메뉴 건너뛰기




Volumn 53, Issue 2, 2012, Pages 292-299

8R-Lipoxygenase-catalyzed synthesis of a prominent cis-epoxyalcohol from dihomo-γ-linolenic acid: A distinctive transformation compared with S-lipoxygenases

Author keywords

18O 2 incorporation; Arachidonic acid; Gas liquid chromatography mass spectrometry; Hepoxilin; Plexaura homomalla; Sharpless epoxidation; Total synthesis; Trans epoxide

Indexed keywords

ALCOHOL DERIVATIVE; ALLENE OXIDE SYNTHASE; DIHOMO GAMMA LINOLENIC ACID; EPOXYALCOHOL; LIPOXYGENASE; SYNTHETASE; UNCLASSIFIED DRUG;

EID: 84855671060     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.M022863     Document Type: Article
Times cited : (9)

References (49)
  • 1
    • 0014623298 scopus 로고
    • 2and its acetate, methyl ester) in the gorgonian Plexaura homomalla
    • 2 and its acetate, methyl ester) in the gorgonian Plexaura homomalla. Tetrahedron Lett. 59: 5185-5188.
    • (1969) Tetrahedron Lett. , vol.59 , pp. 5185-5188
    • Weinheimer, A.J.1    Spraggins, R.L.2
  • 5
    • 0023665336 scopus 로고
    • On non-cyclooxygenase prostaglandin synthesis in the sea whip coral Plexaura homomalla: An 8(R)-lipoxygenase pathway leads to formation of an α-ketol and a racemic prostanoid
    • Brash, A. R., S. W. Baertschi, C. D. Ingram, and T. M. Harris. 1987. On non-cyclooxygenase prostaglandin synthesis in the sea whip coral Plexaura homomalla: An 8(R)-lipoxygenase pathway leads to formation of an α-ketol and a racemic prostanoid. J. Biol. Chem. 262: 15829-15839.
    • (1987) J. Biol. Chem. , vol.262 , pp. 15829-15839
    • Brash, A.R.1    Baertschi, S.W.2    Ingram, C.D.3    Harris, T.M.4
  • 6
    • 0035831484 scopus 로고    scopus 로고
    • The basis of prostaglandin synthesis in coral. Molecular cloning and expression of a cyclooxygenase from the Arctic soft coral Gersemia fruticosa
    • Koljak, R., I. Järving, R. Kurg, W. E. Boeglin, K. Varvas, K. Valmsen, M. Ustav, A. R. Brash, and N. Samel. 2001. The basis of prostaglandin synthesis in coral. Molecular cloning and expression of a cyclooxygenase from the Arctic soft coral Gersemia fruticosa. J. Biol. Chem. 276: 7033-7040.
