Preparative enzymatic solid phase synthesis of cis(+)-12-oxo-phytodienoic acid - physical interaction of AOS and AOC is not necessary

Phytochemistry

Volumn 68, Issue 2, 2007, Pages 229-236

  Zerbe, Philipp ^a   Weiler, Elmar W ^a   Schaller, Florian ^a  

^a RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

12 Oxo phytodienoic acid; Allene oxide cyclase; Allene oxide synthase; Jasmonates; Jasmonic acid; Octadecanoid pathway; Oxylipins; Plant hormones

Indexed keywords

12 OXOPHYTODIENOIC ACID; 12-OXOPHYTODIENOIC ACID; CYCLOPENTANE DERIVATIVE; HYDROPEROXIDE ISOMERASE; IMMOBILIZED ENZYME; ISOMERASE; JASMONIC ACID; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID;

ARTICLE; BIOSYNTHESIS; CHEMISTRY; METABOLISM; PROTEIN BINDING; STEREOISOMERISM;

CYCLOPENTANES; ENZYMES, IMMOBILIZED; FATTY ACIDS, UNSATURATED; INTRAMOLECULAR OXIDOREDUCTASES; PROTEIN BINDING; STEREOISOMERISM;

EID: 33845877465     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2006.10.010     Document Type: Article

References (38)

