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Volumn 53, Issue 2, 2012, Pages 247-256

Primary fatty acid amide metabolism: Conversion of fatty acids and an ethanolamine in N 18TG 2 and SCP cells

Author keywords

Choroid plexus cells; N acylethanolamine as PFAM precursors; N fatty acylglycine oxidation; Oleamide metabolism

Indexed keywords

AMIDE; ETHANOLAMINE; FATTY ACID; LINOLEAMIDE; N TRIDECANOYLETHANOLAMINE; OLEAMIDE; PALMITAMIDE; PALMITOLEAMIDE; TRIDECANAMIDE; UNCLASSIFIED DRUG;

EID: 84862965840     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.M018606     Document Type: Article
Times cited : (34)

References (63)
  • 1
    • 34548725416 scopus 로고
    • Thudichum and the medical chemistry of the 1860s to 1880s
    • McIlwain, H. 1958. Thudichum and the medical chemistry of the 1860s to 1880s. Proc. R. Soc. Med. 51: 127-132.
    • (1958) Proc. R. Soc. Med. , vol.51 , pp. 127-132
    • McIlwain, H.1
  • 2
    • 45849107005 scopus 로고
    • Sphingomyelin. III
    • Levene, P. A. 1916. Sphingomyelin. III. J. Biol. Chem. 24: 69-89.
    • (1916) J. Biol. Chem. , vol.24 , pp. 69-89
    • Levene, P.A.1
  • 3
    • 0024366156 scopus 로고
    • Identification of fatty acid amides in human plasma
    • DOI 10.1016/0024-3205(89)90278-6
    • Arafat, E. S., J. W. Trimble, R. N. Andersen, C. Dass, and D. M. Desiderio. 1989. Identification of fatty acid amides in human plasma. Life Sci. 45: 1679-1687. (Pubitemid 19275496)
    • (1989) Life Sciences , vol.45 , Issue.18 , pp. 1679-1687
    • Arafat, E.S.1    Trimble, J.W.2    Andersen, R.N.3    Dass, C.4    Desiderio, D.M.5
  • 5
    • 0036111752 scopus 로고    scopus 로고
    • A comparison of oleamide in the brains of hibernating and non-hibernating Richardson's ground squirrel (Spermophilus richardsonii) and its inability to bind to brain fatty acid binding protein
    • DOI 10.1016/S0306-4565(01)00093-6, PII S0306456501000936
    • Stewart, J. M., N. M. Boudreau, J. A. Blakely, and K. B. Storey. 2002. A comparison of oleamide in the brains of hibernating and non-hibernating Richard's ground squirrel (Spermophilus richardsonii) and its inability to bind to brain fatty acid binding protein. J. Therm. Biol. 27: 309-315. (Pubitemid 34548676)
    • (2002) Journal of Thermal Biology , vol.27 , Issue.4 , pp. 309-315
    • Stewart, J.M.1    Boudreau, N.M.2    Blakely, J.A.3    Storey, K.B.4
  • 6
    • 0031425481 scopus 로고    scopus 로고
    • The sleep-inducing lipid oleamide deconvolutes gap junction communication and calcium wave transmission in glial cells
    • DOI 10.1083/jcb.139.7.1785
    • Guan, X., B. F. Cravatt, C. R. Ehring, J. E. Hall, D. L. Boger, R. A. Lerner, and N. B. Gilula. 1997. The sleep-inducing lipid oleamide deconvolutes gap junction communication and calcium wave transmission in glial cells. J. Cell Biol. 139: 1785-1792. (Pubitemid 28079242)
    • (1997) Journal of Cell Biology , vol.139 , Issue.7 , pp. 1785-1792
    • Guan, X.1    Cravatt, B.F.2    Ehring, G.R.3    Hall, J.E.4    Boger, D.L.5    Lerner, R.A.6    Gilula, N.B.7