    • (2001) J. Biol. Chem. , vol.276 , pp. 7033-7040
    • Koljak, R.1    Järving, I.2    Kurg, R.3    Boeglin, W.E.4    Varvas, K.5    Valmsen, K.6    Ustav, M.7    Brash, A.R.8    Samel, N.9
  • 8
    • 0022606976 scopus 로고
    • Discovery of an arachidonic acid C-8 lipoxygenase in the gorgonian coral Pseudoplexaura porosa
    • Bundy, G. L., E. G. Nidy, D. E. Epps, S. A. Mizsak, and R. J. Wnuk. 1986. Discovery of an arachidonic acid C-8 lipoxygenase in the gorgonian coral Pseudoplexaura porosa. J. Biol. Chem. 261: 747-751. (Pubitemid 16161735)
    • (1986) Journal of Biological Chemistry , vol.261 , Issue.2 , pp. 747-751
    • Bundy, G.L.1    Nidy, E.G.2    Epps, D.E.3
  • 9
    • 0023939605 scopus 로고
    • Biosynthesis of 8-R-HPETE and preclavulone A from arachidonate in several species of Caribbean coral. A widespread route to marine prostanoids
    • Corey, E. J., S. P. T. Matsuda, R. Nagata, and M. B. Cleaver. 1988. Biosynthesis of 8-R-HPETE and preclavulone A from arachidonate in several species of Caribbean coral. A widespread route to marine prostanoids. Tetrahedron Lett. 29: 2555-2558.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 2555-2558
    • Corey, E.J.1    Matsuda, S.P.T.2    Nagata, R.3    Cleaver, M.B.4
  • 10
    • 0036669864 scopus 로고    scopus 로고
    • Lipoxygenase-catalyzed formation of R-configuration hydroperoxides
    • DOI 10.1016/S0090-6980(02)00041-2, PII S0090698002000412
    • Schneider, C., and A. R. Brash. 2002. Lipoxygenase-catalyzed formation of R-configuration hydroperoxides. Prostaglandins Other Lipid Mediat. 68-69: 291-301. (Pubitemid 35247402)
    • (2002) Prostaglandins and Other Lipid Mediators , vol.68-69 , pp. 291-301
    • Schneider, C.1    Brash, A.R.2
  • 11
    • 66149155333 scopus 로고    scopus 로고
    • Autosomal recessive congenital ichthyosis
    • Fischer, J. 2009. Autosomal recessive congenital ichthyosis. J. Invest. Dermatol. 129: 1319-1321.
    • (2009) J. Invest. Dermatol. , vol.129 , pp. 1319-1321
    • Fischer, J.1
  • 12
    • 79959906412 scopus 로고    scopus 로고
    • Lipoxygenases mediate the effect of essential fatty acid in skin barrier formation: A proposed role in releasing omega-hydroxyceramide for construction of the corneocyte lipid envelope
    • Zheng, Y., H. Yin, W. E. Boeglin, P. M. Elias, D. Crumrine, D. R. Beier, and A. R. Brash. 2011. Lipoxygenases mediate the effect of essential fatty acid in skin barrier formation: A proposed role in releasing omega-hydroxyceramide for construction of the corneocyte lipid envelope. J. Biol. Chem. 286: 24046-24056.
    • (2011) J. Biol. Chem. , vol.286 , pp. 24046-24056
    • Zheng, Y.1    Yin, H.2    Boeglin, W.E.3    Elias, P.M.4    Crumrine, D.5    Beier, D.R.6    Brash, A.R.7
  • 13
    • 0000376312 scopus 로고
    • Intermediacy of 8- (R) -HPETE in the conversion of arachidonic acid to pre-clavulone A by Clavularia viridis. Implications for the biosynthesis of marine prostanoids
    • Corey, E. J., M. d'Alarcao, S. P. T. Matsuda, and P. T. Lansbury, Jr. 1987. Intermediacy of 8- (R) -HPETE in the conversion of arachidonic acid to pre-clavulone A by Clavularia viridis. Implications for the biosynthesis of marine prostanoids. J. Am. Chem. Soc. 109: 289-290.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 289-290
    • Corey, E.J.1    D'Alarcao, M.2    Matsuda, S.P.T.3    Lansbury Jr., P.T.4
  • 14
    • 0020455745 scopus 로고
    • Clavulones, new type of prostanoids from the Stolonifer Clavularia viridis Quoy and Gaimard
    • DOI 10.1016/S0040-4039(00)85788-3
