glyceryl ethers

Summary

Summary: Compounds in which one or more of the three hydroxyl groups of glycerol are in ethereal linkage with a saturated or unsaturated aliphatic alcohol; one or two of the hydroxyl groups of glycerol may be esterified. These compounds have been found in various animal tissue.

Top Publications

  1. Damsté J, Schouten S, Hopmans E, van Duin A, Geenevasen J. Crenarchaeol: the characteristic core glycerol dibiphytanyl glycerol tetraether membrane lipid of cosmopolitan pelagic crenarchaeota. J Lipid Res. 2002;43:1641-51 pubmed
    ..This prevents the dense packing characteristic for the cyclopentane ring-containing GDGTs membrane lipids used by hyperthermophilic crenarchaeota to adjust their membrane fluidity to high temperatures...
  2. Jahn U, Summons R, Sturt H, Grosjean E, Huber H. Composition of the lipids of Nanoarchaeum equitans and their origin from its host Ignicoccus sp. strain KIN4/I. Arch Microbiol. 2004;182:404-13 pubmed
    ..Sugar residues were mainly mannose and small amounts of glucose. Consistent 13C fractionation patterns of isoprenoid chains of N. equitans and its host indicated that the N. equitans lipids were synthesized in the host cells...
  3. Pedrono F, Saïag B, Moulinoux J, Legrand A. 1-O-alkylglycerols reduce the stimulating effects of bFGF on endothelial cell proliferation in vitro. Cancer Lett. 2007;251:317-22 pubmed
    ..Inhibition of bFGF-stimulated endothelial proliferation could support anti-angiogenic activity of alkyl-Gro...
  4. Sprott G, Dicaire C, Côté J, Whitfield D. Adjuvant potential of archaeal synthetic glycolipid mimetics critically depends on the glyco head group structure. Glycobiology. 2008;18:559-65 pubmed publisher
    ..This first study on synthetic archaeal lipid adjuvants reveals potential for this class of regulatory friendly, easily scalable, inexpensive, and potent glyco-adjuvant...
  5. Pedrono F, Cheminade C, Legrand A. Natural 1-O-alkylglycerols reduce platelet-activating factor-induced release of [3H]-serotonin in rabbit platelets. Prostaglandins Leukot Essent Fatty Acids. 2004;71:19-23 pubmed
    ..These data show that alkylglycerols inhibit partially and specifically PAF-induced platelet stimulation and suggest that this effect could result from interfering with PAF receptors...
  6. Erdlenbruch B, Schinkhof C, Kugler W, Heinemann D, Herms J, Eibl H, et al. Intracarotid administration of short-chain alkylglycerols for increased delivery of methotrexate to the rat brain. Br J Pharmacol. 2003;139:685-94 pubmed
    ..4 In summary, intracarotid short-chain alkylglycerols constitute a very effective and low toxic strategy for transient opening of the BBB to overcome the limited access of cytotoxic drugs to the brain...
  7. Zoeller R, Grazia T, LaCamera P, Park J, Gaposchkin D, Farber H. Increasing plasmalogen levels protects human endothelial cells during hypoxia. Am J Physiol Heart Circ Physiol. 2002;283:H671-9 pubmed
    ..These data also demonstrate that HG can protect cells during hypoxia and other ROS-mediated stress, likely due to the resulting increase in these antioxidant phospholipids...
  8. Martín D, Morán Valero M, Señoráns F, Reglero G, Torres C. In vitro intestinal bioaccessibility of alkylglycerols versus triacylglycerols as vehicles of butyric acid. Lipids. 2011;46:277-85 pubmed publisher
    ..Additionally, such a product would integrate both bioactive compounds, butyric acid and alkylglycerol, within the same molecule. Free butyric acid and AKG would be also released, which are lipid products of interest as well. ..
  9. Upasani V, Desai S, Moldoveanu N, Kates M. Lipids of extremely halophilic archaeobacteria from saline environments in India: a novel glycolipid in Natronobacterium strains. Microbiology. 1994;140 ( Pt 8):1959-66 pubmed
    ..Hydroxylated lipid cores have previously been identified only in some methanogenic archaeobacteria...

