Volatile Oxylipins and Related Compounds Formed Under Stress in Plants

Matsui, Kenji; Sugimoto, Koh‐ichi; Kakumyan, Pattana; Khorobrykh, Sergey; Mano, Junichi

doi:10.1007/978-1-60761-325-1_2

Cited by 24 publications

(30 citation statements)

References 15 publications

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“…Carbonyls in the extract were derivatized with 2,4-dinitrophenylhydrazine, and the dinitrophenylhydrazone derivatives were extracted and analyzed by HPLC as described (Yin et al, 2010). We identified dinitrophenylhydrazone derivatives of carbonyls by their retention times and determined their contents by a comparison with authentic compounds (Matsui et al, 2009 BY-2 cells, collected with a brief centrifugation followed by a washing with distilled water, were incubated in 20 mM H 2 DCF diacetate (Molecular Probes) in PBS at 37°C for 30 min or 50 mM BES-H 2 O 2 -Ac (Wako Pure Chemical) for 30 min in darkness. The cells were washed twice with PBS.…”

Section: Detection and Quantification Of Carbonyls Using Hplcmentioning

confidence: 99%

Lipid Peroxide-Derived Short-Chain Carbonyls Mediate Hydrogen Peroxide-Induced and Salt-Induced Programmed Cell Death in Plants

2015

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Lipid peroxide-derived toxic carbonyl compounds (oxylipin carbonyls), produced downstream of reactive oxygen species (ROS), were recently revealed to mediate abiotic stress-induced damage of plants. Here, we investigated how oxylipin carbonyls cause cell death. When tobacco (Nicotiana tabacum) Bright Yellow-2 (BY-2) cells were exposed to hydrogen peroxide, several species of short-chain oxylipin carbonyls [i.e. 4-hydroxy-(E)-2-nonenal and acrolein] accumulated and the cells underwent programmed cell death (PCD), as judged based on DNA fragmentation, an increase in terminal deoxynucleotidyl transferase dUTP nick end labeling-positive nuclei, and cytoplasm retraction. These oxylipin carbonyls caused PCD in BY-2 cells and roots of tobacco and Arabidopsis (Arabidopsis thaliana). To test the possibility that oxylipin carbonyls mediate an oxidative signal to cause PCD, we performed pharmacological and genetic experiments. Carnosine and hydralazine, having distinct chemistry for scavenging carbonyls, significantly suppressed the increase in oxylipin carbonyls and blocked PCD in BY-2 cells and Arabidopsis roots, but they did not affect the levels of ROS and lipid peroxides. A transgenic tobacco line that overproduces 2-alkenal reductase, an Arabidopsis enzyme to detoxify a,b-unsaturated carbonyls, suffered less PCD in root epidermis after hydrogen peroxide or salt treatment than did the wild type, whereas the ROS level increases due to the stress treatments were not different between the lines. From these results, we conclude that oxylipin carbonyls are involved in the PCD process in oxidatively stressed cells. Our comparison of the ability of distinct carbonyls to induce PCD in BY-2 cells revealed that acrolein and 4-hydroxy-(E)-2-nonenal are the most potent carbonyls. The physiological relevance and possible mechanisms of the carbonyl-induced PCD are discussed.

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Section: Detection and Quantification Of Carbonyls Using Hplcmentioning

confidence: 99%

Lipid Peroxide-Derived Short-Chain Carbonyls Mediate Hydrogen Peroxide-Induced and Salt-Induced Programmed Cell Death in Plants

2015

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“…Because each oxylipin carbonyl has distinct chemical reactivity and hence toxicity Reynolds 1977), it is important to identify the chemial species and determine the amount of every carbonyl generated in the cells. To obtain detailed insights into the oxylipin carbonyl metabolism in plants, we previously established a HPLC analytical method (Matsui et al 2009). In this method, carbonyls extracted from plants are derivatized with 2,4-dinitrophenylhydrazine (DNPH), the resulting hydrazone are extracted, separated on a reverse-phase chromatography and determined with a ultraviolet detector.…”

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confidence: 99%

Acrolein is formed from trienoic fatty acids in chloroplast: A targeted metabolomics approach

Mano

Khorobrykh

Matsui

et al. 2014

Plant Biotechnology

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Aldehydes and ketones produced from lipid peroxides (oxylipin carbonyls) exhibit a variety of biological activities ranging from the induction of defense genes to the irreversible damage to cells. Short oxylipin carbonyls such as acrolein and (E)-2-pentenal are responsible for tissue injury under environmental stress, but their production mechanism remains unclear. In this study, we elucidated the source fatty acids of short oxylipin carbonyls in leaves. We first established a comprehensive analysis of oxylipin carbonyls for quantitation and structural estimation. Carbonyls were extracted from rosette leaves of Arabidopsis thaliana, derivatized with 2,4-dinitrophenylhydrazine and separated with a reverse-phase HPLC equipped with a photodiode array detector and an Fourier transform ion cyclotron resonance mass spectrometer. Thirty-three distinct carbonyls were detected, in which 19 species were identified on the MS/MS spectrum. Using this analysis system, we compared the carbonyl composition in the leaves between two A. thaliana lines that have different fatty acid composition. The mutant fad7fad8, which lacks the biosynthesis of trienoic fatty acids in the plastid, contained significantly lower amounts of malondialdehyde, acrolein and (E)-2-pentenal and higher amounts of acetone, 3-pentanone, and n-hexanal than the wild type Col-0. This difference in the carbonyl composition agreed with the oxidative degradation of dienoic and trienoic fatty acids in vitro, showing that similar non-enzymatic reactions occur in the thylakoid membrane. Consideration of the formation mechanism of acrolein from trienoic fatty acid suggests that membrane lipids in chloroplasts are constitutively oxidized by singlet oxygen.

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“…Six-carbon aldehydes formed after complete disruption of Arabidopsis leaves were quantified by HPLC after derivatization of the aldehydes with 2,4-dinitrophenylhydrazine, as described previously (32). Under these experimental conditions, (Z)-3-hexenal was the main product, accounting for ϳ85% of the GLVs formed (8).…”

Section: Methodsmentioning

confidence: 99%

Traumatin- and Dinortraumatin-containing Galactolipids in Arabidopsis

Nakashima

Reuß

Tasaka

et al. 2013

Journal of Biological Chemistry

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Background:The pathway to form green leaf volatiles is important for plant defense against pathogens and herbivores. Results: Galactolipids with truncated oxoacids are formed as counterparts of green leaf volatiles. Conclusion: Galactolipid-hydroperoxides are substrates for hydroperoxide lyase. Significance: The biosynthetic pathway partly proceeds directly with galactolipids, without the involvement of lipases, to form free fatty acids.

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Volatile Oxylipins and Related Compounds Formed Under Stress in Plants

Cited by 24 publications

References 15 publications

Lipid Peroxide-Derived Short-Chain Carbonyls Mediate Hydrogen Peroxide-Induced and Salt-Induced Programmed Cell Death in Plants

Lipid Peroxide-Derived Short-Chain Carbonyls Mediate Hydrogen Peroxide-Induced and Salt-Induced Programmed Cell Death in Plants

Acrolein is formed from trienoic fatty acids in chloroplast: A targeted metabolomics approach

Traumatin- and Dinortraumatin-containing Galactolipids in Arabidopsis

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