  • 9
    • 2642561321 scopus 로고    scopus 로고
    • Functional characterization of Cx43 based gap junctions during spermatogenesis
    • DOI 10.1002/jcp.10473
    • Decrouy, X., J. M. Gasc, G. Pointis, and D. Segretain. 2004. Functional characterization of Cx43 based gap junctions during spermatogenesis. J. Cell. Physiol. 200: 146-154. (Pubitemid 38720630)
    • (2004) Journal of Cellular Physiology , vol.200 , Issue.1 , pp. 146-154
    • Decrouy, X.1    Gasc, J.-M.2    Pointis, G.3    Sgretain, D.4
  • 10
    • 33745598855 scopus 로고    scopus 로고
    • Gap junction communications influence upon fibroblast synthesis of type I collagen and fibronectin
    • DOI 10.1002/jcb.20852
    • Ehrlich, H. P., B. Sun, G. C. Saggers, and F. Kromath. 2006. Gap junction commications influence upon fibroblast synthesis of type I collagen and fibronectin. J. Cell. Biochem. 98: 735-743. (Pubitemid 43993392)
    • (2006) Journal of Cellular Biochemistry , vol.98 , Issue.4 , pp. 735-743
    • Ehrlich, H.P.1    Sun, B.2    Saggers, G.C.3    Kromath, F.4
  • 11
    • 0036246584 scopus 로고    scopus 로고
    • The sleep hormone oleamide modulates inhibitory ionotropic receptors in mammalian CNS in vitro
    • Coyne, L., G. Lees, R. A. Nicholson, J. Zheng, and K. D. Neufield. 2002. The sleep hormone oleamide modulates inhibitory ionotropic receptors in mammalian CNS in vitro. Br. J. Pharmacol. 135: 1977-1987. (Pubitemid 34478310)
    • (2002) British Journal of Pharmacology , vol.135 , Issue.8 , pp. 1977-1987
    • Coyne, L.1    Lees, G.2    Nicholson, R.A.3    Zheng, J.4    Neufield, K.D.5
  • 12
    • 0029836767 scopus 로고    scopus 로고
    • Brain lipids that induce sleep are novel modulators of 5-hydroxytryptamine receptors
    • Huidobro-Toro, J. P., and R. A. Harris. 1996. Brain lipids that induce sleep are novel modulators of 5-hydroxytryptamine receptors. Proc. Natl. Acad. Sci. USA. 93: 8078-8082.
    • (1996) Proc. Natl. Acad. Sci. USA , vol.93 , pp. 8078-8082
    • Huidobro-Toro, J.P.1    Harris, R.A.2
  • 13
    • 0032702510 scopus 로고    scopus 로고
    • 7 receptors
    • DOI 10.1016/S0006-2952(99)00274-9, PII S0006295299002749
    • Hedlund, P. B., M. J. Carson, J. G. Sutcliffe, and E. A. Thomas. 1999. Allosteric regulation by oleamide of the binding properties of 5-hydroxytryptamine 7 receptors. Biochem. Pharmacol. 58: 1807-1813. (Pubitemid 29505422)
    • (1999) Biochemical Pharmacology , vol.58 , Issue.11 , pp. 1807-1813
    • Hedlund, P.B.1    Carson, M.J.2    Sutcliffe, J.G.3    Thomas, E.A.4
  • 14
    • 33645115275 scopus 로고    scopus 로고
    • Fatty acid amide hydrolase(-/-) mice exhibit an increased sensitivity to the disruptive effects of anandamide or oleamide in a working memory water maze task
    • Varvel, S. A., B. F. Cravatt, A. E. Engram, and A. H. Lichtman. 2006. Fatty acid amide hydrolase(-/-) mice exhibit an increased sensitivity to the disruptive effects of anandamide or oleamide in a working memory water maze task. J. Pharmacol. Exp. Ther. 317: 251-257.
