Purification and Characterization of Allene Oxide Cyclase from Dry Corn Seeds

Overview

Journal Plant Physiol

Specialty Physiology

Date 1997 Jun 1

PMID 12223729

Citations 24

Authors

J Ziegler

M Hamberg

O Miersch

B Parthier

Affiliations

Soon will be listed here.

Abstract

Allene oxide cyclase (AOC; EC 5.3.99.6) catalyzes the cyclization of 12,13(S)-epoxy-9(Z),11,15(Z)-octadecatrienoic acid to 12-oxo- 10,15(Z)-phytodienoic acid, the precursor of jasmonic acid (JA). This soluble enzyme was purified 2000-fold from dry corn (Zea mays L.) kernels to apparent homogeneity. The dimeric protein has a molecular mass of 47 kD. Allene oxide cyclase activity was not affected by divalent ions and was not feedback-regulated by its product, 12-oxo-l0,15(Z)-phytodienoic acid, or by JA. ([plus or minus])-cis- 12,13-Epoxy-9(Z)-octadecenoic acid, a substrate analog, strongly inhibited the enzyme, with 50% inhibition at 20 [mu]M. Modification of the inhibitor, such as methylation of the carboxyl group or a shift in the position of the epoxy group, abolished the inhibitory effect, indicating that both structural elements and their position are essential for binding to AOC. Nonsteroidal anti-inflammatory drugs, which are often used to interfere with JA biosynthesis, did not influence AOC activity. The purified enzyme catalyzed the cyclization of 12,13(S)-epoxy-9(Z),11,15(Z)-octadecatrienoic acid derived from linolenic acid, but not that of 12,13(S)-epoxy-9(Z),11- octadecadienoic acid derived from linoleic acid.

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References

Pan Z, Durst F, Werck-Reichhart D, Gardner H, Camara B, Cornish K . The major protein of guayule rubber particles is a cytochrome P450. Characterization based on cDNA cloning and spectroscopic analysis of the solubilized enzyme and its reaction products. J Biol Chem. 1995; 270(15):8487-94. DOI: 10.1074/jbc.270.15.8487. View

Farmer E, Ryan C . Octadecanoid Precursors of Jasmonic Acid Activate the Synthesis of Wound-Inducible Proteinase Inhibitors. Plant Cell. 1992; 4(2):129-134. PMC: 160114. DOI: 10.1105/tpc.4.2.129. View

Laemmli U . Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 1970; 227(5259):680-5. DOI: 10.1038/227680a0. View

Song W, Funk C, Brash A . 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. 1993; 90(18):8519-23. PMC: 47388. DOI: 10.1073/pnas.90.18.8519. View

Vick B, Zimmerman D . The biosynthesis of jasmonic acid: a physiological role for plant lipoxygenase. Biochem Biophys Res Commun. 1983; 111(2):470-7. DOI: 10.1016/0006-291x(83)90330-3. View

Grechkin A, Hamberg M . Divinyl ether synthase from garlic (Allium sativum L.) bulbs: sub-cellular localization and substrate regio-and stereospecificity. FEBS Lett. 1996; 388(2-3):112-4. DOI: 10.1016/0014-5793(96)00536-4. View

Hamberg M, Gardner H . Oxylipin pathway to jasmonates: biochemistry and biological significance. Biochim Biophys Acta. 1992; 1165(1):1-18. DOI: 10.1016/0005-2760(92)90069-8. View

Creelman R, Mullet J . Jasmonic acid distribution and action in plants: regulation during development and response to biotic and abiotic stress. Proc Natl Acad Sci U S A. 1995; 92(10):4114-9. PMC: 41895. DOI: 10.1073/pnas.92.10.4114. View

Blechert S, Brodschelm W, Holder S, KAMMERER L, Kutchan T, Mueller M . The octadecanoic pathway: signal molecules for the regulation of secondary pathways. Proc Natl Acad Sci U S A. 1995; 92(10):4099-105. PMC: 41893. DOI: 10.1073/pnas.92.10.4099. View

10.

Hamberg M, Hamberg G . Hydroperoxide-dependent epoxidation of unsaturated fatty acids in the broad bean (Vicia faba L.). Arch Biochem Biophys. 1990; 283(2):409-16. DOI: 10.1016/0003-9861(90)90662-i. View

11.

Doares S, Narvaez-Vasquez J, Conconi A, Ryan C . Salicylic Acid Inhibits Synthesis of Proteinase Inhibitors in Tomato Leaves Induced by Systemin and Jasmonic Acid. Plant Physiol. 1995; 108(4):1741-1746. PMC: 157556. DOI: 10.1104/pp.108.4.1741. View

12.

Gardner H . Recent investigations into the lipoxygenase pathway of plants. Biochim Biophys Acta. 1991; 1084(3):221-39. DOI: 10.1016/0005-2760(91)90063-n. View

13.

Kauss H, Jeblick W, Ziegler J, Krabler W . Pretreatment of Parsley (Petroselinum crispum L.) Suspension Cultures with Methyl Jasmonate Enhances Elicitation of Activated Oxygen Species. Plant Physiol. 1994; 105(1):89-94. PMC: 159332. DOI: 10.1104/pp.105.1.89. View

14.

Song W, Brash A . Purification of an allene oxide synthase and identification of the enzyme as a cytochrome P-450. Science. 1991; 253(5021):781-4. DOI: 10.1126/science.1876834. View

15.

Galliard T, Phillips D . The enzymic 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. 1972; 129(3):743-53. PMC: 1174176. DOI: 10.1042/bj1290743. View

16.

Conconi A, Miquel M, Browse J, Ryan C . Intracellular Levels of Free Linolenic and Linoleic Acids Increase in Tomato Leaves in Response to Wounding. Plant Physiol. 1996; 111(3):797-803. PMC: 157897. DOI: 10.1104/pp.111.3.797. View

17.

Laudert D, Pfannschmidt U, Lottspeich F, Hollander-Czytko H, Weiler E . 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. 1996; 31(2):323-35. DOI: 10.1007/BF00021793. View

18.

Doares S, Syrovets T, Weiler E, Ryan C . Oligogalacturonides and chitosan activate plant defensive genes through the octadecanoid pathway. Proc Natl Acad Sci U S A. 1995; 92(10):4095-8. PMC: 41892. DOI: 10.1073/pnas.92.10.4095. View

19.

Nojiri H, Sugimori M, Yamane H, Nishimura Y, Yamada A, Shibuya N . Involvement of Jasmonic Acid in Elicitor-Induced Phytoalexin Production in Suspension-Cultured Rice Cells. Plant Physiol. 1996; 110(2):387-392. PMC: 157731. DOI: 10.1104/pp.110.2.387. View

20.

Franceschi V, Grimes H . Induction of soybean vegetative storage proteins and anthocyanins by low-level atmospheric methyl jasmonate. Proc Natl Acad Sci U S A. 1991; 88(15):6745-9. PMC: 52165. DOI: 10.1073/pnas.88.15.6745. View