Skip to main content
NCBI home page
Journal of Bacteriology logoLink to Journal of Bacteriology
. 1981 Jul;147(1):80–90. doi: 10.1128/jb.147.1.80-90.1981

Isolation and characterization of several unique lipids from Azotobacter vinelandii cysts.

C J Su, R N Reusch, H L Sadoff
PMCID: PMC216010  PMID: 7240098

Abstract

Unique cyclic compounds were found in the lipid fraction of Azotobacter vinelandii cysts. In addition to two major molecular species which had already been identified, 5-n-alkylresorcinol and its galactoside derivative, five other molecular species (two alkyl side chain homologs of each) were isolated, and their structures were established by infrared, ultraviolet, nuclear magnetic resonance, and mass spectroscopy. These 10 compounds were 6-n-heneicosylresorcylic acid methyl ester and 6-n-tricosylresorcylic acid methyl ester, 5-n-(2-hydroxy)heneicosylresorcinol and 5-n-(2-hydroxy-tricosylresorcinol, 5-n-heneicosyl-4-acetylresorcinol and 5-n-tricosyl-4-acetylresorcinol, 6-n-heneicosyl-4-hydroxypyran-2-one and 6-n-tricosyl-4-hydroxypyran-2-one, and 6-(2-oxotricosyl)-4-hydroxy-pyran-2-one and 6-(2-oxopentacosyl)-4-hydroxypyran-2-one.

Full text

PDF
80

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Acker T. E., Brenneisen P. E., Tanenbaum S. W. Isolation, structure, and radiochemical synthesis of 3,6-dimethyl-4-hydroxy-2-pyrone. J Am Chem Soc. 1966 Feb 20;88(4):834–837. doi: 10.1021/ja00956a041. [DOI] [PubMed] [Google Scholar]
  2. BLIGH E. G., DYER W. J. A rapid method of total lipid extraction and purification. Can J Biochem Physiol. 1959 Aug;37(8):911–917. doi: 10.1139/o59-099. [DOI] [PubMed] [Google Scholar]
  3. Bentley R., Ghaphery J. A., Keil J. G. Effect of ethionine on tropolone biosynthesis in Penicillium stipitatum. Arch Biochem Biophys. 1965 Jul;111(1):80–87. doi: 10.1016/0003-9861(65)90325-5. [DOI] [PubMed] [Google Scholar]
  4. Bentley R., Zwitkowits P. M. Biosynthesis of tropolones in Penicillium stipitatum. VII. The formation of polyketide lactones and other nontropolone compounds as a result of ethionine inhibition. J Am Chem Soc. 1967 Feb 1;89(3):676–680. doi: 10.1021/ja00979a036. [DOI] [PubMed] [Google Scholar]
  5. Hitchins V. M., Sadoff H. L. Morphogenesis of cysts in Azotobacter vinelandii. J Bacteriol. 1970 Oct;104(1):492–498. doi: 10.1128/jb.104.1.492-498.1970. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Kumagai M., Suhara Y., Aoyagi T., Umezawa H. An enzyme inhibitor, panosialin, produced by Streptomyces. II. Chemistry of panosialin, 5-alkylbenzene-1,3-disulfates. J Antibiot (Tokyo) 1971 Dec;24(12):870–875. doi: 10.7164/antibiotics.24.870. [DOI] [PubMed] [Google Scholar]
  7. Langworthy T. A., Smith P. F., Mayberry W. R. Lipids of Thermoplasma acidophilum. J Bacteriol. 1972 Dec;112(3):1193–1200. doi: 10.1128/jb.112.3.1193-1200.1972. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Lin L. P., Sadoff H. L. Chemical composition of Azotobacter vinelandii cysts. J Bacteriol. 1969 Oct;100(1):480–486. doi: 10.1128/jb.100.1.480-486.1969. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Lin L. P., Sadoff H. L. Encystment and polymer production by Azotobacter vinelandii in the presence of beta-hydroxybutyrate. J Bacteriol. 1968 Jun;95(6):2336–2343. doi: 10.1128/jb.95.6.2336-2343.1968. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Lin L. P., Sadoff H. L. Preparation and ultrastructure of the outer coats of Azotobacter vinelandii cysts. J Bacteriol. 1969 Jun;98(3):1335–1341. doi: 10.1128/jb.98.3.1335-1341.1969. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Reusch R. N., Sadoff H. L. 5-n-Alkylresorcinols from encysting Azotobacter vinelandii: isolation and characterization. J Bacteriol. 1979 Aug;139(2):448–453. doi: 10.1128/jb.139.2.448-453.1979. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Reusch R. N., Sadoff H. L. Lipid metabolism during encystment of Azotobacter vinelandii. J Bacteriol. 1981 Feb;145(2):889–895. doi: 10.1128/jb.145.2.889-895.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. WILLIAMSON D. H., WILKINSON J. F. The isolation and estimation of the poly-beta-hydroxybutyrate inclusions of Bacillus species. J Gen Microbiol. 1958 Aug;19(1):198–209. doi: 10.1099/00221287-19-1-198. [DOI] [PubMed] [Google Scholar]
  14. Yalpani M., Willecke K., Lynen F. Triacetic acid lactone, a derailment product of fatty acid biosynthesis. Eur J Biochem. 1969 Apr;8(4):495–502. doi: 10.1111/j.1432-1033.1969.tb00554.x. [DOI] [PubMed] [Google Scholar]

Articles from Journal of Bacteriology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES