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. 1995 Sep;109(1):269–275. doi: 10.1104/pp.109.1.269

N-acylphosphatidylethanolamine in dry and imbibing cottonseeds. Amounts, molecular species, and enzymatic synthesis.

J A Sandoval 1, Z H Huang 1, D C Garrett 1, D A Gage 1, K D Chapman 1
PMCID: PMC157585  PMID: 7480326

Abstract

N-Acylphosphatidylethanolamine (NAPE), an unusual acylated derivative of phosphatidylethanolamine (PE), was recently shown to be synthesized from PE and free fatty acids in cotyledons of cotton (Gossypium hirsutum L.) seedlings (K.D. Chapman, T.S. Moore [1993] Plant Physiol 102: 761-769). Here we report that NAPE is present in dry seeds of cotton and increases with time of imbibition from 2.31 nmol/seed in dry seeds to 4.26 nmol/seed in 4-h-soaked seeds. Total phospholipid/seed also increased such that the relative percentage of NAPE was similar in dry and soaked seeds (2.3 mol% compared to 2.6 mol%, respectively). The major molecular species of NAPE were identified in both dry and soaked seeds by fast atom bombardment mass spectrometry and collisionally activated dissociation tandem mass spectrometry as 16:0/18:2-PE(N-palmitoyl), 16:0/18:2-PE(N-linoleoyl), and 18:2/18:2-PE(N-palmitoyl). The specific activity of NAPE synthase in seed extracts increased with increasing time of imbibition from 35 pmol h-1 mg-1 protein in dry seeds to 129 pmol h-1 mg-1 protein in 4-h-soaked seeds. Collectively, our results indicate that NAPE is present in dry cottonseeds and synthesized during imbibition. The biosynthesis of NAPE provides a mechanism for maintaining membrane integrity during seed rehydration and may indicate that NAPE plays a protective role in intracellular membranes of plant tissues, as has been suggested for intracellular membranes of animal tissues.

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Selected References

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  1. Bomstein R. A. A new class of phosphatides isolated from soft wheat flour. Biochem Biophys Res Commun. 1965 Oct 8;21(1):49–54. doi: 10.1016/0006-291x(65)90424-9. [DOI] [PubMed] [Google Scholar]
  2. Borochov A., Walker M. A., Kendall E. J., Pauls K. P., McKersie B. D. Effect of a freeze-thaw cycle on properties of microsomal membranes from wheat. Plant Physiol. 1987 May;84(1):131–134. doi: 10.1104/pp.84.1.131. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Chapman K. D., Lin I., DeSouza A. D. Metabolism of cottonseed microsomal N-acylphosphatidylethanolamine. Arch Biochem Biophys. 1995 Apr 20;318(2):401–407. doi: 10.1006/abbi.1995.1246. [DOI] [PubMed] [Google Scholar]
  4. Chapman K. D., Moore T. S., Jr Isozymes of cottonseed microsomal N-acylphosphatidylethanolamine synthase: detergent solubilization and electrophoretic separation of active enzymes with different properties. Biochim Biophys Acta. 1994 Feb 10;1211(1):29–36. doi: 10.1016/0005-2760(94)90135-x. [DOI] [PubMed] [Google Scholar]
  5. Chapman K. D., Moore T. S., Jr N-acylphosphatidylethanolamine synthesis in plants: occurrence, molecular composition, and phospholipid origin. Arch Biochem Biophys. 1993 Feb 15;301(1):21–33. doi: 10.1006/abbi.1993.1110. [DOI] [PubMed] [Google Scholar]
  6. Crowe J. H., Hoekstra F. A., Crowe L. M. Membrane phase transitions are responsible for imbibitional damage in dry pollen. Proc Natl Acad Sci U S A. 1989 Jan;86(2):520–523. doi: 10.1073/pnas.86.2.520. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Domingo J. C., Mora M., Africa de Madariaga M. Incorporation of N-acylethanolamine phospholipids into egg phosphatidylcholine vesicles: characterization and permeability properties of the binary systems. Biochim Biophys Acta. 1993 Jun 5;1148(2):308–316. doi: 10.1016/0005-2736(93)90144-o. [DOI] [PubMed] [Google Scholar]
  8. Epps D. E., Natarajan V., Schmid P. C., Schmid H. O. Accumulation of N-acylethanolamine glycerophospholipids in infarcted myocardium. Biochim Biophys Acta. 1980 Jun 23;618(3):420–430. doi: 10.1016/0005-2760(80)90260-x. [DOI] [PubMed] [Google Scholar]
  9. Epps D. E., Schmid P. C., Natarajan V., Schmid H. H. N-Acylethanolamine accumulation in infarcted myocardium. Biochem Biophys Res Commun. 1979 Sep 27;90(2):628–633. doi: 10.1016/0006-291x(79)91281-6. [DOI] [PubMed] [Google Scholar]
  10. Gray G. M. Phosphatidyl-(N-acyl)-ethanolamine. A lipid component of mammalian epidermis. Biochim Biophys Acta. 1976 Apr 22;431(1):1–8. doi: 10.1016/0005-2760(76)90253-8. [DOI] [PubMed] [Google Scholar]
  11. Lafrance D., Marion D., Pézolet M. Study of the structure of N-acyldipalmitoylphosphatidylethanolamines in aqueous dispersion by infrared and Raman spectroscopies. Biochemistry. 1990 May 15;29(19):4592–4599. doi: 10.1021/bi00471a013. [DOI] [PubMed] [Google Scholar]
  12. Schmid H. H., Schmid P. C., Natarajan V. N-acylated glycerophospholipids and their derivatives. Prog Lipid Res. 1990;29(1):1–43. doi: 10.1016/0163-7827(90)90004-5. [DOI] [PubMed] [Google Scholar]
  13. Senaratna T., McKersie B. D., Stinson R. H. Association between Membrane Phase Properties and Dehydration Injury in Soybean Axes. Plant Physiol. 1984 Nov;76(3):759–762. doi: 10.1104/pp.76.3.759. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Uemura M., Steponkus P. L. A Contrast of the Plasma Membrane Lipid Composition of Oat and Rye Leaves in Relation to Freezing Tolerance. Plant Physiol. 1994 Feb;104(2):479–496. doi: 10.1104/pp.104.2.479. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Van Bilsen DGJL., Hoekstra F. A., Crowe L. M., Crowe J. H. Altered Phase Behavior in Membranes of Aging Dry Pollen May Cause Imbibitional Leakage. Plant Physiol. 1994 Apr;104(4):1193–1199. doi: 10.1104/pp.104.4.1193. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Webb M. S., Uemura M., Steponkus P. L. A Comparison of Freezing Injury in Oat and Rye: Two Cereals at the Extremes of Freezing Tolerance. Plant Physiol. 1994 Feb;104(2):467–478. doi: 10.1104/pp.104.2.467. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. de la Roche I. A., Andrews C. J. Changes in Phospholipid Composition of a Winter Wheat Cultivar during Germination at 2 C and 24 C. Plant Physiol. 1973 Mar;51(3):468–473. doi: 10.1104/pp.51.3.468. [DOI] [PMC free article] [PubMed] [Google Scholar]

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