1887

Abstract

Pentacyclic triterpenoids of the hopane family were found in about half of some 100 strains of prokaryotes belonging to diverse taxonomic groups, such a wide distribution indicating the biological significance of these compounds. Hopanoids were found in almost all the cyanobacteria and obligate methylotrophs examined, in all the purple non-sulphur bacteria studied and in many taxonomically diverse Gram-negative or Gram-positive chemohetero-trophs. They were absent in all archaebacteria and purple sulphur bacteria examined as well as in various other Gram-positive or Gram-negative genera. The C hopanoids, diploptene and diplopterol, are present in almost all hopanoid-containing prokaryotes. The major compounds are always the C bacteriohopanepolyols, which are present at a level of 0.1-2 mg per g dry weight, the most common one being bacteriohopanetetrol. Because of their structural characteristics and their influence on the properties of biological membrane models, these compounds might be the structural equivalents of the sterols found in eukaryotes.

Loading

Article metrics loading...

/content/journal/micro/10.1099/00221287-130-5-1137
1984-05-01
2021-10-27
Loading full text...

Full text loading...

/deliver/fulltext/micro/130/5/mic-130-5-1137.html?itemId=/content/journal/micro/10.1099/00221287-130-5-1137&mimeType=html&fmt=ahah

References

  1. Adachi K., Suzuki I. 1977; Purification and properties of glutamate synthase from Thiobacillus thioparus. Journal of Bacteriology 129:1173–1182
    [Google Scholar]
  2. Anding C., Rohmer M., Ourisson G. 1976; Non-specific biosynthesis of hopane triterpenes in a cell-free system from Acetobacter rancens. Journal of the American Chemical Society 94:3257–3259
    [Google Scholar]
  3. Asselineau J. 1962 Les Lipides Bacteriens pp. 162287 Paris: Hermann;
    [Google Scholar]
  4. Bird C. W., Lynch J. M., Pirt S. J., Reid W. W. 1971; The identification of hop-22 (29)-ene in prokaryotic organisms. Tetrahedron Letters3189–3190
    [Google Scholar]
  5. Blsseret P. 1982 Membranes et évolution: études méthodologiques. Thèse d’État, Université Louis Pasteur, Strasbourg, France
    [Google Scholar]
  6. Bisseret P., Wolff G., Albrecht A. M., Tanaka T., Nakatani Y., Ourisson G. 1983; A direct study of the cohesion of lecithin bilayers. The effect of hopanoids and α,ω-dihydroxycarotenoids. Biochemical and Biophysical Research Communications 110:320–324
    [Google Scholar]
  7. Bouvier P. 1978 Biosynthèse de stéroïdes et triterpén-oïdes chez les procaryotes et les eucaryotes. Thèse d’Etat, Université Louis Pasteur, Strasbourg, France
    [Google Scholar]
  8. Bouvier P., Rohmer M., Benveniste P., Ourisson G. 1976; Δ8(14)-Steroids in the bacterium Methylococcus capsulatus. Biochemical Journal 159:267–271
    [Google Scholar]
  9. Bouvier P., Berger Y., Rohmer M., Ourisson G. 1980; Non-specific biosynthesis of gammacerane derivatives by a cell-free system from the protozoon Tetrahymena pyriformis. European Journal of Biochemistry 112:549–556
    [Google Scholar]
  10. Brandt R. D., Pryce R. J., Anding C., Ourisson A. 1970; Sterol biosynthesis in Euglena gracilis Z. Comparative study of free and bound sterols in light and dark grown Euglena gracilis Z. European Journal of Biochemistry 17:344–349
    [Google Scholar]
  11. Conner R. L., Landrey J. R., Burns C. H., Mallory F. B. 1968; Cholesterol inhibition of pentacyclic triterpene biosynthesis in Tetrahymena pyriformis. Journal of Protozoology 15:600–605
