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. 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.
Highlights
Sulfonate sphingoids or sulfonolipids are bioactive unusual compounds found in members of the Bacteroidetes family
Electrospray ionization-mass spectrometry (ESI-MS) analyses of the total lipid extract of S. ruber showed a prominent peak in the high-mass range of the spectrum at m/z 660.7, which was identified as a novel sulfonolipid [7]
Individual polar lipid components were identified by staining behavior, by comparison of their Rf values with those of the total lipid extract of the previously characterized extremely halophilic bacterium S. ruber [5], and by electrospray interface (ESI)-MS analyses
Summary
Sulfonate sphingoids or sulfonolipids are bioactive unusual compounds found in members of the Bacteroidetes family. Electrospray ionization-mass spectrometry (ESI-MS) analyses (negative ion) of the total lipid extract of S. ruber showed a prominent peak in the high-mass range of the spectrum at m/z 660.7, which was identified as a novel sulfonolipid [7].
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