    • (2006) J. Pharmacol. Exp. Ther. , vol.317 , pp. 251-257
    • Varvel, S.A.1    Cravatt, B.F.2    Engram, A.E.3    Lichtman, A.H.4
  • 16
    • 34447292290 scopus 로고    scopus 로고
    • Neuropharmacological effects of oleamide in male and female mice
    • DOI 10.1016/j.bbr.2007.05.006, PII S0166432807002537
    • Akanmu, M. A., S. O. Adesun, and O. R. Ilesanmi. 2007. Neuropharmacological effects of oleamide in male and female mice. Behav. Brain Res. 182: 88-94. (Pubitemid 47042195)
    • (2007) Behavioural Brain Research , vol.182 , Issue.1 , pp. 88-94
    • Akanmu, M.A.1    Adeosun, S.O.2    Ilesanmi, O.R.3
  • 18
    • 0035211628 scopus 로고    scopus 로고
    • Effect of oleamide on sleep and its relationship to blood pressure, body temperature, and locomotor activity in rats
    • DOI 10.1006/exnr.2001.7792
    • Huitrón-Reséndiz, S., L. Gombart, B. F. Cravatt, and S. J. Henriksen. 2001. Effect of oleamide on sleep and its relationship to blood pressure, body temperature, and locomotor activity in rats. Exp. Neurol. 172: 235-243. (Pubitemid 33141169)
    • (2001) Experimental Neurology , vol.172 , Issue.1 , pp. 235-243
    • Huitron-Resendiz, S.1    Gombart, L.2    Cravatt, B.F.3    Henriksen, S.J.4
  • 20
    • 33644827806 scopus 로고    scopus 로고
    • Vasorelaxant effects of oleamide in rat small mesenteric artery indicate action at a novel cannabinoid receptor
    • DOI 10.1038/sj.bjp.0706643, PII 0706643
    • Hoi, P. M., and C. R. Hiley. 2006. Vasorelaxant effects of oleamide in rat small mesenteric artery indicate action at a novel cannabinoid receptor. Br. J. Pharmacol. 147: 560-568. (Pubitemid 43355054)
    • (2006) British Journal of Pharmacology , vol.147 , Issue.5 , pp. 560-568
    • Hoi, P.M.1    Hiley, C.R.2
  • 21
    • 62149085894 scopus 로고    scopus 로고
    • Mechanisms involved in oleamide-induced vasorelaxation in rat mesenteric resistance arteries
    • Sudhahar, V., S. Shaw, and J. D. Imig. 2009. Mechanisms involved in oleamide-induced vasorelaxation in rat mesenteric resistance arteries. Eur. J. Pharmacol. 607: 143-150.
    • (2009) Eur. J. Pharmacol. , vol.607 , pp. 143-150
    • Sudhahar, V.1    Shaw, S.2    Imig, J.D.3
  • 22
    • 0035060264 scopus 로고    scopus 로고
    • Anticonvulsant activity of N-palmitoylethanolamide, a putative endocannabinoid, in mice
    • DOI 10.1046/j.1528-1157.2001.41499.x
    • Lambert, D. M., S. Vandevoorde, G. Diependaele, S. J. Govaerts, and A. R. Robert. 2001. Anticonvulsant activity of N-palmitoyle thanolamide, a putative endocannabinoid, in mice. Epilepsia. 42: 321-327. (Pubitemid 32275910)
    • (2001) Epilepsia , vol.42 , Issue.3 , pp. 321-327
    • Lambert, D.M.1    Vandevoorde, S.2    Diependaele, G.3    Govaerts, S.J.4    Robert, A.R.5
  • 23
    • 0035910310 scopus 로고    scopus 로고
    • 2+ levels in MDCK renal tubular cells
    • 2+ levels in MDCK renal tubular cells. Life Sci. 68: 997-1004.
    • (2001) Life Sci. , vol.68 , pp. 997-1004
    • Huang, J.K.1    Jan, C.R.2
  • 26
    • 0037323296 scopus 로고    scopus 로고
    • Erucamide as a modulator of water balance: New function of a fatty acid amide
    • DOI 10.1023/A:1022364830421
    • Hamberger, A., and G. Stenhagen. 2003. Erucamide as a modulator of water balance: new function of a fatty acid amide. Neurochem. Res. 28: 177-185. (Pubitemid 36207343)
    • (2003) Neurochemical Research , vol.28 , Issue.2 , pp. 177-185
    • Hamberger, A.1    Stenhagen, G.2
  • 29
    • 45849097898 scopus 로고    scopus 로고
    • Biosynthesis, degradation, and pharmacological importance of the fatty acid amides
    • Farrell, E. K., and D. J. Merkler. 2008. Biosynthesis, degradation, and pharmacological importance of the fatty acid amides. Drug Discov. Today. 13: 558-568.
