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Example of an ethanolamine plasmalogen with the characteristic vinyl ether linkage at the sn-1 position and an ester linkage at the sn-2 position
Glycerophospholipids of biochemical relevance are divided into three subclasses based on the substitution present at the sn-1 position of the glycerol backbone: acyl, alkyl and alkenyl.[1] Of these, the alkyl and alkenyl moiety in each case form an ether bond, which makes for two types of ether phospholipids, plasmanyl (alkyl moiety at sn-1), and plasmenyl (alkenyl moiety with vinyl ether linkage at sn-1). Plasmalogens are plasmenyls with an ester (acyl group) linked lipid at the sn-2 position of the glycerol backbone,[2][3] chemically designated 1-0(1Z-alkenyl)-2-acyl-glycerophospholipids.[4] The lipid attached to the vinyl ether at sn-1 can be C16:0, C18:0, or C18:1 (saturated and monounsaturated),[4][2] and the lipid attached to the acyl group at sn-2 can be C22:6 ω-3 (docosahexaenoic acid) or C20:4 ω-6 (arachidonic acid), (both are polyunsaturated acids).[5] Plasmalogens are classified according to their head group, mainly as PC plasmalogens (plasmenylcholines) and PE plasmalogens (plasmenylethalomines)[6][7] Plasmalogens should not be confused with plasmanyls.
Plasmalogens are commonly found in cell membranes in the nervous, immune, and cardiovascular systems.[8][9][10]
^Yamashita S, Honjo A, Aruga M, Nakagawa K, Miyazawa T (2014). "Preparation of marine plasmalogen and selective identification of molecular species by LC-MS/MS". J Oleo Sci. 63 (5): 423–30. doi:10.5650/jos.ess13188. PMID 24717546.
^ abWallner S, Schmitz G (September 2011). "Plasmalogens the neglected regulatory and scavenging lipid species". Chem Phys Lipids. 164 (6): 573–89. doi:10.1016/j.chemphyslip.2011.06.008. PMID 21723266.
^Hu C, Wang M, Han X (August 2017). "Shotgun lipidomics in substantiating lipid peroxidation in redox biology: Methods and applications". Redox Biol. 12: 946–955. doi:10.1016/j.redox.2017.04.030. PMC 5423350. PMID 28494428.
^ abBraverman NE, Moser AB (September 2012). "Functions of plasmalogen lipids in health and disease". Biochim Biophys Acta. 1822 (9): 1442–52. doi:10.1016/j.bbadis.2012.05.008. PMID 22627108.
^Fuchs B (May 2015). "Analytical methods for (oxidized) plasmalogens: Methodological aspects and applications". Free Radic Res. 49 (5): 599–617. doi:10.3109/10715762.2014.999675. PMID 25536419. S2CID 5443009.
^Maeba R, Nishimukai M, Sakasegawa S, Sugimori D, Hara H (2015). "Plasma/Serum Plasmalogens: Methods of Analysis and Clinical Significance". Adv Clin Chem. 70: 31–94. doi:10.1016/bs.acc.2015.03.005. PMID 26231485.
^Messias, Márcia Cristina Fernandes; Mecatti, Giovana Colozza; Priolli, Denise Gonçalves; De Oliveira Carvalho, Patrícia (2018). "Plasmalogen lipids: Functional mechanism and their involvement in gastrointestinal cancer". Lipids in Health and Disease. 17 (1): 41. doi:10.1186/s12944-018-0685-9. PMC 5842581. PMID 29514688.
^Nagan, N.; Zoeller, R. A. (2001). "Plasmalogens: Biosynthesis and functions". Progress in Lipid Research. 40 (3): 199–229. doi:10.1016/S0163-7827(01)00003-0. PMID 11275267.
^Gorgas, K.; Teigler, A.; Komljenovic, D.; Just, W. W. (2006). "The ether lipid-deficient mouse: Tracking down plasmalogen functions". Biochimica et Biophysica Acta (BBA) - Molecular Cell Research. 1763 (12): 1511–26. doi:10.1016/j.bbamcr.2006.08.038. PMID 17027098.
