{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T23:56:20Z","timestamp":1792108580638,"version":"4.4.0"},"reference-count":93,"publisher":"Springer Science and Business Media LLC","issue":"6","license":[{"start":{"date-parts":[[2021,11,11]],"date-time":"2021-11-11T00:00:00Z","timestamp":1636588800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2021,11,11]],"date-time":"2021-11-11T00:00:00Z","timestamp":1636588800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"name":"doe great lakes bioenergy research center","award":["DE-SC0018409"],"award-info":[{"award-number":["DE-SC0018409"]}]},{"DOI":"10.13039\/501100000923","name":"australian research council","doi-asserted-by":"crossref","award":["DP180101011"],"award-info":[{"award-number":["DP180101011"]}],"id":[{"id":"10.13039\/501100000923","id-type":"DOI","asserted-by":"crossref"}]},{"name":"novo nordisk foundation distinguished investigator grant","award":["NNF 0054563"],"award-info":[{"award-number":["NNF 0054563"]}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Planta"],"published-print":{"date-parts":[[2021,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:sec>\n                <jats:title>Main conclusion<\/jats:title>\n                <jats:p><jats:bold>Developmental and organ-specific expression of genes in dhurrin biosynthesis, bio-activation, and recycling offers dynamic metabolic responses optimizing growth and defence responses in Sorghum<\/jats:bold>.\n<\/jats:p>\n              <\/jats:sec><jats:sec>\n                <jats:title>Abstract<\/jats:title>\n                <jats:p>Plant defence models evaluate the costs and benefits of resource investments at different stages in the life cycle. Poor understanding of the molecular regulation of defence deployment and remobilization hampers accuracy of the predictions. Cyanogenic glucosides, such as dhurrin are phytoanticipins that release hydrogen cyanide upon bio-activation. In this study, RNA-seq was used to investigate the expression of genes involved in the biosynthesis, bio-activation and recycling of dhurrin in <jats:italic>Sorghum bicolor<\/jats:italic>. Genes involved in dhurrin biosynthesis were highly expressed in all young developing vegetative tissues (leaves, leaf sheath, roots, stems), tiller buds and imbibing seeds and showed gene specific peaks of expression in leaves during diel cycles. Genes involved in dhurrin bio-activation were expressed early in organ development with organ-specific expression patterns. Genes involved in recycling were expressed at similar levels in the different organ during development, although post-floral initiation when nutrients are remobilized for grain filling, expression of <jats:italic>GSTL1<\/jats:italic> decreased\u2009&gt;\u2009tenfold in leaves and <jats:italic>NITB2<\/jats:italic> increased\u2009&gt;\u2009tenfold in stems. Results are consistent with the establishment of a pre-emptive defence in young tissues and regulated recycling related to organ senescence and increased demand for nitrogen during grain filling. This detailed characterization of the transcriptional regulation of dhurrin biosynthesis, bioactivation and remobilization genes during organ and plant development will aid elucidation of gene regulatory networks and signalling pathways that modulate gene expression and dhurrin levels. In-depth knowledge of dhurrin metabolism could improve the yield, nitrogen use efficiency and stress resilience of <jats:italic>Sorghum<\/jats:italic>.\n<\/jats:p>\n              <\/jats:sec>","DOI":"10.1007\/s00425-021-03774-2","type":"journal-article","created":{"date-parts":[[2021,11,11]],"date-time":"2021-11-11T11:05:52Z","timestamp":1636628752000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["Regulation of dhurrin pathway gene expression during Sorghum\u00a0bicolor development"],"prefix":"10.1007","volume":"254","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4756-0411","authenticated-orcid":false,"given":"Roslyn M.","family":"Gleadow","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7105-9649","authenticated-orcid":false,"given":"Brian A.","family":"McKinley","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1919-6982","authenticated-orcid":false,"given":"Cecilia K.","family":"Blomstedt","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0083-637X","authenticated-orcid":false,"given":"Austin C.","family":"Lamb","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3252-3119","authenticated-orcid":false,"given":"Birger Lindberg","family":"M\u00f8ller","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2502-2671","authenticated-orcid":false,"given":"John E.","family":"Mullet","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2021,11,11]]},"reference":[{"issue":"1","key":"3774_CR1","doi-asserted-by":"publisher","first-page":"343","DOI":"10.1007\/s11033-018-4477-0","volume":"46","author":"MA Akbudak","year":"2019","unstructured":"Akbudak MA, Filiz E, Uylas S (2019) Identification of O-acetylserine(thiol)lyase (OASTL) genes in sorghum (Sorghum bicolor) and gene expression analysis under cadmium stress. Mol Biol Rep 46(1):343\u2013354. https:\/\/doi.org\/10.1007\/s11033-018-4477-0","journal-title":"Mol Biol Rep"},{"issue":"3","key":"3774_CR2","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1023\/A:1005915507497","volume":"36","author":"S