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Investigation of the chemical structure and biological activity of oligosaccharides isolated from rough-type Xanthomonas campestris pv. campestris B100 lipopolysaccharide

Division of Structural Biochemistry, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel, Germany

Sebastian Braun

Abteilung 7, Proteom- und Metabolomforschung, Fakultät für Biologie, Universität Bielefeld, Bielefeld, Germany

Buko Lindner

Division of Immunochemistry, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel, Germany

Karsten Niehaus

Abteilung 7, Proteom- und Metabolomforschung, Fakultät für Biologie, Universität Bielefeld, Bielefeld, Germany

Otto Holst

Division of Structural Biochemistry, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel, Germany, oholst{at}fz-borstel.de

The rough-type lipopolysaccharide (LPS) of the phytopathogenic bacterium Xanthomonas campestris pv. campestris B 100 was isolated utilizing the hot phenol-water method and successively de-acylated by treatment with hydrazine and hot potassium hydroxide. Four compounds were separated by preparative high-performance anion-exchange chromatography and studied by sugar analysis and by 1D and 2D homonuclear and heteronuclear ¹H-, ¹³C- and ³¹P-NMR spectroscopy as well as ESI FT-MS. The two main products were a heptasaccharide and a pentasaccharide of the structures -D-Manp-(13)--D-Man p-(14)-ß-D-Glcp-(14)--D-Manp-3P -(15)--Kdo-(26)-ß-D-GlcpN-4P-(16)--D-Glc pN-1P (1) and ß-D-Glcp-(14)--D-Man p-3P-(15)--Kdo-(26)-ß-D-GlcpN-4 P-(16)--D-GlcpN-1P (2), respectively. The products in smaller amounts were a heptasaccharide and pentasaccharide possessing the above structures plus a phosphate group at C-4 of the Kdo residue (compounds 3 and 4). Both, heptasaccharide 1 and pentasaccharide 2 were able to induce an oxidative burst in cell cultures of the non-host plant tobacco.

Key Words: Lipopolysaccharides • Xanthomonas campestris pv. campestris • structural analysis • NMR spectroscopy • ESI FT-MS • oxidative burst

Journal of Endotoxin Research, Vol. 13, No. 2, 101-108 (2007)
DOI: 10.1177/0968051907079121


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