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Chemical Compound Review

HMDB08899     2-aminoethoxy-[(2R)-2- icosanoyloxy-3...

Synonyms: KB-63681, LMGP02010463, AC1L9K72, PE(15:0/20:0), 39382-08-6, ...
 
 
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Disease relevance of phosphatidylethanolamine

  • Upon expression of the bradyrhizobial pmtA gene in Escherichia coli, predominantly monomethylphosphatidylethanolamine was formed from PE [1].
  • Phosphatidylethanolamine (PE) was isolated from Bacillus megaterium grown at 20 and 55 degrees C (PE-20 and PE-55) [2].
  • This method was applied to the separation of PE isolated from HT29 human colon cancer cells and roughly 30 PE species were resolved [3].
  • Fusion between Sendai virus and liposomes containing phosphatidylethanolamine (PE) and different mole fractions of ganglioside GD1a has been investigated [4].
  • In both M.9.1.1 and hepatoma cells transfected with PSS2 cDNA the rate of synthesis of PtdSer and PtdSer-derived PtdEtn did not exceed that in parental CHO cells or control McArdle cells respectively, in contrast to cells expressing similar levels of murine PSS1 [5].
 

High impact information on phosphatidylethanolamine

 

Biological context of phosphatidylethanolamine

  • The combined results indicate that the selective methylation of PE species by the methyltransferases plays an important role in shaping the steady-state profile of PC molecular species in yeast [9].
  • Control experiments showed that differences in [3H]PS and -PE molecular species profiles are not due to (i) incorporation of 3H label to some PE species via alternative pathways, (ii) differences in degradation or remodeling among species, or (iii) selective decarboxylation of PS molecular species by the enzyme [10].
  • The BK effect was significantly higher in old cells and, very likely, PKC-independent, since phorbol 12-myristate 13-acetate failed to induce PtdEtn hydrolysis [11].
  • Late pregnancy in the rat (gestational ages 16-21 days) was accompanied by a specific increase in hepatic phosphatidylcholine (PC) and phosphatidylethanolamine (PE) molecular species containing C16:0 at the sn-1 position and polyunsaturated essential fatty acids (PUFA), in particular C22:6(n-3), at the sn-2 position [12].
  • In summary, our results indicate that serum cholesterol and phospholipid fractions (except PE) are increased during hibernation in bears [13].
 

Anatomical context of phosphatidylethanolamine

  • Interestingly, the hydrophilic diacyl molecular species were found to be much more abundant in PE than in PS, suggesting that hydrophilic PS species may be more readily transported to mitochondria than the hydrophobic ones [10].
  • In strains with a psd1Delta allele for the mitochondrial PtdSer decarboxylase, the conversion of nascent PtdSer to PtdEtn can serve as an indicator of lipid transport to the locus of PtdSer decarboxylase 2 (Psd2p) in the Golgi/vacuole [14].
  • A similar preferential conversion of di-C16:1 PE to PC was found in vitro upon incubating isolated microsomes with S-adenosyl[methyl-D3]methionine [9].
  • In addition, the impaired VLDL secretion from the choline-deficient hepatocytes could also be corrected by supplementation of betaine (0.2 mM) and homocysteine (0.2 mM), indicating the utilization of a methyl group from betaine for PC formation via methylation of PE [15].
  • In the ROS disk membranes the value for S perpendicular was marginally higher than in the PC membranes, perhaps reflecting the influence of PE [16].
 

