{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T02:25:50Z","timestamp":1791944750927,"version":"4.3.4"},"reference-count":84,"publisher":"Oxford University Press (OUP)","issue":"1","license":[{"start":{"date-parts":[[2021,10,27]],"date-time":"2021-10-27T00:00:00Z","timestamp":1635292800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Max-Planck Society"},{"name":"the Swiss National Science Foundation","award":["160786"],"award-info":[{"award-number":["160786"]}]},{"name":"US Department of Agriculture, National Institute of Food and Agriculture","award":["2018-67013-28125"],"award-info":[{"award-number":["2018-67013-28125"]}]},{"name":"National Science Foundation, Plant\u2013Biotic Interactions Program","award":["1758976"],"award-info":[{"award-number":["1758976"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2022,1,20]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Fungal infection of grasses, including rice (Oryza sativa), sorghum (Sorghum bicolor), and barley (Hordeum vulgare), induces the formation and accumulation of flavonoid phytoalexins. In maize (Zea mays), however, investigators have emphasized benzoxazinoid and terpenoid phytoalexins, and comparatively little is known about flavonoid induction in response to pathogens. Here, we examined fungus-elicited flavonoid metabolism in maize and identified key biosynthetic enzymes involved in the formation of O-methylflavonoids. The predominant end products were identified as two tautomers of a 2-hydroxynaringenin-derived compound termed xilonenin, which significantly inhibited the growth of two maize pathogens, Fusarium graminearum and Fusarium verticillioides. Among the biosynthetic enzymes identified were two O-methyltransferases (OMTs), flavonoid OMT 2 (FOMT2), and FOMT4, which demonstrated distinct regiospecificity on a broad spectrum of flavonoid classes. In addition, a cytochrome P450 monooxygenase (CYP) in the CYP93G subfamily was found to serve as a flavanone 2-hydroxylase providing the substrate for FOMT2-catalyzed formation of xilonenin. In summary, maize produces a diverse blend of O-methylflavonoids with antifungal activity upon attack by a broad range of fungi.<\/jats:p>","DOI":"10.1093\/plphys\/kiab496","type":"journal-article","created":{"date-parts":[[2021,10,25]],"date-time":"2021-10-25T07:08:41Z","timestamp":1635145721000},"page":"167-190","source":"Crossref","is-referenced-by-count":74,"title":["Biosynthesis and antifungal activity of fungus-induced\n                    <i>O<\/i>\n                    -methylated flavonoids in maize"],"prefix":"10.1093","volume":"188","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6028-3060","authenticated-orcid":false,"given":"Christiane","family":"F\u00f6rster","sequence":"first","affiliation":[{"name":"Department of Biochemistry, Max Planck Institute for Chemical Ecology, Jena D-07745, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vinzenz","family":"Handrick","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Max Planck Institute for Chemical Ecology, Jena D-07745, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5903-1870","authenticated-orcid":false,"given":"Yezhang","family":"Ding","sequence":"additional","affiliation":[{"name":"Section of Cell and Developmental Biology, University of California, San Diego, California 92093-0380, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yoko","family":"Nakamura","sequence":"additional","affiliation":[{"name":"Research Group Biosynthesis\/NMR, Max Planck Institute for Chemical Ecology, Jena D-07745, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christian","family":"Paetz","sequence":"additional","affiliation":[{"name":"Research Group Biosynthesis\/NMR, Max Planck Institute for Chemical Ecology, Jena D-07745, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4788-1565","authenticated-orcid":false,"given":"Bernd","family":"Schneider","sequence":"additional","affiliation":[{"name":"Research Group Biosynthesis\/NMR, Max Planck Institute for Chemical Ecology, Jena