Partial structure and immunological properties of lipopolysaccharide from marine-derived Pseudomonas stutzeri KMM 226.

The partial structure and immunology of the lipopolysaccharide (LPS) of Pseudomonas stutzeri KMM 226, a bacterium isolated from a seawater sample collected at a depth of 2000 m, was characterised. The O-polysaccharide was built up of disaccharide repeating units constituted by L-Rhap and D-GlcpNAc: →2)-α-L-Rhap-(1→3)-α-D-GlcpNAc-(1→. The structural analysis of the lipid A showed a mixture of different species. The major species were hexa-acylated and penta-acylated lipids A, bearing the 12:0(3-OH) in amide linkage and 10:0(3-OH) in ester linkage, while the secondary fatty acids were present only as 12:0. The presence of 12:0(2-OH) was not detected. The immunology experiments demonstrated that P. stutzeri KMM 226 LPS displayed a low ability to induce TNF-α, IL-1ß, IL-6, IL-8 and IL-10 cytokine production and acted as an antagonist of hexa-acylated Escherichia coli LPS in human blood in vitro.

A pseudoaminic acid-containing O-specific polysaccharide from a marine bacterium Cellulophaga fucicola.

The O-polysaccharide was isolated from the lipopolysaccharide of Cellulophaga fucicola and studied by chemical analyses along with (1)H and (13)C NMR spectroscopy. The following new structure of the O-polysaccharide of C. fucicola containing 5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-L-manno-non-2-ulosonic acid residue (pseudoaminic acid, Psep) was elucidated as the following:

Structure of the O-specific polysaccharide from a marine bacterium Cellulophaga algicola.

The O-polysaccharide was isolated from the lipopolysaccharide of Cellulophaga algicola and studied by chemical analyses along with 1H and 13C NMR spectroscopy, including 2D 1H, 1H COSY, TOCSY, ROESY, 1Н, 13С HSQC, HMBC experiments. It was found that the polysaccharide is built up of branched pentasaccharide repeating units, containing D-mannose (Man), D-glucuronic acid (GlcA), N-acetyl-D-glucosamine (GlcNAc), two L-rhamnose (Rha) residues and O-acetyl groups in a non-stoichiometric amount and has the following structure.

Structure and in vitro anticancer activity of sulfated O-polysaccharide from marine bacterium Poseidonocella pacifica KMM 9010T.

We presented the structure of the sulfated polysaccharide moiety and anticancer activity in vitro of the О-deacylated lipopolysaccharide (DPS) isolated from the marine bacterium Poseidonocella pacifica KMM 9010T. The structure of O-polysaccharide was investigated by chemical methods along with 1H and 13C NMR spectroscopy. The O-polysaccharide was built up of sulfated disaccharide repeating units consisted of d-rhamnose (d-Rhaр) and 3-deoxy-d-manno-oct-2-ulosonic acid (Kdop): →7)-ß-Kdoр4Ac5S-(2→3)-ß-d-Rhaр2S-(1→. We demonstrated that the DPS from P. pacifica KMM 9010T non-toxic for normal mouse epidermal cells (JB6 Cl41 cell line) and inhibited colony formation of human colorectal carcinoma HT-29, breast adenocarcinoma MCF-7 and melanoma SK-MEL-5 cells in a dose-dependent manner.

Structure of the O-specific polysaccharide from a marine bacterium Echinicola pacifica КММ 6172(Т) containing 2,3-diacetamido-2,3-dideoxy-D-glucuronic acid.

The O-polysaccharide was isolated from the lipopolysaccharide of Echinicola pacifica KMM 6172(T) and studied by chemical analyses along with (1)H and (13)C NMR spectroscopy, including (1)H, (1)H COSY, 1D and 2D TOCSY, ROESY, (1)H, (13)С HMQC, HMBC and H2BC experiments. It was found that the polysaccharide is built up of branched pentasaccharide repeating units, containing D-galactose (Gal), L-rhamnose (Rha), 2-acetamido-2-deoxy-D-glucose (GlcNAc), two residues of 2,3-diacetamido-2,3-dideoxy-D-glucuronic acid (GlcNAc3NAcA) and O-acetyl group in nonstoichiometric amount and has the following structure [Structure: see text].

Structure of polysaccharide moiety of Pseudomonas xanthomarina KMM 1447T lipopolysaccharide.