More Information

Publications62

  1. Torres C, Vazquez L, Señoráns F, Reglero G. Study of the analysis of alkoxyglycerols and other non-polar lipids by liquid chromatography coupled with evaporative light scattering detector. J Chromatogr A. 2005;1078:28-34 pubmed
    ..The present methodology not only separates 18 different lipid classes with a good reproducibility, but it is also able to estimate the relative proportion in which they are found in a broad range of concentrations...
  2. Tarui M, Tanaka N, Tomura K, Ohga M, Morii H, Koga Y. Lipid component parts analysis of the hyperthermophilic sulfate-reducing archaeon Archaeoglobus fulgidus. J UOEH. 2007;29:131-9 pubmed
    ..An amino group containing phospholipid was found for the first time in an archaeon other than methanogenic archaea...
  3. Moncla B, Pryke K, Isaacs C. Killing of Neisseria gonorrhoeae, Streptococcus agalactiae (group B streptococcus), Haemophilus ducreyi, and vaginal Lactobacillus by 3-O-octyl-sn-glycerol. Antimicrob Agents Chemother. 2008;52:1577-9 pubmed publisher
    ..Octylglycerol concentrations must exceed the binding capacity of any human serum albumin to be effective...
  4. Sun X, Wu Q, Wang N, Cai Y, Lin X. Novel mutual pro-drugs of 2',3'-dideoxyinosine with 3-octadecyloxy-propane-1,2-diol by straightforward enzymatic regioselective synthesis in acetone. Biotechnol Lett. 2005;27:113-7 pubmed
  5. Sato Y, Moriuchi H, Hishiyama S, Otsuka Y, Oshima K, Kasai D, et al. Identification of three alcohol dehydrogenase genes involved in the stereospecific catabolism of arylglycerol-beta-aryl ether by Sphingobium sp. strain SYK-6. Appl Environ Microbiol. 2009;75:5195-201 pubmed publisher
    ..Disruption of the genes indicated that ligD is essential for the degradation of (alphaR,betaS)-GGE and (alphaR,betaR)-GGE and that both ligL and ligN contribute to the degradation of the two other GGE stereoisomers...
  6. Anadón A, Martinez M, Ares I, Ramos E, Señoráns F, Reglero G, et al. Acute and repeated dose (28 days) oral safety studies of an alkoxyglycerol extract from shark liver oil in rats. J Agric Food Chem. 2010;58:2040-6 pubmed publisher
    ..It is concluded that the AKG-1 extract is well tolerated in rats at an acute dose of 2000 mg kg(-1) and at a subchronic (28 days) dose of 1000 mg kg(-1)...
  7. Krishnan L, Sad S, Patel G, Sprott G. The potent adjuvant activity of archaeosomes correlates to the recruitment and activation of macrophages and dendritic cells in vivo. J Immunol. 2001;166:1885-93 pubmed
    ..Thus, the recruitment and activation of professional APCs by archaeosomes constitutes an efficient self-adjuvanting process for induction of Ag-specific responses to encapsulated Ags...
  8. Morilla M, Gomez D, Cabral P, Cabrera M, Balter H, Tesoriero M, et al. M cells prefer archaeosomes: an in vitro/in vivo snapshot upon oral gavage in rats. Curr Drug Deliv. 2011;8:320-9 pubmed
  9. Pollet S, Bottex Gauthier C, Li M, Potier P, Favier A, Vidal D. Insight into some of the signaling pathways triggered by a lipid immunomodulator. Immunopharmacol Immunotoxicol. 2002;24:527-46 pubmed
    ..DiHDA-glycerol induced a strong activation of neutral sphingomyelinase, suggesting an important role of sphingolipids in the regulatory responses induced by diHDA-glycerol...
  10. Honda T, Yoshida S, Arai M, Masuda T, Yamashita M. Synthesis and anti-influenza evaluation of polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives. Bioorg Med Chem Lett. 2002;12:1929-32 pubmed
    ..These multivalent conjugates 9 and 10 showed enhancement of antiviral activity against infuenza A virus and more potent efficacy in vivo relative to a monomeric sialidase inhibitor...
