메뉴 건너뛰기




Volumn 152, Issue 2, 2008, Pages 122-130

Monoepoxy octadecadienoates and monoepoxy octadecatrienoates. 1: NMR spectral characterization

Author keywords

1H and 13C NMR; Epoxide; Epoxy fatty acids; HPLC; Mass spectrometry; Polyunsaturated fatty acids

Indexed keywords

2 CHLOROPERBENZOIC ACID; BENZOIC ACID DERIVATIVE; CARBENE; EPOXIDE; GAMMA LINOLENIC ACID; LINOLENIC ACID; MONOEPOXYOCTADECADIENOATE DERIVATIVE; MONOEPOXYOCTADECATRIENOATE DERIVATIVE; POLYUNSATURATED FATTY ACID; STEARIDONIC ACID; UNCLASSIFIED DRUG;

EID: 41549145253     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2008.02.003     Document Type: Article
Times cited : (13)

References (33)
  • 1
    • 0030051805 scopus 로고    scopus 로고
    • Identification of epoxyeicosatrienoic acids as endothelium-derived hyperpolarizing factors
    • Campbell W.B., Gebremedhin D., Pratt P.F., and Harder D.R. Identification of epoxyeicosatrienoic acids as endothelium-derived hyperpolarizing factors. Circ. Res. 78 (1996) 415-423
    • (1996) Circ. Res. , vol.78 , pp. 415-423
    • Campbell, W.B.1    Gebremedhin, D.2    Pratt, P.F.3    Harder, D.R.4
  • 2
    • 0032582707 scopus 로고    scopus 로고
    • Epoxyeicosatrienoic acids and their sulfonimide derivatives stimulate tyrosine phosphorylation and induce mitogenesis in renal epithelial cells
    • Chen J.K., Falck J.R., Reddy K.M., Capdevila J., and Harris R.C. Epoxyeicosatrienoic acids and their sulfonimide derivatives stimulate tyrosine phosphorylation and induce mitogenesis in renal epithelial cells. J. Biol. Chem. 273 (1998) 29254-29261
    • (1998) J. Biol. Chem. , vol.273 , pp. 29254-29261
    • Chen, J.K.1    Falck, J.R.2    Reddy, K.M.3    Capdevila, J.4    Harris, R.C.5
  • 3
    • 34147222432 scopus 로고    scopus 로고
    • Mitogenic activity and signaling mechanism of 2-(14,15-epoxyeicosatrienoyl) glycerol, a novel cytochrome p450 arachidonate metabolite
    • Chen J., Chen J.K., Falck J.R., Anjaiah S., Capdevila J.H., and Harris R.C. Mitogenic activity and signaling mechanism of 2-(14,15-epoxyeicosatrienoyl) glycerol, a novel cytochrome p450 arachidonate metabolite. Mol. Cell. Biol. 27 8 (2007) 3023-3034
    • (2007) Mol. Cell. Biol. , vol.27 , Issue.8 , pp. 3023-3034
    • Chen, J.1    Chen, J.K.2    Falck, J.R.3    Anjaiah, S.4    Capdevila, J.H.5    Harris, R.C.6
  • 4
    • 41549130111 scopus 로고    scopus 로고
    • Christie, W.W., 2007. www.lipidlibrary.co.uk.
    • Christie, W.W., 2007. www.lipidlibrary.co.uk.
  • 5
    • 0016213422 scopus 로고
    • Synthesis of (±)-eicosa-cis-8,9-(11,12- and 14,15-) epoxy-cis-11,14-(8,14- and 8.11-) dienoic acids and attempted bioconversion to prostaglandins
    • Chung S.K., and Scott A.I. Synthesis of (±)-eicosa-cis-8,9-(11,12- and 14,15-) epoxy-cis-11,14-(8,14- and 8.11-) dienoic acids and attempted bioconversion to prostaglandins. Tetrahedron Lett. 35 (1974) 3023-3024
    • (1974) Tetrahedron Lett. , vol.35 , pp. 3023-3024
    • Chung, S.K.1    Scott, A.I.2
  • 6
    • 41549103270 scopus 로고    scopus 로고
