Phytochemistry Reviews

, Volume 5, Issue 2, pp 347–357

Formation of oxylipins by CYP74 enzymes

Original Paper

DOI: 10.1007/s11101-006-9038-9

Cite this article as:
Stumpe, M. & Feussner, I. Phytochem Rev (2006) 5: 347. doi:10.1007/s11101-006-9038-9

Abstract

Lipid peroxidation is common to all biological systems, both appearing in developmentally and environmentally regulated processes. Products are hydroperoxy polyunsaturated fatty acids and metabolites derived there from collectively named oxylipins. They may either originate from chemical oxidation or are synthesized by the action of various enzymes, such as lipoxygenases. Cloning of many lipoxygenases and other key enzymes metabolizing oxylipins revealed new insights on oxylipin functions, new reactions and the first hints on enzyme mechanisms. These aspects are reviewed with respect to metabolism of fatty acid hydroperoxides by an atypical P450 subfamily: the CYP74. Up to now this protein family contains three different enzyme activities: (i) allene oxide synthase leading to the formation of unstable allene oxides which react to ketol and cyclopentenone fatty acids, (ii) hydroperoxide lyase producing hemiacetals decomposing to aldehydes and ω-oxo fatty acids and (iii) divinyl ether synthase which forms divinyl ethers. Signalling compounds such as jasmonates, antimicrobial and antifungal compounds such as leaf aldehydes or divinyl ethers, and a plant-specific blend of volatiles including leaf alcohols are among their numerous products.

Keywords

Allene oxide synthaseDivinyl ether synthaseFatty acid hydroperoxidesHydroperoxide lyaseLipoxygenase

Abbreviations

AOC

Allene oxide cyclase

AOS

Allene oxide synthase

DES

Divinyl ether synthase

9-HPOTE

(9S,10E,12Z,15Z)-9-Hydroperoxy-10,12,15-octadecatrienoic acid

13-HPOTE

(9Z,11E,13S,15Z)-13-Hydroperoxy-9,11,15-octadecatrienoic acid

HPO(D/T)E

Hydroperoxy linole(n)ic acid

HPL

Hydroperoxide lyase

JA

Jasmonic acid

KO(D/T)E

Keto linole(n)ic acid

LA

Linoleic acid

LeA

Linolenic acid

LOX

Lipoxygenase

OPDA

(9S,13S)-12-Oxo phytodienoic acid

PUFA

Polyunsaturated fatty acids

Copyright information

© Springer Science+Business Media B.V. 2006

Authors and Affiliations

  1. 1.Department of Plant Biochemistry, Albrecht-von-Haller-Institute for Plant SciencesGeorg-August-University GöttingenGöttingenGermany