The structural analysis of a polysaccharide moiety of Pseudomonas xanthomarina KMM 1447T lipopolysaccharide (LPS) was carried out. Mild acid degradation of LPS resulted in identification of two polysaccharides. The major one was built of ß-D-GlcpNAcA residues amidated with L-Ala and Gly residues randomly. The minor polysaccharide was composed of branched tetrasaccharide repeating units constituted by two D-Galр, D-GalpNAc and ether of D-Glc with (2R,4R)-2,4-dihydroxypentanoic acid lactone (2R,4R-Dhpl): →3)-α-D-Galр-(1 â†’ 3)-ß-D-Galр-(1 â†’ 3)-[ß-D-Glcp4(2R,4R-Dhpl)-(1 â†’ 4)]-ß-D-GalpNAc-(1 â†’ .

Structure of the O-specific polysaccharide from the marine bacterium Rheinheimera japonica KMM 9513(T), containing N-glycosidic bond between monosaccharides.

The O-specific polysaccharide was isolated from the lipopolysaccharide of type strain Rheinheimera japonica KMM 9513(T) and studied by sugar analysis, Smith degradation, and two-dimensional (1)H and (13)C NMR spectroscopy including (1)H,(1)H-TOCSY, (1)H,(1)H-COSY, (1)H,(1)H-ROESY, (1)H,(13)C-HSQC, (1)H,(13)C-HMBC, (1)H,(13)C-H2BC and (1)H,(13)C-HSQC-TOCSY experiments. The new structure of the O-specific polysaccharide of R. japonica KMM 9513(T) containing N-glycosidic bond was established.

Structure and anticancer activity of sulfated O-polysaccharide from marine bacterium Cobetia litoralis KMM 3880(T).

We presented the structure of the polysaccharide moiety and anticancer activity in vitro of the sulfated lipopolysaccharide isolated from the marine bacterium Cobetia litoralis KMM 3880(T). The structure of O-polysaccharide was investigated by chemical methods along with (1)H and (13)C NMR spectroscopy. The O-polysaccharide was built up of branched trisaccharide repeating units consist of D-glucose (D-Glcр), D-mannose (D-Manр) and sulfated 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo5S): →7-ß-Kdoр4Ac5S-(2→4)-[ß-d-Glcp-(1→2)-]-ß-d-Manр6Ac-1→. We demonstrated that the lipopolysaccharide and О-deacetylated O-polysaccharide from Cobetia litoralis KMM 3880(T) inhibited a colony formation of human melanoma SK-MEL-28 and colorectal carcinoma HTC-116 cells.

Structure of the O-specific polysaccharide from a marine bacterium Echinicola vietnamensis KММ 6221Т.

The O-specific polysaccharide was isolated from the lipopolysaccharide of Echinicola vietnamensis and studied by chemical methods along with 1H and 13C NMR spectroscopy, including 2D 1H, 1H COSY, TOCSY, ROESY, 1H, 13C HSQC, HMBC, and H2BC experiments. It was found that the polysaccharide is built up of branched tetrasaccharide repeating units, containing 2-acetamido-2-deoxy-D-glucuronic acid (GlcNAcA), 2-acetamido-2-deoxy-D-galactose (GalNAc), and D-glucuronic acid (GlcA) with a terminal residue of 3,6-dideoxy-L-xylo-hexose (colitose, Col) and has the following structure. α-Colp1-->2-->4)-ß-D-GlcpNAcA-(1-->4)-ß-D-GlcpA-(1-->3)-α-D-GalpNAc-(1-->

Structure of the O-specific polysaccharide from a marine bacterium Cellulophaga tyrosinoxydans.

The O-polysaccharide was isolated from the lipopolysaccharide of Cellulophaga tyrosinoxydans and studied by chemical analyses along with (1)H and (13)C NMR spectroscopy, including 2D (1)H, (1)H COSY, TOCSY, ROESY, (1)Н, (13)С HSQC, HMBC and H2BC experiments. The following new structure of the O-polysaccharide of C. tyrosinoxydans containing l-fucose (Fuc), N-acetyl-d-glucosamine (GlcNAc), 4-acetamido-4,6-dideoxy-d-glucose (Qui4NAc) and two l-rhamnose residues (Rha) was established:.

Structure of the O-specific polysaccharide from the deep-sea marine bacterium Idiomarina abyssalis КММ 227(T) containing a 2-O-sulfate-3-N-(4-hydroxybutanoyl)-3,6-dideoxy-d-glucose.

