Linoleic and linolenic acid hydroperoxides interact differentially with biomimetic plant membranes in a lipid specific manner

Deleu, Magali; Deboever, Estelle; Nasir, Mehmet Nail; Crowet, Jean-Marc; Dauchez, Manuel; Ongena, Marc; Jijakli, Haïssam; Fauconnier, Marie‐Laure; Lins, Laurence

doi:10.1016/j.colsurfb.2018.12.014

Cited by 18 publications

(45 citation statements)

References 64 publications

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“…Although hundreds of studies have investigated PO biosynthesis, to the best of our knowledge no studies have investigated the trafficking of POs at the subcellular level during pathogen attack, and it remains unclear how POs contact and interact with plant cells or pathogens after being released into cellular compartments. Recently, a study reported that HPOs can interact with biomimetic plant plasma membranes (PM) by modifying domains' lateral organisation, in a lipid-dependent manner [78]. The chemical structure and subsequent conformation of HPOs seems to be involved, thereby implicating a structure-activity relationship.…”

Section: Are Membranes Active Actors or Passive Filters In Po Biocidamentioning

confidence: 99%

Plant–Pathogen Interactions: Underestimated Roles of Phyto-oxylipins

Deboever

Deleu

Mongrand

et al. 2020

Trends in Plant Science

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Almost 30 years ago, the term 'oxylipin' (see Glossary) appeared in the literature and since then, publications on the topic have increased steadily. Oxylipins are found in almost all organisms and are present in free forms, esterified to phospholipids or galactolipids, or combined with other compounds (e.g., methyl groups, isoleucine) [1-10]. The precursors of oxylipin synthesis vary among organisms, as do the enzymes that will oxidise them. Because aerobic biological systems are continuously subject to autooxidation, oxylipins (e.g., phytoprostanes) are also produced through nonenzymatic routes in the presence of singlet oxygen or reactive oxygen species (ROS) [3,11-15]. Both pathways have been extensively reviewed. Figure 1 summarises the enzymatic production pathways of oxylipins (free forms) in mammals, fungi, and flowering plants (for detailed information see [8,13-21]).

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Section: Are Membranes Active Actors or Passive Filters In Po Biocidamentioning

confidence: 99%

Plant–Pathogen Interactions: Underestimated Roles of Phyto-oxylipins

Deboever

Deleu

Mongrand

et al. 2020

Trends in Plant Science

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“…The ΔΠ vs. Πi curves (data not shown) decreased linearly with increasing values of Π i , suggesting that a higher packing of lipid molecules at the air-water interface leads to a weaker adsorption of 13-HPOT into the monolayer, as observed for various amphiphilic molecules [24,49,50]. All the MIP values are higher than the lateral pressure supposed to prevail within biological membranes (30-35 mN/m) [68] ( Fig.…”

Section: Involvement Of Specific Lipids In Bpm − 13-hpot Interactionsmentioning

confidence: 77%

“…As many antibacterial molecules have proved their efficiency through specific membrane interactions [22,23], such behavior can be expected with phyto-oxylipins including 13-HPOT. Indeed, in a previous work based on HPOs interactions with plant biomimetic plasma membranes, we have demonstrated that 13-HPOT has more affinity for model bilayer and displays a faster adsorption kinetic as compared to 13-HPOD [24]. The presence of three double bonds seems to be the key structural trait as 13-HPOT has a higher biocidal effect in in vitro assays [17].…”

Section: Introductionmentioning

confidence: 85%

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Linolenic fatty acid hydroperoxide acts as biocide on plant pathogenic bacteria: Biophysical investigation of the mode of action