    • Kikuchi, H., Y. Tsukitani, K. Iguchi, and Y. Yamada. 1982. Clavulones, new type of prostanoids from the stolonifer Clavularis viridis Quoy and Gaimard. Tetrahedron Lett. 23: 5171-5174. (Pubitemid 13202962)
    • (1982) Tetrahedron Letters , vol.23 , Issue.49 , pp. 5171-5174
    • Kikuchi, H.1    Tsukitani, Y.2    Iguchi, K.3    Yamada, Y.4
  • 16
    • 0021871120 scopus 로고
    • Identification of a new eicosanoid from in vitro biosynthetic experiments with clavularia viridis, implications for the biosynthesis of clavulones
    • DOI 10.1016/S0040-4039(00)98982-2
    • Corey, E. J., P. T. Lansbury, Jr., and Y. Yamada. 1985. Identification of a new eicosanoid from in vitro biosynthetic experiments with Clavularia viridis. Implications for the biosynthesis of clavulones. Tetrahedron Lett. 26: 4171-4174. (Pubitemid 15011099)
    • (1985) Tetrahedron Letters , vol.26 , Issue.35 , pp. 4171-4174
    • Corey, E.J.1    Lansbury Jr., P.T.2    Yamada, Y.3
  • 19
    • 0030796446 scopus 로고    scopus 로고
    • Identification of a naturally occurring peroxidase-lipoxygenase fusion protein
    • DOI 10.1126/science.277.5334.1994
    • Koljak, R., O. Boutaud, B-H. Shieh, N. Samel, and A. R. Brash. 1997. Identification of a naturally occurring peroxidase-lipoxygenase fusion protein. Science. 277: 1994-1996. (Pubitemid 27449141)
    • (1997) Science , vol.277 , Issue.5334 , pp. 1994-1996
    • Koljak, R.1    Boutaud, O.2    Shieh, B.-H.3    Samel, N.4    Brash, A.R.5
  • 20
    • 0033584952 scopus 로고    scopus 로고
    • Purification and catalytic activities of the two domains of the allene oxide synthase-lipoxygenase fusion protein of the coral Plexaura homomalla
    • Boutaud, O., and A. R. Brash. 1999. Purification and catalytic activities of the two domains of the allene oxide synthase-lipoxygenase fusion protein of the coral Plexaura homomalla. J. Biol. Chem. 274: 33764-33770. (Pubitemid 129511693)
    • (1999) Journal of Biological Chemistry , vol.274 , Issue.47 , pp. 33764-33770
    • Boutaud, O.1    Brash, A.R.2
  • 21
    • 0029808212 scopus 로고    scopus 로고
    • Purification and molecular cloning of an 8R-lipoxygenase from the coral Plexaura homomalla reveal the related primary structures of R- and S- lipoxygenases
    • DOI 10.1074/jbc.271.34.20949
    • Brash, A. R., W. E. Boeglin, M. S. Chang, and B-H. Shieh. 1996. Purification and molecular cloning of an 8 R -lipoxygenase from the coral Plexaura homomalla reveal the related primary structures of R-and S -lipoxygenases. J. Biol. Chem. 271: 20949-20957. (Pubitemid 26281886)
    • (1996) Journal of Biological Chemistry , vol.271 , Issue.34 , pp. 20949-20957
    • Brash, A.R.1    Boeglin, W.E.2    Chang, M.S.3    Shieh, B.-H.4
  • 22
    • 1042297292 scopus 로고
    • Comportement d'hydroperoxydes allyliques a longue chaine en presence de complexes de certains metaux de transition. II. Structure des époxy-alcools formés à partir d'hydroperoxydes d'octadécène-9 oates de méthyle cis et trans en présence d'acétylacétonate de vanadyle
    • Mercier, J., and B. Agoh. 1974. Comportement d'hydroperoxydes allyliques a longue chaine en presence de complexes de certains metaux de transition. II. Structure des époxy-alcools formés à partir d'hydroperoxydes d'octadécène-9 oates de méthyle cis et trans en présence d'acétylacétonate de vanadyle. Chem. Phys. Lipids. 12: 239-248.
    • (1974) Chem. Phys. Lipids. , vol.12 , pp. 239-248
    • Mercier, J.1    Agoh, B.2
  • 23
    • 0028950166 scopus 로고
    • Hepoxilins: A review on their enzymatic formation, metabolism and chemical synthesis
    • Pace-Asciak, C. R., D. Reynaud, and P. M. Demin. 1995. Hepoxilins: a review on their enzymatic formation, metabolism and chemical synthesis. Lipids. 30: 107-114.
