Open AccessChemical characterization of the ester-linked 3-hydroxy fatty acyl-containing lipids in Mycobacterium tuberculosis
Author(s) -
Srinivas Alugupalli,
MarieAntoinette Lanéelle,
Lennart Larsson,
Mamadou Daffé
Publication year - 1995
Publication title -
journal of bacteriology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.652
H-Index - 246
eISSN - 1067-8832
pISSN - 0021-9193
DOI - 10.1128/jb.177.15.4566-4570.1995
Subject(s) - glycolipid , trehalose , mycobacterium tuberculosis , biochemistry , biology , mycobacterium , fatty acid , ethanolamine , bacillus (shape) , phospholipid , bacteria , microbiology and biotechnology , tuberculosis , membrane , medicine , genetics , pathology
In a previous study (S. Alugupalli, F. Portaels, and L. Larsson, J. Bacteriol. 176:2962-2969, 1994), we reported the occurrence of 21 3-hydroxy fatty acids (3-OH-FAs) in the methanolysis products of different mycobacterial species. The present study was undertaken in order to chemically characterize the ester-linked complex native forms of these acids in Mycobacterium tuberculosis. Three 3-OH-FA-containing lipids were purified by chromatography and analyzed by one- and two-dimensional nuclear magnetic resonance spectroscopy, by fast atom bombardment-mass spectrometry, and by various conventional chemical analysis techniques. 3-OH-2,4,6-trimethyl-FAs were found in 2,3-diacyl trehalose and 2,3,6,6'-tetra-acyl-2'-sulfate trehalose (sulfatide I), two specific glycolipids of the tubercle bacillus, explaining the specific occurrence of these fatty acids in the methanolysis products of virulent strains of M. tuberculosis. Straight-chain 3-OH-FAs were localized in phosphatidyl ethanolamine but not in the other phospholipids, suggesting a possible role of this class of phospholipids in the metabolism of fatty acids in actinomycetes.