Skip to main content
Plant Physiology logoLink to Plant Physiology
. 1975 Jan;55(1):120–129. doi: 10.1104/pp.55.1.120

Characterization of Inositol-containing Phosphosphingolipids from Tobacco Leaves

Isolation and Identification of Two Novel, Major Lipids: N-Acetylglucosamidoglucuronidoinositol Phosphorylceramide and Glucosamidoglucuronidoinositol Phosphorylceramide 1

Karan Kaul a, Robert L Lester a
PMCID: PMC541565  PMID: 16659016

Abstract

A method for a large scale extraction of phosphoglycosphingolipids from the leaves of Nicotiana tabacum L. has been developed. The phosphosphingolipid concentrate consists of a dozen or more polar lipids as judged by thin layer chromatography. Two of these lipids were purified by chromatography on porous silica beads and partially characterized. These lipids are formulated as: N-acetylglucosamidoglucuronidoinositol phosphorylceramide and glucosamidoglucuronidoinositol phosphorylceramide. Although not fully characterized, the other lipids in the concentrate are inositol-containing phosphosphingolipids with a higher carbohydrate content.

Full text

PDF
120

Selected References

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

  1. BARTLETT G. R. Phosphorus assay in column chromatography. J Biol Chem. 1959 Mar;234(3):466–468. [PubMed] [Google Scholar]
  2. BITTER T., MUIR H. M. A modified uronic acid carbazole reaction. Anal Biochem. 1962 Oct;4:330–334. doi: 10.1016/0003-2697(62)90095-7. [DOI] [PubMed] [Google Scholar]
  3. Banks T. E., Shafer J. A. S methylation of thiols by O-methylisourea. Biochemistry. 1970 Aug 18;9(17):3343–3348. doi: 10.1021/bi00819a008. [DOI] [PubMed] [Google Scholar]
  4. CARTER H. E., BETTS B. E., STROBACH D. R. BIOCHEMISTRY OF THE SPHINGOLIPIDS. XVII. THE NATURE OF THE OLIGOSACCHARIDE COMPONENT OF PHYTOGLYCOLIPID. Biochemistry. 1964 Aug;3:1103–1107. doi: 10.1021/bi00896a016. [DOI] [PubMed] [Google Scholar]
  5. CARTER H. E., GIGG R. H., LAW J. H., NAKAYAMA T., WEBER E. Biochemistry of the sphingolipides. XI. Structure of phytoglycolipide. J Biol Chem. 1958 Dec;233(6):1309–1314. [PubMed] [Google Scholar]
  6. Carter H. E., Gaver R. C. Improved reagent for trimethylsilylation of sphingolipid bases. J Lipid Res. 1967 Jul;8(4):391–395. [PubMed] [Google Scholar]
  7. Carter H. E., Hirschberg C. B. Phytosphingosines and branched sphingosines in kidney. Biochemistry. 1968 Jun;7(6):2296–2300. doi: 10.1021/bi00846a036. [DOI] [PubMed] [Google Scholar]
  8. Carter H. E., Kisic A. Countercurrent distribution of inosol lipids of plant seeds. J Lipid Res. 1969 Jul;10(4):356–362. [PubMed] [Google Scholar]
  9. Carter H. E., Koob J. L. Sphingolipids in bean leaves (Phaseolus vulgaris). J Lipid Res. 1969 Jul;10(4):363–369. [PubMed] [Google Scholar]
  10. Carter H. E., Strobach D. R., Hawthorne J. N. Biochemistry of the sphingolipids. 18. Complete structure of tetrasaccharide phytoglycolipid. Biochemistry. 1969 Jan;8(1):383–388. doi: 10.1021/bi00829a053. [DOI] [PubMed] [Google Scholar]
  11. Desnick R. J., Sweeley C. C., Krivit W. A method for the quantitative determination of neutral glycosphingolipids in urine sediment. J Lipid Res. 1970 Jan;11(1):31–37. [PubMed] [Google Scholar]