Bak","year":"1998","unstructured":"Bak S, Kahn RA, Nielsen HL, M\u00f8ller BL, Halkier BA (1998) Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin. Plant Mol Biol 36(3):393\u2013405","journal-title":"Plant Mol Biol"},{"issue":"4","key":"3774_CR3","doi-asserted-by":"crossref","first-page":"1437","DOI":"10.1104\/pp.123.4.1437","volume":"123","author":"S Bak","year":"2000","unstructured":"Bak S, Olsen CE, Halkier BA, M\u00f8ller BL (2000) Transgenic tobacco and Arabidopsis plants expressing the two multifunctional sorghum cytochrome P450 enzymes, CYP79A1 and CYP71E1, are cyanogenic and accumulate metabolites derived from intermediates in dhurrin biosynthesis. Plant Physiol 123(4):1437\u20131448","journal-title":"Plant Physiol"},{"key":"3774_CR4","doi-asserted-by":"crossref","first-page":"261","DOI":"10.1007\/s10886-005-9001-z","volume":"32","author":"D Ballhorn","year":"2006","unstructured":"Ballhorn D, Heil M, Lieberei R (2006) Phenotypic plasticity of cyanogenesis in lima bean Phaseolus lunatus\u2014activity and activation of \u03b2-glucosidase. J Chem Ecol 32:261\u2013275","journal-title":"J Chem Ecol"},{"key":"3774_CR5","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1111\/ele.12744","volume":"20","author":"KE Barton","year":"2017","unstructured":"Barton KE, Boege K (2017) Future directions in the ontogeny of plant defence: understanding the evolutionary causes and consequences. Ecol Lett 20:403\u2013411","journal-title":"Ecol Lett"},{"issue":"6","key":"3774_CR6","doi-asserted-by":"publisher","first-page":"1109","DOI":"10.1111\/tpj.13923","volume":"94","author":"N Bjarnholt","year":"2018","unstructured":"Bjarnholt N, Neilson EHJ, Crocoll C, J\u00f8rgensen K, Motawia MS, Olsen CE, Dixon DP, Edwards R, M\u00f8ller BL (2018) Glutathione transferases catalyze recycling of auto-toxic cyanogenic glucosides in Sorghum. Plant J 94(6):1109\u20131125. https:\/\/doi.org\/10.1111\/tpj.13923","journal-title":"Plant J"},{"issue":"7","key":"3774_CR7","doi-asserted-by":"publisher","first-page":"705","DOI":"10.1071\/FP17227","volume":"45","author":"CK Blomstedt","year":"2018","unstructured":"Blomstedt CK, Rosati VC, Lindberg M\u00f8ller B, Gleadow R (2018) Counting the costs: nitrogen partitioning in Sorghum mutants. Funct Plant Biol 45(7):705\u2013718. https:\/\/doi.org\/10.1071\/FP17227","journal-title":"Funct Plant Biol"},{"issue":"8","key":"3774_CR8","doi-asserted-by":"publisher","first-page":"441","DOI":"10.1016\/j.tree.2005.05.001","volume":"20","author":"K Boege","year":"2005","unstructured":"Boege K, Marquis RJ (2005) Facing herbivory as you grow up: the ontogeny of resistance in plants. Trends Ecol Evol 20(8):441\u2013448. https:\/\/doi.org\/10.1016\/j.tree.2005.05.001","journal-title":"Trends Ecol Evol"},{"key":"3774_CR9","doi-asserted-by":"publisher","first-page":"1056","DOI":"10.2135\/cropsci2012.09.0520","volume":"53","author":"JJ Burke","year":"2013","unstructured":"Burke JJ, Chen J, Burow G, Mechref Y, Rosenow D, Payton P, Xin Z, Hayes CM (2013) Leaf dhurrin content is a quantitative measure of the level of pre- and postflowering drought tolerance in sorghum. Crop Sci 53:1056\u20131065. https:\/\/doi.org\/10.2135\/cropsci2012.09.0520","journal-title":"Crop Sci"},{"key":"3774_CR10","doi-asserted-by":"crossref","first-page":"1222","DOI":"10.1104\/pp.000687","volume":"129","author":"PK Busk","year":"2002","unstructured":"Busk PK, M\u00f8ller BL (2002) Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants. Plant Physiol 129:1222\u20131231","journal-title":"Plant Physiol"},{"issue":"11","key":"3774_CR11","doi-asserted-by":"publisher","DOI":"10.1002\/pld3.85","volume":"2","author":"AL Casto","year":"2018","unstructured":"Casto AL, McKinley BA, Yu KMJ, Rooney WL, Mullet JE (2018) Sorghum stem aerenchyma formation is regulated by SbNAC_D during internode development. Plant Direct 2(11):e00085. https:\/\/doi.org\/10.1002\/pld3.85","journal-title":"Plant Direct"},{"issue":"4","key":"3774_CR12","doi-asserted-by":"crossref","first-page":"1469","DOI":"10.1104\/pp.116.4.1469","volume":"116","author":"M Cicek","year":"1998","unstructured":"Cicek M, Esen A (1998) Structure and expression of a dhurrinase (beta-glucosidase) from Sorghum. Plant Physiol (rockville) 116(4):1469\u20131478","journal-title":"Plant Physiol (rockville)"},{"issue":"1","key":"3774_CR13","doi-asserted-by":"publisher","first-page":"420","DOI":"10.1186\/s12864-019-5734-x","volume":"20","author":"EA Cooper","year":"2019","unstructured":"Cooper EA, Brenton ZW, Flinn BS, Jenkins J, Shu S, Flowers D, Luo F, Wang Y, Xia P, Barry K, Daum C, Lipzen A, Yoshinaga Y, Schmutz J, Saski C, Vermerris W, Kresovich S (2019) A new reference genome for Sorghum bicolor reveals high levels of sequence similarity between sweet and grain genotypes: implications for the genetics of sugar metabolism. BMC Genomics 20(1):420. https:\/\/doi.org\/10.1186\/s12864-019-5734-x","journal-title":"BMC Genomics"},{"key":"3774_CR14","doi-asserted-by":"crossref","first-page":"112645","DOI":"10.1016\/j.phytochem.2020.112645","volume":"184","author":"M Cowan","year":"2021","unstructured":"Cowan M, Blomstedt CK, M\u00f8ller BL, Henry R, Gleadow RM (2021) Variation in production of cyanogenic glucosides