Structure-activity relationship of volatile compounds that induce defense-related genes in maize seedlings

References

• Zhou S, Jander G, Ort D. Molecular ecology of plant volatiles in interactions with insect herbivores. J Exp Bot. 2022;73(2):449–9. doi:10.1093/jxb/erab413.
   PubMed Web of Science ®Google Scholar
• Brosset A, Blande JD, Rosenkranz M. Volatile-mediated plant–plant interactions: volatile organic compounds as modulators of receiver plant defence, growth, and reproduction. J Exp Bot. 2022;73(2):511–528. doi:10.1093/jxb/erab487.
   PubMed Web of Science ®Google Scholar
• Karban R, Yang LH, Edwards KF. Volatile communication between plants that affects herbivory: a meta-analysis. Ecol Lett. 2014;17(1):44–52. doi:10.1111/ele.12205.
   PubMed Web of Science ®Google Scholar
• Matsui K, Engelberth J. Green leaf volatiles—the forefront of plant responses against biotic attack. Plant Cell Physiol. 2022;63(10):1378–1390. doi:10.1093/pcp/pcac117.
   PubMed Web of Science ®Google Scholar
• Tanaka T, Ikeda A, Shiojiri K, Ozawa R, Shiki K, Nagai-Kunihiro N, Fujita K, Sugimoto K, Yamato KT, Dohra H, et al. Identification of a hexenal reductase that modulates the composition of green leaf volatiles. Plant Physiol. 2018;178(2):552–564. doi:10.1104/pp.18.00632.
   PubMed Web of Science ®Google Scholar
• D’Auria JC, Pichersky E, Schaub A, Hansel A, Gershenzon J. Characterization of a BAHD acyltransferase responsible for producing the green leaf volatile (Z)-3-hexen-1-yl acetate in Arabidopsis thaliana. Plant J. 2007;49(2):194–207. doi:10.1111/j.1365-313X.2006.02946.x.
   PubMed Web of Science ®Google Scholar
• Shiojiri K, Kishimoto K, Ozawa R, Kugimiya S, Urashimo S, Arimura G, Horiuchi J, Nishika T, Matsui K, Takabayashi J. Changing green leaf volatile biosynthesis in plants: an approach for improving plant resistance against both herbivores and pathogens. Proc Natl Acad Sci USA. 2006;103(45):16672–16676. doi:10.1073/pnas.0607780103.
   PubMed Web of Science ®Google Scholar
• Sugimoto K, Matsui K, Iijima Y, Akakabe Y, Muramoto S, Ozawa R, Uefune M, Sasaki R, Alamgir KM, Akitake S, et al. Intake and transformation to a glycoside of (Z)-3-hexenol from infested neighbors reveals a mode of plant odor reception and defense. Proc Natl Acad Sci USA. 2014;111(19):7144–7149. doi:10.1073/pnas.1320660111.
   PubMed Web of Science ®Google Scholar
• Sugimoto K, Ono E, Inaba T, Tsukahara T, Matsui K, Horikawa M, Toyonaga H, Fujikawa K, Osawa T, Homma S, et al. Identification of a tomato UDP-arabinosyltransferase for airborne volatile reception. Nat Commun. 2023;14:677. doi:10.1038/s41467-023-36381-8.
   PubMed Web of Science ®Google Scholar
• Hu L, Zhang K, Wu Z, Xu J, Erb M. Plant volatiles as regulators of plant defense and herbivore immunity: molecular mechanisms and unanswered questions. Curr Opin Plant Biol. 2021;44:82–88. doi:10.1016/j.cois.2021.03.010.
   Google Scholar
• Zebelo SA, Matsui K, Ozawa R, Maffei ME. Plasma membrane potential depolarization and cytosolic calcium flux are early events involved in tomato (Solanum lycopersicon) plant-to-plant communication. Plant Sci. 2012;196:93–100. doi:10.1016/j.plantsci.2012.08.006.
   PubMed Web of Science ®Google Scholar
• Engelberth J, Contreras CF, Dalvi C, Li T, Engelberth M, Heil M. Early transcriptome analyses of Z-3-hexenol-treated Zea mays revealed distinct transcriptional networks and anti-herbivore defense potential of green leaf volatiles. PLoS One. 2013;8(10):e77465. doi:10.1371/journal.pone.0077465.
   PubMed Web of Science ®Google Scholar
• Yamauchi Y, Kunishima M, Mizutani M, Sugimoto Y. Reactive short-chain leaf volatiles act as powerful inducers of abiotic stress-related gene expression. Sci Rep. 2015;5:8030. doi:10.1038/srep08030.
   PubMed Web of Science ®Google Scholar
• Alméras E, Stolz S, Vollenweider S, Reymond P, Méne-Saffrané L, Farmer EE. Reactive electrophile species activate defense gene expression in Arabidopsis. Plant J. 2003;34(2):205–216. doi:10.1046/j.1365-313X.2003.01718.x.
   PubMed Web of Science ®Google Scholar
• Matsui K, Sugimoto K, Mano J, Ozawa R, Takabayashi J, Bonaventure G. Differential metabolisms of green leaf volatiles in injured and intact parts of a wounded leaf meet distinct ecophysiological requirement. PLoS One. 2012;7(4):e36433. doi:10.1371/journal.pone.0036433.
   PubMed Web of Science ®Google Scholar
• Ameye M, Allmann S, Verwaeren J, Smagghe G, Haesaert G, Schuurink RC, Audenaert K. Green leaf volatile production by plants: a meta-analysis. New Phytol. 2018;220(3):666–683. doi:10.1111/nph.14671.