D-07745, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3504-0980","authenticated-orcid":false,"given":"Gabriel","family":"Castro-Falc\u00f3n","sequence":"additional","affiliation":[{"name":"Scripps Institution of Oceanography, University of California, San Diego, California 92093, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7000-6438","authenticated-orcid":false,"given":"Chambers C","family":"Hughes","sequence":"additional","affiliation":[{"name":"Scripps Institution of Oceanography, University of California, San Diego, California 92093, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katrin","family":"Luck","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Max Planck Institute for Chemical Ecology, Jena D-07745, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sowmya","family":"Poosapati","sequence":"additional","affiliation":[{"name":"Section of Cell and Developmental Biology, University of California, San Diego, California 92093-0380, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Grit","family":"Kunert","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Max Planck Institute for Chemical Ecology, Jena D-07745, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3886-8433","authenticated-orcid":false,"given":"Alisa","family":"Huffaker","sequence":"additional","affiliation":[{"name":"Section of Cell and Developmental Biology, University of California, San Diego, California 92093-0380, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1812-1551","authenticated-orcid":false,"given":"Jonathan","family":"Gershenzon","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Max Planck Institute for Chemical Ecology, Jena D-07745, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2837-734X","authenticated-orcid":false,"given":"Eric A","family":"Schmelz","sequence":"additional","affiliation":[{"name":"Section of Cell and Developmental Biology, University of California, San Diego, California 92093-0380, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7037-904X","authenticated-orcid":false,"given":"Tobias G","family":"K\u00f6llner","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Max Planck Institute for Chemical Ecology, Jena D-07745, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2021,10,27]]},"reference":[{"key":"2022012018123332600_kiab496-B1","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1104\/pp.111.180224","article-title":"Benzoxazinoid metabolites regulate innate immunity against aphids and fungi in maize","volume":"157","author":"Ahmad","year":"2011","journal-title":"Plant Physiol"},{"key":"2022012018123332600_kiab496-B2","doi-asserted-by":"crossref","first-page":"287","DOI":"10.1016\/S0014-5793(98)00781-9","article-title":"Identification of a cytochrome P450 cDNA encoding (2S)-flavanone 2-hydroxylase of licorice (Glycyrrhiza echinata L.; Fabaceae) which represents licodione synthase and flavone synthase II","volume":"431","author":"Akashi","year":"1998","journal-title":"FEBS Lett"},{"key":"2022012018123332600_kiab496-B3","doi-asserted-by":"crossref","first-page":"2331","DOI":"10.1016\/S0031-9422(00)91021-5","article-title":"Studies on plant cultures .34. biosynthesis of a retrochalcone, echinating - involvement of O-methyltransferase to licodione","volume":"19","author":"Ayabe","year":"1980","journal-title":"Phytochemistry"},{"key":"2022012018123332600_kiab496-B4","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1111\/tpj.12114","article-title":"Induced resistance in maize is based on organ-specific defence responses","volume":"74","author":"Balmer","year":"2013","journal-title":"Plant J"},{"key":"2022012018123332600_kiab496-B5","doi-asserted-by":"crossref","first-page":"1052","DOI":"10.1104\/pp.112.204164","article-title":"A set of regioselective O-methyltransferases gives rise to the complex pattern of methoxylated flavones in sweet basil","volume":"160","author":"Berim","year":"2012","journal-title":"Plant Physiol"},{"key":"2022012018123332600_kiab496-B6","doi-asserted-by":"crossref","first-page":"2633","DOI":"10.1093\/bioinformatics\/btm308","article-title":"TASSEL: software for association mapping of complex traits in diverse samples","volume":"23","author":"Bradbury","year":"2007","journal-title":"Bioinformatics"},{"key":"2022012018123332600_kiab496-B7","doi-asserted-by":"crossref","first-page":"3909","DOI":"10.1016\/S0040-4020(01)86431-0","article-title":"The camalexins - new phytoalexins produced in the leaves of Camelina Sativa (Cruciferae)","volume":"47","author":"Browne","year":"1991","journal-title":"Tetrahedron"},{"key":"2022012018123332600_kiab496-B8","doi-asserted-by":"crossref","first-page":"1297","DOI":"10.1105\/tpc.16.00003","article-title":"Identification and characterization of maize salmon silks genes involved in insecticidal maysin biosynthesis","volume":"28","author":"Casas","year":"2016","journal-title":"Plant Cell"},{"key":"2022012018123332600_kiab496-B9","doi-asserted-by":"crossref","first-page":"219","DOI":"10.1023\/A:1005985609313","article-title":"A flavonoid 7-O-methyltransferase is expressed in barley leaves in response to pathogen attack","volume":"36","author":"Christensen","year":"1998","journal-title":"Plant Mol Biol"},{"key":"2022012018123332600_kiab496-B10","volume-title":"The R Book","author":"Crawley","year":"2013"},{"key":"2022012018123332600_kiab496-B11","doi-asserted-by":"crossref","first-page":"857","DOI":"10.1104\/pp.19.00683","article-title":"The acetate pathway supports flavonoid and lipid biosynthesis in Arabidopsis","volume":"182","author":"de Souza","year":"2020","journal-title":"Plant Physiol"},{"key":"2022012018123332600_kiab496-B12","doi-asserted-by":"crossref","first-page":"1043","DOI":"10.1038\/s41477-019-0509-6","article-title":"Multiple genes recruited from hormone pathways partition maize diterpenoid defences","volume":"5","author":"Ding","year":"2019","journal-title":"Nat Plants"},{"key":"2022012018123332600_kiab496-B13","doi-asserted-by":"crossref","first-page":"1455","DOI":"10.1104\/pp.17.00879","article-title":"Selinene volatiles are essential precursors for maize defense promoting fungal pathogen resistance","volume":"175","author":"Ding","year":"2017","journal-title":"Plant Physiol"},{"key":"2022012018123332600_kiab496-B14","doi-asserted-by":"crossref","first-page":"1375","DOI":"10.1038\/s41477-020-00787-9","article-title":"Genetic elucidation of interconnected antibiotic pathways mediating maize innate immunity","volume":"6","author":"Ding","year":"2020","journal-title":"Nat Plants"},{"key":"2022012018123332600_kiab496-B15","doi-asserted-by":"crossref","first-page":"324","DOI":"10.1104\/pp.110.161042","article-title":"CYP93G2 is a flavanone 2-hydroxylase required for C-glycosylflavone biosynthesis in rice","volume":"154","author":"Du","year":"2010","journal-title":"Plant Physiol"},{"key":"2022012018123332600_kiab496-B16","doi-asserted-by":"crossref","first-page":"983","DOI":"10.1093\/jxb\/erp364","article-title":"Identification of flavone phytoalexins and a pathogen-inducible flavone synthase II gene (SbFNSII) in sorghum","volume":"61","author":"Du","year":"2010","journal-title":"J Exp Bot"},{"key":"2022012018123332600_kiab496-B17","doi-asserted-by":"crossref","first-page":"31678","DOI":"10.1074\/jbc.M113.510040","article-title":"Identification of a bifunctional maize C- and O-glucosyltransferase","volume":"288","author":"Falcone-Ferreyra","year":"2013","journal-title":"J Biol Chem"},{"key":"2022012018123332600_kiab496-B18","doi-asserted-by":"crossref","first-page":"1054","DOI":"10.1111\/j.1365-313X.2005.02591.x","article-title":"Maize association population: a high-resolution platform for quantitative trait locus dissection","volume":"44","author":"Flint-Garcia","year":"2005","journal-title":"Plant J"},{"key":"2022012018123332600_kiab496-B19","doi-asserted-by":"crossref","first-page":"1797","DOI":"10.1007\/BF00019493","article-title":"A putative O-methyltransferase from barley is induced by fungal pathogens and Uv-light","volume":"26","author":"Gregersen","year":"1994","journal-title":"Plant Mol Biol"},{"key":"2022012018123332600_kiab496-B20","doi-asserted-by":"crossref","DOI":"10.1007\/978-0-387-28822-2","volume-title":"The