Wounding stimulates the accumulation of glycerolipids containing oxophytodienoic acid and dinor-oxophytodienoic acid in Arabidopsis leaves. Plant Physiol

Division of Biology, Kansas State University, Manhattan, 66506, USA.
Plant physiology (Impact Factor: 6.84). 10/2006; 142(1):28-39. DOI: 10.1104/pp.106.082115
Source: PubMed


Although oxylipins can be synthesized from free fatty acids, recent evidence suggests that oxylipins are components of plastid-localized polar complex lipids in Arabidopsis (Arabidopsis thaliana). Using a combination of electrospray ionization (ESI) collisionally induced dissociation time-of-flight mass spectrometry (MS) to identify acyl chains, ESI triple-quadrupole (Q) MS in the precursor mode to identify the nominal masses of complex polar lipids containing each acyl chain, and ESI Q-time-of-flight MS to confirm the identifications of the complex polar lipid species, 17 species of oxylipin-containing phosphatidylglycerols, monogalactosyldiacylglycerols (MGDG), and digalactosyldiacylglycerols (DGDG) were identified. The oxylipins of these polar complex lipid species include oxophytodienoic acid (OPDA), dinor-OPDA (dnOPDA), 18-carbon ketol acids, and 16-carbon ketol acids. Using ESI triple-Q MS in the precursor mode, the accumulation of five OPDA- and/or dnOPDA-containing MGDG and two OPDA-containing DGDG species were monitored as a function of time in mechanically wounded leaves. In unwounded leaves, the levels of these oxylipin-containing complex lipid species were low, between 0.001 and 0.023 nmol/mg dry weight. However, within the first 15 min after wounding, the levels of OPDA-dnOPDA MGDG, OPDA-OPDA MGDG, and OPDA-OPDA DGDG, each containing two oxylipin chains, increased 200- to 1,000-fold. In contrast, levels of OPDA-hexadecatrienoic acid MGDG, linolenic acid (18:3)-dnOPDA MGDG, OPDA-18:3 MGDG, and OPDA-18:3 DGDG, each containing a single oxylipin chain, rose 2- to 9-fold. The rapid accumulation of high levels of galactolipid species containing OPDA-OPDA and OPDA-dnOPDA in wounded leaves is consistent with these lipids being the primary products of plastidic oxylipin biosynthesis.

