Distribution of Phthiocerol Diester, Phenolic Mycosides and Related Compounds in Mycobacteria Free

Abstract

Among 28 mycobacterial species studied, only and produced waxes yielding long-chain -diol components (called phthiocerol and companions) and polymethyl-branched fatty acids on saponification. The same mycobacterial species also produced diesters of phenol phthiocerol and companions. Fatty acids esterifying these fatty alcohols in and were found to belong to the phthioceranic series (dextrorotatory fatty acids), in contrast to those of the other species (laevorotatory fatty acids called mycocerosic acids), both groups having the same chain length and methyl-branched positions. and contained the same waxes with identical structures, as did and Neither the type strain of , nor that of or accumulated the strain-specific phenolic glycolipids.

Loading

Article metrics loading...

/content/journal/micro/10.1099/00221287-134-7-2049
1988-07-01
2024-03-28
Loading full text...

Full text loading...

/deliver/fulltext/micro/134/7/mic-134-7-2049.html?itemId=/content/journal/micro/10.1099/00221287-134-7-2049&mimeType=html&fmt=ahah

References

  1. Asselineau C., Asselineau J. 1984; waxes, mycosides and related compounds. In The Mycobacteria: a Source Book, part A pp. 345–359 Kubica G. P., Wayne L. G. Edited by New York: Marcel Dekker;
    [Google Scholar]
  2. Asselineau C., Daffé M., David H. L., Laneelle M. A., Rastogi N. 1984; Lipids as taxonomic markers for bacteria derived from leprosy infections. Acta leprologica 95:121–127
    [Google Scholar]
  3. Asselineau J. 1954; Sur quelques substances à 60 atomes de carbone isolés des lipides de soucheshumaines de Mycobacterium tuberculosis . Bulletin de la Société Chimique de France 21:108–112
    [Google Scholar]
  4. Brennan P. J. 1983; The phthiocerol-containing surface lipids of Mycobacterium leprae -a perspective of past and present work. International Journal of Leprosy 51:387–396
    [Google Scholar]
  5. Brett S. J., Lowe C., Payne S. N., Draper P. 1984; Phenolic glycolipid 1 of Mycobacterium leprae causes nonspecific inflammation but has no effect on cell-mediated reponses in mice. Infection and Immunity 46:802–808
    [Google Scholar]
  6. Daffé M., Laneelle M. A., Asselineau C., Levy-Frebault V., David H. 1983; Intérêt taxonomique des acidesgras des mycobactéries: proposition d’une méthode d’analyse. Annales de microbiologie 134B:241–256
    [Google Scholar]
  7. Daffé M., Laneelle M. A., Roussel J., Asselineau C. 1984; Lipides specifiques de Mycobacterium ulcerans . Annales de microbiologie 135A:191–201
    [Google Scholar]
  8. Daffé M., Lacave C., Laneelle M. A., Laneelle G. 1987; Structure of the major triglycosyl phenol- phthiocerol of Mycobacterium tuberculosis (strain Canetti). European Journal of Biochemistry 167:155–160
    [Google Scholar]
  9. Demarteau-Ginsburg H., Ginsburg A., Lederer E. 1953; Sur troisnouvelles substances naturelles apparentées au phtiocerol. Biochimica et biophysica acta 12:587–588
    [Google Scholar]
  10. Demarteau-Ginsburg H., Lederer E. 1963; Sur la structure chimique du mycoside B. Biochimica et biophysica acta 70:442–451
    [Google Scholar]
  11. Dobson G., Minnikin D. E., Parlett J. H., Goodfellow M., Ridell M., Magnusson M. 1985; Systematic analysis of complex mycobacterial lipids. In Chemical Methods in Bacterial Systematics pp. 237–265 Goodfellow M., Minnikin D. E. Edited by London: Academic Press;
    [Google Scholar]
  12. Draper P., Dobson G., Minnikin D. E., Minnikin S. M. 1982; The mycolic acids of Mycobacterium leprae harvested from experimentally infected nine-banded armadillos. Annales de microbiologie 133B:39–47
    [Google Scholar]
  13. Draper P., Payne S. N., Dobson G., Minnikin D. E. 1983; Isolation of a characteristic phthioceroldimycocerosate from Mycobacterium leprae . Journal of General Microbiology 129:859–863
    [Google Scholar]
  14. Etemadi A. H., Convit J. 1974; Mycolic acids from ‘non-cultivable’ mycobacteria. Infection and Immunity 10:236–239
    [Google Scholar]
  15. Fournié J. J., Rivière M., Puzo G. 1987; lipid from Mycobacterium kansasii. I. Evidence for tetrasaccharide structure of the oligosaccharide moiety. Journal of Biological Chemistry 262:3174–3179