   PubMed Web of Science ®Google Scholar
• Hu L, Ye M, Erb M. Integration of two herbivore-induced plant volatiles results in synergistic effects on plant defence and resistance. Plant, Cell & Environ. 2019;42(3):959–971. doi:10.1111/pce.13443.
   PubMed Web of Science ®Google Scholar
• Widhalm JR, Shih ML, Morgan JA, Dudareva N. Two-way communication: volatile emission and uptake occur through the same barriers. Mol Plant. 2023;16(1):1–3. doi:10.1016/j.molp.2022.11.006.
   PubMed Web of Science ®Google Scholar
• Matsui M, Furuhata A, Tade H, Hayashi K. 1979. 3-Hexynyl and cis-3-hexenyl ethers, their preparation and use. JPS5412309. (in Japanese).
   Google Scholar
• Erb M, Veyrat N, Robert CA, Xu H, Frey M, Ton J, Turlings TCJ. Indole is an essential herbivore-induced volatile priming signal in maize. Nat Commun. 2015;6(1):6273. doi:10.1038/ncomms7273.
   PubMedGoogle Scholar
• Engelberth J, Alborn HA, Schmelz EA, Tumlinson JH. Airborne signals prime plants against insect herbivore attack. Proc Natl Acad Sci USA. 2004;101(6):1781–1785. doi:10.1073/pnas.0308037100.
   PubMed Web of Science ®Google Scholar
• Nagashima A, Higaki T, Koeduka T, Ishigami K, Hosokawa S, Watanabe H, Matsui K, Hasezawa S, Touhara K. Transcriptional regulators involved in responses to volatile organic compounds in plants. J Biol Chem. 2019;294(7):2256–2266. doi:10.1074/jbc.RA118.005843.
   PubMed Web of Science ®Google Scholar
• von Merey G, Veyrat N, Mahuku G, Valdez RL, Turlings TCJ, D’Alessandro M. Dispensing synthetic green leaf volatiles in maize fields increases the release of sesquiterpenes by the plants, but has little effect on the attraction of pest and beneficial insects. Phytochemistry. 2011;72(14–15):1838–1847. doi:10.1016/j.phytochem.2011.04.022.
   PubMed Web of Science ®Google Scholar
• Farag MA, Foker M, Abd H, Zhang H, Allen RD, Paré PW. (Z)-3-Hexenol induces defense genes and downstream metabolites in maize. Planta. 2005;220(6):900–909. doi:10.1007/s00425-004-1404-5.
   PubMed Web of Science ®Google Scholar
• Ton J, D’Alessandro M, Jourdie V, Jakab G, Karlen D, Held M, Mauch-Mani B, Turlings TCJ. Priming by airborne signals boosts direct and indirect resistance in maize. Plant J. 2007;49(1):16–26. doi:10.1111/j.1365-313X.2006.02935.x.
   PubMed Web of Science ®Google Scholar
• Cofer TM, Erb M, Tumlinson JH. The Arabidopsis thaliana carboxyesterase AtCXE12 converts volatile (Z)-3-hexenyl acetate to (Z)-3-hexenol. bioRxiv. 2023. doi:10.1101/2023.03.14.532512.
   Google Scholar
• Goulet C, Mageroy MH, Lam NB, Floystad A, Tieman DM, Klee HJ. Role of an esterase in flavor volatile variation within the tomato clade. Proc Natl Acad Sci USA. 2012;109(46):19009–19014. doi:10.1073/pnas.1216515109.
   PubMed Web of Science ®Google Scholar
• Gershater M, Sharples K, Edwards R. Carboxyesterase activities toward pesticide esters in crops and weeds. Phytochemistry. 2006;67(23):2561–2567. doi:10.1016/j.phytochem.2006.09.019.
   PubMed Web of Science ®Google Scholar
• Heil M, Lion U, Boland W. Defense-inducing volatiles: In search of the active motif. J Chem Ecol. 2008;34(5):601–604. doi:10.1007/s10886-008-9464-9.
   PubMed Web of Science ®Google Scholar
• Engelberth J. Selective inhibition of jasmonic acid accumulation by a small α,β-unsaturated carbonyl and phenidone reveals different modes of octadecanoid signalling activation in response to insect elicitors and green leaf volatiles in Zea mays. BMC Res Notes. 2011;4:377. doi:10.1186/1756-0500-4-377.
   PubMedGoogle Scholar
• Grahovac J, Pajcin I, Vlajkov V. Bacillus VOCs in the context of biological control. Antibiotics. 2023;12:581. doi:10.3390/antibiotics12030581.
   Google Scholar
• Liao P, Maoz I, Shih ML, Lee JH, Huang XQ, Morgan JA, Dudareva N. Emission of floral volatiles is facilitated by cell wall non-specific lipid transfer proteins. Nat Commun. 2023;14(1):330. doi:10.1038/s41467-023-36027-9.
   PubMed Web of Science ®Google Scholar
• Sugimoto K, Matsui K, Takabayashi J. Conversion of volatile alcohols into their glucosides in Arabidopsis. Commun Integr Biol. 2015;8(1):e992731. doi:10.4161/19420889.2014.992731.
   PubMedGoogle Scholar
• Li Z, Hao P, Li L, Tna CYJ, Cheng X, Chen GYJ, Sze SK, Shen HM, Yao SQ. Design and synthesis of minimalist terminal alkyne-containing diazirine photo-crosslinkers and their incorporation into kinase inhibitors for cell- and tissue-based proteome profiling. Angew Chem Int Ed Engl. 2013;52(33):8551–8556. doi:10.1002/anie.201300683.
   PubMed Web of Science ®Google Scholar