Download full-text


Available from: Ruth Welti,
  • Source
    • "Moreover, the accumulation of these hydroxy-oxylipins occurred concomitantly with the oxidative burst, as found in L. digitata (Küpper et al. 2009). These authors further illustrated that although it is not known whether the oxidation of PUFAs occurs after or before their release from membranes, the latter possibility is more pronounced as LOX isoforms that oxidizes PUFAs attached to lipids, such as MGDG, DGDG, PG and PC, are already reported in higher plants (Buseman et al. 2006, Vu et al. 2011). The untargeted profiling of oxidized lipids may help in gaining insight in this regard in macroalgae. "
    [Show abstract] [Hide abstract]
    ABSTRACT: The role of exogenously added methyl jasmonate (MeJA), a lipid-derived signaling compound, in inducing oxidative stress in the marine red macroalga Gracilaria dura was investigated. MeJA at a concentration of 1-100 µM was a strong stimulant of reactive oxygen species (H2O2, HO· and O(2) (·-)) (P < 0.05) causing considerable oxidative stress in G. dura. This further led to lipid peroxidation and degradation of the pigments Chl a and phycocyanin, with a concomitant increase in phycoerythrin. The MeJA-induced oxidative burst also led to the induction of a fatty acid oxidation cascade, resulting in the synthesis of hydroxy-oxylipins and the up-regulation of the 13-lipoxygenase pathway. Electrospray ionization-mass spectrometry-based shotgun lipidomic analysis revealed that monogalactosyldiacylglycerol (a chloroplastic glycerolipid) and phosphatidylcholine (extrachloroplastidic phopholipid) were the most affected lipid classes. The degradation of 18:3-fatty acid-containing monogalactosyldiacylglycerol inferred that it provided fatty acyl chains for the biosynthesis of 13-hydroperoxylinolenic acid, which was further directed towards either the jasmonate pathway or other alternative pathways of the fatty acid oxidation cascade, analogous to higher plants. Also, G. dura modulated the lipid acyl chains in such a way that no significant change was observed in the fatty acid profile of the treated thalli as compared with those of the control, except for C16:0, C16:1 (n-9), C20:3 (n-6) and C20:4 (n-6) (P < 0.05). Furthermore, MeJA caused the accumulation of phenolic compounds and the up-regulation of enzymes involved in secondary metabolism such as polyphenol oxidase, shikimate dehydrogenase and phenylalanine ammonia-lyase, indicating a shift towards secondary metabolism as a defense strategy to combat the induced oxidative stress.
    Plant and Cell Physiology 08/2015; DOI:10.1093/pcp/pcv115 · 4.93 Impact Factor
  • Source
    • "Mono-and digalactosyldiacylglycerols (MGDG and DGDG) that contain OPDA and/or 12- oxodinorphytodienoic acid (a 16-carbon analog of OPDA) (collectively known as arabidopsides) have been identified in Arabidopsis (Buseman et al. 2006; Stelmach et al. 2001) (Figure 3). Phospholipids and galactolipids containing divinyl ether residues (linolipins) (Figure 3) have also been found in potato tubers and flax seedlings, respectively (Chechetkin et al. 2009; Fauconnier et al. 2003). "
    [Show abstract] [Hide abstract]
    ABSTRACT: Green leaf volatiles (GLVs) are six-carbon volatile compounds. They are formed from fatty acids by a dioxygenation reaction catalyzed by lipoxygenase and a subsequent cleavage reaction catalyzed by hydroperoxide lyase. GLVs are involved in direct and indirect plant defense against herbivores and pathogens. In intact plant tissues, GLVs are usually present at low concentrations, but upon wounding, GLVs are synthesized rapidly: within seconds to minutes. It has been hypothesized that this ‘GLV burst’ is supported by activation of pre-existing enzymes on endogenous substrates; however, the detailed mechanism of the GLV burst has not been elucidated. Recently, we found that a certain portion of GLVs is formed without liberation of free fatty acids from lipids. Accordingly, we hypothesized that lipoxygenase plays an essential role in the GLV burst. In particular, direct oxygenation by lipoxygenase on membrane lipids seems to be responsible. Lipoxygenase is also a target for controlling GLV levels in food derived from plants.
    Plant Biotechnology 12/2014; 31(5):445-452. DOI:10.5511/plantbiotechnology.14.0924a · 0.87 Impact Factor
  • Source
    • "escribed as free oxylipins ( Bohlmann et al . , 1982 , 1983 ; Ohashi et al . , 2005 ; Tamayo - Castillo et al . , 1989 ; Zdero et al . , 1991 ) , as oxylipins esterified with a number of other mole - cules in the cell , like glycerolipids ( glycolipids , phospholipids , and neutral lipids ) ( Andersson et al . , 2006 ; Bottcher and Weiler , 2007 ; Buseman et al . , 2006 ; Göbel and Feussner , 2009 ; Stelmach et al . , 2001 ) , and oxylipins conjugated to amino acids and other metabolites , such as sulfate , glutathione , ethanolamine , and carbo - hydrates ( Mosblech et al . , 2009 ) . The compounds present in the exudate material of S . adenophora were free oxylipins . Compound 5 was isolated as an am"
    [Show abstract] [Hide abstract]
    ABSTRACT: From the aerial parts of Salvia adenophora Fernald four derivatives of 12-oxo-phytodienoic acid (1-4) together with five clerodane diterpenoids (5, 6, 8-10), and one known diterpene (7) have been isolated. Compounds 1-6 and 8-10 are described for the first time. The structures were established by extensive 1D, 2D NMR and HRESI-TOFMS spectroscopic methods. Finally, the absolute configuration has been established by comparing of experimental and quantum chemical calculation of ECD spectra. Despite a total lack of antimicrobial activity of the plant extract, hinting to the existence of antagonistic interactions in the crude material, three oxylipins (2-4) displayed a promising inhibition on Gram-positive multidrug-resistant clinical strains including Staphylococcus aureus, Streptococcus agalactiae and, particularly, Staphylococcus epidermidis, while the compounds 9 and 10 revealed a specific and strain-dependent activity against S. epidermidis. Interestingly, the inhibition provided by these compounds was independent of the resistance patterns of these pathogens to classic antibiotics. No action was reported on Gram-negative strains nor on Candida albicans. These results confirm that clerodanes and, particularly, prostaglandin-like compounds can be considered as interesting antimicrobial agents deserving further study. Copyright © 2014 Elsevier Ltd. All rights reserved.
    Phytochemistry 11/2014; 110. DOI:10.1016/j.phytochem.2014.10.033 · 2.55 Impact Factor
Show more