  11. Tokumura A, Sinomiya J, Kishimoto S, Tanaka T, Kogure K, Sugiura T, et al. Human platelets respond differentially to lysophosphatidic acids having a highly unsaturated fatty acyl group and alkyl ether-linked lysophosphatidic acids. Biochem J. 2002;365:617-28 pubmed
    ..These results indicated that human platelets express acyl-LPA-selective and alkyl-LPA-selective receptors on their plasma membrane...
  12. Batrakov S, Pivovarova T, Esipov S, Sheichenko V, Karavaiko G. Beta-D-glucopyranosyl caldarchaetidylglycerol is the main lipid of the acidophilic, mesophilic, ferrous iron-oxidising archaeon Ferroplasma acidiphilum. Biochim Biophys Acta. 2002;1581:29-35 pubmed
  13. Lecollinet G, Gulik A, Mackenzie G, Goodby J, Benvegnu T, Plusquellec D. Supramolecular self-assembling properties of membrane-spanning archaeal tetraether glycolipid analogues. Chemistry. 2002;8:585-93 pubmed
  14. Panteghini M, Bonora R, Pagani F. Measurement of pancreatic lipase activity in serum by a kinetic colorimetric assay using a new chromogenic substrate. Ann Clin Biochem. 2001;38:365-70 pubmed
    ..The estimated reference interval was 6-38 U/L. The unique characteristics of the chromogenic substrate qualify the present method as an innovative approach to serum lipase analysis...
  15. Shrestha R, Shrestha L, Aramaki K, Abe M. SAXS and rheometry studies of diglycerol monolurate reverse micelles in styrene. J Oleo Sci. 2011;60:393-401 pubmed
    ..As anticipated reverse micelles swelled with water causing two dimensional micellar growth; both the maximum dimension and maximum core radius increase with water...
  16. Perales E, García J, Pires E, Aldea L, Lomba L, Giner B. Ecotoxicity and QSAR studies of glycerol ethers in Daphnia magna. Chemosphere. 2017;183:277-285 pubmed publisher
    ..There is a correlation between the lipophilicity and the increase of the toxic effect in the crustacean biomodel. Furthermore, the length and the number of the alkyl substituents and ecotoxicity are highly related. ..
  17. Kudsiova L, Fridrich B, Ho J, Mustapa M, Campbell F, Welser K, et al. Lipopolyplex ternary delivery systems incorporating C14 glycerol-based lipids. Mol Pharm. 2011;8:1831-47 pubmed publisher
    ..The more fluid, cis lipids were thought to confer better activity in this formulation due to allowing more of the targeting peptide sequence to protrude...
  18. Parmentier J, Becker M, Heintz U, Fricker G. Stability of liposomes containing bio-enhancers and tetraether lipids in simulated gastro-intestinal fluids. Int J Pharm. 2011;405:210-7 pubmed publisher
    ..This type of liposomes could be a versatile tool for the oral delivery of drug substances with poor stability in the GI tract and low permeability...
  19. Mussmann M, Brito I, Pitcher A, Sinninghe Damsté J, Hatzenpichler R, Richter A, et al. Thaumarchaeotes abundant in refinery nitrifying sludges express amoA but are not obligate autotrophic ammonia oxidizers. Proc Natl Acad Sci U S A. 2011;108:16771-6 pubmed publisher
    ..These data demonstrate that some amoA-carrying group I.1b Thaumarchaeota are not obligate chemolithoautotrophs...
  20. Xie S, Lipp J, Wegener G, Ferdelman T, Hinrichs K. Turnover of microbial lipids in the deep biosphere and growth of benthic archaeal populations. Proc Natl Acad Sci U S A. 2013;110:6010-4 pubmed publisher
    ..These constraints on microbial growth are an important step toward understanding the relationship between the deep biosphere and the carbon cycle...
  21. Tao J, Zhang Y, Huang H, Jiang X. Activation of corticotropin-releasing factor 2 receptor inhibits Purkinje neuron P-type calcium currents via G(o)alpha-dependent PKC epsilon pathway. Cell Signal. 2009;21:1436-43 pubmed publisher
    ..In summary, activation of CRFR2 inhibits P-currents in Purkinje neurons via G(o)alpha-dependent PLC/PKCepsilon pathway, which might contribute to its physiological functions in the cerebellum...