    • (1995) Lipids , vol.30 , pp. 107-114
    • Pace-Asciak, C.R.1    Reynaud, D.2    Demin, P.M.3
  • 24
    • 0027460286 scopus 로고
    • Formation of epoxyalcohols by a purified allene oxide synthase. Implications for the mechanism of allene oxide synthesis
    • Song, W-C., S. W. Baertschi, W. E. Boeglin, T. M. Harris, and A. R. Brash. 1993. Formation of epoxyalcohols by a purified allene oxide synthase. Implications for the mechanism of allene oxide biosynthesis. J. Biol. Chem. 268: 6293-6298. (Pubitemid 23099322)
    • (1993) Journal of Biological Chemistry , vol.268 , Issue.9 , pp. 6293-6298
    • Song, W.-C.1    Baertschi, S.W.2    Boeglin, W.E.3    Harris, T.M.4    Brash, A.R.5
  • 25
    • 69249109193 scopus 로고    scopus 로고
    • Evidence for an ionic intermediate in the transformation of fatty acid hydroperoxide by a catalase-related allene oxide synthase from the cyanobacterium Acaryochloris marina
    • Gao, B., W. E. Boeglin, Y. Zheng, C. Schneider, and A. R. Brash. 2009. Evidence for an ionic intermediate in the transformation of fatty acid hydroperoxide by a catalase-related allene oxide synthase from the cyanobacterium Acaryochloris marina. J. Biol. Chem. 284: 22087-22098.
    • (2009) J. Biol. Chem. , vol.284 , pp. 22087-22098
    • Gao, B.1    Boeglin, W.E.2    Zheng, Y.3    Schneider, C.4    Brash, A.R.5
  • 26
    • 52149110322 scopus 로고    scopus 로고
    • Structural insights into the evolutionary paths of oxylipin biosynthetic enzymes
    • Lee, D. S., P. Nioche, M. Hamberg, and C. S. Raman. 2008. Structural insights into the evolutionary paths of oxylipin biosynthetic enzymes. Nature. 455: 363-368.
    • (2008) Nature. , vol.455 , pp. 363-368
    • Lee, D.S.1    Nioche, P.2    Hamberg, M.3    Raman, C.S.4
  • 27
    • 0028209428 scopus 로고
    • The dioxygenation rate in lipoxygenase catalysis is determined by the amount of iron(III) lipoxygenase in solution
    • Schilstra, M. J., G. A. Veldink, and J. F. G. Vliegenthart. 1994. The dioxygenation rate in lipoxygenase catalysis is determined by the amount of iron(Iii) lipoxygenase in solution. Biochemistry. 33: 3974-3979. (Pubitemid 24125363)
    • (1994) Biochemistry , vol.33 , Issue.13 , pp. 3974-3979
    • Schilstra, M.J.1    Veldink, G.A.2    Vliegenthart, J.F.G.3
  • 29
    • 78650037229 scopus 로고    scopus 로고
    • Dioxygenase activity of epidermal lipoxygenase-3 unveiled: Typical and atypical features of its catalytic activity with natural and synthetic polyunsaturated fatty acids
    • Zheng, Y., and A. R. Brash. 2010. Dioxygenase activity of epidermal lipoxygenase-3 unveiled: Typical and atypical features of its catalytic activity with natural and synthetic polyunsaturated fatty acids. J. Biol. Chem. 285: 39866-39875.
    • (2010) J. Biol. Chem. , vol.285 , pp. 39866-39875
    • Zheng, Y.1    Brash, A.R.2
  • 30
    • 78650074364 scopus 로고    scopus 로고
    • On the role of molecular oxygen in lipoxygenase activation: Comparison and contrast of epidermal lipoxygenase-3 with soybean lipoxygenase-1
    • Zheng, Y., and A. R. Brash. 2010. On the role of molecular oxygen in lipoxygenase activation: Comparison and contrast of epidermal lipoxygenase-3 with soybean lipoxygenase-1. J. Biol. Chem. 285: 39876-39887.
