The acylhalocapnines of halophilic bacteria: Structural details of unusual sulfonate sphingoids

Maristella Baronio, Veronica M.T. Lattanzio, Natalie Vaisman, Aharon Oren, Angela Corcelli*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Sulfonate sphingoids or sulfonolipids are bioactive unusual compounds found in members of the Bacteroidetes family. The present report describes the structures of sulfonolipids of halophilic bacteria, sharing structural similarity with compounds of fungal origin inhibiting the serine palmitoyl transferase and with capnines, known as antagonists of von Willebrandt factor. Two sulfonolipids (SL1 and SL2) were isolated from the lipid extract of the halophile Salisaeta longa and analyzed by ESI-MS/MS. SL1 and SL2 structures have in common the long chain aminosulfonate 2-carboxy-2-amino-3,4-hydroxy-17 methyloctadec-5-ene-1-sulfonic for which the common name of halocapnine is suggested. The hydroxyl group on carbon 3 of aminosulfonate moiety is acylated: iso C15 and iso hydroxy C15 chains are present in SL1 and SL2, respectively.jlr The levels of the two different sulfonolipids in the bacterium were found to be modulated by the proportion of sodium and magnesium ions in the environment.

Original languageAmerican English
Pages (from-to)1878-1885
Number of pages8
JournalJournal of Lipid Research
Volume51
Issue number7
DOIs
StatePublished - 1 Jul 2010

Keywords

  • Bacteroidetes
  • Capnine
  • Halocapnine
  • Sulfonolipids

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