Associations of phosphatidylethanolamine with other chemical compounds

 

Gene context of phosphatidylethanolamine

 

Analytical, diagnostic and therapeutic context of phosphatidylethanolamine

  • The cells were pulse labeled with [3H]serine whereafter the distribution of the labels among PS and PE molecular species was determined by reverse phase high performance liquid chromatography and liquid scintillation counting [10].
  • To investigate how these biosynthetic enzymes contribute to the composition of the PC species profile, the precursor-product relationships between PE and newly synthesized PC were determined at the level of the molecular species by using electrospray ionization tandem mass spectrometry and stable isotope labeling [9].
  • Ca2(+)-dependent binding of adseverin to PS liposomes but not to PC or PE liposomes was observed by a centrifugation assay [25].
  • This conclusion was substantiated by analysing the molecular species by electrospray ionization-mass spectrometry (ESI-MS/MS), which revealed that PE and NaCl-induced PBut share a unique (18 : 1)2-structure [26].
  • Using receptor-based microtiter well immunoassays, we observed binding to be equal, specific, and saturable for PE and Gg 4 but low and nonspecific for PS [27].

References

  1. Phosphatidylcholine levels in Bradyrhizobium japonicum membranes are critical for an efficient symbiosis with the soybean host plant. Minder, A.C., de Rudder, K.E., Narberhaus, F., Fischer, H.M., Hennecke, H., Geiger, O. Mol. Microbiol. (2001) [Pubmed]
  2. Regulation and phase equilibria of membrane lipids from Bacillus megaterium and Acholeplasma laidlawii strain A containing methyl-branched acyl chains. Rilfors, L., Hauksson, J.B., Lindblom, G. Biochemistry (1994) [Pubmed]
  3. Analysis of aminophospholipid molecular species by methyl-beta-cyclodextrin modified micellar electrokinetic capillary chromatography with laser-induced fluorescence detection. Zhang, L., Hu, S., Cook, L., Dovichi, N.J. Electrophoresis (2002) [Pubmed]
  4. Kinetic studies of Sendai virus-target membrane interactions: independent analysis of binding and fusion. Tsao, Y.S., Huang, L. Biochemistry (1986) [Pubmed]
  5. Cloning and expression of murine liver phosphatidylserine synthase (PSS)-2: differential regulation of phospholipid metabolism by PSS1 and PSS2. Stone, S.J., Vance, J.E. Biochem. J. (1999) [Pubmed]
  6. Electrospray ionization tandem mass spectrometry (ESI-MS/MS) analysis of the lipid molecular species composition of yeast subcellular membranes reveals acyl chain-based sorting/remodeling of distinct molecular species en route to the plasma membrane. Schneiter, R., Brügger, B., Sandhoff, R., Zellnig, G., Leber, A., Lampl, M., Athenstaedt, K., Hrastnik, C., Eder, S., Daum, G., Paltauf, F., Wieland, F.T., Kohlwein, S.D. J. Cell Biol. (1999) [Pubmed]
  7. Early embryonic lethality in mice with targeted deletion of the CTP:phosphocholine cytidylyltransferase alpha gene (Pcyt1a). Wang, L., Magdaleno, S., Tabas, I., Jackowski, S. Mol. Cell. Biol. (2005) [Pubmed]
  8. Disruption of the phosphatidylserine decarboxylase gene in mice causes embryonic lethality and mitochondrial defects. Steenbergen, R., Nanowski, T.S., Beigneux, A., Kulinski, A., Young, S.G., Vance, J.E. J. Biol. Chem. (2005) [Pubmed]
  9. The yeast phospholipid N-methyltransferases catalyzing the synthesis of phosphatidylcholine preferentially convert di-C16:1 substrates both in vivo and in vitro. Boumann, H.A., Chin, P.T., Heck, A.J., De Kruijff, B., De Kroon, A.I. J. Biol. Chem. (2004) [Pubmed]
