Isolation and stomatal opening activity of two oxylipins from Ipomoea tricolor

Ohashi, Teruhisa; Ito, Yoshinori; Okada, Masahiro; Sakagami, Youji

doi:10.1016/j.bmcl.2004.10.088

Cited by 26 publications

(23 citation statements)

References 9 publications

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“…In line with this observation, we found that β-CC led to an increase in the tolerance of Arabidopsis to a subsequent photooxidative stress treatment. Moreover, the β-CC-induced changes in gene expression were not accompanied by visible symptoms of toxicity (e.g., leaf necrosis) or by effects on photosynthetic electron transport or stomatal conductance, although the latter processes are known to be sensitive to RES (27,39). This observation confirms that the amounts of volatile β-CC that penetrated inside the leaves were low, as also inferred from the gene expression levels, which were less pronounced than expression levels induced by high light stress (compare Figs.…”

Section: Discussionmentioning

confidence: 99%

Carotenoid oxidation products are stress signals that mediate gene responses to singlet oxygen in plants

Ramel

Birtić

Giniès

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

609

665

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1 O 2 (singlet oxygen) is a reactive O 2 species produced from triplet excited chlorophylls in the chloroplasts, especially when plants are exposed to excess light energy. Similarly to other active O 2 species, 1 O 2 has a dual effect: It is toxic, causing oxidation of biomolecules, and it can act as a signal molecule that leads to cell death or to acclimation. Carotenoids are considered to be the main 1 O 2 quenchers in chloroplasts, and we show here that light stress induces the oxidation of the carotenoid β-carotene in Arabidopsis plants, leading to the accumulation of different volatile derivatives. One such compound, β-cyclocitral, was found to induce changes in the expression of a large set of genes that have been identified as 1 O 2 responsive genes. In contrast, β-cyclocitral had little effect on the expression of H 2 O 2 gene markers. β-Cyclocitral–induced reprogramming of gene expression was associated with an increased tolerance to photooxidative stress. The results indicate that β-cyclocitral is a stress signal produced in high light that is able to induce defense mechanisms and represents a likely messenger involved in the 1 O 2 signaling pathway in plants.

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Section: Discussionmentioning

confidence: 99%

Carotenoid oxidation products are stress signals that mediate gene responses to singlet oxygen in plants

Ramel

Birtić

Giniès

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

609

665

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“…Here an extra OPDA molecule is esterified to the galactosyl moiety in addition to the one at the sn 1 and sn 2 postion (Ara-G; note that in case of Ara-E, dnOPDA is esterified at the sn 2 position). Additionally, OPDA linked to monogalactosyl monoacylglycerol MGM was found in Ipomoea tricolor (heavenly blue; Ohashi et al, 2005). Besides the above described galactolipid species, one phospholipid, namely phosphatidylglycerol (PG) has also been demonstrated to contain OPDA esterified at the sn 1 position and hexadecenoic acid (16:1) or hexadecanoic acid (16:0) at sn 2 position (Buseman et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

The alphabet of galactolipids in Arabidopsis thaliana

Ibrahim¹

2011

Front. Plant Sci.

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Galactolipids constitute the major lipid class in plants. In recent years oxygenated derivatives of galactolipids have been detected. They are discussed as signal molecules during leaf damage, since they accumulate in wounded leaves in high levels. Using different analytical methods such as nuclear magnetic resonance, infra-red spectroscopy, and high performance liquid chromatography/mass spectrometry (HPLC/MS) earlier reports focused on the analysis of either oxidized or non-oxidized species and needed high levels of analytes. Here, we report on the analysis of the galactolipid subfraction of the Arabidopsis leaf lipidome by an improved HPLC/MS2-based method that is fast, robust, and comparatively simple in its performance. Due to a combination of phase partitioning, solid phase fractionation, liquid chromatography, and MS2 experiments this method has high detection sensitivity and requires only low amounts of plant material. With this method 167 galactolipid species were detected in leaves of Arabidopsis thaliana. Out of these 79 being newly described species. From all species the head group and acyl side chains were identified via MS2 experiments. Moreover, the structural identification was supported by HPLC/time-of-flight (TOF)-MS and gas chromatography (GC)/MS analysis. The quantification of different galactolipid species that accumulated 30 min after a mechanical wounding in A. thaliana leaves showed that the oxidized acyl side chains in galactolipids are divided into 65% cyclopentenones, 27% methyl-branched ketols, 3.8% hydroperoxides/straight-chain ketols, 2.0% hydroxides, and 2.6% phytoprostanes. In comparison to the free cyclopentenone derivatives, the esterified forms occur in a 149-fold excess supporting the hypothesis that galactolipids might function as storage compounds for cyclopentenones. Additional analysis of the ratio of non-oxidized to oxidized galactolipid species in leaves of wounded plants was performed resulting in a ratio of 2.0 in case of monogalactosyl diacylglycerol (MGD), 8.1 in digalactosyl diacylglycerol (DGD), and 0.6 in the acylated MGD. This indicates that galactolipid oxidation is a major and rapid metabolic process that occurs class specific.

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“…It was shown that OPDA was more active than JA in eliciting the tendril coiling response in Bryonia dioica (Blechert et al, 1999). More recently, OPDA was shown to induce stomatal opening (Ohashi et al, 2005). However, little is known about OPDA-dependent gene expression or other possible functions of OPDA.…”

mentioning

confidence: 99%

12-Oxo-Phytodienoic Acid Triggers Expression of a Distinct Set of Genes and Plays a Role in Wound-Induced Gene Expression in Arabidopsis

et al. 2005

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Jasmonic acid (JA) and methyl jasmonate (MeJA), collectively known as JAs, regulate diverse physiological processes in plants, including the response to wounding. Recent reports suggest that a cyclopentenone precursor of JA, 12-oxo-phytodienoic acid (OPDA), can also induce gene expression. However, little is known about the physiological significance of OPDA-dependent gene expression. We used microarray analysis of approximately 21,500 Arabidopsis (Arabidopsis thaliana) genes to compare responses to JA, MeJA, and OPDA treatment. Although many genes responded identically to both OPDA and JAs, we identified a set of genes (OPDA-specific response genes [ORGs]) that specifically responded to OPDA but not to JAs. ORGs primarily encoded signaling components, transcription factors, and stress response-related genes. One-half of the ORGs were induced by wounding. Analysis using mutants deficient in the biosynthesis of JAs revealed that OPDA functions as a signaling molecule in the wounding response. Unlike signaling via JAs, OPDA signaling was CORONATINE INSENSITIVE 1 independent. These results indicate that an OPDA signaling pathway functions independently of JA/MeJA signaling and is required for the wounding response in Arabidopsis.

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Isolation and stomatal opening activity of two oxylipins from Ipomoea tricolor

Cited by 26 publications

References 9 publications

Carotenoid oxidation products are stress signals that mediate gene responses to singlet oxygen in plants

Carotenoid oxidation products are stress signals that mediate gene responses to singlet oxygen in plants

The alphabet of galactolipids in Arabidopsis thaliana

12-Oxo-Phytodienoic Acid Triggers Expression of a Distinct Set of Genes and Plays a Role in Wound-Induced Gene Expression in Arabidopsis

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