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The antifungal activities of these metabolites against the phytopathogens <jats:italic>Alternaria brassicicola<\/jats:italic>, <jats:italic>Leptosphaeria maculans<\/jats:italic> and <jats:italic>Sclerotinia sclerotiorum<\/jats:italic> established that tryptanthrin is a much stronger growth inhibitor of <jats:italic>L. maculans<\/jats:italic> than the phytoalexin camalexin. The biosynthetic precursors of tryptanthrin and <jats:italic>N<\/jats:italic>\u2010formylanthranilic acid are proposed based on the deuterium incorporations of isotopically labeled compounds. The overall results suggest that tryptanthrin is a phytoalexin and indirubin and <jats:italic>N<\/jats:italic>\u2010formylanthranilic acid are phytoanticipins in the plant species <jats:italic>I. indigotica<\/jats:italic> and that chemical diversity and biodiversity are intimately connected.<\/jats:p>","DOI":"10.1002\/cbdv.201800579","type":"journal-article","created":{"date-parts":[[2018,12,17]],"date-time":"2018-12-17T17:27:03Z","timestamp":1545067623000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Ecological Roles of Tryptanthrin, Indirubin and <i>N<\/i>\u2010Formylanthranilic Acid in <i>Isatis indigotica<\/i>: Phytoalexins or Phytoanticipins?"],"prefix":"10.1002","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9510-2215","authenticated-orcid":false,"given":"M. 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Huy","family":"To","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Saskatchewan  110 Science Place Saskatoon SK S7N 5C9 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chintamani","family":"Thapa","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Saskatchewan  110 Science Place Saskatoon SK S7N 5C9 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2019,2,8]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"crossref","unstructured":"I.\u2005A. Al-Shehbaz M.\u2005A. Beilstein E.\u2005A. Kellogg \u2018Systematics and phylogeny of the Brassicaceae (Cruciferae): an overview\u2019 Plant Syst. Evol.2006 259 89\u2013120.","DOI":"10.1007\/s00606-006-0415-z"},{"key":"e_1_2_8_2_1","doi-asserted-by":"crossref","unstructured":"L. Yang G. Wang M. Wang H. Jiang L. Chen F. Zhao F. 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