    • (2008) Drug Discov. Today , vol.13 , pp. 558-568
    • Farrell, E.K.1    Merkler, D.J.2
  • 31
    • 0037207093 scopus 로고    scopus 로고
    • The enzymatic inactivation of the fatty acid amide class of signaling lipids
    • DOI 10.1016/S0009-3084(02)00147-0, PII S0009308402001470
    • Cravatt, B. F., and A. H. Lichtman. 2002. The enzymatic inactivation of the fatty acid amide class of signaling lipids. Chem. Phys. Lipids. 121: 135-148. (Pubitemid 36044548)
    • (2002) Chemistry and Physics of Lipids , vol.121 , Issue.1-2 , pp. 135-148
    • Cravatt, B.F.1    Lichtman, A.H.2
  • 32
    • 22244484464 scopus 로고    scopus 로고
    • Structure and function of fatty acid amide hydrolase
    • DOI 10.1146/annurev.biochem.74.082803.133450
    • McKinney, M. K., and B. F. Cravatt. 2005. Structure and function of fatty acid amide hydrolase. Annu. Rev. Biochem. 74: 411-432. (Pubitemid 40995513)
    • (2005) Annual Review of Biochemistry , vol.74 , pp. 411-432
    • McKinney, M.K.1    Cravatt, B.E.2
  • 33
    • 34447532944 scopus 로고    scopus 로고
    • Oleamide synthesizing activity from rat kidney: Identification as cytochrome c
    • DOI 10.1074/jbc.M610070200
    • Driscoll, W. J., S. Chaturvedi, and G. P. Mueller. 2007. Oleamide synthesizing activity from rat kidney. Identification as cytochrome c. J. Biol. Chem. 282: 22353-22363. (Pubitemid 47267327)
    • (2007) Journal of Biological Chemistry , vol.282 , Issue.31 , pp. 22353-22363
    • Driscoll, W.J.1    Chaturvedi, S.2    Mueller, G.P.3
  • 34
    • 0030008554 scopus 로고    scopus 로고
    • Fatty acid amide biosynthesis: A possible new role for peptidylglycine α-amidating enzyme and acyl-coenzyme A:Glycine N-acyltransferase
    • Merkler, D. J., K. A. Merkler, W. Stern, and F. F. Fleming. 1996. Fatty acid amide biosynthesis: a possible new role for peptidylglycine α-amidating enzyme and acyl-coenzyme A:glycine N-acyltransferase. Arch. Biochem. Biophys. 330: 430-434.
    • (1996) Arch. Biochem. Biophys. , vol.330 , pp. 430-434
    • Merkler, D.J.1    Merkler, K.A.2    Stern, W.3    Fleming, F.F.4
  • 38
    • 0023028516 scopus 로고
    • Inhibition of peptide amidation by disulfiram and diethyldithiocarbamate
    • Mains, R. E., L. P. Park, and B. A. Eipper. 1986. Inhibition of peptide amidation by disulfiram and diethyldithiocarbamate. J. Biol. Chem. 261: 11938-11941. (Pubitemid 17202744)
    • (1986) Journal of Biological Chemistry , vol.261 , Issue.26 , pp. 11938-11941
    • Mains, R.E.1    Park, L.P.2    Eipper, B.A.3
  • 39
    • 67651166648 scopus 로고    scopus 로고
    • Novel endogenous N-acyl glycines: Identification and characterization
    • Bradshaw, H. B., N. Rimmerman, S. S. Hu, S. Burstein, and J. M. Walker. 2009. Novel endogenous N-acyl glycines: identification and characterization. Vitam. Horm. 81: 191-205.
    • (2009) Vitam. Horm. , vol.81 , pp. 191-205
    • Bradshaw, H.B.1    Rimmerman, N.2    Hu, S.S.3    Burstein, S.4    Walker, J.M.5
  • 42
    • 77952731052 scopus 로고    scopus 로고
    • N-Arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor
    • McHugh, D., S. S. Hu, N. Rimmerman, A. Juknat, Z. Vogel, J. M. Walker, and H. B. Bradshaw. 2010. N-Arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor. BMC Neurosci. 11: 44.
    • (2010) BMC Neurosci. , vol.11 , pp. 44
    • McHugh, D.1    Hu, S.S.2    Rimmerman, N.3    Juknat, A.4    Vogel, Z.5    Walker, J.M.6    Bradshaw, H.B.7
  • 43
    • 77955792986 scopus 로고    scopus 로고
    • Identification of glycine N-acyltranferase-like 2 (GLYATL2) as a transferase that produces N-acyl glycines in humans
    • Waluk, D. P., N. Schultz, and M. C. Hunt. 2010. Identification of glycine N-acyltranferase-like 2 (GLYATL2) as a transferase that produces N-acyl glycines in humans. FASEB J. 24: 2795-2803.
    • (2010) FASEB J. , vol.24 , pp. 2795-2803
    • Waluk, D.P.1    Schultz, N.2    Hunt, M.C.3
  • 44
    • 57749083298 scopus 로고    scopus 로고
    • Alcohol dehydrogenase-catalyzed in vitro oxidation of anandamide to N-arachidonoyl glycine, a lipid mediator: Synthesis of N-acyl glycinals
    • Aneetha, H., D. K. O'Dell, B. Tan, J. M. Walker, and T. D. Hurley. 2009. Alcohol dehydrogenase-catalyzed in vitro oxidation of anandamide to N-arachidonoyl glycine, a lipid mediator: synthesis of N-acyl glycinals. Bioorg. Med. Chem. Lett. 19: 237-241.
