Phytochemistry Reviews

, Volume 5, Issue 2–3, pp 347–357 | Cite as

Formation of oxylipins by CYP74 enzymes

  • Michael Stumpe
  • Ivo Feussner
Original Paper


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.


Allene oxide synthase Divinyl ether synthase Fatty acid hydroperoxides Hydroperoxide lyase Lipoxygenase 



Allene oxide cyclase


Allene oxide synthase


Divinyl ether synthase


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


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


Hydroperoxy linole(n)ic acid


Hydroperoxide lyase


Jasmonic acid


Keto linole(n)ic acid


Linoleic acid


Linolenic acid




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


Polyunsaturated fatty acids



The authors apologize to scientists whose work we overlooked or were not able to include because of length limitations. We are grateful for the constructive help of two anonymous reviewers. Our work was supported by the Deutsche Forschungsgemeinschaft and the European Community.


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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

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