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14 pages, 1705 KiB

Open AccessArticle

Wheat Oxylipins in Response to Aphids, CO₂ and Nitrogen Regimes

by Mari Merce Cascant-Vilaplana, Eduardo Viteritti, Víctor Sadras, Sonia Medina, María Puerto Sánchez-Iglesias, Camille Oger, Jean-Marie Galano, Thierry Durand, José Antonio Gabaldón, Julian Taylor, Federico Ferreres, Manuel Sergi and Angel Gil-Izquierdo

Molecules 2023, 28(10), 4133; https://doi.org/10.3390/molecules28104133 - 16 May 2023

Viewed by 2012

Abstract

Wheat is critical for food security, and is challenged by biotic stresses, chiefly aphids and the viruses they transmit. The objective of this study was to determine whether aphids feeding on wheat could trigger a defensive plant reaction to oxidative stress that involved plant oxylipins. Plants were grown in chambers with a factorial combination of two nitrogen rates (100% N vs. 20% N in Hoagland solution), and two concentrations of CO₂ (400 vs. 700 ppm). The seedlings were challenged with Rhopalosiphum padi or Sitobion avenae for 8 h. Wheat leaves produced phytoprostanes (PhytoPs) of the F₁ series, and three types of phytofurans (PhytoFs): ent-16(RS)-13-epi-ST-Δ¹⁴-9-PhytoF, ent-16(RS)-9-epi-ST-Δ¹⁴-10-PhytoF and ent-9(RS)-12-epi-ST-Δ¹⁰-13-PhytoF. The oxylipin levels varied with aphids, but not with other experimental sources of variation. Both Rhopalosiphum padi and Sitobion avenae reduced the concentrations of ent-16(RS)-13-epi-ST-Δ¹⁴-9-PhytoF and ent-16(RS)-9-epi-ST-Δ¹⁴-10-PhytoF in relation to controls, but had little or no effect on PhytoPs. Our results are consistent with aphids affecting the levels of PUFAs (oxylipin precursors), which decreased the levels of PhytoFs in wheat leaves. Therefore, PhytoFs could be postulated as an early indicator of aphid hosting for this plant species. This is the first report on the quantification of non-enzymatic PhytoFs and PhytoPs in wheat leaves in response to aphids. Full article

(This article belongs to the Special Issue Molecules in 2023)

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16 pages, 1659 KiB

Open AccessArticle

Exogenous Application of Salicylic Acid Modulates Oxidative Stress during the Seed Development of Rice (Oryza sativa L.) Grain

by María Pinciroli, Raúl Domínguez-Perles, Sonia Medina, Camille Oger, Alexandre Guy, Thierry Durand, Mari Merce Cascant-Vilaplana, José Antonio Gabaldón-Hernández, Federico Ferreres and Ángel Gil-Izquierdo

Agronomy 2023, 13(3), 636; https://doi.org/10.3390/agronomy13030636 - 23 Feb 2023

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Abstract

The present study aimed to discover the effects of exogenously foliar-applied salicylic acid (SA) in concentrations of 0, 1 and 15 mM (applied 7 and 21 days after heading) on oxidative stress. The effects were monitored through the concentrations of phytoprostanes (PhytoPs) and phytofurans (PhytoFs) in immature and mature grains of three genotypes of rice (‘R52’, ‘R45’ and ‘Yerua’), and their influence on grains per panicle and chalkiness. Chromatographic separation of PhytoPs and PhytoFs was performed using a UHPLC coupled to triple quadrupole-MS/MS (Agilent Technologies, Germany). The concentrations of oxylipins showed differences in both harvest times (immature and mature) for each genotype. The advanced lines, ‘R52’ and ‘R45’, showed concentrations that were 24.0 and 79.0% lower than those of the immature grains, respectively. The PhytoFs concentration in “R45” was 46.0% lower in the mature grains. In unripe grains, SA reduced a single oxylipin of all those analyzed, while in mature grains, a significant decrease in six of the ten monitored biomarkers was observed. The SA produced an increase in grains per panicle, and a decrease in chalkiness. Therefore, salicylic acid-mediated antioxidant regulatory capacities due to oxylipin down-regulation could favor grain filling and, hence, rice production. Full article

(This article belongs to the Special Issue Crop and Vegetable Physiology under Environmental Stresses)

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31 pages, 2915 KiB

Open AccessReview

Therapeutic Potential of Plant Oxylipins

by Tatyana Savchenko, Evgeny Degtyaryov, Yaroslav Radzyukevich and Vlada Buryak

Int. J. Mol. Sci. 2022, 23(23), 14627; https://doi.org/10.3390/ijms232314627 - 23 Nov 2022