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 237-241
    • Aneetha, H.1    O'Dell, D.K.2    Tan, B.3    Walker, J.M.4    Hurley, T.D.5
  • 49
    • 32944472868 scopus 로고    scopus 로고
    • New role for urea as a surfactant headgroup promoting self-assembly in water
    • DOI 10.1021/cm0522681
    • Fong, C., D. Wells, I. Krodkiewska, P. G. Hartley, and C. J. Drummond. 2006. New role for urea as a surfactant headgroup promoting self-assembly in water. Chem. Mater. 18: 594-597. (Pubitemid 43260091)
    • (2006) Chemistry of Materials , vol.18 , Issue.3 , pp. 594-597
    • Fong, C.1    Wells, D.2    Krodkiewska, I.3    Hartley, P.G.4    Drummond, C.J.5
  • 50
    • 28944445904 scopus 로고    scopus 로고
    • Sample preparation and gas chromatography of primary fatty acid amides
    • DOI 10.1016/j.chroma.2005.10.027, PII S0021967305019825
    • Sultana, T., and M. E. Johnson. 2006. Sample preparation and gas chromatography of primary fatty acid amides. J. Chromatogr. A. 1101: 278-285. (Pubitemid 41785560)
    • (2006) Journal of Chromatography A , vol.1101 , Issue.1-2 , pp. 278-285
    • Sultana, T.1    Johnson, M.E.2
  • 53
    • 70350532440 scopus 로고    scopus 로고
    • Method for the determination of fatty acid amides in polyethylene packaging materials-gas chromatography/mass spectrometry
    • Lv, G., L. Wang, and S. Li. 2009. Method for the determination of fatty acid amides in polyethylene packaging materials-gas chromatography/mass spectrometry. J. Chromatogr. A. 1216: 8545-8548.
    • (2009) J. Chromatogr. A , vol.1216 , pp. 8545-8548
    • Lv, G.1    Wang, L.2    Li, S.3
  • 54
    • 0014949207 scopus 로고
    • Cleavage of structural proteins during the assembly of the head of bacteriophage T4
    • Laemmli, U. K. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 227: 680-685.
    • (1970) Nature , vol.227 , pp. 680-685
    • Laemmli, U.K.1
  • 55
    • 0020671509 scopus 로고
    • Trans unsaturated fatty acids in natural products and processed foods
    • Sommerfeld, M. 1983. Trans unsaturated fatty acids in natural products and processed foods. Prog. Lipid Res. 22: 221-233.
    • (1983) Prog. Lipid Res. , vol.22 , pp. 221-233
    • Sommerfeld, M.1
  • 56
  • 57
    • 0035918311 scopus 로고    scopus 로고
    • The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism
    • De Petrocellis, L., T. Bisogno, M. Maccarrone, J. B. Davis, A. Finazzi-Agrò, and V. Di Marzo. 2001. The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism. J. Biol. Chem. 276: 12856-12863.
    • (2001) J. Biol. Chem. , vol.276 , pp. 12856-12863
    • De Petrocellis, L.1    Bisogno, T.2    Maccarrone, M.3    Davis, J.B.4    Finazzi-Agrò, A.5    Di Marzo, V.6
  • 59
    • 0029619298 scopus 로고
    • Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma 'anandamide amidohydrolase'
    • DOI 10.1016/0014-5793(95)01311-3
    • Maurelli, S., T. Bisogno, L. De Petrocellis, A. Di Luccia, G. Marino, and V. Di Marzo. 1995. Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma 'anandamide hydrolase'. FEBS Lett. 377: 82-86. (Pubitemid 26009779)
    • (1995) FEBS Letters , vol.377 , Issue.1 , pp. 82-86
    • Maurelli, S.1    Bisogno, T.2    De Petrocellis, L.3    Di, L.A.4    Marino, G.5    Di, M.V.6
  • 60
    • 0028903996 scopus 로고
    • Anandamide amidohydrolase activity in rat brain microsomes
    • Desarnaud, F., H. Cadas, and D. Piomelli. 1995. Anandamide amidohydrolase activity in rat brain microsomes. J. Biol. Chem. 270: 6030-6035.
    • (1995) J. Biol. Chem. , vol.270 , pp. 6030-6035
    • Desarnaud, F.1    Cadas, H.2    Piomelli, D.3


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