during early plant development: a comparison of wild and domesticated Sorghum. Phytochemistry 184:112645","journal-title":"Phytochemistry"},{"issue":"4","key":"3774_CR15","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1038\/nmeth.3317","volume":"12","author":"K Daehwan","year":"2015","unstructured":"Daehwan K, Langmead B, Salzberg S (2015) HISAT: a fast spliced aligner with low memory requirements. Nat Methods 12(4):357\u2013360","journal-title":"Nat Methods"},{"issue":"1","key":"3774_CR16","doi-asserted-by":"publisher","first-page":"37079","DOI":"10.1038\/srep37079","volume":"6","author":"B Darbani","year":"2016","unstructured":"Darbani B, Motawia MS, Olsen CE, Nour-Eldin HH, M\u00f8ller BL, Rook F (2016) The biosynthetic gene cluster for the cyanogenic glucoside dhurrin in Sorghum bicolor contains its co-expressed vacuolar MATE transporter. Sci Rep 6(1):37079. https:\/\/doi.org\/10.1038\/srep37079","journal-title":"Sci Rep"},{"issue":"12","key":"3774_CR150","doi-asserted-by":"crossref","first-page":"971","DOI":"10.1111\/j.1744-7909.2011.01086.x","volume":"53","author":"C Diezel","year":"2011","unstructured":"Diezel C, Allmann S, Baldwin IT (2011) Mechanisms of optimal defense patterns in Nicotiana attenuata: flowering attenuates herbivory-elicited Ethylene and Jasmonate Signaling F. J Integr Plant Biol 53(12):971\u2013983","journal-title":"J Integr Plant Biol"},{"issue":"1","key":"3774_CR17","doi-asserted-by":"crossref","first-page":"135","DOI":"10.21475\/ajcs.18.12.01.pne790","volume":"12","author":"Y Emendack","year":"2018","unstructured":"Emendack Y, Burke J, Sanchez J, Laza HE, Hayes C (2018) Agro-morphological characterization of diverse sorghum lines for pre-and post-flowering drought tolerance. Aust J Crop Sci 12(1):135\u2013150","journal-title":"Aust J Crop Sci"},{"key":"3774_CR18","doi-asserted-by":"publisher","first-page":"33151","DOI":"10.1038\/srep33151","volume":"5","author":"Y Fang","year":"2016","unstructured":"Fang Y, Mei H, Zhou B, Xiao X, Yang M, Huang Y, Long X, Hu S, Tang C (2016) De novo transcriptome analysis reveals distinct defense mechanisms by young and mature leaves of Hevea brasiliensis (para rubber tree). Sci Rep 5:33151. https:\/\/doi.org\/10.1038\/srep33151","journal-title":"Sci Rep"},{"key":"3774_CR19","first-page":"1","volume":"54","author":"D Ganjewala","year":"2010","unstructured":"Ganjewala D, Kumar S, Devi SA, Ambika K (2010) Advances in cyanogenic glycosides biosynthesis and analyses in plants: a review. Acta Biologica Szegediensis 54:1\u201314","journal-title":"Acta Biologica Szegediensis"},{"key":"3774_CR20","first-page":"105","volume-title":"Insect-plant interactions","author":"J Gershenzon","year":"1989","unstructured":"Gershenzon J (1989) The cost of plant chemical defense against herbivory: a biochemical perspective. In: Bernays EA (ed) Insect-plant interactions, vol 5. CRC Press, Bacon Raton, pp 105\u2013173"},{"issue":"3","key":"3774_CR21","doi-asserted-by":"publisher","first-page":"1026","DOI":"10.1007\/s12155-014-9445-5","volume":"7","author":"JR Gill","year":"2014","unstructured":"Gill JR, Burks PS, Staggenborg SA, Odvody GN, Heiniger RW, Macoon B, Moore KJ, Barrett M, Rooney WL (2014) Yield results and stability analysis from the sorghum regional biomass feedstock trial. BioEnergy Res 7(3):1026\u20131034. https:\/\/doi.org\/10.1007\/s12155-014-9445-5","journal-title":"BioEnergy Res"},{"issue":"1","key":"3774_CR22","doi-asserted-by":"publisher","first-page":"155","DOI":"10.1146\/annurev-arplant-050213-040027","volume":"65","author":"RM Gleadow","year":"2014","unstructured":"Gleadow RM, M\u00f8ller BL (2014) Cyanogenic glycosides: synthesis, physiology, and phenotypic plasticity. Annu Rev Plant Biol 65(1):155\u2013185. https:\/\/doi.org\/10.1146\/annurev-arplant-050213-040027","journal-title":"Annu Rev Plant Biol"},{"key":"3774_CR23","doi-asserted-by":"crossref","first-page":"1301","DOI":"10.1023\/A:1016298100201","volume":"28","author":"RM Gleadow","year":"2002","unstructured":"Gleadow RM, Woodrow IE (2002) Constraints on effectiveness of cyanogenic glycosides in herbivore defense. J Chem Ecol 28:1301\u20131313","journal-title":"J Chem Ecol"},{"key":"3774_CR24","doi-asserted-by":"crossref","first-page":"12","DOI":"10.1046\/j.1365-3040.1998.00258.x","volume":"21","author":"RM Gleadow","year":"1998","unstructured":"Gleadow RM, Foley WJ, Woodrow IE (1998) Enhanced CO2 alters the relationship between photosynthesis and defence in cyanogenic Eucalyptus cladocalyx F. Muell. Plant Cell Environ 21:12\u201322","journal-title":"Plant Cell Environ"},{"key":"3774_CR25","doi-asserted-by":"publisher","first-page":"97","DOI":"10.1016\/j.fcr.2015.10.010","volume":"185","author":"RM Gleadow","year":"2016","unstructured":"Gleadow RM, Ottman MJ, Kimball BA, Wall GW, Pinter PJ Jr, LaMorte RL, Leavitt SW (2016) Drought-induced changes in nitrogen partitioning between cyanide and nitrate in leaves and stems of Sorghum grown at elevated CO2 are age dependent. Field Crop Res 185:97\u2013102. https:\/\/doi.org\/10.1016\/j.fcr.2015.10.010","journal-title":"Field Crop Res"},{"issue":"4","key":"3774_CR26","doi-asserted-by":"crossref","first-page":"1552","DOI":"10.1104\/pp.90.4.1552","volume":"90","author":"BA Halkier","year":"1989","unstructured":"Halkier