title: Polyphthienoyl trehalose, glycolipids specific for virulent strains of the tubercle bacillus.
abstract: Phthienoic acids constitute a family of dextro-rotary odd-numbered unsaturated fatty acids isolated exclusively from virulent strains of human and bovine tubercle bacilli. In the bacterial cell they are not free and a search for their linked form in complex wall lipids of Mycobacterium tuberculosis (strain Canetti) showed that they esterified trehalose. Structural elucidation of the major phthienoyl trehalose showed the occurrence of five acyl residues located at 2, 2', 3', 4 and 6' positions of trehalose. The acyl substituents were mainly 2,4,6-trimethyl tetracos-2-enoic acid (C27 phthienoic acid) accompanied by its homologs. In addition to these branched fatty acids, straight-chain C16 and C18 acyls composed about 20% of the substituents. The proposed structure is a new one, both for the mycobacterial-specific glycolipid and for the substituted positions on trehalose. Other minor acyl trehaloses were detected in M. tuberculosis (strain Canetti), differing from the major component by the occurrence of an additional hydroxy fatty acid (3-hydroxy-2,4,6-trimethyl tetracosanoic acid) or by the number of acyl substituents. The major glycolipid presented a weak activity in vitro on mitochondrial oxidative phosphorylation. These glycolipids and phthienoic acids could serve as virulence indicators.
mesh_terms: D000215:Acylation; D000818:Animals; D002241:Carbohydrates / Q000302:isolation & purification; D002417:Cattle; D002473:Cell Wall / Q000032:analysis; D004187:Disaccharides; D006017:Glycolipids / Q000302:isolation & purification*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008928:Mitochondria / Q000378:metabolism; D009169:Mycobacterium tuberculosis / Q000032:analysis* / Q000472:pathogenicity; D010085:Oxidative Phosphorylation; D013329:Structure-Activity Relationship; D014199:Trehalose / Q000031:analogs & derivatives* / Q000302:isolation & purification; D014774:Virulence
chemical_list: D002241:Carbohydrates; D004187:Disaccharides; D006017:Glycolipids; D014199:Trehalose