The O-specific polysaccharide was isolated from the lipopolysaccharide of type strain Idiomarina abyssalis КММ 227(T) and studied by sugar analysis, Smith degradation, and two-dimensional (1)H and (13)C NMR spectroscopy including (1)H,(1)H-TOCSY, (1)H,(1)H-COSY, (1)H,(1)H-ROESY, (1)H,(13)C-HSQC, (1)H,(13)C-HMBC, (1)H,(13)C-H2BC and (1)H,(13)C-HSQC-TOCSY experiments. The new structure of the O-specific polysaccharide of I. abyssalis КММ 227(T) containing 2-O-sulfate-3-N-(4-hydroxybutanoyl)-3,6-dideoxy-d-glucose was established.

The O-specific polysaccharide from the marine bacterium Pseudoalteromonas agarivorans KMM 255(T).

The O-specific polysaccharide was isolated from the lipopolysaccharide of a marine bacterium Pseudoalteromonas agarivorans KMM 255(T) and studied by chemical methods along with (1)H and (13)C NMR spectroscopies. The following new structure of the O-specific polysaccharide from P. agarivorans KMM 255(T) containing 2-acetamido-2-deoxy-D-glucose (D-GlcNAc), D-glucose (D-Glc), D-glucuronic acid (D-GlcA) and two residues of D-galactose (D-Gal) was established: Formula: see text].

Structure of the O-polysaccharide of Idiomarina zobellii KMM 231T containing two unusual amino sugars with the free amino group, 4-amino-4,6-dideoxy-D-glucose and 2-amino-2-deoxy-L-guluronic acid.

Mild acid degradation of the lipopolysaccharide of the bacterium Idiomarina zobellii, type strain KMM 231T, with aq 2% HOAc at 100 degrees C, yielded an oligosaccharide, which represents one repeating unit of the O-polysaccharide. A polysaccharide was obtained by mild base degradation of the lipopolysaccharide. The following structure of the O-polysaccharide was elucidated by 1H and 13C NMR spectroscopy of the oligosaccharide and base-degraded lipopolysaccharide, including COSY, TOCSY, ROESY, 1H, 13C HSQC, HSQC-TOCSY and HMBC experiments: [-->3)-alpha-D-Quip4N-(1-->4)-alpha-D-GlcpA-(1-->6)-alpha-D-GlcpNAc-(1-->4)-alpha-L-GulpNA-(1-->3)-beta-D-FucpNAc-(1-->] The O-polysaccharide is distinguished by the presence of two unusual amino sugars, 4-amino-4,6-dideoxy-D-glucose (D-Qui4N) and 2-amino-2-deoxy-L-guluronic acid (L-GulNA), both having the free amino group. The unexpectedly high acid lability of the glycosidic linkage of 2-acetamido-2,6-dideoxy-D-galactose (D-FucNAc) could be associated with the presence of a free amino group adjacent to the site of attachment of FucNAc to Qui4N.

Structures of polysaccharides and oligosaccharides of some Gram-negative marine Proteobacteria.

The chemical structures of polysaccharides and LPS core oligosaccharides, isolated from various Gram-negative marine bacteria from the genera Pseudoalteromonas and Shewanella belonging to the Alteromonadaceae family and gamma-subclass of Proteobacteria, are reviewed. The polysaccharides are distinguished by the acidic character (e.g., due to the presence of hexuronic and aldulosonic acids and their derivatives) and the occurrence of unusual sugars, including N-acyl derivatives of 6-deoxyamino sugars, such as N-acetyl-D-quinovosamine, N-acetyl-L-fucosamine and N-acetyl-6-deoxy-L-talosamine, and higher sugars like 2,6-dideoxy-2-acetamido-4-C-(3'-carboxamide-2',2'-dihydroxypropyl)-D-galactopyranose (shewanellose). Many constituent sugars have various uncommon non-sugar substituents, such as alanine, formic, lactic and hydroxybutyric acids, sulfate, phosphate, and 2-aminopropane-1,3-diol.

The new sulfated O-specific polysaccharide from marine bacterium Cobetia pacifica KMM 3878, containing 3,4-O-[(S)-1-carboxyethylidene]-D-galactose and 2,3-O-disulfate-D-galactose.

The O-specific polysaccharide was isolated from the lipopolysaccharide of Cobetia pacifica KMM 3878 and studied by chemical methods along with (1)H and (13)C NMR spectroscopy, including, 1D TOCSY and 2D (1)H, (1)H COSY, (1)H, (13)C HSQC, (1)H, (1)H ROESY, (1)H, (13)C HMBC and (1)H, (13)C H2BC experiments. The following new structure of the sulfated O-polysaccharide from C. pacifica KMM 3878 containing 3,4-O-[(S)-1-carboxyethylidene]-D-galactose and 2,3-O-disulfate-D-galactose was established: →4)-ß-D-Gal2,3R-(1→6)-ß-D-Gal3,4(S-Pyr)-(1→6)-ß-D-Gal-(1→ Where R is -SO3H.