BA, M\u00f8ller BL (1989) Biosynthesis of the cyanogenic glucoside dhurrin in seedlings of Sorghum bicolor (L.) Moench and partial purification of the enzyme system involved. Plant Physiol 90(4):1552\u20131559","journal-title":"Plant Physiol"},{"issue":"1","key":"3774_CR27","doi-asserted-by":"publisher","first-page":"104","DOI":"10.2135\/cropsci2015.06.0379","volume":"56","author":"CM Hayes","year":"2016","unstructured":"Hayes CM, Weers BD, Thakran M, Burow G, Xin Z, Emendack Y, Burke JJ, Rooney WL, Mullet JE (2016) Discovery of a dhurrin QTL in Sorghum: co-localization of dhurrin biosynthesis and a novel stay-green QTL. Crop Sci 56(1):104\u2013112. https:\/\/doi.org\/10.2135\/cropsci2015.06.0379","journal-title":"Crop Sci"},{"key":"3774_CR28","doi-asserted-by":"publisher","DOI":"10.3835\/plantgenome2014.09.0048","author":"CM Hayes","year":"2015","unstructured":"Hayes CM, Burow GB, Brown PJ, Thurber C, Xin Z, Burke JJ (2015) Natural variation in synthesis and catabolism genes influences dhurrin content in sorghum. Plant Genome. https:\/\/doi.org\/10.3835\/plantgenome2014.09.0048","journal-title":"Plant Genome"},{"issue":"1","key":"3774_CR29","doi-asserted-by":"publisher","first-page":"2691","DOI":"10.1038\/s41598-018-20928-7","volume":"8","author":"P Heraud","year":"2018","unstructured":"Heraud P, Cowan MF, Marzec KM, M\u00f8ller BL, Blomstedt CK, Gleadow R (2018) Label-free Raman hyperspectral imaging analysis localizes the cyanogenic glucoside dhurrin to the cytoplasm in Sorghum cells. Sci Rep 8(1):2691. https:\/\/doi.org\/10.1038\/s41598-018-20928-7","journal-title":"Sci Rep"},{"key":"3774_CR30","doi-asserted-by":"crossref","first-page":"152","DOI":"10.1016\/0003-9861(87)90019-1","volume":"252","author":"W H\u00f6sel","year":"1987","unstructured":"H\u00f6sel W, Tober I, Eklund SH, Conn EE (1987) Characterisation of betaglucosidases with high specificity for the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench seedlings. Arch Biochem Biophys 252:152\u2013162","journal-title":"Arch Biochem Biophys"},{"issue":"47","key":"3774_CR31","doi-asserted-by":"publisher","first-page":"18848","DOI":"10.1073\/pnas.0709315104","volume":"104","author":"R Jenrich","year":"2007","unstructured":"Jenrich R, Trompetter I, Bak S, Olsen CE, M\u00f8ller BL, Piotrowski M (2007) Evolution of heteromeric nitrilase complexes in Poaceae with new functions in nitrile metabolism. Proc Natl Acad Sci 104(47):18848\u201318853. https:\/\/doi.org\/10.1073\/pnas.0709315104","journal-title":"Proc Natl Acad Sci"},{"issue":"50","key":"3774_CR32","doi-asserted-by":"publisher","first-page":"35483","DOI":"10.1074\/jbc.274.50.35483","volume":"274","author":"PR Jones","year":"1999","unstructured":"Jones PR, M\u00f8ller BL, Hoj PB (1999) The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor isolation, cloning, heterologous expression, and substrate specificity. J Biol Chem 274(50):35483\u201335491. https:\/\/doi.org\/10.1074\/jbc.274.50.35483","journal-title":"J Biol Chem"},{"key":"3774_CR33","doi-asserted-by":"crossref","first-page":"280","DOI":"10.1016\/j.pbi.2005.03.014","volume":"8","author":"K J\u00f8rgensen","year":"2005","unstructured":"J\u00f8rgensen K, Rasmussen AV, Morant M, Nielsen AH, Bjarnholt N, Zagrobelny M, Bak S, M\u00f8ller BL (2005) Metabolon formation and metabolic channeling in the biosynthesis of plant natural products. Curr Opin Plant Biol 8:280\u2013291","journal-title":"Curr Opin Plant Biol"},{"key":"3774_CR34","doi-asserted-by":"publisher","first-page":"19466","DOI":"10.7554\/eLife.19466","volume":"6","author":"M J\u00f8rgensen","year":"2017","unstructured":"J\u00f8rgensen M, Xu D, Crocoll C, Ernst H, Ram\u00edrez D, Motawia M, Olsen C, Mirza O, Nour-Eldin H, Halkier B (2017) Origin and evolution of transporter substrate specificity within the NPF family. Elife 6:19466. https:\/\/doi.org\/10.7554\/eLife.19466","journal-title":"Elife"},{"issue":"4","key":"3774_CR35","doi-asserted-by":"crossref","first-page":"1661","DOI":"10.1104\/pp.115.4.1661","volume":"115","author":"RA Kahn","year":"1997","unstructured":"Kahn RA, Bak S, Svendsen I, Halkier BA, M\u00f8ller BL (1997) Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from Sorghum. Plant Physiol 115(4):1661\u20131670","journal-title":"Plant Physiol"},{"issue":"1","key":"3774_CR36","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1006\/abbi.1998.1068","volume":"363","author":"R Kahn","year":"1999","unstructured":"Kahn R, Fahrendorf T, Halkier B, M\u00f8ller B (1999) Substrate specificity of the cytochrome P450 enzymes CYP79A1 and CYP71E1 involved in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench. Archives Biochem Biophys 363(1):9\u201318","journal-title":"Archives Biochem Biophys"},{"key":"3774_CR37","doi-asserted-by":"crossref","first-page":"2232","DOI":"10.1104\/pp.16.00014","volume":"170","author":"TH Kebrom","year":"2016","unstructured":"Kebrom TH, Mullet JE (2016) Transcriptome profiling of tiller buds provides new insights into phyb regulation of tillering and indeterminate growth in Sorghum. Plant Physiol 170:2232\u20132250","journal-title":"Plant Physiol"},{"issue":"1","key":"3774_CR38","doi-asserted-by":"publisher","first-page":"159","DOI":"10.1186\/s13068-017-0848-3","volume":"10","author":"TH Kebrom","year":"2017","unstructured":"Kebrom