    • Cui, P.H., Duke, R.K., Tattam, B.N., Duke, C.C., 2008. Monoepoxy octadecadienoates and monoepoxy octadecatrienoates. 2: Mass spectral characterization. Chem. Phys. Lipids., doi:10.1016/j.chemphyslip.2008.02.004.
    • Cui, P.H., Duke, R.K., Tattam, B.N., Duke, C.C., 2008. Monoepoxy octadecadienoates and monoepoxy octadecatrienoates. 2: Mass spectral characterization. Chem. Phys. Lipids., doi:10.1016/j.chemphyslip.2008.02.004.
  • 8
    • 0023816450 scopus 로고
    • cis-9,10-Epoxystearic acid in human leukocytes: isolation and quantitative determination
    • Fahlstadius P. cis-9,10-Epoxystearic acid in human leukocytes: isolation and quantitative determination. Lipids 23 (1988) 1015-1018
    • (1988) Lipids , vol.23 , pp. 1015-1018
    • Fahlstadius, P.1
  • 9
    • 0020956157 scopus 로고
    • Epoxyeicosatrienoic acids stimulate glucagon and insulin release from isolated rat pancreatic islets
    • Falck J.R., Manna S., Moltz J., Chacos N., and Capdevila J. Epoxyeicosatrienoic acids stimulate glucagon and insulin release from isolated rat pancreatic islets. Biochem. Biophys. Res. Commun. 114 (1983) 743-749
    • (1983) Biochem. Biophys. Res. Commun. , vol.114 , pp. 743-749
    • Falck, J.R.1    Manna, S.2    Moltz, J.3    Chacos, N.4    Capdevila, J.5
  • 10
    • 85047676117 scopus 로고
    • Cardiovascular effects of leukotoxin (9,10-epoxy-12-octadecenoate) and free fatty acids in dogs
    • Fukushima A., Hayakawa M., Sugiyama S., Ajioka M., Ito T., Satake T., and Ozawa T. Cardiovascular effects of leukotoxin (9,10-epoxy-12-octadecenoate) and free fatty acids in dogs. Cardiovasc. Res. 22 (1988) 213-218
    • (1988) Cardiovasc. Res. , vol.22 , pp. 213-218
    • Fukushima, A.1    Hayakawa, M.2    Sugiyama, S.3    Ajioka, M.4    Ito, T.5    Satake, T.6    Ozawa, T.7
  • 11
    • 41549111741 scopus 로고
    • Fatty acids, Part 46. PMR spectra of several epoxyoctadecenoic, epoxyoctadecynoic, and diepoxyoctadecanoic
    • Gunstone F.D., and Schuler H.R. Fatty acids, Part 46. PMR spectra of several epoxyoctadecenoic, epoxyoctadecynoic, and diepoxyoctadecanoic. Chem. Phys. Lipids 15 2 (1975) 189-197
    • (1975) Chem. Phys. Lipids , vol.15 , Issue.2 , pp. 189-197
    • Gunstone, F.D.1    Schuler, H.R.2
  • 15
    • 41549136247 scopus 로고
    • Epoxy-triglycerides in soyabean oil
    • Gupta S.A. Epoxy-triglycerides in soyabean oil. Chem. Ind. (Lond.) 6 (1970) 257-258
    • (1970) Chem. Ind. (Lond.) , vol.6 , pp. 257-258
    • Gupta, S.A.1
  • 17
    • 0028092168 scopus 로고
    • Leukotoxin, a linoleate epoxide: its implication in the late death of patients with extensive burns
    • Kosaka K., Suzuki K., Hayakawa M., Sugiyama S., and Ozawa T. Leukotoxin, a linoleate epoxide: its implication in the late death of patients with extensive burns. Mol. Cell. Biochem. 139 (1994) 141-148
    • (1994) Mol. Cell. Biochem. , vol.139 , pp. 141-148
    • Kosaka, K.1    Suzuki, K.2    Hayakawa, M.3    Sugiyama, S.4    Ozawa, T.5
  • 18
    • 18244378308 scopus 로고    scopus 로고
    • Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activators
