Green leaf divinyl ether synthase: Gene detection, molecular cloning and identification of a unique CYP74B subfamily member

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1821, Issue 2, 2012, Pages 287-294

  Gogolev, Yuri V ^a   Gorina, Svetlana S ^a   Gogoleva, Natalia E ^a   Toporkova, Yana Y ^a   Chechetkin, Ivan R ^a   Grechkin, Alexander N ^a  

^a KAZAN INSTITUTE OF BIOCHEMISTRY AND BIOPHYSICS   (Russian Federation)

Author keywords

CYP74B; Divinyl ether synthase; Flax (Linum usitatissimum L.); Molecular cloning; Oxylipins; P450

Indexed keywords

ALLENE OXIDE SYNTHASE; AMINO ACID; CYTOCHROME; CYTOCHROME P450; CYTOCHROME P450 74A; CYTOCHROME P450 74B; CYTOCHROME P450 74B16; DIVINYL ETHER 12 [HEXADIENYLOXY] 9,11 DODECADIENOIC ACID; DIVINYL ETHER SYNTHASE; ESSENTIAL FATTY ACID; ETHEROLENIC ACID; HYDROPEROXIDE; LINOLENIC ACID; LIPOXYGENASE; RECOMBINANT PROTEIN; RECOMBINANT PROTEIN CYTOCHROME P450 74B16; SYNTHETASE; TRANSCRIPTOME; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; ENZYME SUBSTRATE; ENZYME SYNTHESIS; ESCHERICHIA COLI; FLAX; FLAX LEAF; GENE EXPRESSION; GENE IDENTIFICATION; GENE SEQUENCE; MASS SPECTROMETRY; MOLECULAR CLONING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; PLANT GENOME; PLANT LEAF; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; PROTEIN DOMAIN; PSEUDOGENE; TRANSCRIPTOMICS; ULTRAVIOLET SPECTROSCOPY;

AMINO ACID SEQUENCE; BASE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CLONING, MOLECULAR; CYTOCHROME P-450 ENZYME SYSTEM; DNA PRIMERS; DNA, COMPLEMENTARY; FLAX; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GENE EXPRESSION REGULATION, PLANT; GENES, PLANT; HYDROGEN-ION CONCENTRATION; KINETICS; MOLECULAR SEQUENCE DATA; PHYLOGENY; PLANT LEAVES; PLANT PROTEINS; RECOMBINANT PROTEINS; RNA, MESSENGER; SEQUENCE ALIGNMENT; SUBSTRATE SPECIFICITY;

ESCHERICHIA COLI; LINUM USITATISSIMUM;

EID: 83655201580     PISSN: 13881981     EISSN: 18792618     Source Type: Journal    
DOI: 10.1016/j.bbalip.2011.11.003     Document Type: Article

References (43)