    [Google Scholar]
  12. De Rosa M., Gambacorta A., Minale L., Bu’Lock J. D. 1971; Bacterial triterpenes. Chemical Communications619–620
    [Google Scholar]
  13. Devon T. K., Scott A. I. 1972 Handbook of Naturally Occurring Compounds II New York: Academic Press;
    [Google Scholar]
  14. Förster H. J., Biemann K., Haigh W. G., Tattrie H. H., Colvin J. R. 1973; The structure of a novel C35 pentacyclic triterpene from Acetobacter xylinum. Biochemical Journal 135:133–143
    [Google Scholar]
  15. Gelpi E., Schneider H., Mann J., Oro J. 1970; Hydrocarbons of geochemical significance in microscopic algae. Phytochemistry 9:603–612
    [Google Scholar]
  16. Goldfine H. 1972; Comparative aspects of bacterial lipids. Advances in Microbial Physiology 8:1–58
    [Google Scholar]
  17. Haigh N. G., Förster H. J., Biemann K., Tattrie N. H., Colvin J. R. 1973; Induction of orientation of bacterial cellulose microfibrils by a novel terpenoid from Acetobacter xylinum. Biochemical Journal 135:145–149
    [Google Scholar]
  18. Hazeu W. 1972; Some cultural and physiological aspects of methane utilizing bacteria. Antonie van Leeuwenhoek 41:121–134
    [Google Scholar]
  19. Hestrin S., Schramm M. 1954; Synthesis of cellulose by Acetobacter xylinum. Biochemical Journal 58:345–352
    [Google Scholar]
  20. Hippchen B., Röll A., Poralla K. 1981; Occurrence in soil of thermo-acidophilic bacilli possessing cu-cyclohexane fatty acids and hopanoids. Archives of Microbiology 129:53–55
    [Google Scholar]
  21. Howard D. L., Chapman D. J. 1981; Structural elucidation of two hopanoids from the photosynthetic bacterium Rhodomicrobium vannielii. Chemical Communications468–469
    [Google Scholar]
  22. Kannenberg E., Poralla K. 1982; The influence of hopanoids on growth of Mycoplasma mycoides. Archives of Microbiology 133:100–102
    [Google Scholar]
  23. Kohl W., Gloe A., Reichenbach H. 1983; Steroids from the myxobacterium Nannocystis exedens. Journal of General Microbiology 129:1629–1635
    [Google Scholar]
  24. Kratz W. A., Myers J. 1955; Nutrition and growth of several blue-green algae. American Journal of Botany 42:282–287
    [Google Scholar]
  25. Langworthy T. A., Mayberry W. R. 1976; A 1,2,3,4-tetrahydroxypentane substituted pentacyclic triterpene from Bacillus acidocaldarius. Biochimica et biophysica acta 431:570–577
    [Google Scholar]
  26. Langworthy T. A., Mayberry W. R., Smith P. F. 1976; A sulfonolipid and novel glycosamidylglycolipids from the extreme thermoacidophile Bacillus acidocaldarius. Biochimica et biophysica acta 431:550–569
    [Google Scholar]
  27. Natori Y., Kamei T., Nagasaki T. 1981; Occurrence of triterpenes and polyprenyl alcohols in Pseudomonas C 45, a mutant. Agricultural and Biological Chemistry 45:2337–2338
    [Google Scholar]
  28. Ourisson G., Rohmer M. 1982; Prokaryotic polyterpenes: phylogenetic precursors of sterols. Current Topics in Membranes and Transport 17:153–172
    [Google Scholar]
  29. Ourisson G., Albrecht P., Rohmer M. 1979a; The hopanoids: palaeochemistry and biochemistry of a group of natural products. Pure and Applied Chemistry 51:709–729
    [Google Scholar]
  30. Ourisson G., Rohmer M., Anton R. 1979b; From terpenes to sterols: macroevolution and microevolution. Recent Advances in Phytochemistry 13:131–162
    [Google Scholar]
  31. Ourisson G., Albrecht P., Rohmer M. 1982; Predictive microbial biochemistry - from molecular fossils to procaryotic membranes. Trends in Biochemical Sciences 7:236–239