Science of Flavonoids","author":"Grotewold","year":"2006"},{"key":"2022012018123332600_kiab496-B21","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1038\/361153a0","article-title":"Disease resistance results from foreign phytoalexin expression in a novel plant","volume":"361","author":"Hain","year":"1993","journal-title":"Nature"},{"key":"2022012018123332600_kiab496-B22","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1146\/annurev.phyto.37.1.285","article-title":"Phytoalexins: what have we learned after 60 years?","volume":"37","author":"Hammerschmidt","year":"1999","journal-title":"Annu Rev Phytopathol"},{"key":"2022012018123332600_kiab496-B23","first-page":"1682","article-title":"Biosynthesis of 8-O-methylated benzoxazinoid defense compounds in maize","volume":"28","author":"Handrick","year":"2016","journal-title":"Plant Cell"},{"key":"2022012018123332600_kiab496-B24","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1016\/j.phytochem.2016.02.013","article-title":"Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins","volume":"125","author":"Hao","year":"2016","journal-title":"Phytochemistry"},{"key":"2022012018123332600_kiab496-B25","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1016\/S0031-9422(97)01105-9","article-title":"Mode of antibacterial action of retrochalcones from Glycyrrhiza inflata","volume":"48","author":"Haraguchi","year":"1998","journal-title":"Phytochemistry"},{"key":"2022012018123332600_kiab496-B26","doi-asserted-by":"crossref","first-page":"11404","DOI":"10.3390\/molecules190811404","article-title":"Analysis on blast fungus-responsive characters of a flavonoid phytoalexin sakuranetin; accumulation in infected rice leaves, antifungal activity and detoxification by fungus","volume":"19","author":"Hasegawa","year":"2014","journal-title":"Molecules"},{"key":"2022012018123332600_kiab496-B27","first-page":"1689","article-title":"Genetic manipulation of isoflavone 7-O-methyltransferase enhances biosynthesis of 4 '-O-methylated isoflavonoid phytoalexins and disease resistance in alfalfa","volume":"12","author":"He","year":"2000","journal-title":"Plant Cell"},{"key":"2022012018123332600_kiab496-B28","doi-asserted-by":"crossref","first-page":"2082","DOI":"10.1104\/pp.111.179457","article-title":"Novel acidic sesquiterpenoids constitute a dominant class of pathogen-induced phytoalexins in maize","volume":"156","author":"Huffaker","year":"2011","journal-title":"Plant Physiol"},{"key":"2022012018123332600_kiab496-B29","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1023\/A:1005939803300","article-title":"Plant O-methyltransferases: molecular analysis, common signature and classification","volume":"36","author":"Ibrahim","year":"1998","journal-title":"Plant Mol Biol"},{"key":"2022012018123332600_kiab496-B30","doi-asserted-by":"crossref","first-page":"18033","DOI":"10.3390\/molecules191118033","article-title":"Deciphering the role of phytoalexins in plant-microorganism interactions and human health","volume":"19","author":"Jeandet","year":"2014","journal-title":"Molecules"},{"key":"2022012018123332600_kiab496-B31","doi-asserted-by":"crossref","first-page":"27","DOI":"10.3390\/plants5020027","article-title":"Flavones: from biosynthesis to health benefits","volume":"5","author":"Jiang","year":"2016","journal-title":"Plants (Basel)"},{"key":"2022012018123332600_kiab496-B32","doi-asserted-by":"crossref","first-page":"276","DOI":"10.3390\/molecules23020276","article-title":"Xylosylated detoxification of the rice flavonoid phytoalexin sakuranetin by the rice sheath blight fungus Rhizoctonia solani","volume":"23","author":"Katsumata","year":"2018","journal-title":"Molecules"},{"key":"2022012018123332600_kiab496-B33","doi-asserted-by":"crossref","DOI":"10.1002\/cbdv.201600240","article-title":"Identification of sternbin and naringenin as detoxified metabolites from the rice flavanone phytoalexin sakuranetin by Pyricularia oryzae","volume":"14","author":"Katsumata","year":"2017","journal-title":"Chem Biodivers"},{"key":"2022012018123332600_kiab496-B34","doi-asserted-by":"crossref","first-page":"387","DOI":"10.1016\/j.phytochem.2005.11.022","article-title":"Flavonoid 3 '-O-methyltransferase from rice: cDNA cloning, characterization and functional expression","volume":"67","author":"Kim","year":"2006","journal-title":"Phytochemistry"},{"key":"2022012018123332600_kiab496-B35","doi-asserted-by":"crossref","first-page":"321","DOI":"10.1007\/s12374-010-9126-7","article-title":"Plant flavonoid O-methyltransferases: substrate specificity and application","volume":"53","author":"Kim","year":"2010","journal-title":"J Plant Biol"},{"key":"2022012018123332600_kiab496-B36","doi-asserted-by":"crossref","first-page":"3807","DOI":"10.1016\/S0031-9422(00)97532-0","article-title":"Sakuranetin, a flavanone phytoalexin from ultraviolet-irradiated rice leaves","volume":"31","author":"Kodama","year":"1992","journal-title":"Phytochemistry"},{"key":"2022012018123332600_kiab496-B37","doi-asserted-by":"crossref","first-page":"1870","DOI":"10.1093\/molbev\/msw054","article-title":"MEGA7: molecular evolutionary genetics analysis version 7.0 for bigger datasets","volume":"33","author":"Kumar","year":"2016","journal-title":"Mol Biol Evol"},{"key":"2022012018123332600_kiab496-B38","doi-asserted-by":"crossref","first-page":"1315","DOI":"10.1104\/pp.114.239723","article-title":"Cytochrome P450 93G1 is a flavone synthase II that channels flavanones to the biosynthesis of Tricin O-linked conjugates in rice","volume":"165","author":"Lam","year":"2014","journal-title":"Plant Physiol"},{"key":"2022012018123332600_kiab496-B39","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/0048-4059(76)90077-1","article-title":"Production of resveratrol by Vitis Vinifera and other members of Vitaceae as a response to infection or injury","volume":"9","author":"Langcake","year":"1976","journal-title":"Physiol Plant Pathol"},{"key":"2022012018123332600_kiab496-B40","doi-asserted-by":"crossref","first-page":"2397","DOI":"10.1093\/bioinformatics\/bts444","article-title":"GAPIT: genome association and prediction integrated tool","volume":"28","author":"Lipka","year":"2012","journal-title":"Bioinformatics"},{"key":"2022012018123332600_kiab496-B41","doi-asserted-by":"crossref","first-page":"1173","DOI":"10.1093\/pcp\/pcq080","article-title":"Molecular dissection of the pathogen-inducible 3-deoxyanthocyanidin biosynthesis pathway in sorghum","volume":"51","author":"Liu","year":"2010","journal-title":"Plant Cell Physiol"},{"key":"2022012018123332600_kiab496-B42","doi-asserted-by":"crossref","first-page":"858","DOI":"10.3390\/molecules25040858","article-title":"Characterization of a flavonoid 3'\/5'\/7-O-methyltransferase from Citrus reticulata and evaluation of the in vitro cytotoxicity of its methylated products","volume":"25","author":"Liu","year":"2020","journal-title":"Molecules"},{"key":"2022012018123332600_kiab496-B43","doi-asserted-by":"crossref","first-page":"2677","DOI":"10.1104\/pp.17.01351","article-title":"Discovery, biosynthesis and stress-related accumulation of dolabradiene-derived defenses in maize","volume":"176","author":"Mafu","year":"2018","journal-title":"Plant Physiol"},{"key":"2022012018123332600_kiab496-B44","doi-asserted-by":"crossref","first-page":"807","DOI":"10.1016\/j.jplph.2012.01.019","article-title":"Evaluation of candidate reference genes for qPCR in maize","volume":"169","author":"Manoli","year":"2012","journal-title":"J Plant Physiol"},{"key":"2022012018123332600_kiab496-B45","doi-asserted-by":"crossref","first-page":"2399","DOI":"10.1016\/j.phytochem.2005.07.013","article-title":"Flavones and flavone synthases","volume":"66","author":"Martens","year":"2005","journal-title":"Phytochemistry"},{"key":"2022012018123332600_kiab496-B46","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1016\/j.jep.2004.02.030","article-title":"Biological activity of five antibacterial flavonoids from Combretum erythrophyllum (Combretaceae)","volume":"93","author":"Martini","year":"2004","journal-title":"J Ethnopharmacol"},{"key":"2022012018123332600_kiab496-B47","first-page":"429","article-title":"Punch inoculation for measuring resistance of corn leaf tissue to Helminthosporium Maydis","volume":"64","author":"Matsuyama","year":"1974","journal-title":"Phytopathology"},{"key":"2022012018123332600_kiab496-B48","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1126\/science.1174320","article-title":"Genetic properties of the maize nested association mapping population","volume":"325","author":"McMullen","year":"2009","journal-title":"Science"},{"key":"2022012018123332600_kiab496-B49","doi-asserted-by":"crossref","first-page":"2341","DOI":"10.1105\/tpc.113.112409","article-title":"Natural variation in maize aphid resistance is associated with 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside methyltransferase activity","volume":"25","author":"Meihls","year":"2013","journal-title":"Plant Cell"},{"key":"2022012018123332600_kiab496-B50","doi-asserted-by":"crossref","first-page":"2745","DOI":"10.1105\/tpc.112.098004","article-title":"A genome-wide regulatory framework identifies maize pericarp color1 controlled genes","volume":"24","author":"Morohashi","year":"2012","journal-title":"Plant Cell"},{"key":"2022012018123332600_kiab496-B51","doi-asserted-by":"crossref","first-page":"369","DOI":"10.1146\/annurev.py.30.090192.002101","article-title":"Phenolic-compounds and their role in disease resistance","volume":"30","author":"Nicholson","year":"1992","journal-title":"Annu Rev Phytopathol"},{"key":"2022012018123332600_kiab496-B52","doi-asserted-by":"crossref","first-page":"5520","DOI":"10.1073\/pnas.84.16.5520","article-title":"Phytoalexin synthesis by the sorghum mesocotyl in response to infection by pathogenic and nonpathogenic fungi","volume":"84","author":"Nicholson","year":"1987","journal-title":"Proc Natl Acad Sci USA"},{"key":"2022012018123332600_kiab496-B53","doi-asserted-by":"crossref","first-page":"2995","DOI":"10.1016\/j.phytochem.2004.09.006","article-title":"Accumulation of HDMBOA-Glc is induced by biotic stresses prior to the release of MBOA in maize leaves","volume":"65","author":"Oikawa","year":"2004","journal-title":"Phytochemistry"},{"key":"2022012018123332600_kiab496-B54","doi-asserted-by":"crossref","first-page":"18139","DOI":"10.3390\/molecules191118139","article-title":"Antimicrobial activity of UV-induced phenylamides from rice leaves","volume":"19","author":"Park","year":"2014","journal-title":"Molecules"},{"key":"2022012018123332600_kiab496-B55","doi-asserted-by":"crossref","first-page":"391","DOI":"10.1016\/j.phytochem.2004.12.032","article-title":"Metabolism and detoxification of phytoalexins and analogs by phytopathogenic fungi","volume":"66","author":"Pedras","year":"2005","journal-title":"Phytochemistry"},{"key":"2022012018123332600_kiab496-B56","author":"Pinheiro","year":"2020"},{"key":"2022012018123332600_kiab496-B57","first-page":"51","article-title":"Yeast expression of animal and plant P450s in optimized redox environments","volume":"P450","author":"Pompon","year":"1996","journal-title":"Cytochrome"},{"key":"2022012018123332600_kiab496-B58","volume-title":"R Foundation for Statistical Computing","year":"2020"},{"key":"2022012018123332600_kiab496-B59","doi-asserted-by":"crossref","first-page":"1046","DOI":"10.1271\/bbb.60.1046","article-title":"Role of jasmonic acid as a signaling molecule in copper chloride-elicited rice phytoalexin production","volume":"60","author":"Rakwal","year":"1996","journal-title":"Biosci Biotech Bioch"},{"key":"2022012018123332600_kiab496-B60","doi-asserted-by":"crossref","first-page":"1100","DOI":"10.1139\/m79-168","article-title":"A liquid medium for the production of Kabatiella zeae conidia","volume":"25","author":"Reifschneider","year":"1979","journal-title":"Can J Microbiol"},{"key":"2022012018123332600_kiab496-B61","doi-asserted-by":"crossref","first-page":"495","DOI":"10.1111\/pce.13428","article-title":"Apigenin produced by maize flavone synthase I and II protects plants against UV-B-induced damage","volume":"42","author":"Righini","year":"2019","journal-title":"Plant Cell Environ"},{"key":"2022012018123332600_kiab496-B62","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1186\/1472-6750-8-83","article-title":"Induction of multiple pleiotropic drug resistance genes in yeast engineered to produce an increased level of anti-malarial drug precursor, artemisinic acid","volume":"8","author":"Ro","year":"2008","journal-title":"BMC Biotechnol"},{"key":"2022012018123332600_kiab496-B63","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1007\/s10340-006-0151-8","article-title":"The effects of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one on two species of Spodoptera and the growth of Setosphaeria turcica in vitro","volume":"80","author":"Rostas","year":"2007","journal-title":"J Pest Sci"},{"key":"2022012018123332600_kiab496-B64","doi-asserted-by":"crossref","first-page":"555","DOI":"10.1046\/j.1365-313X.2002.01378.x","article-title":"Key amino acid residues required for aryl migration catalysed by the cytochrome P450 2-hydroxyisoflavanone synthase","volume":"31","author":"Sawada","year":"2002","journal-title":"Plant J"},{"key":"2022012018123332600_kiab496-B65","doi-asserted-by":"crossref","first-page":"5455","DOI":"10.1073\/pnas.1014714108","article-title":"Identity, regulation, and activity of inducible diterpenoid phytoalexins in maize","volume":"108","author":"Schmelz","year":"2011","journal-title":"Proc Natl Acad Sci USA"},{"key":"2022012018123332600_kiab496-B66","doi-asserted-by":"crossref","first-page":"19315","DOI":"10.1074\/jbc.M112.351270","article-title":"Purification and identification of naringenin 7-O-methyltransferase, a key enzyme in biosynthesis of flavonoid phytoalexin sakuranetin in rice","volume":"287","author":"Shimizu","year":"2012","journal-title":"J Biol Chem"},{"key":"2022012018123332600_kiab496-B67","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1111\/j.1601-5223.1997.00147.x","article-title":"The role of the barley testa layer and its flavonoid content in resistance to Fusarium infections","volume":"126","author":"Skadhauge","year":"1997","journal-title":"Hereditas"},{"key":"2022012018123332600_kiab496-B68","doi-asserted-by":"crossref","first-page":"463","DOI":"10.1016\/0885-5765(91)90012-7","article-title":"Accumulation of sorghum phytoalexins induced by Colletotrichum Graminicola at the infection site","volume":"39","author":"Snyder","year":"1991","journal-title":"Physiol Mol Plant Pathol"},{"key":"2022012018123332600_kiab496-B69","doi-asserted-by":"crossref","first-page":"1397","DOI":"10.3852\/11-374","article-title":"Zymoseptoria ardabiliae and Z. pseudotritici, two progenitor species of the septoria tritici leaf blotch fungus Z. tritici (synonym: Mycosphaerella graminicola)","volume":"104","author":"Stukenbrock","year":"2012","journal-title":"Mycologia"},{"key":"2022012018123332600_kiab496-B70","doi-asserted-by":"crossref","first-page":"2157","DOI":"10.1101\/gr.118851.110","article-title":"The making of a new pathogen: insights from comparative population genomics of the domesticated wheat pathogen Mycosphaerella graminicola and its wild sister species","volume":"21","author":"Stukenbrock","year":"2011","journal-title":"Genome Res"},{"key":"2022012018123332600_kiab496-B71","doi-asserted-by":"crossref","first-page":"4013","DOI":"10.1093\/jxb\/erx177","article-title":"Current understanding of the pathways of flavonoid biosynthesis in model and crop plants","volume":"68","author":"Tohge","year":"2017","journal-title":"J Exp Bot"},{"key":"2022012018123332600_kiab496-B72","author":"Turner","year":"2014"},{"key":"2022012018123332600_kiab496-B73","doi-asserted-by":"crossref","first-page":"112650","DOI":"10.1016\/j.phytochem.2020.112650","article-title":"Identification of methoxylchalcones produced in response to CuCl2 treatment and pathogen infection in barley","volume":"184","author":"Ube","year":"2021","journal-title":"Phytochemistry"},{"key":"2022012018123332600_kiab496-B74","doi-asserted-by":"crossref","first-page":"1560","DOI":"10.1104\/pp.17.00842","article-title":"Flavan-3-ols are an effective chemical defense against rust infection","volume":"175","author":"Ullah","year":"2017","journal-title":"Plant Physiol"},{"key":"2022012018123332600_kiab496-B75","doi-asserted-by":"crossref","first-page":"1191","DOI":"10.2307\/3869817","article-title":"Two classes of plant antibiotics: phytoalexins versus \u201cphytoanticipins\u201d","volume":"6","author":"VanEtten","year":"1994","journal-title":"Plant Cell"},{"key":"2022012018123332600_kiab496-B76","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1038\/ng1702","article-title":"A unified mixed-model method for association mapping that accounts for multiple levels of relatedness","volume":"38","author":"Yu","year":"2006","journal-title":"Nat Genet"},{"key":"2022012018123332600_kiab496-B77","doi-asserted-by":"crossref","first-page":"741","DOI":"10.1104\/pp.106.095018","article-title":"Flavone synthases from Medicago truncatula are flavanone-2-hydroxylases and are important for nodulation","volume":"144","author":"Zhang","year":"2007","journal-title":"Plant Physiol"},{"key":"2022012018123332600_kiab496-B78","first-page":"1568","article-title":"Different reactive oxygen species scavenging properties of flavonoids determine their abilities to extend the shelf life of tomato","volume":"169","author":"Zhang","year":"2015","journal-title":"Plant Physiol"},{"key":"2022012018123332600_kiab496-B79","doi-asserted-by":"crossref","first-page":"355","DOI":"10.1038\/ng.546","article-title":"Mixed linear model approach adapted for genome-wide association studies","volume":"42","author":"Zhang","year":"2010","journal-title":"Nat Genet"},{"key":"2022012018123332600_kiab496-B80","doi-asserted-by":"crossref","first-page":"915","DOI":"10.1007\/s10600-020-03185-x","article-title":"Flavonoids from Pulicaria vulgaris and their antimicrobial activity","volume":"56","author":"Zhanzhaxina","year":"2020","journal-title":"Chem Nat Compd"},{"key":"2022012018123332600_kiab496-B81","first-page":"981","article-title":"Characterization of a novel flavone O-methyltransferase gene in rice","volume":"1","author":"Zhou","year":"2006","journal-title":"Nat Prod Commun"},{"key":"2022012018123332600_kiab496-B82","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1080\/13880200701729745","article-title":"Characterization of two O-methyltransferase-like genes in barley and maize","volume":"46","author":"Zhou","year":"2008","journal-title":"Pharm Biol"},{"key":"2022012018123332600_kiab496-B83","doi-asserted-by":"crossref","first-page":"1115","DOI":"10.1016\/j.bbagen.2006.02.008","article-title":"Sequential O-methylation of tricetin by a single gene product in wheat","volume":"1760","author":"Zhou","year":"2006","journal-title":"Bba-Gen Subjects"},{"key":"2022012018123332600_kiab496-B84","doi-asserted-by":"crossref","DOI":"10.1007\/978-0-387-87458-6","volume-title":"Mixed Effects Models and Extensions in Ecology with R","author":"Zuur","year":"2009"}],"container-title":["Plant Physiology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/academic.oup.com\/plphys\/advance-article-pdf\/doi\/10.1093\/plphys\/kiab496\/42079900\/kiab496.pdf","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/plphys\/article-pdf\/188\/1\/167\/42248220\/kiab496.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/plphys\/article-pdf\/188\/1\/167\/42248220\/kiab496.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,1,20]],"date-time":"2022-01-20T13:18:14Z","timestamp":1642684694000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/plphys\/article\/188\/1\/167\/6412572"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,10,27]]},"references-count":84,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2021,10,27]]},"published-print":{"date-parts":[[2022,1,20]]}},"URL":"https:\/\/doi.org\/10.1093\/plphys\/kiab496","relation":{},"ISSN":["0032-0889","1532-2548"],"issn-type":[{"value":"0032-0889","type":"print"},{"value":"1532-2548","type":"electronic"}],"subject":[],"published-other":{"date-parts":[[2022,1,1]]},"published":{"date-parts":[[2021,10,27]]}}}