51:
28:
40:
183:
next to the ether linkage. Without specification it generally refers to alkenyl-acylphospholipids, but "neutral plasmalogens" (alkenyldiacylglycerols) and "diplasmalogens" (dialkenylphospholipids) also exist. The prototypical plasmalogen is
432:
Ether phospholipids are major parts of the cell membrane in anaerobic bacteria. These lipids can be variously 1-O-alkyl, 2-O-alkyl, or 1,2-O-dialkyl. Some groups have, like archaea, evolved tetraether lipids.
1018:
Lux H, Heise N, Klenner T, Hart D, Opperdoes FR (November 2000). "Ether--lipid (alkyl-phospholipid) metabolism and the mechanism of action of ether--lipid analogues in
Leishmania".
669:
Villanueva, Laura; von
Meijenfeldt, F. A. Bastiaan; Westbye, Alexander B.; Yadav, Subhash; Hopmans, Ellen C.; Dutilh, Bas E.; Damsté, Jaap S. Sinninghe (January 2021).
1157:"Mono- and dialkyl glycerol ether lipids in anaerobic bacteria: biosynthetic insights from the mesophilic sulfate reducer Desulfatibacillum alkenivorans PF2803T"
901:"Platelet-activating factor. Evidence for 1-O-alkyl-2-acetyl-sn-glyceryl-3-phosphorylcholine as the active component (a new class of lipid chemical mediators)"
371:
consist mostly of ether phospholipids. These lipids have a flipped chirality compared to bacterial and eukaryotic membranes, a conundrum known as the "
164:
1391:
671:"Bridging the membrane lipid divide: bacteria of the FCB group superphylum have the potential to synthesize archaeal ether lipids"
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206:
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761:
570:"Differential metabolism of diradyl glycerol molecular subclasses and molecular species by rabbit brain diglyceride kinase"
467:
202:
726:
501:
17:
848:
141:
on the phosphate connection is called an "archaeal ether lipid". With few (if any) exceptions, it is only found among
1116:"Recent advances in structural research on ether lipids from archaea including comparative and physiological aspects"
940:
Brosche T, Platt D (August 1998). "The biological significance of plasmalogens in defense against oxidative damage".
1352:
1347:
1342:
110:: "ether lipids" in the context of bacteria and eukaryotes refer to this class of lipids. Compared to the usual
163:: a number of other lipids not belonging to any of the classes above contain the ether linkage. For example,
502:"Ether lipids - glyceryl ethers, plasmalogens, aldehydes, structure, biochemistry, composition and analysis"
128:("plasmanylphospholipid"). This class of lipids have important roles in human cell signaling and structure.
375:". The "tail" groups are also not simply n-alkyl groups, but highly methylated chains made up of saturated
312:
metabolism. This antioxidant activity comes from the enol ether double bond being targeted by a variety of
242:
157:: 1-alkyldiacyl-sn-glycerols (alkyldiacylglycerols) are found in significant proportions in marine animals.
120:
Based on whether the sn-1 lipid is unsaturated next to the ether linkage, they can be further divided into
1065:
1240:
276:
that are important in signal transduction. Ether lipids can also act directly in cell signaling, as the
1418:
277:
185:
54:
1320:
983:
Engelmann B (February 2004). "Plasmalogens: targets for oxidants and major lipophilic antioxidants".
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412:
Some such covelant bilayers feature crosslinks between the two chains, giving an H-shaped molecule.
313:
265:
1233:
1215:
216:
Monoalkylglycerol ethers (MAGEs) are also generated from 2-acetyl MAGEs (precursors of PAF) by
233:
Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the
1494:
1155:
Grossi, V; Mollex, D; Vinçon-Laugier, A; Hakil, F; Pacton, M; Cravo-Laureau, C (1 May 2015).
418:
is a tetraether backbone with cyclopentane and cyclohexane rings on the cross-linked "tail"s.
138:
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682:
104:: phospholipids are known to have ether-linked "tails" instead of the usual ester linkage.
8:
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213:. Accordingly, peroxisomal defects often lead to impairment of ether-lipid production.
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Some lipids replace the glycerol backbone with four-carbon polyols (tetriols).
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258:
234:
90:
50:
753:
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1004:
878:
777:
Hajra AK (1995). "Glycerolipid biosynthesis in peroxisomes (microbodies)".
712:
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554:
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398:
372:
347:
has recently been introduced as an oral treatment for the tropical disease
325:
305:
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32:
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Biochimica et
Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids
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parasite with a particularly high ether lipid content in its membranes.
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996:
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Among different groups of archaea, diverse modifications on the basic
245:
anchor of mammalian proteins generally consist of an 1-O-alkyl lipid.
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properties, probably by disrupting membrane structure and acting as
1481:
1268:
406:
387:
380:
217:
146:
78:
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The two tails can be linked together, forming a macrocyclic lipid.