    [Google Scholar]
  32. Palleroni N. J., Kunisawa R., Contopolou R., Doudoroff M. 1973; Nucleic acid homologies in the genus Pseudomonas. International Journal of Systematic Bacteriology 23:333–339
    [Google Scholar]
  33. Patt T. E., Hanson R. S. 1978; Intracytoplasmic membrane, phospholipid and sterol content of Methylobacterium organophilum cells grown under different conditions. Journal of Bacteriology 134:636–644
    [Google Scholar]
  34. Pfennig N. 1977; Phototrophic green and purple bacteria: a comparative systematic survey. Annual Review of Microbiology 31:275–290
    [Google Scholar]
  35. Poralla K., Kannenberg E., Blume A. 1980; A glycolipid containing hopane isolated from Bacillus acidocaldarius has a cholesterol like function in membranes. FEBS Letters 113:107–110
    [Google Scholar]
  36. Rohmer M. 1975 Triterpénoïdes de procaryotes. Thèse d’État, Université Louis Pasteur, Strasbourg, France
    [Google Scholar]
  37. Rohmer M., Ourisson G. 1976a; Structure des bactériohopanetétrols d’Acetobacter xylinum. Tetrahedron Letters3633–3636
    [Google Scholar]
  38. Rohmer M., Ourisson G. 1976b; Dérivés du bactériohopane: variations structurales et répartition. Tetrahedron Letters3637–3640
    [Google Scholar]
  39. Rohmer M., Ourisson G. 1976a; Méthylhopanes d’Acetobacter xylinum et d’Acetobacter rancens: une nouvelle famille de composés triterpéniques. Tetrahedron Letters3641–3644
    [Google Scholar]
  40. Rohmer M., Bouvier P., Ourisson G. 1979; Molecular evolution of biomembranes: structural equivalents and phylogenetic precursors of sterols. Proceedings of the National Academy of Sciences of the United States of America 76:847–851
    [Google Scholar]
  41. Rohmer M., Anding C., Ourisson G. 1980a; Non-specific biosynthesis of hopane triterpenes by a cell-free system from Acetobacter pasteurianum. European Journal of Biochemistry 112:541–547
    [Google Scholar]
  42. Rohmer M., Bouvier P., Ourisson G. 1980b; Non-specific lanosterol and hopanoid biosynthesis by a cell-free system from the bacterium Methylococcus capsulatus. European Journal of Biochemistry 112:557–560
    [Google Scholar]
  43. Skerman V. B. D, Mcgowan V., Sneath P. H. A. 1980; Approved lists of bacterial names. International Journal of Systematic Bacteriology 30:225–420
    [Google Scholar]
  44. Stanier R. Y., Cohen-Bazire G. 1977; Phototrophic procaryotes: the cyanobacteria. Annual Review of Microbiology 31:225–274
    [Google Scholar]
  45. Van Dorsselaer A., Albrecht P., Ourisson G. 1977; Identification of novel (17αH)-hopanes in shales, coals, lignites, sediments and petroleum. Bulletin de la Société chimique de France165–170
    [Google Scholar]
  46. Whittenbury R., Dow C. S. 1977; Morphogenesis and differentiation in Rhodomicrobium vannielii and other budding and prosthecate bacteria. Bacteriological Reviews 41:754–808
    [Google Scholar]
  47. Whittenbury R., Phillips K. C., Wilkinson J. F. 1970; Enrichment, isolation and some properties of methane utilizing bacteria. Journal of General Microbiology 61:205–218
    [Google Scholar]
  48. Winogradskl S. 1949 Microbiologie du Sol p. 761 Paris: Masson & Cie;
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/micro/10.1099/00221287-130-5-1137
Loading
/content/journal/micro/10.1099/00221287-130-5-1137
Loading

Data & Media loading...

Most cited this month Most Cited RSS feed

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error