    • (2010) J. Biol. Chem. , vol.285 , pp. 39876-39887
    • Zheng, Y.1    Brash, A.R.2
  • 31
    • 18944364281 scopus 로고    scopus 로고
    • Dual role of oxygen during lipoxygenase reactions
    • DOI 10.1111/j.1742-4658.2005.04673.x
    • Ivanov, I., J. Saam, H. Kuhn, and H. G. Holzhutter. 2005. Dual role of oxygen during lipoxygenase reactions. FEBS J. 272: 2523-2535. (Pubitemid 40705072)
    • (2005) FEBS Journal , vol.272 , Issue.10 , pp. 2523-2535
    • Ivanov, I.1    Saam, J.2    Kuhn, H.3    Holzhutter, H.-G.4
  • 32
    • 0000209617 scopus 로고
    • Vanadium-catalyzed epoxidations. 1. New selectivity pattern for acyclic allylic alcohols
    • Mihelich, E. D. 1979. Vanadium-catalyzed epoxidations. 1. New selectivity pattern for acyclic allylic alcohols. Tetrahedron Lett. 49: 4729-4732.
    • (1979) Tetrahedron Lett. , vol.49 , pp. 4729-4732
    • Mihelich, E.D.1
  • 33
    • 0028093915 scopus 로고
    • Eicosanoids from the tropical red alga Murrayella periclados
    • DOI 10.1016/S0031-9422(00)89643-0
    • Bernart, M. W., and W. H. Gerwick. 1994. Eicosanoids from the tropical red alga Murrayella periclados. Phytochemistry. 36: 1233-1240. (Pubitemid 2118482)
    • (1994) Phytochemistry , vol.36 , Issue.5 , pp. 1233-1240
    • Bernart, M.W.1    Gerwick, W.H.2
  • 34
    • 0030927441 scopus 로고    scopus 로고
    • Diastereoselective catalytic epoxidation of chiral allylic alcohols by the TS-1 and Ti-beta zeolites: Evidence for a hydrogen-bonded, peroxy-type loaded complex as oxidizing species
    • DOI 10.1021/jo970364i, PII S0022326397003642
    • Adam, W., A. Corma, T. I. Reddy, and M. Renz. 1997. Diastereoselective catalytic epoxidation of chiral allylic alcohols by the TS-1 and Ti-beta zeolites: Evidence for a hydrogen-bonded, peroxy-type loaded complex as oxidizing species. J. Org. Chem. 62: 3631-3637. (Pubitemid 27280604)
    • (1997) Journal of Organic Chemistry , vol.62 , Issue.11 , pp. 3631-3637
    • Adam, W.1    Corma, A.2    Indrasena, R.T.3    Renz, M.4
  • 35
    • 33845557915 scopus 로고
    • Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation - A route to substances of absolute enantiomeric purity
    • Martin, V. S., S. S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, and K. B. Sharpless. 1981. Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation - A route to substances of absolute enantiomeric purity. J. Am. Chem. Soc. 103: 6237-6240.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6237-6240
    • Martin, V.S.1    Woodard, S.S.2    Katsuki, T.3    Yamada, Y.4    Ikeda, M.5    Sharpless, K.B.6
  • 36
    • 49249151283 scopus 로고
    • Stereoselective epoxidation of acyclic allylic alcohols. A correction of our previous work
    • Rossiter, B. E., T. R. Verhoeven, and K. B. Sharpless. 1979. Stereoselective epoxidation of acyclic allylic alcohols. A correction of our previous work. Tetrahedron Lett. 49: 4733-4736.