1. Ausubel F.M., Brent R., Kinston R.E., Moore D.D., Seidmann J.G., Smith J.A., and Struhl K. Current Protocols in Molecular Biology (1995), Wiley, New York
2. Blechert S., Brodschelm W., Hölder S., Kammerer L., Kutchan T.M., Müller M.J., Xia Z.-Q., and Zenk M.H. The octadecanoid pathway: signal molecules for the regulation of secondary pathways. Proc. Natl. Acad. Sci. USA 92 (1995) 4099-4105
3. Bradford M.M. A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
4. Brash A.R., Baertschi S.W., Ingram C.D., and Harris T.M. Isolation and characterization of natural allene oxides: unstable intermediates in the metabolism of lipid hydroperoxides. Proc. Natl. Acad. Sci. USA 85 (1988) 3382-3386
5. Conconi A., Miquel M., Browse J.A., and Ryan C.A. Intracellular levels of free linolenic and linoleic acids increase in tomato leaves in response to wounding. Plant Physiol. 111 (1996) 797-803
6. CruzCastillo M., Marti{dotless}́nez C., Buchala A., Métraux J.P., and León J. Gene-specific involvement of β-oxidation in wound-activated responses in Arabidopsis. Plant Physiol. 135 (2004) 85-94
7. Dathe W., Rönsch H., Preiss A., Schade W., Sembner G., and Schreiber K. Endogenous plant hormones of the broad bean, Vicia faba L. (-)-jasmonic acid, a plant growth inhibitor in peicarp. Planta 153 (1981) 530-535
8. Demole E., Lederer E., and Mercier D. Isolement et détermination de la structure du jasmonate de méthyle, constituant odorant charactéristique de l'essence de jasmin. Helv. Chim. Acta 45 (1962) 675-685
9. Falkenstein E., Groth B., Mithöfer A., and Weiler E.W. Methyljasmonate and α-linolenic acid are potent inducers of tendril coiling. Planta 185 (1991) 316-322
10. Farmer E.E., and Ryan C.A. Interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves. Proc. Natl. Acad. Sci. USA 87 (1990) 7713-7716
11. Farmer E.E., Johnson R.R., and Ryan C.A. Regulation of expression of proteinase inhibitor genes by methyl jasmonate and jasmonic acid. Plant Physiol. 98 (1991) 995-1002
12. Farmer E.E., and Ryan C.A. Octadecanoid-derived signals in plants. Trends Cell Biol. 2 (1992) 236-241
13. Froehlich J.E., Itoh A., and Howe G.A. Tomato allene oxide synthase and fatty acid hydroperoxide lyase, two cytochrome P450s involved in oxylipin metabolism, are targeted to different membranes of chloroplast envelope. Plant Physiol. 125 (2001) 306-317
14. Gerhardt B. Localization of β-oxidation enzymes in peroxisomes isolated from nonfatty plant tissues. Planta 159 (1983) 238-246
15. Graff G., Andersson L.A., and Jackes L.W. Preparation and purification of soybean lipoxygenase-derived unsaturated hydroperoxy and hydroxyl fatty acids and determination of molar absorptivities of hydroxyl fatty acids. Anal. Biochem. 188 (1990) 38-47
16. Hamberg M., and Fahlstadius P. Allene oxide cyclase: a new enzyme in plant lipid metabolism. Arch. Biochem. Biophys. 276 (1990) 518-526
17. Kramell R., Miersch O., Hause B., Ortel B., Parthier B., and Wasternack C. Amino acid conjugates of jasmonic acid induce jasmonate-responsive gene expression in barley (Hordeum vulgare L.) leaves. FEBS Lett. 414 (1997) 197-202
18. Laemmli U.K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227 (1970) 680-685
19. Laudert D., Pfannschmidt U., Lottspeich F., Holländer-Czytko H., and Weiler E.W. Cloning, molecular and functional characterization of Arabidopsis thaliana allene oxide synthase (CYP 74), the first enzyme of the octadecanoid pathway to jasmonates. Plant. Mol. Biol. 31 (1996) 323-335
20. Laudert D., Hennig P., Stelmach B.A., Müller A., Andert L., and Weiler E.W. Analysis of 12-oxo-phytodienoic acid enantiomers in biological samples by capillary gas chromatography-mass spectrometry using cyclodextrin stationary phases. Anal. Biochem. 246 (1997) 211-217
21. Li C., Schilmiller A.L., Liu G.L., Lee G.L., Jayanti S., Sageman C., Vrebalov J., Giovannoni J.J., Yagi K., Kobayashi Y., and Howe G.A. Role of β-oxidation in jasmonate biosynthesis and systemic wound signaling in tomato. Plant Cell 17 (2005) 971-986
22. Meyer A., Miersch O., Büttner C., Dathe W., and Sembdner G. Occurrence of the plant growth regulator jasmonic acid in plants. J. Plant Growth Regul. 3 (1984) 1-8
23. Müller A., Düchting P., and Weiler E.W. A multiplex GC-MS/MS technique for the sensitive and quantitative single-run analysis of acidic phytohormones and related compounds, and its application to Arabidopsis thaliana. Planta 216 (2002) 44-56
24. Mueller M.J., Brodschelm W., Spannagl E., and Zenk M.H. Signaling in the elicitation process is mediated through the octadecanoid pathway leading to jasmonic acid. Proc. Natl. Acad. Sci. USA 90 (1993) 7490-7494
25. Narváez-Vásquez J., Florin-Christensen J., and Ryan C.A. Positional specificity of a phospholipase A2 activity induced by wounding, systemin, and oligosaccharide elicitors in tomato leaves. Plant Cell 11 (1999) 2249-2260
26. Oh K., and Murofushi N. Design and synthesis of novel imidazole derivatives as potent inhibitors of allene oxide synthase (CYP74). Bioorg. Med. Chem. 10 (2002) 3707-3711
27. Schaller F., Biesgen C., Müssig C., Altmann T., and Weiler E.W. 12-oxo-phytodienoate reductase 3 (OPR3) is the isoenzyme involved in jasmonate biosynthesis. Planta 210 (2000) 979-1094
28. Schaller F., Schaller A., and Stintzi A. Biosynthesis and metabolism of jasmonates. J. Plant Growth Regul. 23 (2005) 179-199
29. Stenzel I., Hause B., Miersch O., Kurz T., Maucher H., Weichert H., Ziegler J., Feussner I., and Wasternack C. Jasmonate biosynthesis and the allene oxide cyclase family of Arabidopsis thaliana. Plant Mol. Biol. 51 (2003) 895-911
30. Stintzi A., Weber H., Reymond P., Browse J., and Farmer E.E. Plant defense in the absence of jasmonic acid: the role of cyclopentenones. Proc. Natl. Acad. Sci. USA 98 (2001) 12837-12842
31. Strassner J., Schaller F., Frick U.B., Howe G.A., Weiler E.W., Amrhein N.A., Macheroux P., and Schaller A. Characterization and cDNA-microarray expression analysis of 12-oxo-phytodienoate reductases reveals differential roles for octadecanoid biosynthesis in the local versus the systemic wound response. Plant J. 32 (2002) 585-601
32. Taki N., Sasaki-Sekimoto Y., Obayashi T., Kikuta A., Kobayashi K., Ainai T., Yagi K., Sakurai N., Suzuki H., Masuda T., Takamiya K.-I., Shibata D., Kobayashi Y., and Ohta H. 12-Oxo-phytodienoic acid triggers expression of a distinct set of genes and plays a role in wound-induced gene expression in Arabidopsis. Plant Physiol. 139 (2005) 1268-1283
33. Theodoulou F.L., Job K., Slocombe S.P., Footitt S., Holdsworth M., Baker A., Larson T.R., and Graham I.A. Jasmonic acid levels are reduced in COMATOSE ATP-binding cassette transporter mutants. Implications for transport of jasmonate precursors into peroxisomes. Plant Physiol. 137 (2005) 835-840
34. Towbin H., Staehelin T., and Gordon J. Electrophoretic transfer of proteins from polyacrylamid gels to nitrocellulose sheets: procedure and some applications. Proc. Natl. Acad. Sci. USA 76 (1979) 4350-4354
35. Ueda J., and Kato J. Isolation and identification of a senescence-promoting substance from wormwood (Artemisia absinthium L.). Plant Physiol. 66 (1980) 246-249
36. Vick B.A., and Zimmerman D.C. Biosynthesis of jasmonic acid by several plant species. Plant Physiol. 75 (1984) 458-461
37. Vick B.A., and Zimmerman D.C. Pathway of fatty acid hydroperoxide metabolism in spinach leaf chloroplasts. Plant Physiol. 85 (1987) 1073-1078
38. Weiler E.W., Albrecht T., Groth B., Xia Z.-Q., Luxem M., Liß H., Andert L., and Spengler P. Evidence for the involvement of jasmonates and their octadecanoid precursors in the tendril coiling response of Bryonia dioica. Plant Physiol. 80 (1993) 202-205