TH, McKinley B, Mullet JE (2017) Dynamics of gene expression during development and expansion of vegetative stem internodes of bioenergy sorghum. Biotechnol Biofuels 10(1):159. https:\/\/doi.org\/10.1186\/s13068-017-0848-3","journal-title":"Biotechnol Biofuels"},{"issue":"6","key":"3774_CR39","doi-asserted-by":"publisher","DOI":"10.1002\/pld3.235","volume":"4","author":"TH Kebrom","year":"2020","unstructured":"Kebrom TH, McKinley BA, Mullet JE (2020) Shade signals alter the expression of circadian clock genes in newly-formed bioenergy sorghum internodes. Plant Direct 4(6):e00235. https:\/\/doi.org\/10.1002\/pld3.235","journal-title":"Plant Direct"},{"key":"3774_CR40","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1111\/tpj.13247","volume":"88","author":"E Knoch","year":"2016","unstructured":"Knoch E, Motawie MS, Olsen CE, M\u00f8ller BL, Lyngkj\u00e6r MF (2016) Biosynthesis of the leucine derived a-, b- and c-hydroxynitrile glucosides in barley (Hordeum vulgare L.). Plant J 88:247\u2013256","journal-title":"Plant J"},{"key":"3774_CR41","doi-asserted-by":"crossref","first-page":"1140","DOI":"10.1039\/C8NP00037A","volume":"35","author":"CB Knudsen","year":"2018","unstructured":"Knudsen CB, Gallage NJ, Hansen CC, M\u00f8ller BL, Laursen T (2018) Dynamic metabolic solutions to the sessile life style of plants. Nat Prod Rep 35:1140\u20131155","journal-title":"Nat Prod Rep"},{"key":"3774_CR42","doi-asserted-by":"crossref","first-page":"112214","DOI":"10.1016\/j.phytochem.2019.112214","volume":"170","author":"CB Knudsen","year":"2020","unstructured":"Knudsen CB, Bavishi K, Viborg KM, Drew DP, Simonsen HT, Motawie MS, M\u00f8ller BL, Laursen T (2020) Stabilization of the dhurrin biosynthetic enzymes using a natural deep eutectic solvent. Phytochemistry 170:112214","journal-title":"Phytochemistry"},{"key":"3774_CR43","doi-asserted-by":"crossref","first-page":"1022","DOI":"10.1104\/pp.63.6.1022","volume":"63","author":"M Kojima","year":"1979","unstructured":"Kojima M, Poulton JE, Thayer SS, Conn EE (1979) Tissue distributions of dhurrin and of enzymes involved in its metabolism in leaves of Sorghum bicolor. Plant Physiol 63:1022\u20131028","journal-title":"Plant Physiol"},{"key":"3774_CR44","doi-asserted-by":"crossref","first-page":"730","DOI":"10.1016\/j.phytochem.2009.03.020","volume":"70","author":"P Kongsawadworakul","year":"2009","unstructured":"Kongsawadworakul P, Viboonjun U, Romruensukharom P, Chantuma P, Ruderman S, Chrestin H (2009) The leaf, inner bark and latex cyanide potential of Hevea brasiliensis: evidence for involvement of cyanogenic glucosides in rubber yield. Phytochemistry 70:730\u2013739","journal-title":"Phytochemistry"},{"issue":"5","key":"3774_CR45","doi-asserted-by":"crossref","first-page":"1779","DOI":"10.1073\/pnas.0409233102","volume":"102","author":"C Kristensen","year":"2005","unstructured":"Kristensen C, Morant M, Olsen CE, Ekstr\u00f8m CT, Galbraith DW, M\u00f8ller BL, Bak S (2005) Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome. Proc Natl Acad Sci USA 102(5):1779\u20131784","journal-title":"Proc Natl Acad Sci USA"},{"issue":"2","key":"3774_CR46","doi-asserted-by":"publisher","first-page":"309","DOI":"10.1534\/genetics.113.149567","volume":"195","author":"K Krothapalli","year":"2013","unstructured":"Krothapalli K, Buescher EM, Li X, Brown E, Chapple C, Dilkes BP, Tuinstra MR (2013) Forward genetics by genome sequencing reveals that rapid cyanide release deters insect herbivory of Sorghum bicolor. Genetics 195(2):309\u2013318. https:\/\/doi.org\/10.1534\/genetics.113.149567","journal-title":"Genetics"},{"issue":"2","key":"3774_CR47","doi-asserted-by":"publisher","first-page":"299","DOI":"10.1111\/tpj.12561","volume":"79","author":"D Lai","year":"2014","unstructured":"Lai D, Abou Hachem M, Robson F, Olsen CE, Wang TL, M\u00f8ller BL, Takos AM, Rook F (2014) The evolutionary appearance of non-cyanogenic hydroxynitrile glucosides in the Lotus genus is accompanied by the substrate specialization of paralogous \u03b2\u2013glucosidases resulting from a crucial amino acid substitution. Plant J 79(2):299\u2013311. https:\/\/doi.org\/10.1111\/tpj.12561","journal-title":"Plant J"},{"key":"3774_CR48","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1016\/j.tplants.2014.11.002","volume":"20","author":"T Laursen","year":"2015","unstructured":"Laursen T, M\u00f8ller BL, Bassard J-E (2015) Plasticity of specialized metabolism as mediated by dynamic metabolons. Trends Plant Sci 20:20\u201332","journal-title":"Trends Plant Sci"},{"key":"3774_CR49","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms3320","author":"ES Mace","year":"2013","unstructured":"Mace ES, Tai S, Gilding EK, Li Y, Prentis PJ, Bian L, Campbell BC, Hu W, Innes DJ, Han X, Cruickshank A, Dai C, Fr\u00e8re C, Zhang H, Hunt CH, Wang X, Shatte T, Wang M, Su Z, Li J, Lin X, Godwin ID, Jordan DR, Wang J (2013) Whole-genome sequencing reveals untapped genetic potential in Africa\u2019s indigenous cereal crop sorghum. Nat Commun. https:\/\/doi.org\/10.1038\/ncomms3320","journal-title":"Nat Commun"},{"issue":"W1","key":"3774_CR50","doi-asserted-by":"publisher","first-page":"W636","DOI":"10.1093\/nar\/gkz268","volume":"47","author":"F Madeira","year":"2019","unstructured":"Madeira F, Park