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. 1975 Jul;123(1):302–307. doi: 10.1128/jb.123.1.302-307.1975

Identification of bisphosphatidic acid and its plasmalogen analogues in the phospholipids of a marine bacterium.

D J McAllister, A J De Siervo
PMCID: PMC235720  PMID: 1141198

Abstract

A relatively nonpolar unidentified phospholipid (phospholipid X) , isolated from the gram-negative marine bacterium MB 45, was characterized both chromatographically and by chemical analysis. Phospholipid X was shown to be an acidic phospholipid without vicinal hydroxyl, free-amino, or amide groups. The presence of O-alkenyl groups was indicated by a positive reaction for plasmalogen. Mild alkaline methanolysis of phospholipid X yielded only glycerophosphoryglycerol as the derivative. Acetolysis produced only diacyl-glycerol monoacetate. Clevage of O-alkenyl chains by methanolic hydrochloride resulted in the formation of three lyso derivatives. It was estimated that 18.2% of phospholipid X was plasmalogen. From these data, together with chromatographic comparisons with standards, infrared spectra, a molecular weight estimation, and the determination of the glycerol-phosphate-acyl ester ratio, it was concluded that phospholipid X was bisphosphatidic acid mixed with its plasmalogen analogues.

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Selected References

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  1. AMES B. N., DUBIN D. T. The role of polyamines in the neutralization of bacteriophage deoxyribonucleic acid. J Biol Chem. 1960 Mar;235:769–775. [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. Benns G., Proulx P. Formation of a new phosphatidyl glycerol derivative in E. coli. Biochem Biophys Res Commun. 1971 Jul 16;44(2):382–389. doi: 10.1016/0006-291x(71)90611-5. [DOI] [PubMed] [Google Scholar]
  4. Cho K. S., Benns G., Proulx P. Formation of acyl phosphatidyl glycerol by Escherichia coli extracts. Biochim Biophys Acta. 1973 Dec 20;326(3):355–360. [PubMed] [Google Scholar]
  5. Debuch H., Rotsch E. Uber ein unbekanntes N-freies Glycerinphosphatid aus grünen Blättern von Spinacia oleracea. Hoppe Seylers Z Physiol Chem. 1966;347(1):79–86. [PubMed] [Google Scholar]
  6. Diervo A. J., Reynolds J. W. Phospholipid composition and cardiolipin synthesis in fermentative and nonfermentative marine bacteria. J Bacteriol. 1975 Jul;123(1):294–301. doi: 10.1128/jb.123.1.294-301.1975. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Fischer W., Ishizuka I., Landgraf H. R., Herrmann J. Glycerophosphoryl diglucosyl diglyceride, a new phosphoglycolipid from Streptococci. Biochim Biophys Acta. 1973 Mar 8;296(3):527–545. doi: 10.1016/0005-2760(73)90113-6. [DOI] [PubMed] [Google Scholar]
  8. GOTTFRIED E. L., RAPPORT M. M. The biochemistry of plasmalogens. I. Isolation and characterization of phosphatidal choline, a pure native plasmalogen. J Biol Chem. 1962 Feb;237:329–333. [PubMed] [Google Scholar]
  9. OLLEY J. The lipids of fish. 7. Phosphate esters in the lipids of haddock and cod flesh. Biochem J. 1956 Jan;62(1):107–114. doi: 10.1042/bj0620107. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Olsen R. W., Ballou C. E. Acyl phosphatidylglycerol. A new phospholipid from Salmonella typhimurium. J Biol Chem. 1971 May 25;246(10):3305–3313. [PubMed] [Google Scholar]
  11. RENKONEN O. Determination of glycerol in phosphatides. Biochim Biophys Acta. 1962 Jan 29;56:367–369. doi: 10.1016/0006-3002(62)90580-2. [DOI] [PubMed] [Google Scholar]
  12. RENKONEN O. INDIVIDUAL MOLECULAR SPECIES OF DIFFERENT PHOSPHOLIPID CLASSES. II. A METHOD OF ANALYSIS. J Am Oil Chem Soc. 1965 Apr;42:298–304. doi: 10.1007/BF02540133. [DOI] [PubMed] [Google Scholar]
  13. Rouser G., Kritchevsky G., Knudson A. G., Jr, Simon G. Accumulation of a glycerolphospholipid in classical niemann-pick disease. Lipids. 1968 May;3(3):287–290. doi: 10.1007/BF02531203. [DOI] [PubMed] [Google Scholar]
  14. SNYDER F., STEPHENS N. A simplified spectrophotometric determination of ester groups in lipids. Biochim Biophys Acta. 1959 Jul;34:244–245. doi: 10.1016/0006-3002(59)90255-0. [DOI] [PubMed] [Google Scholar]
  15. Singh H., Spritz N., Geyer B. Studies of brain myelin in the "quaking mouse". J Lipid Res. 1971 Jul;12(4):473–481. [PubMed] [Google Scholar]
  16. Skipski V. P., Smolowe A. F., Barclay M. Separation of neutral glycosphingolipids and sulfatides by thin-layer chromatography. J Lipid Res. 1967 Jul;8(4):295–299. [PubMed] [Google Scholar]
  17. TYLER M. E., BIELLING M. C., PRATT D. B. Mineral requirements and other characters of selected marine bacteria. J Gen Microbiol. 1960 Aug;23:153–161. doi: 10.1099/00221287-23-1-153. [DOI] [PubMed] [Google Scholar]
  18. VORBECK M. L., MARINETTI G. V. SEPARATION OF GLYCOSYL DIGLYCERIDES FROM PHOSPHATIDES USING SILICIC ACID COLUMN CHROMATOGRAPHY. J Lipid Res. 1965 Jan;6:3–6. [PubMed] [Google Scholar]
  19. White D. C., Frerman F. E. Extraction, characterization, and cellular localization of the lipids of Staphylococcus aureus. J Bacteriol. 1967 Dec;94(6):1854–1867. doi: 10.1128/jb.94.6.1854-1867.1967. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Wuthier R. E. Two-dimensional chromatography on silica gel-loaded paper for the microanalysis of polar lipids. J Lipid Res. 1966 Jul;7(4):544–550. [PubMed] [Google Scholar]
  21. Yamamoto A., Adachi S., Kitani T., Shinji Y., Seki K. Drug-induced lipidosis in human cases and in animal experiments. Accumulation of an acidic glycerophospholipid. J Biochem. 1971 Mar;69(3):613–615. [PubMed] [Google Scholar]

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