Plasmalogen

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.
^ ^a ^b Wallner 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.
^ ^a ^b Braverman 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.

[1] 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.

[PMID_21723266-2] Wallner 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.

[3] 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.

[PMID_22627108-4] Braverman 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.

[5] 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.

[6] 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.

[7] 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.

[pmid11275267-8] 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.

[pmid17027098-9] 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.

[pmedid21679470-10] 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.

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