YM, Lee J, Buso N, Gur T, Madhusoodanan N, Basutkar P, Tivey ARN, Potter SC, Finn RD, Lopez R (2019) The EMBL-EBI search and sequence analysis tools APIs in 2019. Nucleic Acids Res 47(W1):W636\u2013W641. https:\/\/doi.org\/10.1093\/nar\/gkz268","journal-title":"Nucleic Acids Res"},{"issue":"2","key":"3774_CR51","doi-asserted-by":"crossref","first-page":"338","DOI":"10.1111\/tpj.13781","volume":"93","author":"RF McCormick","year":"2018","unstructured":"McCormick RF, Truong SK, Sreedasyam A, Jenkins J, Shu S, Sims D, Kennedy M, Amirebrahimi M, Weers BD, McKinley B, Mattison A, Morishige DT, Grimwood J, Schmutz J, Mullet JE (2018) The Sorghum bicolor reference genome: improved assembly, gene annotations, a transcriptome atlas, and signatures of genome organization. Plant J 93(2):338\u2013354","journal-title":"Plant J"},{"key":"3774_CR52","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1086\/282909","volume":"108","author":"D McKey","year":"1974","unstructured":"McKey D (1974) Adaptive patterns in alkaloid physiology. Am Nat 108:305\u2013320","journal-title":"Am Nat"},{"issue":"4","key":"3774_CR53","doi-asserted-by":"publisher","first-page":"662","DOI":"10.1111\/tpj.13269","volume":"88","author":"B McKinley","year":"2016","unstructured":"McKinley B, Rooney W, Wilkerson C, Mullet J (2016) Dynamics of biomass partitioning, stem gene expression, cell wall biosynthesis, and sucrose accumulation during development of Sorghum bicolor. Plant J 88(4):662\u2013680. https:\/\/doi.org\/10.1111\/tpj.13269","journal-title":"Plant J"},{"key":"3774_CR54","doi-asserted-by":"publisher","DOI":"10.1002\/pld3.74","volume":"2","author":"BA McKinley","year":"2018","unstructured":"McKinley BA, Casto AL, Rooney WL, Mullet JE (2018a) Developmental dynamics of stem starch accumulation in Sorghum bicolor. Plant Direct 2:e00074. https:\/\/doi.org\/10.1002\/pld3.74","journal-title":"Plant Direct"},{"issue":"4","key":"3774_CR55","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0195863","volume":"13","author":"BA McKinley","year":"2018","unstructured":"McKinley BA, Olson SN, Ritter KB, Herb DW, Karlen SD, Lu F, Ralph J, Rooney WL, Mullet JE (2018b) Variation in energy Sorghum hybrid TX08001 biomass composition and lignin chemistry during development under irrigated and nonirrigated field conditions. PLoS ONE 13(4):e0195863. https:\/\/doi.org\/10.1371\/journal.pone.0195863","journal-title":"PLoS ONE"},{"key":"3774_CR56","doi-asserted-by":"crossref","first-page":"929","DOI":"10.1111\/pce.12209","volume":"37","author":"RE Miller","year":"2014","unstructured":"Miller RE, Gleadow RM, Cavagnaro T (2014) Age versus stage: does ontogeny modify the effect of phosphorus and arbuscular mycorrhizas on above- and below-ground defence in forage sorghum? Plant Cell Environ 37:929\u2013942","journal-title":"Plant Cell Environ"},{"key":"3774_CR57","doi-asserted-by":"crossref","first-page":"1328","DOI":"10.1126\/science.1194971","volume":"330","author":"BL M\u00f8ller","year":"2010","unstructured":"M\u00f8ller BL (2010) Dynamic metabolons. Science 330:1328","journal-title":"Science"},{"issue":"17","key":"3774_CR58","doi-asserted-by":"crossref","first-page":"8575","DOI":"10.1016\/S0021-9258(19)86931-4","volume":"254","author":"BL M\u00f8ller","year":"1979","unstructured":"M\u00f8ller BL, Conn EE (1979) The biosynthesis of cyanogenic glucosides in higher plants N-Hydroxytyrosine as an intermediate in the biosynthesis of dhurrin by Sorghum bicolor (L.) Moench. J Biol Chem 254(17):8575\u20138583","journal-title":"J Biol Chem"},{"key":"3774_CR59","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1016\/bs.abr.2020.09.006","volume":"97","author":"BL M\u00f8ller","year":"2021","unstructured":"M\u00f8ller BL, Laursen T (2021) Metabolons and bio-condensates: the essence of plant plasticity and the key elements in development of green production systems. Adv Bot Res 97:185\u2013223","journal-title":"Adv Bot Res"},{"key":"3774_CR60","doi-asserted-by":"crossref","first-page":"925","DOI":"10.1104\/pp.19.01357","volume":"183","author":"L Montini","year":"2020","unstructured":"Montini L, Crocoll C, Gleadow R, Motawia M, Janfelt C, Bjarnholt N (2020) Metabolite dynamics during Sorghum grain germination visualised by MALDI-mass spectrometry imaging. Plant Physiol 183:925\u2013942","journal-title":"Plant Physiol"},{"issue":"3","key":"3774_CR61","doi-asserted-by":"publisher","first-page":"1072","DOI":"10.1104\/pp.107.109512","volume":"147","author":"AV Morant","year":"2008","unstructured":"Morant AV, Bjarnholt N, Kragh ME, Kjaergaard CH, Jorgensen K, Paquette SM, Piotrowski M, Imberty A, Olsen CE, M\u00f8ller BL, Bak S (2008a) The \u03b2-Glucosidases responsible for bioactivation of hydroxynitrile glucosides in Lotus japonicus. Plant Physiol 147(3):1072\u20131091. https:\/\/doi.org\/10.1104\/pp.107.109512","journal-title":"Plant Physiol"},{"key":"3774_CR62","doi-asserted-by":"crossref","first-page":"1795","DOI":"10.1016\/j.phytochem.2008.03.006","volume":"69","author":"AV Morant","year":"2008","unstructured":"Morant AV, J\u00f8rgensen K, Kristensen C, Paquette SM, Sanchez-Perez R, M\u00f8ller BL, Bak S (2008b) \u03b2-glucosidases as detonators of plant chemical defense. Phytochemistry 