Daffé M, Varnerot A, Lévy-Frébault V V
Centre de Recherche de Biochimie et de Génétique Cellulaires du CNRS, Toulouse, France.
J Gen Microbiol. 1992 Jan;138(1):131-7. doi: 10.1099/00221287-138-1-131.
Mycobacterium ulcerans and some pathogenic mycobacterial species elaborate wax A consisting of related long-chain beta-diol components (phthiocerol and related compounds) esterified by multimethyl-branched fatty acids. With the exception of M. ulcerans, wax A-containing mycobacteria also synthesize glycosylated phenol phthiocerol diester and related compounds: the so-called phenolic mycosides. In a deliberate effort to characterize this latter class of compounds in M. ulcerans, 20 strains were examined. Phenolic mycosides were found in two strains. Application of chemical analyses, including one- and two-dimensional NMR spectroscopy, allowed the structural elucidation of glycolipids identified as 3-O-methyl-alpha-L-rhamnosyl phenol phthiocerol diphthioceranate investigators. As phenolic mycosides are highly species-specific molecules, this finding stresses the close phylogenetic link between M. marinum and M. ulcerans. Incidentally, a survey of the mycolate content of M. ulcerans showed that methoxymycolate could not be detected in three strains.
溃疡分枝杆菌和一些致病性分枝杆菌物种会合成蜡质A，其由相关的长链β-二醇成分（结核硬脂醇及相关化合物）与多甲基支链脂肪酸酯化而成。除溃疡分枝杆菌外，含蜡质A的分枝杆菌还会合成糖基化的酚基结核硬脂醇二酯及相关化合物，即所谓的酚类霉菌糖苷。为了深入研究溃疡分枝杆菌中的后一类化合物，我们检测了20株菌株。在两株菌株中发现了酚类霉菌糖苷。通过化学分析，包括一维和二维核磁共振光谱，研究人员得以阐明被鉴定为3-O-甲基-α-L-鼠李糖基酚基结核硬脂醇二结核硬脂酸酯的糖脂结构。由于酚类霉菌糖苷是高度物种特异性的分子，这一发现强调了海分枝杆菌和溃疡分枝杆菌之间密切的系统发育联系。顺便提一下，对溃疡分枝杆菌的霉菌酸含量调查显示，在三株菌株中未检测到甲氧基霉菌酸。