    [Google Scholar]
  16. Gastambide-Odier M., Sarda P., Lederer E. 1965; Structure des alglycones des mycosides A et B. Tetrahedron Letters 35:3135–3143
    [Google Scholar]
  17. Gastambide-Odier M., Sarda P., Lederer E. 1967; Biosynthèse des aglycones des mycosides A et B. Bulletin de la Société de Chimie Biologique 49:849–864
    [Google Scholar]
  18. Gastambide-Odier M., Ville C. 1970; Desoxysucres isolés du mycoside A. Bulletin de la Société de Chimie Biologique 47:2047–2067
    [Google Scholar]
  19. Goren M. B., Brokl O., Schaefer W. B. 1974; Lipids of putative relevance to virulence in Mycobacterium tuberculosis:phthioceroldimycocerosate and the attenuation indicator lipid. Infection and Immunity 9:150–158
    [Google Scholar]
  20. Grange J. M. 1982; Koch’s tubercle bacillus. A centenary reappraisal. Zentralblatt für Bakteriologie, Mikrobiologie und Hygiene, Abteilung I, Originale A 251:297–307
    [Google Scholar]
  21. Hunter S. W., Fujiwara T., Brennan P. J. 1982; Structure and antigenicity of the major specific glycolipid antigen of Mycobacterium leprae . Journal of Biological Chemistry 257:15072–15078
    [Google Scholar]
  22. Hunter S. W., Brennan P. J. 1983; Further specific extracellular phenolic glycolipid antigens and a related diacylphthiocerol from Mycobacterium leprae . Journal of Biological Chemistry 258:7556–7562
    [Google Scholar]
  23. Jenkins P. A. 1981; Lipid analysis for the identification of mycobacteria: an appraisal. Reviews of Infectious Diseases 3:862–866
    [Google Scholar]
  24. Minnikin D. E. 1982; Lipids: complex lipids, their chemistry, biosynthesis and roles. In The Biology of the Mycobacteria 1 pp. 95–184 Ratledge C., Standford J. L. Edited by London: Academic Press;
    [Google Scholar]
  25. Minnikin D. E., Minnikin S. M., Parlett J. H., Goodfellow M., Magnusson M. 1984a; Mycolic acids of some species of Mycobacterium . Archives of Microbiology 139:225–231
    [Google Scholar]
  26. Minnikin D. E., Parlett J. H., Magnusson M., Ridell M., Lind A. 1984b; Mycolic acid patterns of representatives of Mycobacterium bovis BCG. Journal of General Microbiology 130:2733–2736
    [Google Scholar]
  27. Minnikin D. E., Dobson G., Goodfellow M., Magnusson M., Ridell M. 1985a; Distribution of some mycobacterial waxes based on the phthiocerol family. Journal of General Microbiology 131:1375–1381
    [Google Scholar]
  28. Minnikin D. E., Dobson G., Goodfellow M., Draper P., Magnusson M. 1985b; Quantitative comparison of the mycolic and fatty acid compositions of Mycobacterium leprae and Mycobacterium gordonae . Journal of General Microbiology 131:2013–2021
    [Google Scholar]
  29. Noll H. 1957; The chemistry of some native constituents of the purified wax of Mycobacterium tuberculosis . Journal of Biological Chemistry 224:149–164
    [Google Scholar]
  30. Pattyn S. R., Portaels F. 1981; Growth of Mycobacterium leprae in experimental animals and on artificial media. Bulletin de l’Institut Pasteur 79:223–250
    [Google Scholar]
  31. Ratledge C. 1982; Lipids: cell composition, fatty acid biosyntheses. In The Biology of the Mycobacteria 1 pp. 53–93 Ratledge C., Stanford J. L. Edited by London: Academic Press;
    [Google Scholar]
  32. Sarda P., Gastambide-Odier M. 1967; Structure chimique de l’aglycone du mycoside G de Mycobacterium marinum . Chemistry and Physics of Lipids 1:434–444
    [Google Scholar]
  33. Stanford J. L., Grange J. M. 1974; The meaning and structure of species as applied to mycobacteria. Tubercle 55:143–152
    [Google Scholar]
  34. Wayne L. G., Kubica G. P. 1986; Genus Mycobacterium Lehmann and Neumann 1896,363AL . In Bergey’s Manual of Systematic Bacteriology 2. pp. 1436–1457 Sneath P. H. A., Mair N. S., Sharpe M. E. Edited by Baltimore: Williams & Wilkins;
    [Google Scholar]
  35. Young D. B. 1981; Detection of mycobacterial lipids in skin biopsies from leprosy patients. International Journal of Leprosy 49:198–204
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/micro/10.1099/00221287-134-7-2049
Loading
/content/journal/micro/10.1099/00221287-134-7-2049
Loading

Data & Media loading...

Most cited Most Cited RSS feed