69:1795\u20131813","journal-title":"Phytochemistry"},{"issue":"13","key":"3774_CR63","doi-asserted-by":"publisher","first-page":"3479","DOI":"10.1093\/jxb\/eru229","volume":"65","author":"J Mullet","year":"2014","unstructured":"Mullet J, Morishige D, McCormick R, Truong S, Hilley J, McKinley B, Anderson R, Olson SN, Rooney W (2014) Energy Sorghum\u2014a genetic model for the design of C4 grass bioenergy crops. J Exp Bot 65(13):3479\u20133489. https:\/\/doi.org\/10.1093\/jxb\/eru229","journal-title":"J Exp Bot"},{"issue":"16","key":"3774_CR64","doi-asserted-by":"publisher","first-page":"469","DOI":"10.1073\/pnas.1106212108","volume":"108","author":"RL Murphy","year":"2011","unstructured":"Murphy RL, Klein RR, Morishige DT, Brady JA, Rooney WL, Miller FR, Dugas DV, Klein PE, Mullet JE (2011) Coincident light and clock regulation of pseudoresponse regulator protein 37 (PRR37) controls photoperiodic lowering in sorghum. Proc Natl Acad Sci USA 108(16):469\u2013474. https:\/\/doi.org\/10.1073\/pnas.1106212108","journal-title":"Proc Natl Acad Sci USA"},{"key":"3774_CR65","doi-asserted-by":"crossref","first-page":"153393","DOI":"10.1016\/j.jplph.2021.153393","volume":"258","author":"H Myrans","year":"2021","unstructured":"Myrans H, Vandegeer RK, Henry RJ, Gleadow RM (2021) Nitrogen availability and allocation in sorghum and its wild relatives: divergent roles for cyanogenic glucosides. J Plant Physiol JPLPH 258:153393","journal-title":"J Plant Physiol JPLPH"},{"issue":"5","key":"3774_CR66","doi-asserted-by":"crossref","first-page":"250","DOI":"10.1016\/j.tplants.2013.01.001","volume":"18","author":"EH Neilson","year":"2013","unstructured":"Neilson EH, Goodger JQD, Woodrow IE, M\u00f8ller BL (2013) Plant chemical defense: at what cost? Trends Plant Sci 18(5):250\u2013258","journal-title":"Trends Plant Sci"},{"key":"3774_CR67","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/j.phytochem.2007.06.033","volume":"69","author":"KA Nielsen","year":"2008","unstructured":"Nielsen KA, Tattersall DB, Jones PR, M\u00f8ller BL (2008) Metabolon formation in dhurrin biosynthesis. Phytochemistry 69:88\u201398","journal-title":"Phytochemistry"},{"key":"3774_CR68","doi-asserted-by":"crossref","first-page":"1021","DOI":"10.1186\/s12864-016-3360-4","volume":"17","author":"LJ Nielsen","year":"2016","unstructured":"Nielsen LJ, Stuart P, Pi\u010dmanov\u00e1 M, Rasmussen S, Olsen CE, Harholt J, M\u00f8ller BL, Bjarnholt N (2016) Dhurrin metabolism in the developing grain of Sorghum bicolor (L.) Moench investigated by metabolite profiling and novel clustering analyses of time-resolved transcriptomic data. BMC Genomics 17:1021","journal-title":"BMC Genomics"},{"issue":"7412","key":"3774_CR69","doi-asserted-by":"publisher","first-page":"531","DOI":"10.1038\/nature11285","volume":"488","author":"HH Nour-Eldin","year":"2012","unstructured":"Nour-Eldin HH, Andersen TG, Burow M, Madsen SR, J\u00f8rgensen ME, Olsen CE, Dreyer I, Hedrich R, Geiger D, Halkier BA (2012) NRT\/PTR transporters are essential for translocation of glucosinolate defence compounds to seeds. Nature 488(7412):531\u2013534. https:\/\/doi.org\/10.1038\/nature11285","journal-title":"Nature"},{"key":"3774_CR70","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/j.plaphy.2013.09.001","volume":"73","author":"NH O'Donnell","year":"2013","unstructured":"O\u2019Donnell NH, M\u00f8ller BL, Neale AD, Hamill JD, Blomstedt CK, Gleadow RM (2013) Effects of PEG-induced osmotic stress on growth and dhurrin levels of forage Sorghum. Plant Physiol Biochem 73:83\u201392","journal-title":"Plant Physiol Biochem"},{"issue":"6","key":"3774_CR71","doi-asserted-by":"publisher","first-page":"640","DOI":"10.1002\/bbb.1357","volume":"6","author":"SN Olson","year":"2012","unstructured":"Olson SN, Ritter K, Rooney W, Kemanian A, McCarl BA, Zhang Y, Hall S, Packer D, Mullet J (2012) High biomass yield energy Sorghum: developing a genetic model for C4 grass bioenergy crops. Biofuels Bioprod Biorefin 6(6):640\u2013655. https:\/\/doi.org\/10.1002\/bbb.1357","journal-title":"Biofuels Bioprod Biorefin"},{"key":"3774_CR72","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1038\/nature07723","volume":"457","author":"AH Paterson","year":"2009","unstructured":"Paterson AH, Bowers JE, Bruggmann R, Dubchak I, Grimwood J, Gundlach H, Haberer G, Hellsten U, Mitros T, Poliakov A, Schmutz J, Spannagl M, Tang H, Wang X, Wicker T, Bharti AK, Chapman J, Feltus FA, Gowik U, Grigoriev IV, Lyons E, Maher CA, Martis M, Narechania A, Otillar RP, Penning BW, Salamov AA, Wang Y, Zhang L, Carpita NC, Freeling M, Gingle AR, Hash T, Keller B, Klein P, Kresovich S, McCann MC, Ming R, Peterson DG, Mehboob-ur-Rahman WD, Westhoff P, Mayer KFX, Messing J, Rokhsar DS (2009) The Sorghum bicolor genome and the diversification of grasses. Nature 457:551\u2013556","journal-title":"Nature"},{"issue":"3","key":"3774_CR73","doi-asserted-by":"publisher","first-page":"290","DOI":"10.1038\/nbt.3122","volume":"33","author":"M Pertea","year":"2015","unstructured":"Pertea M, Pertea GM, Antonescu CM, Chang T-C, Mendell JT, Salzberg SL (2015) StringTie enables improved reconstruction of a transcriptome from RNA-seq reads. Nat Biotechnol 33(3):290\u2013295. https:\/\/doi.org\/10.1038\/nbt.3122","journal-title":"Nat