2-hexenal--z-isomer and methyl-jasmonate

The medicinal herbal plant Achyranthes bidentata (A. bidentata) produces the sweet-odor ester - methyl (E)-2-hexenoate (1) as the major volatile in response to methyl jasmonate (MeJA). Here, we investigated the biosynthetic pathway of methyl (E)-2-hexenoate (1). The common plant precursor (Z)-3-hexenal was only slightly metabolized into methyl (E)-2-hexenoate (1), and its application scarcely enhanced the production of this ester. By contrast, a structurally related alcohol, (Z)-2-hexenol, as well as a deuteride derivative thereof could be efficiently metabolized into methyl (E)-2-hexenoate (1). Thus, we hypothesize that A. bidentata possess a specific pathway for the production of methyl (E)-2-hexenoate (1) from (Z)-2-hexenol in response to MeJA.

Topics: Acetates; Achyranthes; Aldehydes; Cyclopentanes; Esters; Isoleucine; Oxylipins; Plants, Medicinal

Plant injuries activate signal transduction cascades mediated by the plant hormones, which lead to enhanced expression of defence related genes and/or to changes in the emission of volatile organic compounds that can act as semiochemicals. In this research we demostrated that infection with the biotrophic pathogen Golovinomyces cichoracearum (DC.) V.P. Heluta (ex Erysiphe cichoracearum DC.), the causal agent of powdery mildew, led in the susceptible host Nicotiana tabacum L. cv Havana 425 to an increased emission of volatile compounds including Methyl-jasmonate (MeJA), (E)-2-hexenal and (E)-β-ocimene. Furthermore we investigated the role of these volatiles in the plant-pathogen interaction. Exogenous application of MeJA induced in tobacco an increase in the transcripts level of the defence related genes lipoxygenase, allene oxide cyclase and defensin and a decrease in the severity of the infection. Qualitative and quantitative differences in volatile compounds emission were showed also in MeJA-treated plants, where the emission of (E)-β-ocimene was significantly increased instead (E)-2-hexenal was not detected. Application of (E)-2-hexenal reduced the severity of powdery mildew while application of (E)-β-ocimene did not. Since (E)-2-hexenal did not activate in tobacco the accumulation of the above reported genes transcripts and the plant cell death, the reduction of the infection severity could be attributable to its inhibitory activity on the fungal germ tube growth. Our data highlight the contributions of natural substances that can act, directly or indirectly, against phytopathogens. In the global context of sustainability, food safety and environmental protection, such semiochemicals represent an alternative and promising approach to integrated pest management.

Topics: Acetates; Acyclic Monoterpenes; Aldehydes; Alkenes; Anti-Infective Agents; Ascomycota; Cyclopentanes; Defensins; Gene Expression Regulation, Plant; Host-Pathogen Interactions; Intramolecular Oxidoreductases; Lipoxygenase; Nicotiana; Oils, Volatile; Oxylipins; Plant Diseases; Plant Growth Regulators; Plant Immunity; Plant Leaves; Plant Oils; Plant Proteins; Signal Transduction; Time Factors

Plants emit green leaf volatiles (GLVs) in response to insect or pathogen damage. GLVs consist of C6 and C9 aldehydes, alcohols, and their acetate esters, and play important roles in the plant defense response. One of the functions of GLVs in the defense response is priming. Plants pretreated by GLVs can induce a defense response more rapidly and effectively than unpretreated plants when they are damaged by pathogens or insects. In this study, we focused on the priming effects of GLVs on jasmonic acid response involved in the defense response. When Arabidopsis was pretreated with aldehyde GLVs, especially with (E)-2-hexenal, the anthocyanin content was significantly increased by a subsequent methyl jasmonate (MeJA) treatment. On the other hand, no effect of anthocyanin accumulation was observed for plants pretreated with alcohol GLVs. These results suggest that aldehyde GLVs, especially (E)-2-hexenal, could enhance sensitivity to MeJA in Arabidopsis.

