Distribution of Some Mycobacterial Waxes Based on the Phthiocerol Family

Abstract

Characteristic waxes, based on methoxy and keto long-chain diols, members of the phthiocerol family, have been isolated from representatives of Mycobacterium bovis, M. kansasii, M. marinum, M. microti and M. tuberculosis. M. kansasii produced essentially di-esters of the ketodiol phthiodiolone A, but the remaining species also had waxes based on the methoxy-diols phthiocerol A and phthiocerol B. Gas chromatography of derivatives of the components of the waxes showed that the phthiocerol A components from M. bovis, M. microti and M. microti and M. tuberculosis were qualitatively similar, being mainly C34 and C36, but potentially significant differences were seen in the proportions of the components from M. bovis. The phthiocerols A from M. marinum were C28 and C30 and the phthiodiolones A from M. kansasii were C25 and C27. The multimethyl-branched acids from the waxes of M. bovis were quantitatively different from those of M. microti and M. tuberculosis but all these mycocerosic acids ranged in size from C23 or C24 to C32, with C29 or C30 being the major component in most cases. M. marinum and M. kansasii strains had mainly C26 or C27 and C29 or C30 multimethyl-branched acids, respectively.

Pathophysiological Implications of Cell Envelope Structure in Mycobacterium tuberculosis and Related Taxa

“…The PDIMs from the M. tuberculosis complex are relatively large in comparison with those of other taxa. Other interesting cases are the so-called "Beijing" variants of M. tuberculosis [37] and M. kansasii [32,33,35] where only restricted selections of members of the phthiocerol family are encountered. Figure 4).…”

“…The phthiocerol and phenolphthiocerol long-chain diols are esterified by multimethylbranched "mycocerosic" acids whose chiral centres have R absolute configuration in members of the M. tuberculosis complex and M. kansasii ( Figure 4) [32][33][34][35]. Phthiocerol dimycocerosates (PDIMs) are mainly based on long-chain diols, the phthiocerol As and phthiodiolones ( Figure 4).…”

Characterization of phthiocerol and phthiodiolone dimycocerosate esters of M. tuberculosis by multiple-stage linear ion-trap MS

“…For example, Minnikin et al ( 10,(24)(25)(26) and Daffe et al ( 9,(27)(28)(29) used GC/MS analysis together with NMR spectroscopy for complete characterization of DIMs, following extraction steps, chromato graphic separations, and chemical reactions. Recently, MALDI-TOF ( 16,29,30 ) and ESI-Fourier transform ion cyclotron resonance ( 31 ) MS have also been applied for profi ling PDIM and PGLs.…”

“…A previous report indicates that M. tuberculosis produced mainly diesters of phthiocerol A and phthiodiolone A, and phthiocerol B diesters were present in very small amounts so that their detection was unreliable ( 10 ). High-resolution mass measurements (supplementary Fig.…”

“…Briefl y, the dried sample was resuspended in 20 l ice-cold acetonitrile/N,N-dimethylformamide PDIM ( Fig. 1 ) and PGL respectively consist of a longchain 3-methoxy, 4-methyl, 9,11-dihydroxy glycol (phthiocerol) and a p -glycosylated phenylglycol (glycosyl phenolphthiocerol) backbone diesterifi ed with di-, tri-, and tetra-methyl-branched long-chain mycocerosic (mycoceranic) acids ( 10,19,20 ). Dependent on the species, the long-chain diol backbone ranges in size from C 25 to C 36 , and the mycocerosic acid chain ranges from C 23 or C 24 to C 32 ( 3,4,10,21,22 ).…”