    • Lauterbach B., Barbosa-Sicard E., Wang M.H., Honeck H., Kargel E., and Theuer I. Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activators. Hypertension 39 (2002) 609-613
    • (2002) Hypertension , vol.39 , pp. 609-613
    • Lauterbach, B.1    Barbosa-Sicard, E.2    Wang, M.H.3    Honeck, H.4    Kargel, E.5    Theuer, I.6
  • 19
    • 0033588034 scopus 로고    scopus 로고
    • Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids
    • Node K., Huo Y., Ruan X., Yang B., Spiecker M., Ley K., Zeldin D.C., and Liao J.K. Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science 285 (1999) 1276-1279
    • (1999) Science , vol.285 , pp. 1276-1279
    • Node, K.1    Huo, Y.2    Ruan, X.3    Yang, B.4    Spiecker, M.5    Ley, K.6    Zeldin, D.C.7    Liao, J.K.8
  • 20
    • 0019979537 scopus 로고
    • Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates
    • Oliw E.H., Guengerich F.P., and Oates J.A. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. J. Biol. Chem. 257 7 (1982) 3771-3781
    • (1982) J. Biol. Chem. , vol.257 , Issue.7 , pp. 3771-3781
    • Oliw, E.H.1    Guengerich, F.P.2    Oates, J.A.3
  • 22
    • 0037013216 scopus 로고    scopus 로고
    • Cytochrome P450 2C9-induced endothelia cell proliferation involves induction of mitogen-activated protein (MAP) kinase phosphatase-1, inhibition of the c-Jun N-terminal kinase, and up-regulation of cylin D1
    • Potente M., Michaelis U.R., Fisslthaler B., Busse R., and Fleming I. Cytochrome P450 2C9-induced endothelia cell proliferation involves induction of mitogen-activated protein (MAP) kinase phosphatase-1, inhibition of the c-Jun N-terminal kinase, and up-regulation of cylin D1. J. Biol. Chem. 277 18 (2002) 15671-15676
    • (2002) J. Biol. Chem. , vol.277 , Issue.18 , pp. 15671-15676
    • Potente, M.1    Michaelis, U.R.2    Fisslthaler, B.3    Busse, R.4    Fleming, I.5
  • 23
    • 0000864898 scopus 로고
    • Synthesis and properties of methyl 9,12,15-octadecatrienoate genetric isomers
    • Rakoff H., and Emken E.A. Synthesis and properties of methyl 9,12,15-octadecatrienoate genetric isomers. Chem. Phys. Lipids 31 (1982) 215-225
    • (1982) Chem. Phys. Lipids , vol.31 , pp. 215-225
    • Rakoff, H.1    Emken, E.A.2
  • 24
    • 84970556042 scopus 로고
    • A series of new diterpenes from the brown alga Dilophus marginatus (Dictyotaceae)
    • Ravi B.N., and Wells R.J. A series of new diterpenes from the brown alga Dilophus marginatus (Dictyotaceae). Aust. J. Chem. 35 1 (1982) 129-144
    • (1982) Aust. J. Chem. , vol.35 , Issue.1 , pp. 129-144
    • Ravi, B.N.1    Wells, R.J.2
  • 25
    • 0017391656 scopus 로고
    • Oxygenated fatty acid constituents of soybean phosphatidylcholines
    • Sessa D.J., Gardner H.W., Kleiman R., and Weisleder D. Oxygenated fatty acid constituents of soybean phosphatidylcholines. Lipids 12 7 (1976) 613-619
    • (1976) Lipids , vol.12 , Issue.7 , pp. 613-619
    • Sessa, D.J.1    Gardner, H.W.2    Kleiman, R.3    Weisleder, D.4
  • 26
    • 0034471543 scopus 로고    scopus 로고
    • Inhibition of polyunsaturated fatty acid accumulation in plants expressing a fatty acid epoxygenase