167:, a vital part of the testes and sperm cells, has a ether linkage.
124:("plasmenylphospholipid", 1-0-alk-1’-enyl-2-acyl-sn-glycerol) and
1507:
368:
201:
The formation of the ether bond in mammals requires two enzymes,
142:
1066:"Archaeal phospholipids: Structural properties and biosynthesis"
296:
Another possible function of the plasmalogen ether lipids is as
1154:
261:
238:
39:
27:
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94:
82:
74:
46:. Note ether at first position, and ester at second position.
812:
Paltauf F (December 1994). "Ether lipids in biomembranes".
58:
898:
280:
is an ether lipid signaling molecule that is involved in
332:
of enzymes within signal transmission pathways, such as
899:
Demopoulos CA, Pinckard RN, Hanahan DJ (October 1979).
114:(DAG), the sn-1 linkage is replaced with an ester bond.
308:
and these lipids might therefore play a role in serum
145:. The part excluding the phoshphate group is known as
746:
Omega 3 fatty acids in brain and neurological health
1017:
77:in which the lipid "tail" group is attached to the
1064:Caforio, Antonella; Driessen, Arnold J.M. (2017).
849:"Membrane lipid composition and cellular function"
727:"Di- and Tetra-Alkyl Ether Lipids of the Archaea"
619:"Structural and functional roles of ether lipids"
521:"Structural and functional roles of ether lipids"
1534:
743:
441:Some ether lipids found in marine animals are S-
319:
1063:
664:
662:
1241:
401:), with two glycerol units connected by two C
264:might be involved in the generation of lipid
939:
846:
1120:Bioscience, Biotechnology, and Biochemistry
659:
85:at any position. In contrast, conventional
35:. Note ether at first and second positions.
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1234:
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257:of ether glycerophospholipids by specific
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1218:at the U.S. National Library of Medicine
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203:dihydroxyacetonephosphate acyltransferase
561:
179:linkage, i.e. ones with a carbon-carbon
49:
38:
26:
1046:
847:Spector AA, Yorek MA (September 1985).
811:
480:
397:Bipolar macrocyclic tetraether lipids (
207:alkyldihydroxyacetonephosphate synthase
14:
1535:
1161:Applied and Environmental Microbiology
1020:Molecular and Biochemical Parasitology
744:Watson RR, De Meester F, eds. (2014).
175:" can refer to any ether lipid with a
1229:
776:
617:Dean, JM; Lodhi, IJ (February 2018).
499:
468:Glycerol dialkyl glycerol tetraether
57:. Note ether at first position, and
905:The Journal of Biological Chemistry
574:The Journal of Biological Chemistry
519:Dean JM, Lodhi IJ (February 2018).
324:Synthetic ether lipid analogs have
248:
24:
25:
1554:
1209:
1114:Koga Y, Morii H (November 2005).
436:
985:Biochemical Society Transactions
300:, as protective effects against
191:
155:Ether analogues of triglycerides
1148:
1107:
1011:
976:
933:
892:
840:
814:Chemistry and Physics of Lipids
568:Ford DA, Gross RW (July 1990).
196:
805:
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610:
512:
427:
291:
13:
1:
1032:10.1016/S0166-6851(00)00278-4
954:10.1016/S0531-5565(98)00014-X
918:10.1016/S0021-9258(19)83523-8
866:10.1016/S0022-2275(20)34276-0
587:10.1016/S0021-9258(19)38342-5
473:
362:
343:A toxic ether lipid analogue
320:Synthetic ether lipid analogs
228:
1085:10.1016/j.bbalip.2016.12.006
826:10.1016/0009-3084(94)90054-X
791:10.1016/0163-7827(95)00013-5
243:glycosylphosphatidylinositol
223:
209:(ADAPS), that reside in the
108:Ether on sn-1, ester on sn-2
97:. Structural types include:
7:
1296:-ethanolamine/cephalin (PE)
748:. Elsevier Academic Press.
456:
10:
1559:
1419:Platelet-activating factor
779:Progress in Lipid Research
695:10.1038/s41396-020-00772-2
304:have been demonstrated in
284:function in the mammalian
278:platelet-activating factor
186:platelet-activating factor
137:: this class with flipped
55:Platelet-activating factor
1503:
1490:
1472:
1465:
1446:
1429:
1403:
1332:
1285:
1267:
853:Journal of Lipid Research
635:10.1007/s13238-017-0423-5
537:10.1007/s13238-017-0423-5
122:alkenyl-acylphospholipids
61:group at second position.
1220:Medical Subject Headings
942:Experimental Gerontology
326:cytostatic and cytotoxic
266:second messenger systems
253:Differences between the
754:10.1016/C2012-0-06006-1
390:backbone have emerged.