  22. Buckles L, Villanueva L, Weijers J, Verschuren D, Damsté J. Linking isoprenoidal GDGT membrane lipid distributions with gene abundances of ammonia-oxidizing Thaumarchaeota and uncultured crenarchaeotal groups in the water column of a tropical lake (Lake Challa, East Africa). Environ Microbiol. 2013;15:2445-62 pubmed publisher
    ..e. tex86 )...
  23. Pitcher A, Villanueva L, Hopmans E, Schouten S, Reichart G, Sinninghe Damsté J. Niche segregation of ammonia-oxidizing archaea and anammox bacteria in the Arabian Sea oxygen minimum zone. ISME J. 2011;5:1896-904 pubmed publisher
  24. Xiao W, Scott T, Feng L, Yu Z, Wang L, Hughes J, et al. Acetylated low-density lipoprotein-encapsulated cholesteryl 1,3-diiopanoate glyceryl ether for the detection of atherosclerosis in rabbits. J Nucl Med. 2003;44:770-3 pubmed
    ..A cholesteryl ester analog, cholesteryl 1,3-diiopanoate glyceryl ether (C2I), was synthesized and investigated for its potential use for the detection of atherosclerotic lesions in rabbits...
  25. Uda I, Sugai A, Itoh Y, Itoh T. Characterization of caldarchaetidylglycerol analogs, dialkyl-type and trialkyl-type, from Thermoplasma acidophilum. Lipids. 2000;35:1155-7 pubmed
    ..The structure of PL-T was characterized as trialkyl-type caldarchaetidylglycerol, PL-Y as caldarchaetidylglycerol, and PL-X as archaetidylglycerol...
  26. Slater S, Seiz J, Stagliano B, Cook A, Milano S, Ho C, et al. Low- and high-affinity phorbol ester and diglyceride interactions with protein kinase C: 1-O-alkyl-2-acyl-sn-glycerol enhances phorbol ester- and diacylglycerol-induced activity but alone does not induce activity. Biochemistry. 2001;40:6085-92 pubmed
    ..The results reveal HAG to be a member of a new class of "nonactivating" compounds that modulate PKC activity by interacting with the low-affinity phorbol ester binding site...
  27. Raggers R, Vogels I, van Meer G. Multidrug-resistance P-glycoprotein (MDR1) secretes platelet-activating factor. Biochem J. 2001;357:859-65 pubmed
    ..While efficient transport of PAF across the apical plasma membrane may be physiologically relevant in MDR1-expressing epithelia, PAF secretion in multidrug-resistant tumours may stimulate angiogenesis and thereby tumour growth...
  28. Oka S, Tsuchie A, Tokumura A, Muramatsu M, Suhara Y, Takayama H, et al. Ether-linked analogue of 2-arachidonoylglycerol (noladin ether) was not detected in the brains of various mammalian species. J Neurochem. 2003;85:1374-81 pubmed
    ..It is rather questionable whether 2-AG ether is present in appreciable amounts in the brain and acts as an 'endogenous' cannabinoid receptor ligand...
  29. Ranasinghe S, Bolsover S. Microglial calcium responses to platelet-activating factor are inhibited by analogue CAS 99103-16-9 and dihydropyridine PCA 4248 but not by ginkgolide A. Basic Clin Pharmacol Toxicol. 2004;95:87-91 pubmed
  30. Novgorodtseva T, Kas ianov S, Vitkina T, Gvozdenko T. [Biological effects of a natural alkyl-diacylglyceride preparation in rats with experimental cardioangiopathy]. Eksp Klin Farmakol. 2005;68:55-8 pubmed
  31. Houck K, Fox T, Sandirasegarane L, Kester M. Ether-linked diglycerides inhibit vascular smooth muscle cell growth via decreased MAPK and PI3K/Akt signaling. Am J Physiol Heart Circ Physiol. 2008;295:H1657-68 pubmed publisher
    ..Taken together, our studies identify ether-linked DGs as potential adjuvant therapies to limit vascular smooth muscle migration and mitogenesis in atherosclerotic and restenotic models...