^Moser, A. B.; Steinberg, S. J.; Watkins, P. A.; Moser, H. W.; Ramaswamy, K.; Siegmund, K. D.; Lee, D. R.; Ely, J. J.; Ryder, O. A.; Hacia, J. G. (2011). "Human and great ape red blood cells differ in plasmalogen levels and composition". Lipids in Health and Disease. 10: 101. doi:10.1186/1476-511X-10-101. PMC 3129581. PMID 21679470.
polyunsaturated acids). Plasmalogens are classified according to their head group, mainly as PC plasmalogens (plasmenylcholines) and PE plasmalogens (plasmenylethalomines)...
but "neutral plasmalogens" (alkenyldiacylglycerols) and "diplasmalogens" (dialkenylphospholipids) also exist. The prototypical plasmalogen is platelet-activating...
In enzymology, a plasmalogen synthase (EC 2.3.1.25) is an enzyme that catalyzes the chemical reaction acyl-CoA + 1-O-alk-1-enyl-glycero-3-phosphocholine...
and polyamines. Peroxisomes also play a role in the biosynthesis of plasmalogens: ether phospholipids critical for the normal function of mammalian brains...
with unsaturated fatty acids in the 1-sn and/or 3-sn position. PlasmalogensPlasmalogens are a type of phosphoglyceride. The first carbon of glycerol has...
cataracts. The cause is a genetic mutation that results in low levels of plasmalogens, which are a type of lipid found in cell membranes throughout the body...
to substantiate, and in many cases has refuted, the xanthine oxidase/plasmalogen depletion hypothesis." Mercola.com has featured positive presentations...
fatty acids, but there are also alkyl-linked and 1Z-alkenyl-linked (plasmalogen) glycerophospholipids, as well as dialkylether variants in archaebacteria...
discussed above. In addition, these individuals can show deficient levels of plasmalogens, ether-phospholipids that are especially important for brain and lung...
Hypochlorous acid also reacts with a subclass of glycerophospholipids called plasmalogens, yielding chlorinated fatty aldehydes which are capable of protein modification...
branched chain fatty acids, D-amino acids, polyamines, and biosynthesis of plasmalogens, ether phospholipids, which are found in mammalian brains and lungs....
lung, and hexadecyl glyceryl ether participates in the biosynthesis of plasmalogens. Cetane index Isocetane Higher alkanes CID 11006 from PubChem Haynes...
fatty acids and branched chain fatty acids (such as phytanic acid) and plasmalogen biosynthesis. Since phytanic acid is not endogenously produced in the...
phytanic acid. In addition, PBD-ZSD patients show deficient levels of plasmalogens, ether-phospholipids necessary for normal brain and lung function.[citation...
dehydrogenation catalyzed unsaturases to give the vinyl ethers called plasmalogens: HOCH2CH(OH)CH2OC18H37 + [O] → HOCH2CH(OH)CH2OCH=CHC16H35 + H2O Sutter...
chains. Many strictly anoxic bacteria and a few aerobic species contain plasmalogens (Pla), which has an alkyl chain bound to sn-1 position of the glycerol...
plant desaturases. Mice lacking plasmanylethanolamine desaturase lack plasmalogens in their tissues and have reduced body weight. Werner, Ernst R.; Keller...
dehydrogenation catalyzed unsaturases to give the vinyl ethers called plasmalogens: HOCH2CH(OH)CH2OC18H37 + [O] → HOCH2CH(OH)CH2OCH=CHC16H35 + H2O Silyl...
bovine milk xanthine oxidase: a critique of the hypothesis relating to plasmalogen depletion and cardiovascular disease". Am. J. Clin. Nutr. 38 (2): 327–332...
discussed below. In addition, these individuals can show deficient levels of plasmalogens, ether-phospholipids that are especially important for brain, lung, and...
(dihydrosphingosine), an effective donor of the alk-1-enyl chain of plasmalogens". Hoppe-Seyler's Z. Physiol. Chem. 351 (7): 875–83. doi:10.1515/bchm2...
M. (1963). "Incorporation of Isobutyrate and Valerate into Cellular Plasmalogen by Bacteroides succinogenes". Journal of Bacteriology. 85: 53–61. doi:10...
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