  12. Jungalwala F. B., Freinkel N., Dawson R. M. The metabolism of phosphatidylinositol in the thyroid gland of the pig. Biochem J. 1971 Jun;123(1):19–33. doi: 10.1042/bj1230019. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Lester R. L., Smith S. W., Wells G. B., Rees D. C., Angus W. W. The isolation and partial characterization of two novel sphingolipids from Neurospora crassa: di(inositolphosphoryl)ceramide and ((gal)3glu)ceramide. J Biol Chem. 1974 Jun 10;249(11):3388–3394. [PubMed] [Google Scholar]
  14. Lester R. L., Steiner M. R. The occurrence of diphosphoinositide and triphosphoinositide in Saccharomyces cerevisiae. J Biol Chem. 1968 Sep 25;243(18):4889–4893. [PubMed] [Google Scholar]
  15. Mahadevan V., Stenroos L. Quantitative analysis of volatile fatty acids in aqueous solution by gas chromatography. Anal Chem. 1967 Nov;39(13):1652–1654. doi: 10.1021/ac50156a046. [DOI] [PubMed] [Google Scholar]
  16. RONDLE C. J., MORGAN W. T. The determination of glucosamine and galactosamine. Biochem J. 1955 Dec;61(4):586–589. doi: 10.1042/bj0610586. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. SAMBASIVARAO K., MCCLUER R. H. THIN-LAYER CHROMATOGRAPHIC SEPARATION OF SPHINGOSINE AND RELATED BASES. J Lipid Res. 1963 Jan;4:106–108. [PubMed] [Google Scholar]
  18. SCHWEIGER A. [Separation of simple sugars on cellulose lavers]. J Chromatogr. 1962 Nov;9:374–376. doi: 10.1016/s0021-9673(00)80803-1. [DOI] [PubMed] [Google Scholar]
  19. SHAFIZADEH F. Formation and cleavage of the oxygen ring in sugars. Adv Carbohydr Chem. 1958;13:9–61. doi: 10.1016/s0096-5332(08)60351-3. [DOI] [PubMed] [Google Scholar]
  20. SVENNERHOLM L. Quantitative estimation of sialic acids. II. A colorimetric resorcinol-hydrochloric acid method. Biochim Biophys Acta. 1957 Jun;24(3):604–611. doi: 10.1016/0006-3002(57)90254-8. [DOI] [PubMed] [Google Scholar]
  21. Siakotos A. N., Kulkarni S., Passo S. The quantitative analysis of sphingolipids by determination of long chain base as the trinitrobenzene sulfonic acid derivative. Lipids. 1971 Apr;6(4):254–259. doi: 10.1007/BF02538397. [DOI] [PubMed] [Google Scholar]
  22. Steiner S., Lester R. L. Studies on the diversity of inositol-containing yeast phospholipids: incorporation of 2-deoxyglucose into lipid. J Bacteriol. 1972 Jan;109(1):81–88. doi: 10.1128/jb.109.1.81-88.1972. [DOI] [PMC free article] [PubMed] [Google Scholar]
  23. Steiner S., Smith S., Waechter C. J., Lester R. L. Isolation and partial characterization of a major inositol-containing lipid in baker's yeast, mannosyl-diinositol, diphosphoryl-ceramide. Proc Natl Acad Sci U S A. 1969 Nov;64(3):1042–1048. doi: 10.1073/pnas.64.3.1042. [DOI] [PMC free article] [PubMed] [Google Scholar]
  24. Talwalkar R. T., Lester R. L. The response of diphosphoinositide and triphosphoinostitide to perturbations of the adenylate energy charge in cells of Saccharomyces cerevisiae. Biochim Biophys Acta. 1973 Jun 21;306(3):412–421. doi: 10.1016/0005-2760(73)90180-x. [DOI] [PubMed] [Google Scholar]
  25. Taylor R. L., Shively J. E., Conrad H. E., Cifonelli J. A. Uronic acid composition of heparins and heparan sulfates. Biochemistry. 1973 Sep 11;12(19):3633–3637. doi: 10.1021/bi00743a010. [DOI] [PubMed] [Google Scholar]
  26. WEISSBACH The enzymic determination of myo-inositol. Biochim Biophys Acta. 1958 Mar;27(3):608–611. doi: 10.1016/0006-3002(58)90393-7. [DOI] [PubMed] [Google Scholar]

Articles from Plant Physiology are provided here courtesy of Oxford University Press

RESOURCES