title: Chemical characterization of the ester-linked 3-hydroxy fatty acyl-containing lipids in Mycobacterium tuberculosis.
abstract: 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.
authors.affiliation: Department of Medical Microbiology, University of Lund, Sweden.
authors.forename: S
authors.initials: S
authors.lastname: Alugupalli
authors.forename: M A
authors.initials: MA
authors.lastname: Lanéelle
authors.forename: L
authors.initials: L
authors.lastname: Larsson
authors.forename: M
authors.initials: M
authors.lastname: Daffé
mesh_terms: D002845:Chromatography; D005227:Fatty Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009169:Mycobacterium tuberculosis / Q000737:chemistry*; D010714:Phosphatidylethanolamines / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013433:Sulfoglycosphingolipids / Q000737:chemistry; D014199:Trehalose / Q000031:analogs & derivatives / Q000737:chemistry
chemical_list: D005227:Fatty Acids; D010714:Phosphatidylethanolamines; D013433:Sulfoglycosphingolipids; D014199:Trehalose