The sulfated O-specific polysaccharide from the marine bacterium Cobetia pacifica KMM 3879(T.).

The O-specific polysaccharide was isolated from the lipopolysaccharide of Cobetia pacifica KMM 3879(T) and studied by chemical methods along with (1)H and (13)C NMR spectroscopy, including 1D TOCSY and 2D (1)H, (1)H-COSY, ROESY, (1)H, (13)C-HSQC, HMBC, H2BC and HMQC-TOCSY experiments. The following new structure of the sulfated O-polysaccharide from the C. pacifica KMM 3879(T) containing rhamnose (Rha), glucose (Glc), and galactose (Gal) was established: where R is -SO3H.

The O-specific polysaccharide of the marine bacterium Rheinheimera pacifica KММ 1406T containing D- and L-2-acetamido-2-deoxy-galacturonic acids.

The O-specific polysaccharide was isolated from the lipopolysaccharide of Rheinheimera pacifica KММ 1406T and studied by chemical methods along with 1H and 13C NMR spectroscopy. It was shown that the polysaccharide contains one residue each of 2-acetamido-2-deoxy-D-galactose (D-GalNAc), 2-acetamido-2-deoxy-D- and 2-acetamido-2-deoxy-L-galacturonic acids (D-GalNAcA, L-GalNAcA), 2,4-diacetamido-2,4,6-trideoxy-D-glucose (D-QuiNAc4NAc), and 4-(N-acetyl-D-alanyl)amino-4,6-dideoxy-D-glucose (D-Qui4NAlaAc) and has the following structure: →4)-α-D-GalpNAc-(1→4)-α-L-GalpNAcA-(1→3)-ß-D-QuipNAc4NAc-(1→2)-ß-D-Quip4NDAlaAc-(1→4)-α-D-GalpNAcA-(1→

The structure of the O-specific polysaccharide from marine bacterium Litorimonas taeanensis G5T containing 2-acetamido-4-((3S,5S)-3,5-dihydroxyhexanamido)-2,4-dideoxy-D-quinovose and 2-acetamido-2,6-dideoxy-L-xylo-hexos-4-ulose.

The O-polysaccharide was isolated from the lipopolysaccharide of Litorimonas taeanensis G5(T) and studied by chemical methods along with (1)H and (13)C NMR spectroscopy, including (1)H, (1)H COSY, 1D and 2D TOCSY, NOESY, (1)H, (13)C HSQC, HMBC, and H2BC experiments. The following new structure of the O-polysaccharide of L. taeanensis G5(T) containing 2-acetamido-2-deoxy-D-galacturonic acid (D-GalNAcA), 2-acetamido-4-((3S,5S)-3,5-dihydroxyhexanamido)-2,4-dideoxy-D-quinovose (D-QuiNAc4NR), and 2-acetamido-2,6-dideoxy-L-xylo-hexos-4-ulose (L-Sug) was established: →4)-α-D-GalpNAcA-(1→3)-α-D-QuiNAc4NR-(1→3)-α-L-Sug-(1→ where R is (3S,5S)-3,5-dihydroxyhexanoic acid.

Structure of the O-specific polysaccharide from a marine bacterium Cellulophaga pacifica containing rarely occurred sugars, Fuc4NAc and ManNAcA.

The O-polysaccharide was isolated from the lipopolysaccharide of Cellulophaga pacifica and studied by chemical methods including Smith degradation as well as (1)H and (13)C NMR spectroscopy. The following structure of the O-polysaccharide of Cellulophaga pacifica containing N-acetyl-d-glucosamine (GlcNAc), 4-acetamido-4,6-dideoxy-d-galactose (Fuc4NAc) and two residues of 2-acetamido-2-deoxy-d-mannuronic acid (ManNAcA) was established. (Formula see text).

Structure of the O-specific polysaccharide from a marine bacterium Oceanisphaeralitoralis KMM 3654(T) containing ManNAcA.

The O-specific polysaccharide was isolated from the lipopolysaccharide of a marine bacterium Oceanisphaeralitoralis KMM 3654(T) and studied by chemical methods along with (1)H and (13)C NMR spectroscopy. The following new structure of the O-specific polysaccharide of O. litoralis containing D-glucose and two residues of 2-acetamido-2-deoxy-D-mannuronic acid was established: →4)-α-D-Glcp-(1→4)-ß-D-ManpNAcA-(1→4)-ß-D-ManpNAcA-(1→.