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An Iron 13S-Lipoxygenase with an α-Linolenic Acid Specific Hydroperoxidase Activity from Fusarium oxysporum

Jasmonates constitute a family of lipid-derived signaling molecules that are abundant in higher plants. The biosynthetic pathway leading to plant jasmonates is initiated by 13-lipoxygenase-catalyzed oxygenation of α-linolenic acid into its 13-hydroperoxide derivative. A number of plant pathogenic fu...

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Autores principales: Brodhun, Florian, Cristobal-Sarramian, Alvaro, Zabel, Sebastian, Newie, Julia, Hamberg, Mats, Feussner, Ivo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3669278/
https://www.ncbi.nlm.nih.gov/pubmed/23741422
http://dx.doi.org/10.1371/journal.pone.0064919
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author Brodhun, Florian
Cristobal-Sarramian, Alvaro
Zabel, Sebastian
Newie, Julia
Hamberg, Mats
Feussner, Ivo
author_facet Brodhun, Florian
Cristobal-Sarramian, Alvaro
Zabel, Sebastian
Newie, Julia
Hamberg, Mats
Feussner, Ivo
author_sort Brodhun, Florian
collection PubMed
description Jasmonates constitute a family of lipid-derived signaling molecules that are abundant in higher plants. The biosynthetic pathway leading to plant jasmonates is initiated by 13-lipoxygenase-catalyzed oxygenation of α-linolenic acid into its 13-hydroperoxide derivative. A number of plant pathogenic fungi (e.g. Fusarium oxysporum) are also capable of producing jasmonates, however, by a yet unknown biosynthetic pathway. In a search for lipoxygenase in F. oxysporum, a reverse genetic approach was used and one of two from the genome predicted lipoxygenases (FoxLOX) was cloned. The enzyme was heterologously expressed in E. coli, purified via affinity chromatography, and its reaction mechanism characterized. FoxLOX was found to be a non-heme iron lipoxygenase, which oxidizes C(18)-polyunsaturated fatty acids to 13S-hydroperoxy derivatives by an antarafacial reaction mechanism where the bis-allylic hydrogen abstraction is the rate-limiting step. With α-linolenic acid as substrate FoxLOX was found to exhibit a multifunctional activity, because the hydroperoxy derivatives formed are further converted to dihydroxy-, keto-, and epoxy alcohol derivatives.
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spelling pubmed-36692782013-06-05 An Iron 13S-Lipoxygenase with an α-Linolenic Acid Specific Hydroperoxidase Activity from Fusarium oxysporum Brodhun, Florian Cristobal-Sarramian, Alvaro Zabel, Sebastian Newie, Julia Hamberg, Mats Feussner, Ivo PLoS One Research Article Jasmonates constitute a family of lipid-derived signaling molecules that are abundant in higher plants. The biosynthetic pathway leading to plant jasmonates is initiated by 13-lipoxygenase-catalyzed oxygenation of α-linolenic acid into its 13-hydroperoxide derivative. A number of plant pathogenic fungi (e.g. Fusarium oxysporum) are also capable of producing jasmonates, however, by a yet unknown biosynthetic pathway. In a search for lipoxygenase in F. oxysporum, a reverse genetic approach was used and one of two from the genome predicted lipoxygenases (FoxLOX) was cloned. The enzyme was heterologously expressed in E. coli, purified via affinity chromatography, and its reaction mechanism characterized. FoxLOX was found to be a non-heme iron lipoxygenase, which oxidizes C(18)-polyunsaturated fatty acids to 13S-hydroperoxy derivatives by an antarafacial reaction mechanism where the bis-allylic hydrogen abstraction is the rate-limiting step. With α-linolenic acid as substrate FoxLOX was found to exhibit a multifunctional activity, because the hydroperoxy derivatives formed are further converted to dihydroxy-, keto-, and epoxy alcohol derivatives. Public Library of Science 2013-05-31 /pmc/articles/PMC3669278/ /pubmed/23741422 http://dx.doi.org/10.1371/journal.pone.0064919 Text en © 2013 Brodhun et al http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are properly credited.
spellingShingle Research Article
Brodhun, Florian
Cristobal-Sarramian, Alvaro
Zabel, Sebastian
Newie, Julia
Hamberg, Mats
Feussner, Ivo
An Iron 13S-Lipoxygenase with an α-Linolenic Acid Specific Hydroperoxidase Activity from Fusarium oxysporum
title An Iron 13S-Lipoxygenase with an α-Linolenic Acid Specific Hydroperoxidase Activity from Fusarium oxysporum
title_full An Iron 13S-Lipoxygenase with an α-Linolenic Acid Specific Hydroperoxidase Activity from Fusarium oxysporum
title_fullStr An Iron 13S-Lipoxygenase with an α-Linolenic Acid Specific Hydroperoxidase Activity from Fusarium oxysporum
title_full_unstemmed An Iron 13S-Lipoxygenase with an α-Linolenic Acid Specific Hydroperoxidase Activity from Fusarium oxysporum
title_short An Iron 13S-Lipoxygenase with an α-Linolenic Acid Specific Hydroperoxidase Activity from Fusarium oxysporum
title_sort iron 13s-lipoxygenase with an α-linolenic acid specific hydroperoxidase activity from fusarium oxysporum
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3669278/
https://www.ncbi.nlm.nih.gov/pubmed/23741422
http://dx.doi.org/10.1371/journal.pone.0064919
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