methyl-jasmonate and 3-hexen-1-ol

Vegetation emits a class of oxygenated hydrocarbons--the green leaf volatiles (GLVs)--under stress or damage. Under foggy conditions GLVs might be a source of secondary organic aerosol (SOA) via aqueous reactions with hydroxyl radical (OH), singlet oxygen ((1)O2*), and excited triplet states ((3)C*). To examine this, we determined the aqueous kinetics and SOA mass yields for reactions of (3)C* and (1)O2* with five GLVs: methyl jasmonate (MeJa), methyl salicylate (MeSa), cis-3-hexenyl acetate (HxAc), cis-3-hexen-1-ol (HxO), and 2-methyl-3-butene-2-ol (MBO). Second-order rate constants with (3)C* and (1)O2* range from (0.13-22) × 10(8) M(-1) s(-1) and (8.2-60) × 10(5) M(-1) s(-1) at 298 K, respectively. Rate constants with (3)C* are independent of temperature, while values with (1)O2* show significant temperature dependence (Ea = 20-96 kJ mol(-1)). Aqueous SOA mass yields for oxidation by (3)C* are (84 ± 7)%, (80 ± 9)%, and (38 ± 18)%, for MeJa, MeSa, and HxAc, respectively; we did not measure yields for other conditions because of slow kinetics. The aqueous production of SOA from GLVs is dominated by (3)C* and OH reactions, which form low volatility products at a rate that is approximately half that from the parallel gas-phase reactions of GLVs.

Topics: Acetates; Aerosols; Cyclopentanes; Hexanols; Hydroxyl Radical; Kinetics; Oxygen; Oxylipins; Pentanols; Plant Leaves; Salicylates; Singlet Oxygen; Temperature; Volatile Organic Compounds; Volatilization; Water

Green leaf volatiles (GLV), which are rapidly emitted by plants in response to insect herbivore damage, are now established as volatile defense signals. Receiving plants utilize these molecules to prime their defenses and respond faster and stronger when actually attacked. To further characterize the biological activity of these compounds we performed a microarray analysis of global gene expression. The focus of this project was to identify early transcriptional events elicited by Z-3-hexenol (Z-3-HOL) as our model GLV in maize (Zea mays) seedlings. The microarray results confirmed previous studies on Z-3-HOL -induced gene expression but also provided novel information about the complexity of Z-3-HOL -induced transcriptional networks. Besides identifying a distinct set of genes involved in direct and indirect defenses we also found significant expression of genes involved in transcriptional regulation, Ca(2+)-and lipid-related signaling, and cell wall reinforcement. By comparing these results with those obtained by treatment of maize seedlings with insect elicitors we found a high degree of correlation between the two expression profiles at this early time point, in particular for those genes related to defense. We further analyzed defense gene expression induced by other volatile defense signals and found Z-3-HOL to be significantly more active than methyl jasmonate, methyl salicylate, and ethylene. The data presented herein provides important information on early genetic networks that are activated by Z-3-HOL and demonstrates the effectiveness of this compound in the regulation of typical plant defenses against insect herbivores in maize.

Topics: Acetates; Animals; Cyclopentanes; Ethylenes; Gene Expression Profiling; Gene Expression Regulation, Plant; Gene Regulatory Networks; Genes, Plant; Herbivory; Hexanols; Oligonucleotide Array Sequence Analysis; Oxylipins; Plant Leaves; Reproducibility of Results; RNA, Messenger; Salicylates; Time Factors; Volatile Organic Compounds; Zea mays

In response to insect feeding, corn plants (Zea mays cv. Delprim) release elevated levels of volatile organic compounds (VOCs), including the C(6)-volatile (Z)-3-hexenol. The level of mRNA accumulation for a series of defense genes was monitored in response to application of (Z)-3-hexenol (50 nmol) to undamaged plants. The induction of transcripts for hpl (hydroperoxide lyase), fps (farnesyl pyrophosphate synthase), pal (phenylalanine ammonia-lyase), lox (lipoxygenase), igl (indole-3-glycerol phosphate lyase) and mpi (maize proteinase inhibitor) were compared with metabolites generated from the respective pathways. While headspace VOC analysis showed an increase in (Z)-3-hexenyl acetate and methyl salicylate with lox and pal induction, respectively, MPI accumulation was not observed with an increase in mpi transcripts. Moreover, (Z)-3-hexenol treatment did not elevate sesquiterpene emissions or activate fps transcription. Chemical labeling and bioassay experiments established that exogenous (Z)-3-hexenol can be taken up and converted to a less active acetylated form. These data indicate that (Z)-3-hexenol can serve as a signaling molecule that triggers defense responses in maize and can rapidly be turned over in planta.

Topics: Acetates; Animals; Blotting, Western; Cyclopentanes; Gene Expression Regulation, Plant; Hexanols; Indoles; Lipoxygenase; Oxylipins; Phenylalanine Ammonia-Lyase; Plant Diseases; Plant Proteins; RNA, Messenger; Sesquiterpenes; Signal Transduction; Spodoptera; Volatilization; Zea mays