  32. McCartney C, Bull I, Waters S, Dewhurst R. Technical note: Comparison of biomarker and molecular biological methods for estimating methanogen abundance. J Anim Sci. 2013;91:5724-8 pubmed publisher
    ..Archaeol analysis was a useful adjunct to molecular biology methods, but it seems that a valid specific primer for M. ruminantium would be more useful than a biased primer for total methanogens. ..
  33. Schouten S, Hopmans E, Pancost R, Damste J. Widespread occurrence of structurally diverse tetraether membrane lipids: evidence for the ubiquitous presence of low-temperature relatives of hyperthermophiles. Proc Natl Acad Sci U S A. 2000;97:14421-6 pubmed
    ..The structures of some of the new GDGTs point to the hybridization of both typical archaeal and eubacterial biosynthetic pathways in single organisms...
  34. Liu X, Summons R, Hinrichs K. Extending the known range of glycerol ether lipids in the environment: structural assignments based on tandem mass spectral fragmentation patterns. Rapid Commun Mass Spectrom. 2012;26:2295-302 pubmed publisher
  35. Knappy C, Barilla D, de Blaquiere J, Morgan H, Nunn C, Suleman M, et al. Structural complexity in isoprenoid glycerol dialkyl glycerol tetraether lipid cores of Sulfolobus and other archaea revealed by liquid chromatography-tandem mass spectrometry. Chem Phys Lipids. 2012;165:648-55 pubmed publisher
    ..Moreover, the results emphasise that tandem mass spectrometry provides a unique capability for assigning the structures of intact tetraether lipid cores for co-eluting species during chromatographic separation...
  36. Phleger C, Nelson M, Mooney B, Nichols P. Interannual variations in the lipids of the Antarctic pteropods Clione limacina and Clio pyramidata. Comp Biochem Physiol B Biochem Mol Biol. 2001;128:553-64 pubmed
    ..DAGE was not detected in C. pyramidata, which had mainly polar lipid and triacy1glycerol. 1-O-Alkyl glyceryl ethers (GE) derived from the DAGE consisted primarily of 15:0 and 16:0, with lower 17:0 and a17:0...
  37. Shimotoyodome A, Suzuki J, Kumamoto Y, Hase T, Isogai A. Regulation of postprandial blood metabolic variables by TEMPO-oxidized cellulose nanofibers. Biomacromolecules. 2011;12:3812-8 pubmed publisher
    ..Thus, TOCNs were found to exhibit characteristic biological activities when administered to mice and may have potential applications in biomedical fields for human health...
  38. Endo Y, Tagiri Endo M, Seo H, Fujimoto K. Identification and quantification of molecular species of diacyl glyceryl ether by reversed-phase high-performance liquid chromatography with refractive index detection and mass spectrometry. J Chromatogr A. 2001;911:39-45 pubmed
  39. Vidawati S, Sitterberg J, Rothe U, Bakowsky U. Stability of monomolecular films of archaebacterial tetraether lipids on silicon wafers: a comparison of physisorbed and chemisorbed monolayers. Colloids Surf B Biointerfaces. 2011;87:209-16 pubmed publisher
    ..The hydrophobic effect with hydrophobic surfaces appears to support the formation of stronger caldarchaeol-PO(4) films on silicon wafer substrates, with increased resistance and stability...
  40. Schouten S, van der Meer M, Hopmans E, Rijpstra W, Reysenbach A, Ward D, et al. Archaeal and bacterial glycerol dialkyl glycerol tetraether lipids in hot springs of yellowstone national park. Appl Environ Microbiol. 2007;73:6181-91 pubmed
    ..Finally, the distribution of bacterial branched GDGTs suggests that they may be derived from the geothermally heated soils surrounding the hot springs...
  41. Chang J, Nomura D, Cravatt B. A potent and selective inhibitor of KIAA1363/AADACL1 that impairs prostate cancer pathogenesis. Chem Biol. 2011;18:476-84 pubmed publisher
    ..These findings indicate that the KIAA1363-MAGE pathway is important for prostate cancer pathogenesis and designate JW480 as a versatile pharmacological probe for disrupting this pro-tumorigenic metabolic pathway...
  42. Nomikos T, Iatrou C, Demopoulos C. Application of a TCA-precipitation method for the determination of 1-alkyl-sn-glycero-3-phosphate: Acetyl-CoA acetyltransferase in human renal tissue. Prostaglandins Other Lipid Mediat. 2004;73:123-40 pubmed
    ..Cortical and medullary acetyltransferases share similar biochemical properties and there is no statistical difference between the two activities...