1. A.N. Grechkin Recent developments in biochemistry of the plant lipoxygenase pathway Prog. Lipid Res. 37 1998 317 352
2. I. Feussner, and C. Wasternack The lipoxygenase pathway Annu Rev. Plant Biol. 53 2002 275 297 (Pubitemid 36257496)
3. M. Stumpe, and I. Feussner Formation of oxylipins by CYP74 enzymes Phytochem. Rev. 5 2006 347 357 (Pubitemid 44900353)
4. N. Tijet, and A.R. Brash Allene oxide synthases and allene oxides Prostaglandins Other Lipid Mediat. 68-69 2002 423 431 (Pubitemid 35247412)
5. A.N. Grechkin Hydroperoxide lyase and divinyl ether synthase Prostaglandins Other Lipid Mediat. 68-69 2002 457 470 (Pubitemid 35247414)
6. A.R. Brash Mechanistic aspects of CYP74 allene oxide synthases and related cytochrome P450 enzymes Phytochemistry 70 2009 1522 1531
7. M. Hamberg Hidden stereospecificity in the biosynthesis of divinyl ether fatty acids FEBS J. 272 2005 736 743 (Pubitemid 40208876)
8. A.N. Grechkin, and M. Hamberg The "heterolytic hydroperoxide lyase" is an isomerase producing a short-lived fatty acid hemiacetal, Biochim. Biophys. Acta-Mol. Cell Biol Lipids 1636 2004 47 58 (Pubitemid 38231004)
9. A.N. Grechkin, F. Brühlmann, L.S. Mukhtarova, Y.V. Gogolev, and M. Hamberg Hydroperoxide lyases (CYP74C and CYP74B) catalyze the homolytic isomerization of fatty acid hydroperoxides into hemiacetals, Biochim. Biophys. Acta-Mol. Cell Biol Lipids 1761 2006 1419 1428 (Pubitemid 44821906)
10. H. Weber, A. Chételat, D. Caldelari, and E.E. Farmer Divinyl ether fatty acid synthesis in late blight-diseased potato leaves Plant Cell 11 1999 485 494
11. G. Granér, M. Hamberg, and J. Meijer Screening of oxylipins for control of oilseed rape (Brassica napus) fungal pathogens Phytochemistry 63 2003 89 95 (Pubitemid 36427444)
12. T. Cowley, and D. Walters Local and systemic effects of oxylipins on powdery mildew infection in barley Pest Manage. Sci. 61 2005 572 576 (Pubitemid 40748205)
13. D. Nelson Progress in tracing the evolutionary paths of cytochrome P450 Biochim. Biophys. Acta 1814 2011 14 18
14. D. Nelson, and D. Werck-Reichhart A P450-centric view of plant evolution Plant J. 66 2011 194 211
15. G. Gullner, A. Künstler, L. Király, M. Pogány, and I. Tóbiás Up-regulated expression of lipoxygenase and divinyl ether synthase genes in pepper leaves inoculated with Tobamoviruses Physiol. Mol. Plant Pathol. 74 2010 387 393
16. D.-S. Lee, P. Nioche, M. Hamberg, and C.S. Raman Structural insights into the evolutionary paths of oxylipin biosynthetic enzymes Nature 455 2008 363 368
17. T. Galliard, and D.R. Phillips The enzymatic conversion of linoleic acid into 9-(nona-1,3-dienoxy)-non-8-enoic acid, a novel unsaturated ether derivative isolated from homogenates of Solanum tuberosum tubers Biochem. J. 129 1972 743 753
18. T. Galliard, D.R. Phillips, and D.J. Frost Novel divinyl ether fatty acids in extracts of Solanum tuberosum Chem. Phys. Lipids 11 1973 173 180
19. T. Galliard, and J.A. Mathew Enzymic reactions of fatty acid hydroperoxides in extracts of potato tuber. I. Comparison 9D- and 13L-hydroperoxyoctadecadienoic acids as substrates for the formation of a divinyl ether derivative Biochim. Biophys. Acta 398 1975 1 9
20. A. Itoh, and G.A. Howe Molecular cloning of a divinyl ether synthase. Identification as a CYP74 cytochrome P-450 J. Biol. Chem. 276 2001 3620 3627
21. M. Stumpe, R. Kandzia, C. Göbel, S. Rosahl, and I. Feussner A pathogen-inducible divinyl ether synthase (CYP74D) from elicitor-treated potato suspension cells FEBS Lett. 507 2001 371 376 (Pubitemid 33030268)
22. A. Fammartino, F. Cardinale, C. Göbel, L. Mène- Saffrané, J. Fournier, I. Feussner, and M.T. Esquerré- Tugayé Characterization of a divinyl ether biosynthetic pathway specifically associated with pathogenesis in tobacco Plant Physiol. 143 2007 378 388 (Pubitemid 46133642)
23. M. Hamberg A pathway for biosynthesis of divinyl ether fatty acids in green leaves Lipids 33 1998 1061 1071 (Pubitemid 28559977)
