by a Vibrio alginolyticus Strain

Abstract

Vibrio alginolyticus (CNCM I-4994) secretes an exopolysaccharide that can be used as an ingredient in cosmetic applications. The structure was resolved using chromatography and one- and two-dimensional NMR spectroscopy experiments. The results show that the carbohydrate backbone is made of two residues: d-galacturonic acid and N-acetyl-d-glucosamine (GlcNac), which together constitute a tetrasaccharide repetition unit: [→3)-α-d-GalA-(1→4)-α-d-GalA-(1→3)-α-d-GalA-(1→3)-β-GlcNAc(1→]. Two amino acids, alanine and serine, are linked to GalA residues via amido linkages. The position and the distribution of the amino acids were characterized by two-dimensional NMR spectroscopy. To our knowledge, this is the first description of a structure for a marine exopolysaccharide decorated with an amino acid.

Structure of the Exopolysaccharide Secreted by a Marine Strain Vibrio alginolyticus

“…Exploring the “carbohydrate structure database” (CSDB, , [ 9 ]), several structures of Vibrio sp. polysaccharides presented alanine derivatives, including V. ordalii [ 10 ], V. cholera [ 11 ], V. parahaemolyticus [ 12 ], V. anguillarum [ 13 ], and V. alginolyticus [ 14 ]. Similarly, Vibrio spp decorated by S-lactate were reported for strains of V. cholerae O144 and O76 strains [ 15 , 16 ], R-lactate in V. fluvialis [ 17 ] and uncharacterized lactate in V. cholerae O:1 [ 18 ].…”

Exopolysaccharides from Marine and Marine Extremophilic Bacteria: Structures, Properties, Ecological Roles and Applications

“…The glycosyl composition for the purified polymer indicated only neutral and amino sugars ( Table 2 ). Instead, the EPS isolated from the strain CNCM I-4994 of V. alginolyticus was composed of galacturonic and N-acetyl glucosamine monosaccharides ( Table 2 , Figure 4 q) [ 124 ]. This polymer is produced on an industrial scale as an ingredient for cosmetic applications for its mattifying and anti-inflammatory properties [ 124 ].…”

“…Instead, the EPS isolated from the strain CNCM I-4994 of V. alginolyticus was composed of galacturonic and N-acetyl glucosamine monosaccharides ( Table 2 , Figure 4 q) [ 124 ]. This polymer is produced on an industrial scale as an ingredient for cosmetic applications for its mattifying and anti-inflammatory properties [ 124 ]. The most interesting feature of the repeating unit is the amino acidic decoration, which has also been reported for both C. psychrerythraea 34H CPS and EPS [ 37 , 79 ].…”

Structure of the Polysaccharide Secreted by Vibrio alginolyticus CNCM I-5035 (Epidermist 4.0TM)

“…In conclusion, the structure investigated in this study is the third exopolysaccharide structure secreted by a V. alginolyticus strain [ 7 , 8 ]. The composition of the repetition unit determined as well as the sequence of residues have no similarities, suggesting that the biosynthetic pathways of these polysaccharides probably have no common ancestor.…”

“…These technical advantages are not sufficient for the development of novel marine EPSs as gelling or thickening agents which are facing the already marketed terrestrial bacterial EPSs, such as xanthan ( Xanthomonas campestris ) or gellan ( Sphingomonas paucimobilis ) Recently, marine EPSs showing both interesting rheological properties and biological properties could be valorized in niche applications in the biomedical and cosmetic sectors. Among them, the elucidation of the structures of two EPSs secreted by two distinct Vibrio alginolyticus strains used as bioactive ingredients in cosmetic applications revealed original structures presenting decoration of the polysaccharide backbone by amino acids (strain CNCM I-4994) and the occurrence of the rare “nosturonic acid” residue (strain CNCM I-5034) [ 7 , 8 ].…”