Deboever

Lins

Ongena

et al. 2020

Bioorganic Chemistry

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Fatty acid hydroperoxides (HPO) are free phyto-oxylipins known for their crucial role as signalling molecules during plant defense mechanisms. They were also demonstrated to have direct biocidal activities against plant pathogens including gram negative bacteria. In the present work, the biocidal effect of one linolenic fatty acid hydroperoxide, namely 13-HPOT has been investigated on three plant pathogen gram negative bacteria: Pectobacterium carotovorum, Pseudomonas syringae and Xanthomonas translucens. We showed that 13-HPOT has a strong dose response effect on those phytopathogens. In a second part, the molecular mechanism behind the antibacterial effect of 13-HPOT was investigated at a molecular level using an integrative biophysical approach combining in vitro and in silico methods. Since other antimicrobial amphiphilic molecules have been shown to target the lipid membrane of the organisms they act on, we focused our study on the interaction of 13-HPOT with biomimetic membranes. In a first step, we hypothesized that the inner membrane of the bacteria was the main site of action of 13-HPOT and hence we used lipids representative of this membrane to form our models. Our results indicated that 13-HPOT can interact with the lipid representative of the inner bacterial plasma membrane. A strong membrane insertion is suggested but no major permeabilization of the membrane is observed. Phosphatidylethanolamine (PE) and cardiolipin (CL), present in the bacterial plasma membrane, appear to play important roles in this interaction. We suggest that the mode of action of 13-HPOT should involve either subtle changes in membrane properties, such as its lateral organization and distribution, and/or interactions with membrane proteins.

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“…These experiments have also shown that different oxylipins and their stereoisomers have distinct biological activities against pathogens 4 . Moreover, it was recently reported that some oxylipin-like fatty acid hydroperoxides interact with plant plasma membrane lipids in vitro and can modify the plasma membrane organization 10 . All these reported insights highlight the crucial functions of plant oxylipins in defence responses and the likely role of these compounds in plant-pathogen interactions 4 .…”

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confidence: 99%

Simple liquid chromatography-electrospray ionization ion trap mass spectrometry method for the quantification of galacto-oxylipin arabidopsides in plant samples

Genva

Andersson

Fauconnier

2020

Sci Rep

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A simple and sensitive method to quantify five different arabidopsides by HPLC-ion trap mass spectrometry in complex plant samples was developed and validated. Arabidopsides are oxidized galactolipids first described in Arabidopsis thaliana but also produced by other plant species under stress conditions. External calibration was performed using arabidopsides purified from freezethawed Arabidopsis leaves. Lipids were extracted and pre-purified on an SPE silica column before HPLC-MS analysis. Arabidopsides were separated on a C18 column using a gradient of mQ water and acetonitrile:mQ water (85:15) supplemented with formic acid (0.2%) and ammonium formate (12 mM). The method was validated according to European commission decision 2002/657/CE. LOD, LOQ, linearity, intra-day and inter-day precision and accuracy, selectivity, matrix effects and recoveries were determined for the five metabolites. The established method is highly selective in a complex plant matrix. LOD and LOQ were, respectively, in the range 0.098-0.78 and 0.64-1.56 µM, allowing the arabidopside quantification from 25.6-62.4 nmol/g fresh weight. Calibration curve correlation coefficients were higher than 0.997. Matrix effects ranged from-2.09% to 6.10% and recoveries between 70.7% and 109%. The method was successfully applied to complex plant matrixes: Arabidopsis thaliana and Nasturtium officinale. Oxylipins are structurally diverse plant metabolites produced following the oxidation of unsaturated fatty acids and include aldehydes, divinyl ethers, oxo-, keto-, hydroxyl-and hydroperoxy acids 1-3. These molecules play crucial roles in plants, as they are involved in developmental processes and defence responses 4. Among the different families of plant oxylipins, jasmonates comprise all molecules formed after α-linolenic and hexadecatrienoic acids enzymatic transformation into jasmonic acid and its wide range of derivatives. Indeed, jasmonic acid can be converted by many metabolic pathways into different active, inactive or partially active compounds, showing the high complexity of the jasmonate pathways. Those ubiquitous plant metabolites have been studied for many years, as both jasmonic acid derivatives and some of its precursors modulate plant gene expression, leading in crucial modifications in plant developmental, physiological and defence processes 5. As examples, jasmonic acid derivatives and its precursors are directly implicated in flower development, leaf senescence, seed maturation, the attraction of insects for pollination and defence against herbivores 3-5. Besides functions as signals in planta, in vitro experiments showed high antimicrobial activities of various oxylipins against diverse pathogens: bacteria,

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Linoleic and linolenic acid hydroperoxides interact differentially with biomimetic plant membranes in a lipid specific manner

Cited by 18 publications

References 64 publications

Plant–Pathogen Interactions: Underestimated Roles of Phyto-oxylipins

Plant–Pathogen Interactions: Underestimated Roles of Phyto-oxylipins

Linolenic fatty acid hydroperoxide acts as biocide on plant pathogenic bacteria: Biophysical investigation of the mode of action

Simple liquid chromatography-electrospray ionization ion trap mass spectrometry method for the quantification of galacto-oxylipin arabidopsides in plant samples

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