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It produces a complex mixture of bioactive secondary metabolites, including toxic pyrrolizidine alkaloids (PAs), that protect the plant from insect and livestock herbivory and naphthoquinones (NQs), which suppress competition from weeds, insects and pathogens, and also influence invasion success. However, the extent to which allelochemical production is impacted by environmental factors, thereby influencing plant defense against pests, remains unclear.<\/jats:p><\/jats:sec><jats:sec><jats:title>Results<\/jats:title><jats:p>Following plant stress induced by drought, herbivory and high temperature, extracts of <jats:italic>E. plantagineum<\/jats:italic> shoots and roots were subjected to metabolic profiling by UPLC\u2010MS\u2010DAD\u2010 QToF mass spectrometry. Abundance of NQs, especially deoxyshikonin, shikonin and dimethylacrylshikonin, rapidly increased in roots exposed to elevated temperatures. Water withholding initially increased NQ abundance, but prolonged drought resulted in reduced total PAs and NQs. Intraspecific competition elevated the production of NQs, whereas simulated herbivory had no initial effect on NQs. Following herbivory, the abundance of the PA 3\u2032\u2010<jats:italic>O<\/jats:italic>\u2010acetylechimidine\u2010<jats:italic>N<\/jats:italic>\u2010oxide in seedling shoots was increased.<\/jats:p><\/jats:sec><jats:sec><jats:title>Conclusions<\/jats:title><jats:p>Differential accumulation of defense metabolites by <jats:italic>E. plantagineum<\/jats:italic> following exposure to various stressors suggested stress\u2010dependent biosynthetic regulation, particularly with respect to NQ production, which was rapidly induced following drought, intraspecific competition and high temperature treatment, thereby positively impacting resistance or defense against herbivores, weeds and pathogens. We propose that trade\u2010offs between above\u2010 and below\u2010ground metabolism in <jats:italic>E. plantagineum<\/jats:italic> may facilitate allelochemical production in response to stress, rendering plants with an enhanced ability to defend against other neighboring plants, insects and microbes, with allelochemical production further facilitated by catabolic recycling following lengthier exposure to stress. \u00a9 2019 Society of Chemical Industry<\/jats:p><\/jats:sec>","DOI":"10.1002\/ps.5540","type":"journal-article","created":{"date-parts":[[2019,7,3]],"date-time":"2019-07-03T03:44:56Z","timestamp":1562125496000},"page":"2530-2541","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":29,"title":["Production of pyrrolizidine alkaloids and shikonins in <i>Echium plantagineum<\/i> L. in response to various plant stressors"],"prefix":"10.1002","volume":"75","author":[{"given":"Dominik","family":"Skoneczny","sequence":"first","affiliation":[{"name":"Graham Centre for Agricultural Innovation Charles Sturt University  Wagga Wagga New South Wales Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaocheng","family":"Zhu","sequence":"additional","affiliation":[{"name":"Graham Centre for Agricultural Innovation Charles Sturt University  Wagga Wagga New South Wales Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paul A","family":"Weston","sequence":"additional","affiliation":[{"name":"Graham Centre for Agricultural Innovation Charles Sturt University  Wagga Wagga New South Wales Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5008-7966","authenticated-orcid":false,"given":"Geoff M","family":"Gurr","sequence":"additional","affiliation":[{"name":"Graham Centre for Agricultural Innovation Charles Sturt University  Orange New South Wales Australia"},{"name":"Institute of Applied Ecology Fujian Agriculture &amp; Forestry University  Fuzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ragan M","family":"Callaway","sequence":"additional","affiliation":[{"name":"Division of Biological Science University of Montana  Missoula MT USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1029-7982","authenticated-orcid":false,"given":"Leslie A","family":"Weston","sequence":"additional","affiliation":[{"name":"Graham Centre for Agricultural Innovation Charles Sturt University  Wagga Wagga New South Wales Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,7,29]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0308007101"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.4161\/psb.6.11.17613"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02059810"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1369-5266(02)00264-9"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1046\/j.1469-8137.1999.00423.x"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms140510242"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10886-013-0248-5"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1093\/jxb\/ers054"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1046\/j.1469-8137.2003.00759.x"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.2307\/3870059"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1038\/35081178"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1305848110"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1104\/pp.113.221150"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms140714950"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10886-013-0312-1"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00344-012-9272-x"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1093\/pcp\/pct054"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10886-014-0505-2"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1744-7909.2007.00395.x"},{"key":"e_1_2_9_21_1","first-page":"3","article-title":"The biology of Australian weeds 8. 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