  43. Hodgson D, Bray C, Kindon N. 2-Ene-1,4-diols by dimerization of terminal epoxides using hindered lithium amides. Org Lett. 2005;7:2305-8 pubmed
    ..D-Mannitol and D-iditol were synthesized using this method in three steps from (S)-tritylglycidyl ether...
  44. Lee H, Zhang Y, Pardridge W. Blood-brain barrier disruption following the internal carotid arterial perfusion of alkyl glycerols. J Drug Target. 2002;10:463-7 pubmed
    ..In summary, these studies demonstrate BBB disruption following the internal carotid arterial infusion of high mM concentrations of membrane active alkyl glycerols...
  45. Zhang C, Pearson A, Li Y, Mills G, Wiegel J. Thermophilic temperature optimum for crenarchaeol synthesis and its implication for archaeal evolution. Appl Environ Microbiol. 2006;72:4419-22 pubmed
    ..This warm temperature optimum may have facilitated colonization of the ocean by (hyper)thermophilic Archaea and the major marine radiation of Crenarchaeota...
  46. Boyd E, Pearson A, Pi Y, Li W, Zhang Y, He L, et al. Temperature and pH controls on glycerol dibiphytanyl glycerol tetraether lipid composition in the hyperthermophilic crenarchaeon Acidilobus sulfurireducens. Extremophiles. 2011;15:59-65 pubmed publisher
    ..sulfurireducens responds to increasing temperature and acidity by increasing the number of cyclopentyl rings in GDGT core membrane lipids...
  47. Isaacs C, Jia J. The anti-infective activity of human milk is potentially greater than the sum of its microbicidal components. Adv Exp Med Biol. 2004;554:439-41 pubmed
  48. Pollet S, Bottex Gauthier C, Picot F, Potier P, Vidal D, Favier A. Effect of a synthetic lipid immunomodulator on the regulation of the transcription factor NF-kappaB. Immunopharmacol Immunotoxicol. 2000;22:653-69 pubmed
    ..DiHDA-glycerol is likely acting on many other transcription factors targeting distinct genes implied in up regulation of the immune system...
  49. Watschinger K, Keller M, Hermetter A, Golderer G, Werner Felmayer G, Werner E. Glyceryl ether monooxygenase resembles aromatic amino acid hydroxylases in metal ion and tetrahydrobiopterin dependence. Biol Chem. 2009;390:3-10 pubmed publisher
  50. Aerts O, Verhulst L, Goossens A. Ethylhexylglycerin: a low-risk, but highly relevant, sensitizer in 'hypo-allergenic' cosmetics. Contact Dermatitis. 2016;74:281-8 pubmed publisher
    ..Ethylhexylglycerin is a relatively new cosmetic ingredient that is used for its surfactant, emollient, skin-conditioning and antimicrobial properties. Since 2002, it has been occasionally reported as a contact allergen...
  51. Morii H, Eguchi T, Koga Y. In vitro biosynthesis of ether-type glycolipids in the methanoarchaeon Methanothermobacter thermautotrophicus. J Bacteriol. 2007;189:4053-61 pubmed
    ..The addition of Mg(2+) increased the formation of diglucosyl caldarchaetidylinositol. This suggested that the same enzyme set synthesized the sole sugar moiety of diether-type glycolipids and tetraether-type phosphoglycolipids...
  52. de la Torre J, Walker C, Ingalls A, Könneke M, Stahl D. Cultivation of a thermophilic ammonia oxidizing archaeon synthesizing crenarchaeol. Environ Microbiol. 2008;10:810-8 pubmed publisher
    ..These findings greatly extend the upper temperature limit of nitrification and document that the capacity for ammonia oxidation is broadly distributed among the Crenarchaeota...
  53. Matsuno Y, Sugai A, Higashibata H, Fukuda W, Ueda K, Uda I, et al. Effect of growth temperature and growth phase on the lipid composition of the archaeal membrane from Thermococcus kodakaraensis. Biosci Biotechnol Biochem. 2009;73:104-8 pubmed