Topics: Acetates; Alcohols; Aldehydes; Anthocyanins; Arabidopsis; Cyclopentanes; Hexobarbital; Oxylipins; Plant Leaves; Volatile Organic Compounds

Alcohol acyltransferases (AATs) are key enzymes in ester biosynthesis. Previous studies have found that AAT may be a stress-related gene. To investigate further the function of the apple alcohol acyltransferase gene (MdAAT2), transgenic tobacco plants overexpressing MdAAT2 were generated. Gas chromatography-mass spectroscopy analysis showed that the volatile blends were altered in these transgenic tobacco leaves. Although no apple-fruity volatile esters were detected in transgenic tobacco leaves, methyl caprylate, methyl caprate, and methyl dodecanoate were newly generated, and the concentrations of methyl benzoate and methyl tetradecanoate were significantly increased, suggesting that MdAAT2 may use medium-chain fatty acyl CoA and benzoyl-CoA as acyl donors together with methanol acceptors as substrates. Surprisingly, the concentrations of linalool were significantly increased in transgenic tobacco leaves, which may mediate the repellent effect on Myzus persicae (Sulzer) aphids. Using methyl jasmonate (MeJA) and wounding treatments, we found that MdAAT2 may substitute for the partial ability of MeJA to induce the production of linalool in transgenic plants. These data suggest that MdAAT2 may be involved in the response to the MeJA signal and may play a role in the response to biotic and abiotic stress.

Topics: Acetates; Acyclic Monoterpenes; Acyltransferases; Aldehydes; Animals; Aphids; Cyclopentanes; Esters; Food Preferences; Gas Chromatography-Mass Spectrometry; Genes, Plant; Immunoblotting; Malus; Monoterpenes; Nicotiana; Oxylipins; Plant Leaves; Plants, Genetically Modified; Solid Phase Microextraction; Volatilization

Six-Carbon (C6-) volatiles, including the aldehydes trans-2-hexenal, hexanal and cis-3-hexenal, as well as their corresponding alcohols, are produced from damaged or wounded plant tissue as a product of the enzymatic activity of hydroperoxide lyase (HPL), a component of the lipoxygenase (LOX) pathway. Aerial treatment of Arabidopsis seedlings with 10 microM concentrations of trans-2-hexenal induces several genes known to be involved in the plant's defense response, including phenylpropanoid-related genes as well as genes of the LOX pathway. Genes encoding the pathogenesis-related proteins PR-1 or PR-2, however, were not induced. Trans-2-hexenal induction thus closely mimics the group of genes induced by methyl jasmonate (MeJA), also a LOX-derived volatile. However, unlike MeJA, trans-2-hexenal did not induce hydroxymethylglutaryl-coenzyme A reductase (HMGR) or thionin2-1. The inductive effect seemed to be limited to C6-related volatiles, as C8-, C9- and other related volatiles did not induce LOX mRNA levels. As has been demonstrated for MeJA, trans-2-hexenal quantitatively reduced wild-type seed germination. Trans-2-hexenal also reduced the germination frequency of the MeJA resistant Arabidopsis mutant, jar1-1, supporting the notion that trans-2-hexenal and MeJA are recognized via different mechanisms. In addition, trans-2-hexenal had a moderate inhibitory effect on root length relative to similar concentrations of MeJA and was approximately 10-fold less effective than MeJA at inducing anthocyanin accumulation in Arabidopsis seedlings. These results suggest that C6-volatiles of the LOX pathway act as a wound signal in plants, but result in a moderate plant response relative to MeJA at both the physiological and molecular level.

Topics: Acetates; Aldehydes; Anthocyanins; Arabidopsis; Base Sequence; Cyclopentanes; DNA Primers; Gene Expression Regulation, Plant; Genes, Plant; Hexanols; Lipoxygenase; Oxylipins; Signal Transduction