    • (1979) Tetrahedron Lett. , vol.49 , pp. 4733-4736
    • Rossiter, B.E.1    Verhoeven, T.R.2    Sharpless, K.B.3
  • 37
    • 0037040698 scopus 로고    scopus 로고
    • A density-functional study of the mechanism for the diastereoselective epoxidation of chiral allylic alcohols by the titanium peroxy complexes
    • DOI 10.1021/jo016015c
    • Cui, M., W. Adam, J. H. Shen, X. M. Luo, X. J. Tan, K. X. Chen, R. Y. Ji, and H. L. Jiang. 2002. A density-functional study of the mechanism for the diastereoselective epoxidation of chiral allylic alcohols by the titanium peroxy complexes. J. Org. Chem. 67: 1427-1435. (Pubitemid 34211583)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.5 , pp. 1427-1435
    • Cui, M.1    Adam, W.2    Shen, J.H.3    Luo, X.M.4    Tan, X.J.5    Chen, K.X.6    Ji, R.Y.7    Jiang, H.L.8
  • 38
    • 0024505631 scopus 로고
    • 4from 5(S)-hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic acid. Evidence for an organoiron intermediate
    • 4 from 5(S)-hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic acid. Evidence for an organoiron intermediate. J. Am. Chem. Soc. 111: 1452-1455.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 1452-1455
    • Corey, E.J.1    Wright, S.W.2    Matsuda, S.P.T.3
  • 39
    • 0017293738 scopus 로고
    • The formation of threo -11-hydroxy- trans -12: 13-epoxy-9-cis- octadecenoic acid by enzymic isomerisation of 13-L-hydroperoxy-9-cis, 11- trans -octadecadienoic acid by soybean lipoxygenase-1
    • Garssen, G. J., G. A. Veldink, J. F. G. Vliegenthart, and J. Boldingh. 1976. The formation of threo -11-hydroxy- trans -12: 13-epoxy-9-cis-octadecenoic acid by enzymic isomerisation of 13-L-hydroperoxy-9-cis, 11- trans -octadecadienoic acid by soybean lipoxygenase-1. Eur. J. Biochem. 62: 33-36.
    • (1976) Eur. J. Biochem. , vol.62 , pp. 33-36
    • Garssen, G.J.1    Veldink, G.A.2    Vliegenthart, J.F.G.3    Boldingh, J.4
  • 40
    • 0021970012 scopus 로고
    • 4
    • Bryant, R. W., T. Schewe, S. M. Rapoport, and J. M. Bailey. 1985. Leukotriene formation by a purified reticulocyte lipoxygenase enzyme. Conversion of arachidonic acid and 15-hydroperoxyeicosatetraenoic acid to 14,15-leukotriene A 4. J. Biol. Chem. 260: 3548-3555. (Pubitemid 15114356)
    • (1985) Journal of Biological Chemistry , vol.260 , Issue.6 , pp. 3548-3555
    • Bryan, R.W.1    Schewe, T.2    Rapoport, S.M.3    Bailey, J.M.4
  • 42
    • 46149131094 scopus 로고
    • Stereochemistry of two epoxy alcohols from Saprolegnia parasitica
    • Hamberg, M., R. P. Herman, and U. Jacobsson. 1986. Stereochemistry of two epoxy alcohols from Saprolegnia parasitica. Biochim. Biophys. Acta. 879: 410-418.
    • (1986) Biochim. Biophys. Acta. , vol.879 , pp. 410-418
    • Hamberg, M.1    Herman, R.P.2    Jacobsson, U.3
  • 43
    • 0032764071 scopus 로고    scopus 로고
    • An epoxy alcohol synthase pathway in higher plants: Biosynthesis of antifungal trihydroxy oxylipins in leaves of potato
    • Hamberg, M. 1999. An epoxy alcohol synthase pathway in higher plants: biosynthesis of antifungal trihydroxy oxylipins in leaves of potato. Lipids. 34: 1131-1142.