    • Singh S., Thomaeus S., Lee M., Green A., and Stymne S. Inhibition of polyunsaturated fatty acid accumulation in plants expressing a fatty acid epoxygenase. Biochem. Soc. Trans. 28 6 (2000) 940-942
    • (2000) Biochem. Soc. Trans. , vol.28 , Issue.6 , pp. 940-942
    • Singh, S.1    Thomaeus, S.2    Lee, M.3    Green, A.4    Stymne, S.5
  • 27
    • 41549141061 scopus 로고
    • Oxygenation of unsaturated fatty acids in seeds during storage
    • Spencer G.F., Wolff I.A., and Tallent W.H. Oxygenation of unsaturated fatty acids in seeds during storage. Chem. Phys. Lipids 10 (1973) 191-202
    • (1973) Chem. Phys. Lipids , vol.10 , pp. 191-202
    • Spencer, G.F.1    Wolff, I.A.2    Tallent, W.H.3
  • 28
    • 41549106904 scopus 로고
    • Epoxyoctadecadienoic acid from Crepis conyzaefolia seed oil
    • Spencer G.F. Epoxyoctadecadienoic acid from Crepis conyzaefolia seed oil. Phytochemistry 16 (1977) 282-284
    • (1977) Phytochemistry , vol.16 , pp. 282-284
    • Spencer, G.F.1
  • 29
    • 33845559362 scopus 로고
    • Vacuum liquid chromatography: an alternative to common chromatographic methods
    • Targett N.M., Kilcoyne J.P., and Green P.J. Vacuum liquid chromatography: an alternative to common chromatographic methods. J. Org. Chem. 44 (1979) 4962-4964
    • (1979) J. Org. Chem. , vol.44 , pp. 4962-4964
    • Targett, N.M.1    Kilcoyne, J.P.2    Green, P.J.3
  • 30
    • 0024586630 scopus 로고
    • Synthesis of epoxide and vicinal diol regioisomers from decosahexaenoate methyl esters
    • VanRollins M., Frade P.D., and Carretero O.A. Synthesis of epoxide and vicinal diol regioisomers from decosahexaenoate methyl esters. J. Lipid Res. 30 (1989) 275-286
    • (1989) J. Lipid Res. , vol.30 , pp. 275-286
    • VanRollins, M.1    Frade, P.D.2    Carretero, O.A.3
  • 31
    • 0034923447 scopus 로고    scopus 로고
    • Overexpression of cytochrome P450 CYP2J2 protects against hypoxia-reoxygenation injury in cultured bovine aortic endothelial cells
    • Yang B., Graham L., Dikalov S., Mason R.P., Falck J.R., Liao J.K., and Zeldin D.C. Overexpression of cytochrome P450 CYP2J2 protects against hypoxia-reoxygenation injury in cultured bovine aortic endothelial cells. Mol. Pharmacol. 60 (2001) 310-320
    • (2001) Mol. Pharmacol. , vol.60 , pp. 310-320
    • Yang, B.1    Graham, L.2    Dikalov, S.3    Mason, R.P.4    Falck, J.R.5    Liao, J.K.6    Zeldin, D.C.7
  • 32
    • 0036828147 scopus 로고    scopus 로고
    • Cytochrome p-450 epoxygenase metabolites of docosaheaenoate potently dilate coronary arterioles by activating large-conductance calcium-activated potassium channels
    • Ye D., Zhang D., Oltman C., Dellsperger K., Lee H.C., and VanRollins M. Cytochrome p-450 epoxygenase metabolites of docosaheaenoate potently dilate coronary arterioles by activating large-conductance calcium-activated potassium channels. J. Pharmacol. Exp. Ther. 303 2 (2002) 768-776
    • (2002) J. Pharmacol. Exp. Ther. , vol.303 , Issue.2 , pp. 768-776
    • Ye, D.1    Zhang, D.2    Oltman, C.3    Dellsperger, K.4    Lee, H.C.5    VanRollins, M.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.