POLYPHTHIENOYL TREHALOSE, GLYCOLIPIDS SPECIFIC FOR VIRULENT-STRAINS OF THE TUBERCLE BACILLUS
POLYPHTHIENOYL TREHALOSE, GLYCOLIPIDS SPECIFIC FOR VIRULENT-STRAINS OF THE TUBERCLE BACILLUS
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DOI：
10.1111/j.1432-1033.1988.tb13928.x
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发表时间：
1988-03-15
期刊：
影响因子：
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通讯作者：
LANEELLE, G
中科院分区：
文献类型：
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作者：
DAFFE, M;LACAVE, C;LANEELLE, G
邻苯二甲酸构成了一个家族的双旋奇数不饱和脂肪酸，专门从人类和牛结核杆菌的强毒株中分离出来。在细菌细胞中，它们不是游离的，在结核分枝杆菌（菌株Canetti）的复合壁脂质中对其连接形式的研究表明，它们酯化了海藻糖。对主要的邻苯噻吩酰海藻糖的结构解析表明，在海藻糖的2、2“、3”、4和6“位上存在5个酰基残基。酰基取代基主要是2，4，6-三甲基二十四-2-烯酸（C27邻苯二甲酸）及其同系物。除了这些支链脂肪酸外，直链C16和C18酰基构成约20%的取代基。建议的结构是一个新的，无论是分枝杆菌特异性糖脂和海藻糖的取代位置。在M.结核杆菌（菌株Canetti），与主要成分的区别在于存在额外的羟基脂肪酸（3-羟基-2，4，6-三甲基二十四烷酸）或酰基取代基的数目。主要的糖脂在体外对线粒体氧化磷酸化的活性较弱。这些糖脂和邻苯二甲酸可以作为毒力指标。
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.