Structural Investigation and Biological Activity of the Lipooligosaccharide from the Psychrophilic Bacterium Pseudoalteromonas haloplanktis TAB 23

Authors

  • Sara Carillo,

    1. Dipartimento di Chimica Organica e Biochimica, Università Federico II di Napoli, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli (Italia), Fax: (+39) 081674393
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    • These authors contributed equally to this work.

  • Dr. Giuseppina Pieretti,

    1. Dipartimento di Chimica Organica e Biochimica, Università Federico II di Napoli, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli (Italia), Fax: (+39) 081674393
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    • These authors contributed equally to this work.

  • Dr. Ermenegilda Parrilli,

    1. Dipartimento di Chimica Organica e Biochimica, Università Federico II di Napoli, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli (Italia), Fax: (+39) 081674393
    2. Facoltà di Scienze Biotecnologiche, Università Federico II di Napoli, 80126 Napoli (Italy)
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  • Prof. Dr. Maria L. Tutino,

    1. Dipartimento di Chimica Organica e Biochimica, Università Federico II di Napoli, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli (Italia), Fax: (+39) 081674393
    2. Facoltà di Scienze Biotecnologiche, Università Federico II di Napoli, 80126 Napoli (Italy)
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  • Dr. Sabrina Gemma,

    1. Bluegreen Biotech s.r.l. Via La Masa 19 Milano (Italy)
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  • Dr. Monica Molteni,

    1. Bluegreen Biotech s.r.l. Via La Masa 19 Milano (Italy)
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  • Prof. Dr. Rosa Lanzetta,

    1. Dipartimento di Chimica Organica e Biochimica, Università Federico II di Napoli, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli (Italia), Fax: (+39) 081674393
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  • Prof. Dr. Michelangelo Parrilli,

    1. Dipartimento di Chimica Organica e Biochimica, Università Federico II di Napoli, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli (Italia), Fax: (+39) 081674393
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  • Prof. Dr. Maria M. Corsaro

    Corresponding author
    1. Dipartimento di Chimica Organica e Biochimica, Università Federico II di Napoli, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli (Italia), Fax: (+39) 081674393
    • Dipartimento di Chimica Organica e Biochimica, Università Federico II di Napoli, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli (Italia), Fax: (+39) 081674393
    Search for more papers by this author

Abstract

Pseudoalteromonas haloplanktis TAB 23 is a Gram-negative psychrophilic bacterium isolated from the Antarctic coastal sea. To survive in these conditions psychrophilic bacteria have evolved typical membrane lipids and “antifreeze” proteins to protect the inner side of the microorganism. As for Gram-negative bacteria, the outer membrane is mainly constituted by lipopoly- or lipooligosaccharides (LPS or LOS, respectively), which lean towards the external environment. Despite this, very little is known about the peculiarity of LPS from Gram-negative psychrophilic bacteria and what their role is in adaptation to cold temperature. Here we report the complete structure of the LOS from P. haloplanktis TAB 23. The lipid A was characterized by MALDI-TOF MS analysis and was tested in vitro showing a significant inhibitory effect on the LPS-induced pro-inflammatory cytokine production when added in culture with LPS from Escherichia coli. The product obtained after de-O-acylation of the LPS was analyzed by MALDI-TOF MS revealing the presence of several molecular species, differing in phosphorylation degree and oligosaccharide length. The oligosaccharide portion released after strong alkaline hydrolysis was purified by anion-exchange chromatography–pulsed amperometric detection (HPAEC-PAD) to give three main fractions, characterized by means of 2D NMR spectroscopy, which showed a very short highly phosphorylated saccharidic chain with the following general structure. α-Hepp3R,6R,4R′-(1→5)-α-Kdop4P-(2→6)-β-GlcpN4R-(1→6)-α-GlcpN1P (R=[BOND]H2PO3 or [BOND]H; R′=α-Galp-(1→4)-β-Galp-(1→ or H[BOND]).

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