Mycobacterium tuberculosis has a cell envelope incorporating a
peptidoglycan-linked
arabinogalactan esterified by long-chain
mycolic acids. A range of "free"
lipids are associated with the "bound"
mycolic acids, producing an effective envelope outer membrane. The distribution of these
lipids is discontinuous among mycobacteria and such
lipids have proven potential for
biomarker use in tracing the evolution of
tuberculosis. A plausible evolutionary scenario involves progression from an environmental organism, such as Mycobacterium kansasii, through intermediate "smooth" tubercle bacilli, labelled "Mycobacterium canettii"; cell envelope
lipid composition possibly correlates with such a progression. M. kansasii and "M. canettii" have characteristic
lipooligosaccharides, associated with motility and biofilms, and glycosyl phenolphthiocerol dimycocerosates ("phenolic
glycolipids"). Both these
lipid classes are absent in modern M.
tuberculosis sensu stricto, though simplified phenolic
glycolipids remain in certain current biotypes. Dimycocerosates of the phthiocerol family are restricted to smaller phthiodiolone diesters in M. kansasii. Diacyl and pentaacyl trehaloses are present in "M. canettii" and M.
tuberculosis, accompanied in the latter by related sulfated acyl trehaloses. In comparison with environmental mycobacteria, subtle modifications in
mycolic acid structures in "M. canettii" and M.
tuberculosis are notable. The probability of essential
tuberculosis evolution taking place in Pleistocene megafauna, rather than Homo sapiens, is reemphasised.