  10. Preferential decarboxylation of hydrophilic phosphatidylserine species in cultured cells. Implications on the mechanism of transport to mitochondria and cellular aminophospholipid species compositions. Heikinheimo, L., Somerharju, P. J. Biol. Chem. (1998) [Pubmed]
  11. Potentiated bradykinin-induced increase of 1,2-diacylglycerol generation and phospholipase D activity in human senescent fibroblasts. Meacci, E., Vasta, V., Faraoni, P., Farnararo, M., Bruni, P. Biochem. J. (1995) [Pubmed]
  12. Mechanisms of hepatic phosphatidylcholine synthesis in adult rat: effects of pregnancy. Burdge, G.C., Hunt, A.N., Postle, A.D. Biochem. J. (1994) [Pubmed]
  13. Changes during hibernation in different phospholipid and free and esterified cholesterol serum levels in black bears. Chauhan, V., Sheikh, A., Chauhan, A., Tsiouris, J., Malik, M., Vaughan, M. Biochimie (2002) [Pubmed]
  14. Characterization of phosphatidylserine transport to the locus of phosphatidylserine decarboxylase 2 in permeabilized yeast. Wu, W.I., Voelker, D.R. J. Biol. Chem. (2001) [Pubmed]
  15. Head group specificity in the requirement of phosphatidylcholine biosynthesis for very low density lipoprotein secretion from cultured hepatocytes. Yao, Z.M., Vance, D.E. J. Biol. Chem. (1989) [Pubmed]
  16. Cholesterol dynamics in membranes. Yeagle, P.L., Albert, A.D., Boesze-Battaglia, K., Young, J., Frye, J. Biophys. J. (1990) [Pubmed]
  17. Phospholipase D activity in the intestinal mitochondria: activation by oxygen free radicals. Madesh, M., Ibrahim, S.A., Balasubramanian, K.A. Free Radic. Biol. Med. (1997) [Pubmed]
  18. Polymorphism of POPE/cholesterol system: a 2H nuclear magnetic resonance and infrared spectroscopic investigation. Paré, C., Lafleur, M. Biophys. J. (1998) [Pubmed]
  19. Evidence for two cholesterol ester hydrolases in human cerebrospinal fluid. Johnson, R.C., Shah, S.N. J. Neurochem. (1981) [Pubmed]
  20. Evidence for an intrinsic toxicity of phosphatidylcholine to Sec14p-dependent protein transport from the yeast Golgi complex. Xie, Z., Fang, M., Bankaitis, V.A. Mol. Biol. Cell (2001) [Pubmed]
  21. Phospholipase D1 is up-regulated in the mitochondrial fraction from the brains of Alzheimer's disease patients. Jin, J.K., Kim, N.H., Lee, Y.J., Kim, Y.S., Choi, E.K., Kozlowski, P.B., Park, M.H., Kim, H.S., Min, d.o. .S. Neurosci. Lett. (2006) [Pubmed]
  22. Profiling membrane lipids in plant stress responses. Role of phospholipase D alpha in freezing-induced lipid changes in Arabidopsis. Welti, R., Li, W., Li, M., Sang, Y., Biesiada, H., Zhou, H.E., Rajashekar, C.B., Williams, T.D., Wang, X. J. Biol. Chem. (2002) [Pubmed]
  23. Dietary polyunsaturated Fatty acids in gestation alter fetal cortical phospholipids, Fatty acids and phosphatidylserine synthesis. Tam, O., Innis, S.M. Dev. Neurosci. (2006) [Pubmed]
  24. Interleukin-1 stimulates phosphatidic acid-mediated phospholipase D activity in human mesangial cells. Bursten, S.L., Harris, W.E. Am. J. Physiol. (1994) [Pubmed]
  25. Inhibition of actin regulatory activity of the 74-kDa protein from bovine adrenal medulla (adseverin) by some phospholipids. Maekawa, S., Sakai, H. J. Biol. Chem. (1990) [Pubmed]
  26. Substrate preference of stress-activated phospholipase D in Chlamydomonas and its contribution to PA formation. Arisz, S.A., Valianpour, F., van Gennip, A.H., Munnik, T. Plant J. (2003) [Pubmed]
  27. Adherence to lipids and intestinal mucin by a recently recognized human pathogen, Campylobacter upsaliensis. Sylvester, F.A., Philpott, D., Gold, B., Lastovica, A., Forstner, J.F. Infect. Immun. (1996) [Pubmed]
 
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