Skip to main content
Biochemical Journal logoLink to Biochemical Journal
. 1967 Jan;102(1):221–229. doi: 10.1042/bj1020221

The chemical nature of the products obtained by the action of cabbage-leaf phospholipase D on lysolecithin: the structure of lysolecithin

C Long 1, R Odavić 1,*, Elizabeth J Sargent 1
PMCID: PMC1270232  PMID: 4291559

Abstract

1. Lysolecithin, prepared by the action of snake-venom phospholipase A on ovolecithin, when incubated with Savoy-cabbage phospholipase D, in the presence of Ca2+ ions, gave two degradation products (designated A and B) in the form of their calcium salts. 2. These calcium salts were separated quantitatively by solvent fractionation and converted into the corresponding sodium salts. 3. Substance B proved to be a lysophosphatidic acid of conventional structure (1-monoacyl-l-3-glycerophosphoric acid). When the phosphate group was removed by means of prostatic acid phosphomonoesterase, a 1-monoglyceride was formed quantitatively. Alkaline hydrolysis gave the theoretical yield of l-3-glycerophosphate. 4. Substance A, on the other hand, had all the properties expected for a cyclic phosphate of a 1-monoglyceride. It was unaffected by phosphomonoesterase. On alkaline hydrolysis, the acyl group was removed and ring opening of the presumed cyclic phosphate group gave an approximately equimolar mixture of 2- and l-3-glycerophosphates. 5. The structures of substances A and B confirm lysolecithin as 1-monoacyl-l-3-glycerylphosphorylcholine.

Full text

PDF
224

Selected References

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

  1. BUBLITZ C., KENNEDY E. P. Synthesis of phosphatides in isolated mitochondria. III. The enzymatic phosphorylation of glycerol. J Biol Chem. 1954 Dec;211(2):951–961. [PubMed] [Google Scholar]
  2. Berenblum I., Chain E. An improved method for the colorimetric determination of phosphate. Biochem J. 1938 Feb;32(2):295–298. doi: 10.1042/bj0320295. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. DAVIDSON F. M., LONG C. The structure of the naturally occurring phosphoglycerides. 4. Action of cabbage-leaf phospholipase D on ovolecithin and related substances. Biochem J. 1958 Jul;69(3):458–466. doi: 10.1042/bj0690458. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. GRAY G. M. The structure of the plasmalogens of ox heart. Biochem J. 1958 Nov;70(3):425–433. doi: 10.1042/bj0700425. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. HANAHAN D. J., BROCKERHOFF H., BARRON E. J. The site of attack of phospholipase (lecithinase) A on lecithin: a re-evaluation. Position of fatty acids on lecithins and triglycerides. J Biol Chem. 1960 Jul;235:1917–1923. [PubMed] [Google Scholar]
  6. HANAHAN D. J. The site of action of lecithinase A of lecithin. J Biol Chem. 1954 Apr;207(2):879–884. [PubMed] [Google Scholar]
  7. LONG C., MAGUIRE M. F. The structure of the naturally occurring phosphoglycerides. I. Evidence derived from alkaline-hydrolysis studies. Biochem J. 1953 Jul;54(4):612–617. doi: 10.1042/bj0540612. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. LONG C., PENNY I. F. The structure of the lysolecithin formed by the action of snake venom phospholipase A on ovolecithin. Biochem J. 1954 Jul 16;58(331ST):xv–xv. [PubMed] [Google Scholar]
  9. LONG C., PENNY I. F. The structure of the naturally occurring phosphoglycerides. III. Action of moccasin-venom phospholipase A on ovolecithin and related substances. Biochem J. 1957 Feb;65(2):382–389. doi: 10.1042/bj0650382. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Long C., Odavić R., Sargent E. J. The action of cabbage-leaf phospholipase D upon lysolecithin. Biochem J. 1967 Jan;102(1):216–220. doi: 10.1042/bj1020216. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. O'DEA J. F., GIBBONS R. A. The estimation of small amounts of formaldehyde liberated during the oxidation of carbohydrates and other substances with periodate. Biochem J. 1953 Nov;55(4):580–586. doi: 10.1042/bj0550580. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. SHAPIRO B. Purification and properties of a lysolecithinase from pancreas. Biochem J. 1953 Mar;53(4):663–666. doi: 10.1042/bj0530663. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Urban F., Milder B. Microdetermination of vitamin A and carotenes. Biochem J. 1943 Jul;37(2):295–298. doi: 10.1042/bj0370295. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. de HAAS G., MULDER I., van DEENEN L. On the specificity of phospholipase A. Biochem Biophys Res Commun. 1960 Sep;3:287–291. doi: 10.1016/0006-291x(60)90241-2. [DOI] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES