{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,18]],"date-time":"2026-10-18T11:27:14Z","timestamp":1792322834698,"version":"4.4.0"},"reference-count":62,"publisher":"Oxford University Press (OUP)","issue":"6","license":[{"start":{"date-parts":[[2021,1,19]],"date-time":"2021-01-19T00:00:00Z","timestamp":1611014400000},"content-version":"vor","delay-in-days":4250,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2009,8,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Accumulation of camalexin, the characteristic phytoalexin of Arabidopsis thaliana, is induced by a great variety of plant pathogens. It is derived from Trp, which is converted to indole-3-acetonitrile (IAN) by successive action of the cytochrome P450 enzymes CYP79B2\/B3 and CYP71A13. Extracts from wild-type plants and camalexin biosynthetic mutants, treated with silver nitrate or inoculated with Phytophthora infestans, were comprehensively analyzed by ultra-performance liquid chromatography electrospray ionization quadrupole time-of-flight mass spectrometry. This metabolomics approach was combined with precursor feeding experiments to characterize the IAN metabolic network and to identify novel biosynthetic intermediates and metabolites of camalexin. Indole-3-carbaldehyde and indole-3-carboxylic acid derivatives were shown to originate from IAN. IAN conjugates with glutathione, \u03b3-glutamylcysteine, and cysteine [Cys(IAN)] accumulated in challenged phytoalexin deficient3 (pad3) mutants. Cys(IAN) rescued the camalexin-deficient phenotype of cyp79b2 cyp79b3 and was itself converted to dihydrocamalexic acid (DHCA), the known substrate of CYP71B15 (PAD3), by microsomes isolated from silver nitrate\u2013treated Arabidopsis leaves. Surprisingly, yeast-expressed CYP71B15 also catalyzed thiazoline ring closure, DHCA formation, and cyanide release with Cys(IAN) as substrate. In conclusion, in the camalexin biosynthetic pathway, IAN is derivatized to the intermediate Cys(IAN), which serves as substrate of the multifunctional cytochrome P450 enzyme CYP71B15.<\/jats:p>","DOI":"10.1105\/tpc.109.066670","type":"journal-article","created":{"date-parts":[[2009,6,30]],"date-time":"2009-06-30T22:38:45Z","timestamp":1246401525000},"page":"1830-1845","source":"Crossref","is-referenced-by-count":219,"title":["The Multifunctional Enzyme CYP71B15 (PHYTOALEXIN DEFICIENT3) Converts Cysteine-Indole-3-Acetonitrile to Camalexin in the Indole-3-Acetonitrile Metabolic Network of\n                    <i>Arabidopsis thaliana<\/i>\n                    \u00a0 \u00a0"],"prefix":"10.1093","volume":"21","author":[{"given":"Christoph","family":"Bo\u0308ttcher","sequence":"first","affiliation":[{"name":"Department of Stress and Developmental Biology, Leibniz Institute of Plant Biochemistry, 06120 Halle\/Saale, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lore","family":"Westphal","sequence":"additional","affiliation":[{"name":"Department of Stress and Developmental Biology, Leibniz Institute of Plant Biochemistry, 06120 Halle\/Saale, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Constanze","family":"Schmotz","sequence":"additional","affiliation":[{"name":"Department of Stress and Developmental Biology, Leibniz Institute of Plant Biochemistry, 06120 Halle\/Saale, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elke","family":"Prade","sequence":"additional","affiliation":[{"name":"Lehrstuhl fu\u0308r Genetik, Technische Universita\u0308t Mu\u0308nchen, 85350 Freising, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dierk","family":"Scheel","sequence":"additional","affiliation":[{"name":"Department of Stress and Developmental Biology, Leibniz Institute of Plant Biochemistry, 06120 Halle\/Saale, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Erich","family":"Glawischnig","sequence":"additional","affiliation":[{"name":"Lehrstuhl fu\u0308r Genetik, Technische Universita\u0308t Mu\u0308nchen, 85350 Freising, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2009,6,30]]},"reference":[{"key":"2021040621022110100_b2","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1126\/science.1163732","volume":"323","year":"2009","journal-title":"Science"},{"key":"2021040621022110100_b1","doi-asserted-by":"crossref","first-page":"1058","DOI":"10.1104\/pp.104.057794","volume":"138","year":"2005","journal-title":"Plant Physiol."},{"key":"2021040621022110100_b3","doi-asserted-by":"crossref","first-page":"740","DOI":"10.1111\/j.1365-313X.2006.02993.x","volume":"49","year":"2007","journal-title":"Plant J."},{"key":"2021040621022110100_b4","doi-asserted-by":"crossref","first-page":"2107","DOI":"10.1104\/pp.108.117754","volume":"147","year":"2008","journal-title":"Plant Physiol."},{"key":"2021040621022110100_b5","first-page":"1499","volume":"13","year":"2001","journal-title":"Plant Cell"},{"key":"2021040621022110100_b6","doi-asserted-by":"crossref","first-page":"21102","DOI":"10.1074\/jbc.M801998200","volume":"283","year":"2008","journal-title":"J. Biol. Chem."},{"key":"2021040621022110100_b7","doi-asserted-by":"crossref","first-page":"3909","DOI":"10.1016\/S0040-4020(01)86431-0","volume":"47","year":"1991","journal-title":"Tetrahedron"},{"key":"2021040621022110100_b8","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1016\/j.phytochem.2007.08.027","volume":"69","year":"2008","journal-title":"Phytochemistry"},{"key":"2021040621022110100_b9","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1126\/science.1164627","volume":"323","year":"2009","journal-title":"Science"},{"key":"2021040621022110100_b10","first-page":"65","year":"2006"},{"key":"2021040621022110100_b11","doi-asserted-by":"crossref","first-page":"778","DOI":"10.1038\/nprot.2007.95","volume":"2","year":"2007","journal-title":"Nat. Protocols"},{"key":"2021040621022110100_b12","doi-asserted-by":"crossref","first-page":"367","DOI":"10.1104\/pp.107.095596","volume":"144","year":"2007","journal-title":"Plant Physiol."},{"key":"2021040621022110100_b13","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1016\/j.phytochem.2006.12.005","volume":"68","year":"2007","journal-title":"Phytochemistry"},{"key":"2021040621022110100_b14","doi-asserted-by":"crossref","first-page":"8245","DOI":"10.1073\/pnas.0305876101","volume":"101","year":"2004","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"2021040621022110100_b15","doi-asserted-by":"crossref","first-page":"8955","DOI":"10.1073\/pnas.91.19.8955","volume":"91","year":"1994","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"2021040621022110100_b16","doi-asserted-by":"crossref","first-page":"32338","DOI":"10.1074\/jbc.M704886200","volume":"282","year":"2007","journal-title":"J. Biol. Chem."},{"key":"2021040621022110100_b17","doi-asserted-by":"crossref","first-page":"753","DOI":"10.1073\/pnas.98.2.753","volume":"98","year":"2001","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"2021040621022110100_b18","doi-asserted-by":"crossref","first-page":"369","DOI":"10.1006\/abbi.1995.1477","volume":"322","year":"1995","journal-title":"Arch. Biochem. Biophys."},{"key":"2021040621022110100_b19","doi-asserted-by":"crossref","first-page":"2379","DOI":"10.1073\/pnas.040569997","volume":"97","year":"2000","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"2021040621022110100_b20","first-page":"99","volume":"78","year":"1997","journal-title":"Phytoprotection"},{"key":"2021040621022110100_b21","doi-asserted-by":"crossref","first-page":"280","DOI":"10.1016\/j.pbi.2005.03.014","volume":"8","year":"2005","journal-title":"Curr. Opin. Plant Biol."},{"key":"2021040621022110100_b22","doi-asserted-by":"crossref","first-page":"234","DOI":"10.1186\/1471-2105-7-234","volume":"7","year":"2006","journal-title":"BMC Bioinformatics"},{"key":"2021040621022110100_b23","doi-asserted-by":"crossref","first-page":"1187","DOI":"10.1021\/ac061391o","volume":"79","year":"2007","journal-title":"Anal. Chem."},{"key":"2021040621022110100_b24","doi-asserted-by":"crossref","first-page":"4225","DOI":"10.1093\/jxb\/erm279","volume":"58","year":"2007","journal-title":"J. Exp. Bot."},{"key":"2021040621022110100_b25","doi-asserted-by":"crossref","first-page":"1180","DOI":"10.1126\/science.1119409","volume":"310","year":"2005","journal-title":"Science"},{"key":"2021040621022110100_b26","doi-asserted-by":"crossref","first-page":"2021","DOI":"10.1104\/pp.108.124784","volume":"148","year":"2008","journal-title":"Plant Physiol."},{"key":"2021040621022110100_b27","first-page":"555","volume":"57","year":"2008","journal-title":"Plant J."},{"key":"2021040621022110100_b28","doi-asserted-by":"crossref","first-page":"33712","DOI":"10.1074\/jbc.M001667200","volume":"275","year":"2000","journal-title":"J. Biol. Chem."},{"key":"2021040621022110100_b29","doi-asserted-by":"crossref","first-page":"2915","DOI":"10.1016\/S0031-9422(00)98224-4","volume":"30","year":"1991","journal-title":"Phytochemistry"},{"key":"2021040621022110100_b30","doi-asserted-by":"crossref","first-page":"2039","DOI":"10.1105\/tpc.107.051383","volume":"19","year":"2007","journal-title":"Plant Cell"},{"key":"2021040621022110100_b31","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1111\/j.1365-313X.2006.02938.x","volume":"49","year":"2007","journal-title":"Plant J."},{"key":"2021040621022110100_b33","doi-asserted-by":"crossref","first-page":"3307","DOI":"10.1016\/S0968-0896(02)00208-0","volume":"10","year":"2002","journal-title":"Bioorg. Med. Chem."},{"key":"2021040621022110100_b32","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1016\/S0031-9422(99)00479-3","volume":"53","year":"2000","journal-title":"Phytochemistry"},{"key":"2021040621022110100_b34","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1016\/S0031-9422(99)00494-X","volume":"53","year":"2000","journal-title":"Phytochemistry"},{"key":"2021040621022110100_b35","first-page":"319","volume":"2","year":"2007","journal-title":"Nat. Prod. Commun."},{"key":"2021040621022110100_b36","doi-asserted-by":"crossref","first-page":"2655","DOI":"10.1016\/j.phytochem.2008.08.020","volume":"69","year":"2008","journal-title":"Phytochemistry"},{"key":"2021040621022110100_b37","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1016\/S0076-6879(96)72008-6","volume":"272","year":"1996","journal-title":"Methods Enzymol."},{"key":"2021040621022110100_b38","doi-asserted-by":"crossref","first-page":"2214","DOI":"10.1038\/emboj.2008.147","volume":"27","year":"2008","journal-title":"EMBO J."},{"key":"2021040621022110100_b39","first-page":"3721","volume":"18","year":"2006","journal-title":"Plant Cell"},{"key":"2021040621022110100_b40","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1006\/abbi.2001.2483","volume":"393","year":"2001","journal-title":"Arch. Biochem. Biophys."},{"key":"2021040621022110100_b41","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1016\/j.phytochem.2008.12.010","volume":"70","year":"2009","journal-title":"Phytochemistry"},{"key":"2021040621022110100_b42","doi-asserted-by":"crossref","first-page":"5638","DOI":"10.1073\/pnas.0711301105","volume":"105","year":"2008","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"2021040621022110100_b43","doi-asserted-by":"crossref","first-page":"748","DOI":"10.1094\/MPMI-9-0748","volume":"9","year":"1996","journal-title":"Mol. Plant Microbe Interact."},{"key":"2021040621022110100_b44","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/0378-4347(92)80311-D","volume":"582","year":"1992","journal-title":"J. Chromatogr."},{"key":"2021040621022110100_b45","doi-asserted-by":"crossref","first-page":"774","DOI":"10.1111\/j.1365-313X.2008.03545.x","volume":"55","year":"2008","journal-title":"Plant J."},{"key":"2021040621022110100_b46","doi-asserted-by":"crossref","first-page":"1248","DOI":"10.1104\/pp.106.082024","volume":"141","year":"2006","journal-title":"Plant Physiol."},{"key":"2021040621022110100_b47","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1046\/j.1364-3703.2003.00168.x","volume":"4","year":"2003","journal-title":"Mol. Plant Pathol."},{"key":"2021040621022110100_b48","doi-asserted-by":"crossref","first-page":"3506","DOI":"10.1074\/jbc.270.8.3506","volume":"270","year":"1995","journal-title":"J. Biol. Chem."},{"key":"2021040621022110100_b49","doi-asserted-by":"crossref","first-page":"499","DOI":"10.1111\/j.1365-313X.2009.03794.x","volume":"58","year":"2009","journal-title":"Plant J."},{"key":"2021040621022110100_b50","doi-asserted-by":"crossref","first-page":"731","DOI":"10.1105\/tpc.105.038372","volume":"18","year":"2006","journal-title":"Plant Cell"},{"key":"2021040621022110100_b51","first-page":"1811","volume":"12","year":"2000","journal-title":"Plant Cell"},{"key":"2021040621022110100_b52","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1016\/j.phytochem.2003.12.009","volume":"65","year":"2004","journal-title":"Phytochemistry"},{"key":"2021040621022110100_b53","doi-asserted-by":"crossref","first-page":"504","DOI":"10.1186\/1471-2105-9-504","volume":"9","year":"2008","journal-title":"BMC Bioinformatics"},{"key":"2021040621022110100_b54","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1111\/j.1365-313X.2005.02437.x","volume":"43","year":"2005","journal-title":"Plant J."},{"key":"2021040621022110100_b55","doi-asserted-by":"crossref","first-page":"1304","DOI":"10.1104\/pp.98.4.1304","volume":"98","year":"1992","journal-title":"Plant Physiol."},{"key":"2021040621022110100_b56","doi-asserted-by":"crossref","first-page":"978","DOI":"10.1104\/pp.108.122325","volume":"147","year":"2008","journal-title":"Plant Physiol."},{"key":"2021040621022110100_b57","doi-asserted-by":"crossref","first-page":"508","DOI":"10.1007\/s004250000420","volume":"212","year":"2001","journal-title":"Planta"},{"key":"2021040621022110100_b58","doi-asserted-by":"crossref","first-page":"2160","DOI":"10.1105\/tpc.108.058040","volume":"20","year":"2008","journal-title":"Plant Cell"},{"key":"2021040621022110100_b59","doi-asserted-by":"crossref","first-page":"1457","DOI":"10.1016\/j.phytochem.2008.02.019","volume":"69","year":"2008","journal-title":"Phytochemistry"},{"key":"2021040621022110100_b60","doi-asserted-by":"crossref","first-page":"3100","DOI":"10.1101\/gad.1035402","volume":"16","year":"2002","journal-title":"Genes Dev."},{"key":"2021040621022110100_b61","doi-asserted-by":"crossref","first-page":"2419","DOI":"10.1105\/tpc.11.12.2419","volume":"11","year":"1999","journal-title":"Plant Cell"},{"key":"2021040621022110100_b62","doi-asserted-by":"crossref","first-page":"463","DOI":"10.1104\/pp.113.2.463","volume":"113","year":"1997","journal-title":"Plant Physiol."}],"container-title":["The Plant Cell"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/academic.oup.com\/plcell\/article-pdf\/21\/6\/1830\/36918704\/plcell_v21_6_1830.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"http:\/\/academic.oup.com\/plcell\/article-pdf\/21\/6\/1830\/36918704\/plcell_v21_6_1830.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,3,14]],"date-time":"2024-03-14T19:33:05Z","timestamp":1710444785000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/plcell\/article\/21\/6\/1830\/6095417"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,6,1]]},"references-count":62,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2009,6,30]]},"published-print":{"date-parts":[[2009,8,5]]}},"URL":"https:\/\/doi.org\/10.1105\/tpc.109.066670","relation":{"has-review":[{"id-type":"doi","id":"10.3410\/f.1166481.627469","asserted-by":"object"}]},"ISSN":["1532-298X","1040-4651"],"issn-type":[{"value":"1532-298X","type":"electronic"},{"value":"1040-4651","type":"print"}],"subject":[],"published-other":{"date-parts":[[2009,6,1]]},"published":{"date-parts":[[2009,6,1]]}}}