    • (1999) Lipids , vol.34 , pp. 1131-1142
    • Hamberg, M.1
  • 44
    • 79961209563 scopus 로고    scopus 로고
    • Efficient and specific conversion of 9-lipoxygenase hydroperoxides in the beetroot. Formation of pinellic acid
    • Hamberg, M., and U. Olsson. 2011. Efficient and specific conversion of 9-lipoxygenase hydroperoxides in the beetroot. Formation of pinellic acid. Lipids. 46: 873-878.
    • (2011) Lipids , vol.46 , pp. 873-878
    • Hamberg, M.1    Olsson, U.2
  • 45
    • 0027532881 scopus 로고
    • Mechanism of reaction of fatty acid hydroperoxides with soybean peroxygenase
    • Blée, E., A. L. Wilcox, L. J. Marnett, and F. Schuber. 1993. Mechanism of reaction of fatty acid hydroperoxides with soybean peroxygenase. J. Biol. Chem. 268: 1708-1715. (Pubitemid 23033562)
    • (1993) Journal of Biological Chemistry , vol.268 , Issue.3 , pp. 1708-1715
    • Blee, E.1    Wilcox, A.L.2    Marnett, L.J.3    Schuber, F.4
  • 46
    • 0030067147 scopus 로고    scopus 로고
    • Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds (sequential oxidation of linoleic acid into 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid)
    • Hamberg, M., and G. Hamberg. 1996. Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds (sequential oxidation of linoleic acid into 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid). Plant Physiol. 110: 807-815.
    • (1996) Plant Physiol. , vol.110 , pp. 807-815
    • Hamberg, M.1    Hamberg, G.2
  • 47
    • 0027939491 scopus 로고
    • Endoperoxide pathway in prostaglandin biosynthesis in the soft coral Gersemia fruticosa
    • DOI 10.1016/0040-4039(94)88299-1
    • Varvas, K., R. Koljak, I. Järving, T. Pehk, and N. Samel. 1994. Endoperoxide pathway in prostaglandin biosynthesis in the soft coral Gersemia fruticosa. Tetrahedron Lett. 35: 8267-8270. (Pubitemid 24324320)
    • (1994) Tetrahedron Letters , vol.35 , Issue.44 , pp. 8267-8270
    • Varvas, K.1    Koljak, R.2    Jarving, I.3    Pehk, T.4    Samel, N.5
  • 48
    • 0039180005 scopus 로고    scopus 로고
    • Evidence of a cyclooxygenase-related prostaglandin synthesis in coral. The allene oxide pathway is not involved in prostaglandin synthesis
    • Varvas, K., I. Järving, R. Koljak, K. Valmsen, A. R. Brash, and N. Samel. 1999. Evidence of a cyclooxygenase-related prostaglandin synthesis in coral. The allene oxide pathway is not involved in prostaglandin synthesis. J. Biol. Chem. 274: 9923-9929.
    • (1999) J. Biol. Chem. , vol.274 , pp. 9923-9929
    • Varvas, K.1    Järving, I.2    Koljak, R.3    Valmsen, K.4    Brash, A.R.5    Samel, N.6
  • 49
    • 4544365241 scopus 로고    scopus 로고
    • Structural and functional comparison of 15S- and 15R-specific cyclooxygenases from the coral Plexaura homomalla
    • DOI 10.1111/j.0014-2956.2004.04289.x
    • Valmsen, K., W. E. Boeglin, J. Järving, C. Schneider, K. Varvas, A. R. Brash, and N. Samel. 2004. Structural and functional comparison of 15S- and 15R-specific cyclooxygenases from the coral Plexaura homomalla. Eur. J. Biochem. 271: 3533-3538. (Pubitemid 39215342)
    • (2004) European Journal of Biochemistry , vol.271 , Issue.17 , pp. 3533-3538
    • Valmsen, K.1    Boeglin, W.E.2    Jarving, I.3    Schneider, C.4    Varvas, K.5    Brash, A.R.6    Samel, N.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.