314:reactive oxygen species
126:alkyl-acylphospholipids
1301:-choline/lecithin (PC)
135:Ether on sn-2 and sn-3
112:1,2-diacyl-sn-glycerol
62:
47:
36:
31:Structure of an ether
1495:Lysophosphatidic acid
1275:Glycerophospholipids/
367:The cell membrane of
351:, which is caused by
53:
42:
30:
1181:10.1128/AEM.03794-14
405:"tail" chains, form
87:glycerophospholipids
1216:Ether+phospholipids
1173:2015ApEnM..81.3157G
1133:10.1271/bbb.69.2019
687:2021ISMEJ..15..168V
409:linked 'bilayers'.
102:Ether phospholipids
1477:Inositol phosphate
1333:Phosphoinositides:
997:10.1042/BST0320147
623:Protein & Cell
525:Protein & Cell
161:Other ether lipids
63:
48:
37:
18:Ether phospholipid
1530:
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1442:
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1277:Phosphoglycerides
1079:(11): 1325–1339.
763:978-0-12-410527-0
506:www.lipidmaps.org
16:(Redirected from
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877:. Archived from
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334:protein kinase C
302:oxidative stress
274:arachidonic acid
249:Second messenger
81:backbone via an
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437:In prokaryotes
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192:In eukaryotes
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1405:Ether lipids
1404:
1306:-serine (PS)
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883:. Retrieved
879:the original
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500:Christie W.
440:
431:
416:Crenarchaeol
399:caldarchaeol
385:
379:units (e.g.
373:lipid divide
366:
342:
323:
306:cell culture
298:antioxidants
295:
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197:Biosynthesis
170:
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107:
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70:
67:biochemistry
64:
33:phospholipid
1466:Metabolites
1448:Sphingosine
1434:Cardiolipin
1414:Plasmalogen
1026:(1): 1–14.
428:In bacteria
345:miltefosine
310:lipoprotein
292:Antioxidant
181:double bond
177:vinyl ether
173:plasmalogen
165:seminolipid
71:ether lipid
44:Plasmalogen
1518:Citicoline
885:2007-03-08
474:References
407:covalently
377:isoprenoid
363:In archaea
353:leishmania
330:inhibitors
255:catabolism
229:Structural
211:peroxisome
171:The term "
83:ether bond
357:protozoal
282:leukocyte
224:Functions
139:chirality
1537:Category
1482:Inositol
1450:backbone
1382:PI(4,5)P
1374:PI(3,5)P
1366:PI(3,4)P
1271:backbone
1269:Glycerol
1199:25724965
1142:16306681
1101:27154462
1093:28007654
1040:11087912
1005:14748736
970:20977817
713:32929208
653:28523433
555:28523433
457:See also
449:, and S-
388:archaeol
381:phytanyl
268:such as
218:KIAA1363
147:archaeol
79:glycerol
1508:Choline
1190:4393425
1169:Bibcode
962:9762517
875:3906008
834:7859340
799:8685243
704:7852524
683:Bibcode
644:5818364
604:1042240
596:2165056
546:5818364
369:archaea
262:enzymes
239:mammals
143:archaea
93:are tri
1543:Lipids
1353:PI(5)P
1348:PI(4)P
1343:PI(3)P
1321:glyco-
1257:Lipids
1222:(MeSH)
1197:
1187:
1140:
1099:
1091:
1038:
1003:
968:
960:
927:489536
925:
873:
832:
797:
760:
711:
701:
651:
641:
602:
594:
553:
543:
241:. The
95:esters
1323:(GPI)
1097:S2CID
1069:(PDF)
966:S2CID
600:S2CID
75:lipid
69:, an
1339:PIP
1195:PMID
1138:PMID
1089:PMID
1077:1862
1036:PMID
1001:PMID
958:PMID
923:PMID
871:PMID
830:PMID
795:PMID
758:ISBN
709:PMID
649:PMID
592:PMID
551:PMID
445:, S-
355:, a
336:and
272:and
89:and
59:acyl
1392:PIP
1359:PIP
1185:PMC
1177:doi
1128:doi
1081:doi
1028:doi
1024:111
993:doi
950:doi
913:doi
909:254
861:doi
822:doi
787:doi
750:doi
699:PMC
691:doi
639:PMC
631:doi
582:doi
578:265
541:PMC
533:doi
383:).
237:in
65:In
1539::
1259::
1193:.
1183:.
1175:.
1165:81
1163:.
1159:.
1136:.
1124:69
1122:.
1118:.
1095:.
1087:.
1075:.
1071:.
1048:^
1034:.
1022:.
999:.
989:32
987:.
964:.
956:.
946:33
944:.
921:.
907:.
903:.
869:.
857:26
855:.
851:.
828:.
818:74
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793:.
783:34
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