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Science 16 August 1991:
Vol. 253. no. 5021, pp. 781 - 784
DOI: 10.1126/science.1876834
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Articles

Science, Vol 253, Issue 5021, 781-784
Copyright © 1991 by American Association for the Advancement of Science

articles

Purification of an allene oxide synthase and identification of the enzyme as a cytochrome P-450

WC Song and AR Brash

Department of Pharmacology, Vanderbilt University School of Medicine, Nashville, TN 37232.

Fatty acid hydroperoxides (lipoxygenase products) are metabolized to allene oxides by a type of dehydrase that has been detected in plants, corals, and starfish oocytes. The allene oxides are unstable epoxide precursors of more complex products such as jasmonic acid, the plant growth hormone. Characterization of the dehydrase enzyme of flaxseed revealed that it is a 55-kilodalton hemoprotein. The spectral characteristics of this dehydrase revealed it to be a cytochrome P-450. It operates with the remarkable activity of greater than or equal to 1000 turnovers per second. The results establish a new catalytic activity for a cytochrome P-450 and illustrate the cooperation of different oxygenases in pathways of fatty acid metabolism.


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Identification of PpoA from Aspergillus nidulans as a Fusion Protein of a Fatty Acid Heme Dioxygenase/Peroxidase and a Cytochrome P450.
F. Brodhun, C. Gobel, E. Hornung, and I. Feussner (2009)
J. Biol. Chem. 284, 11792-11805
   Abstract »    Full Text »    PDF »
Modes of heme binding and substrate access for cytochrome P450 CYP74A revealed by crystal structures of allene oxide synthase.
L. Li, Z. Chang, Z. Pan, Z.-Q. Fu, and X. Wang (2008)
PNAS 105, 13883-13888
   Abstract »    Full Text »    PDF »
Specific Adduction of Plant Lipid Transfer Protein by an Allene Oxide Generated by 9-Lipoxygenase and Allene Oxide Synthase.
B. Bakan, M. Hamberg, L. Perrocheau, D. Maume, H. Rogniaux, O. Tranquet, C. Rondeau, J.-P. Blein, M. Ponchet, and D. Marion (2006)
J. Biol. Chem. 281, 38981-38988
   Abstract »    Full Text »    PDF »
The Crystal Structure of Arabidopsis thaliana Allene Oxide Cyclase: Insights into the Oxylipin Cyclization Reaction.
E. Hofmann, P. Zerbe, and F. Schaller (2006)
PLANT CELL 18, 3201-3217
   Abstract »    Full Text »    PDF »
On the Relationship of Coral Allene Oxide Synthase to Catalase: A SINGLE ACTIVE SITE MUTATION THAT INDUCES CATALASE ACTIVITY IN CORAL ALLENE OXIDE SYNTHASE.
T. Tosha, T. Uchida, A. R. Brash, and T. Kitagawa (2006)
J. Biol. Chem. 281, 12610-12617
   Abstract »    Full Text »    PDF »
Variations in CYP74B2 (Hydroperoxide Lyase) Gene Expression Differentially Affect Hexenal Signaling in the Columbia and Landsberg erecta Ecotypes of Arabidopsis.
H. Duan, M.-Y. Huang, K. Palacio, and M. A. Schuler (2005)
Plant Physiology 139, 1529-1544
   Abstract »    Full Text »    PDF »
Endogenous {alpha}-Ketol Linolenic Acid Levels in Short Day-Induced Cotyledons are Closely Related to Flower Induction in Pharbitis nil.
M. Suzuki, S. Yamaguchi, T. Iida, I. Hashimoto, H. Teranishi, M. Mizoguchi, F. Yano, Y. Todoroki, N. Watanabe, and M. Yokoyama (2003)
Plant Cell Physiol. 44, 35-43
   Abstract »    Full Text »    PDF »
Enzymes of the biosynthesis of octadecanoid-derived signalling molecules.
F. Schaller (2001)
J. Exp. Bot. 52, 11-23
   Abstract »    Full Text »    PDF »
Purification and Catalytic Activities of the Two Domains of the Allene Oxide Synthase-Lipoxygenase Fusion Protein of the Coral Plexaura homomalla.
O. Boutaud and A. R. Brash (1999)
J. Biol. Chem. 274, 33764-33770
   Abstract »    Full Text »    PDF »
Inhibition of Wound-Induced Accumulation of Allene Oxide Synthase Transcripts in Flax Leaves by Aspirin and Salicylic Acid.
K. Harms, I. Ramirez, and H. Peña-Cortés (1998)
Plant Physiology 118, 1057-1065
   Abstract »    Full Text »
Aspirin Inhibition and Acetylation of the Plant Cytochrome P450, Allene Oxide Synthase, Resembles that of Animal Prostaglandin Endoperoxide H Synthase.
Z. Pan, B. Camara, H. W. Gardner, and R. A. Backhaus (1998)
J. Biol. Chem. 273, 18139-18145
   Abstract »    Full Text »    PDF »
Specific Soybean Lipoxygenases Localize to Discrete Subcellular Compartments and Their mRNAs Are Differentially Regulated by Source-Sink Status.
L. C. Stephenson, T. W. Bunker, W. E. Dubbs, and H. D. Grimes (1998)
Plant Physiology 116, 923-933
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The Major Protein of Guayule Rubber Particles Is a Cytochrome P450.
Z. Pan, F. Durst, D. Werck-Reichhart, H. W. Gardner, B. Camara, K. Cornish, and R. A. Backhaus (1995)
J. Biol. Chem. 270, 8487-8494
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Molecular Cloning of Allene Oxide Cyclase. THE ENZYME ESTABLISHING THE STEREOCHEMISTRY OF OCTADECANOIDS AND JASMONATES.
J. Ziegler, I. Stenzel, B. Hause, H. Maucher, M. Hamberg, R. Grimm, M. Ganal, and C. Wasternack (2000)
J. Biol. Chem. 275, 19132-19138
   Abstract »    Full Text »    PDF »
Substrate Binding Is the Rate-limiting Step in Thromboxane Synthase Catalysis.
L.-H. Wang, A.-L. Tsai, and P.-Y. Hsu (2001)
J. Biol. Chem. 276, 14737-14743
   Abstract »    Full Text »    PDF »
A Novel Class of Oxylipins, sn1-O-(12-Oxophytodienoyl)-sn2-O-(hexadecatrienoyl)-monogalactosyl Diglyceride, from Arabidopsis thaliana.
B. A. Stelmach, A. Muller, P. Hennig, S. Gebhardt, M. Schubert-Zsilavecz, and E. W. Weiler (2001)
J. Biol. Chem. 276, 12832-12838
   Abstract »    Full Text »    PDF »


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