24. M. Hamberg Biosynthesis of new divinyl ether oxylipins in Ranunculus plants Lipids 37 2002 427 433 (Pubitemid 34441806)
25. M. Hamberg Isolation and structures of two divinyl ether fatty acids from Clematis vitalba Lipids 39 2004 565 569 (Pubitemid 39372353)
26. A.N. Grechkin, F.N. Fazliev, and L.S. Mukhtarova The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: detection of the novel divinyl ether oxylipins FEBS Lett. 371 1995 159 162
27. A.N. Grechkin, and M. Hamberg Divinyl ether synthase from garlic (Allium sativum L.) bulbs: subcellular localization and substrate regio- and stereospecificity FEBS Lett. 388 1996 112 114 (Pubitemid 26226341)
28. A.N. Grechkin, A.V. Ilyasov, and M. Hamberg On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbs Eur. J. Biochem. 245 1997 137 142 (Pubitemid 27142273)
29. M. Stumpe, J.-G. Carsjens, C. Göbel, and I. Feussner Divinyl ether synthesis in garlic bulbs J. Exp. Bot. 59 2008 907 915 (Pubitemid 351644666)
30. A.V. Ogorodnikova, L.R. Latypova, F.K. Mukhitova, L.S. Mukhtarova, and A.N. Grechkin Detection of divinyl ether synthase in Lily-of-the-Valley (Convallaria majalis) roots Phytochemistry 69 2008 2793 2798
31. P.J. Proteau, and W.H. Gerwick Divinyl ethers and hydroxy fatty acids from three species of Laminaria brown algae Lipids 28 1993 783 787 (Pubitemid 23277641)
32. Z.D. Jiang, and W.H. Gerwick Novel oxylipins from the temperate red alga Polyneura latissima: evidence for an arachidonate 9(S)-lipoxygenase Lipids 32 1997 231 235 (Pubitemid 27131755)
33. I.R. Chechetkin, A. Blufard, M. Hamberg, and A.N. Grechkin A lipoxygenase-divinyl ether synthase pathway in flax (Linum usitatissimum L.) leaves Phytochemistry 69 2008 2008 2015
34. I.R. Chechetkin, F.K. Mukhitova, A.S. Blufard, A.Y. Yarin, L.L. Antsygina, and A.N. Grechkin Unprecedented pathogen-inducible complex oxylipins from flax - linolipins A and B FEBS J. 276 2009 4463 4472
35. C. Göbel, I. Feussner, A. Schmidt, D. Scheel, J. Sanchez-Serrano, M. Hamberg, and S. Rosahl Oxylipin profiling reveals the preferential stimulation of the 9-lipoxygenase pathway in elicitor-treated potato cells J. Biol. Chem. 276 2001 6267 6273
36. I. Prost, S. Dhondt, G. Rothe, J. Vicente, M.J. Rodriguez, N. Kift, F. Carbonne, G. Griffiths, M.-T. Esquerré-Tugayé, S. Rosahl, C. Castresana, M. Hamberg, and J. Fournier Evaluation of the antimicrobial activities of plant oxylipins supports their involvement in defense against pathogens Plant Physiol. 139 2005 1902 1913 (Pubitemid 43899826)
37. J.C. Verdonk, C.H.R. de Vos, H.A. Verhoeven, M.A. Haring, A.J. van Tunen, and R.C. Schuurink Regulation of floral scent production in petunia revealed by targeted metabolomics Phytochemistry 62 2003 997 1008 (Pubitemid 36262402)
38. J.B. Schenkman, and I. Jansson Spectral analyses of cytochromes P450 Meth. Mol. Biol. 320 2006 11 18
39. Y.Y. Toporkova, Y.V. Gogolev, L.S. Mukhtarova, and A.N. Grechkin Determinants governing the CYP74 catalysis: conversion of allene oxide synthase into hydroperoxide lyase by site-directed mutagenesis FEBS Lett. 582 2008 3423 3428
40. W.-C. Song, C.D. Funk, and A.R. Brash Molecular cloning of an allene oxide synthase: a cytochrome P450 specialized for the metabolism of fatty acid hydroperoxides Proc. Natl. Acad. Sci. U. S. A. 90 1993 8519 8523 (Pubitemid 23277700)
41. H.A. Lütcke, K.C. Chow, F.S. Mickel, K.A. Moss, H.F. Kern, and G.A. Scheele Selection of AUG initiation codons differs in plants and animals EMBO J. 6 1987 43 48
42. K.B. Cho, W. Lai, M. Hamberg, C.S. Raman, and S. Shaik The reaction mechanism of allene oxide synthase: interplay of theoretical QM/MM calculations and experimental investigations Arch. Biochem. Biophys. 507 2011 14 25
43. O. Gotoh Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences J. Biol. Chem. 267 1992 83 90