Cited by 27 | Viewed by 4618

Abstract

For immobile plants, the main means of protection against adverse environmental factors is the biosynthesis of various secondary (specialized) metabolites. The extreme diversity and high biological activity of these metabolites determine the researchers’ interest in plants as a source of therapeutic agents. Oxylipins, oxygenated derivatives of fatty acids, are particularly promising in this regard. Plant oxylipins, which are characterized by a diversity of chemical structures, can exert protective and therapeutic properties in animal cells. While the therapeutic potential of some classes of plant oxylipins, such as jasmonates and acetylenic oxylipins, has been analyzed thoroughly, other oxylipins are barely studied in this regard. Here, we present a comprehensive overview of the therapeutic potential of all major classes of plant oxylipins, including derivatives of acetylenic fatty acids, jasmonates, six- and nine-carbon aldehydes, oxy-, epoxy-, and hydroxy-derivatives of fatty acids, as well as spontaneously formed phytoprostanes and phytofurans. The presented analysis will provide an impetus for further research investigating the beneficial properties of these secondary metabolites and bringing them closer to practical applications. Full article

(This article belongs to the Special Issue Metabolism and the Biological Functions of Oxylipins)

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13 pages, 3576 KiB

Open AccessArticle

Oxidized Products of α-Linolenic Acid Negatively Regulate Cellular Survival and Motility of Breast Cancer Cells

by Jorge L. Gutierrez-Pajares, Celine Ben Hassen, Camille Oger, Jean-Marie Galano, Thierry Durand and Philippe G. Frank

Biomolecules 2020, 10(1), 50; https://doi.org/10.3390/biom10010050 - 28 Dec 2019

Cited by 11 | Viewed by 4406

Abstract

Despite recent advances in our understanding of the biological processes leading to the development and progression of cancer, there is still a need for new and effective agents to treat this disease. Phytoprostanes (PhytoPs) and phytofurans (PhytoFs) are non-enzymatically oxidized products of α-linolenic acid that are present in seeds and vegetable oils. They have been shown to possess anti-inflammatory and apoptosis-promoting activities in macrophages and leukemia cells, respectively. In this work, seven PhytoPs (PP1–PP7) and one PhytoFs (PF1) were evaluated for their cytotoxic, chemosensitization, and anti-migratory activities using the MCF-7 and MDA-MB-231 breast cancer cell lines. Among the tested compounds, only three PhytoPs had a significant effect on cell viability compared to the control group: Ent-9-L₁-PhytoP (PP6) decreased cell viability in both cell lines, while 16-F_1t-PhytoP (PP1) and 9-L₁-PhytoP (PP5) decreased viability of MCF-7 and MDA-MB-231 cells, respectively. When combined with a sub-cytotoxic dose of doxorubicin, these three PhytoPs displayed significantly enhanced cytotoxic effects on MCF-7 cells while the chemotherapeutic drug alone had no effect. In cellular motility assays, Ent-9-(RS)-12-epi-ST-Δ¹⁰-13-PhytoF could significantly inhibit cellular migration of MDA-MB-231 cells. In addition, Ent-9-(RS)-12-epi-ST-Δ¹⁰-13-PhytoF also enhanced cellular adhesion of MDA-MB-231 cells. Full article

(This article belongs to the Special Issue Antitumor Agents from Natural Sources)

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19 pages, 1106 KiB

Open AccessReview

Structural/Functional Matches and Divergences of Phytoprostanes and Phytofurans with Bioactive Human Oxylipins

by Sonia Medina, Ángel Gil-Izquierdo, Thierry Durand, Federico Ferreres and Raúl Domínguez-Perles

Antioxidants 2018, 7(11), 165; https://doi.org/10.3390/antiox7110165 - 16 Nov 2018

Cited by 31 | Viewed by 4580

Abstract

Structure-activity relationship (SAR) constitutes a crucial topic to discover new bioactive molecules. This approach initiates with the comparison of a target candidate with a molecule or a collection of molecules and their attributed biological functions to shed some light in the details of one or more SARs and subsequently using that information to outline valuable application of the newly identified compounds. Thus, while the empiric knowledge of medicinal chemistry is critical to these tasks, the results retrieved upon dedicated experimental demonstration retrieved resorting to modern high throughput analytical approaches and techniques allow to overwhelm the constraints adduced so far to the successful accomplishment of such tasks. Therefore, the present work reviews critically the evidences reported to date on the occurrence of phytoprostanes and phytofurans in plant foods, and the information available on their bioavailability and biological activity, shedding some light on the expectation waken up due to their structural similarities with prostanoids and isoprostanes. Full article

(This article belongs to the Special Issue Lipid Peroxidation: Analysis and Applications in Biological Systems)

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