Biotechnol"},{"issue":"3","key":"3774_CR74","doi-asserted-by":"publisher","first-page":"375","DOI":"10.1042\/bj20150390","volume":"469","author":"M Pi\u010dmanov\u00e1","year":"2015","unstructured":"Pi\u010dmanov\u00e1 M, Neilson Elizabeth H, Motawia Mohammed S, Olsen Carl E, Agerbirk N, Gray Christopher J, Flitsch S, Meier S, Silvestro D, J\u00f8rgensen K, S\u00e1nchez-P\u00e9rez R, M\u00f8ller Birger L, Bjarnholt N (2015) A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species. Biochem J 469(3):375\u2013389. https:\/\/doi.org\/10.1042\/bj20150390","journal-title":"Biochem J"},{"key":"3774_CR75","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1104\/pp.94.2.401","volume":"94","author":"JE Poulton","year":"1990","unstructured":"Poulton JE (1990) Cyanogenesis in Plants. Plant Physiol 94:401\u2013405","journal-title":"Plant Physiol"},{"key":"3774_CR76","unstructured":"Quinby JR (1974) Sorghum improvement and the genetics of growth. Texas agricultural experiment station"},{"issue":"2","key":"3774_CR77","doi-asserted-by":"publisher","first-page":"147","DOI":"10.1002\/bbb.15","volume":"1","author":"WL Rooney","year":"2007","unstructured":"Rooney WL, Blumenthal J, Bean B, Mullet JE (2007) Designing Sorghum as a dedicated bioenergy feedstock. Biofuels Bioprod Biorefin 1(2):147\u2013157. https:\/\/doi.org\/10.1002\/bbb.15","journal-title":"Biofuels Bioprod Biorefin"},{"key":"3774_CR78","doi-asserted-by":"crossref","first-page":"1458","DOI":"10.3389\/fpls.2019.01458","volume":"10","author":"VC Rosati","year":"2019","unstructured":"Rosati VC, Blomstedt CK, M\u00f8ller BL, Garnett T, Gleadow R (2019) The interplay between drought stress, dhurrin and nitrate in the low-cyanogenic Sorghum mutant adult cyanide deficient class 1. Front Plant Sci 10:1458","journal-title":"Front Plant Sci"},{"key":"3774_CR79","doi-asserted-by":"crossref","first-page":"110","DOI":"10.1016\/j.toxlet.2009.05.007","volume":"189","author":"K Sakurada","year":"2009","unstructured":"Sakurada K, Ikegaya H, Ohta H, Fukushima H, Akutsu T, Watanabea K (2009) Effects of oximes on mitochondrial oxidase activity. Toxicol Lett 189:110","journal-title":"Toxicol Lett"},{"key":"3774_CR80","doi-asserted-by":"crossref","first-page":"154","DOI":"10.1104\/pp.61.2.154","volume":"61","author":"JA Saunders","year":"1978","unstructured":"Saunders JA, Conn EE (1978) Presence of the cyanogenic glucoside dhurrin in isolated vacuoles from Sorghum. Plant Physiol 61:154\u2013157","journal-title":"Plant Physiol"},{"key":"3774_CR81","doi-asserted-by":"publisher","DOI":"10.1002\/pld3.38","author":"FB Schmidt","year":"2018","unstructured":"Schmidt FB, Cho SK, Olsen CE, Yang SW, M\u00f8ller BL, J\u00f8rgensen K (2018) Diurnal regulation of cyanogenic glucoside biosynthesis and endogenous turnover in cassava. Plant Direct. https:\/\/doi.org\/10.1002\/pld3.38","journal-title":"Plant Direct"},{"key":"3774_CR82","doi-asserted-by":"publisher","first-page":"1111","DOI":"10.1093\/treephys\/tpq049","volume":"30","author":"J Simon","year":"2010","unstructured":"Simon J, Gleadow RM, Woodrow IE (2010) Allocation of nitrogen to chemical defence and plant functional traits is constrained by soil N. Tree Physiol 30:1111\u20131117. https:\/\/doi.org\/10.1093\/treephys\/tpq049","journal-title":"Tree Physiol"},{"key":"3774_CR83","doi-asserted-by":"publisher","first-page":"1791","DOI":"10.3390\/plants9121791","volume":"9","author":"MN Sohail","year":"2020","unstructured":"Sohail MN, Blomstedt CK, Gleadow RM (2020) Allocation of resources to cyanogenic glucosides does not incur a growth sacrifice in Sorghum bicolor (L.) Moench. Plants 9:1791. https:\/\/doi.org\/10.3390\/plants9121791","journal-title":"Plants"},{"key":"3774_CR84","doi-asserted-by":"publisher","first-page":"95","DOI":"10.1016\/j.molp.2017.12.014","volume":"11","author":"M S\u00f8rensen","year":"2018","unstructured":"S\u00f8rensen M, Neilson EH, M\u00f8ller BL (2018) Oximes: unrecognized chameleons in general and specialized plant metabolism. Mol Plant 11:95\u2013117. https:\/\/doi.org\/10.1016\/j.molp.2017.12.014","journal-title":"Mol Plant"},{"issue":"7","key":"3774_CR85","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1016\/j.tplants.2012.04.004","volume":"17","author":"AM Takos","year":"2012","unstructured":"Takos AM, Rook F (2012) Why biosynthetic genes for chemical defense compounds cluster. Trends Plant Sci 17(7):383\u2013388. https:\/\/doi.org\/10.1016\/j.tplants.2012.04.004","journal-title":"Trends Plant Sci"},{"issue":"2","key":"3774_CR86","doi-asserted-by":"publisher","first-page":"273","DOI":"10.1111\/j.1365-313X.2011.04685.x","volume":"68","author":"AM Takos","year":"2011","unstructured":"Takos AM, Knudsen C, Lai D, Kannangara R, Mikkelsen L, Motawia MS, Olsen CE, Sato S, Tabata S, J\u00f8rgensen K, M\u00f8ller BL, Rook F (2011) Genomic clustering of cyanogenic glucoside biosynthetic genes aids their identification in Lotus japonicus and suggests the repeated evolution of this chemical defence pathway. Plant J 68(2):273\u2013286. https:\/\/doi.org\/10.1111\/j.1365-313X.2011.04685.x","journal-title":"Plant J"},{"key":"3774_CR87","doi-asserted-by":"publisher","first-page":"1826","DOI":"10.1126\/science.1062249","volume":"293","author":"DB Tattersall","year":"2001","unstructured":"Tattersall DB, Bak S, Jones PR, Olsen CE, Nielsen JK, Hansen ML, Hoj PB, Moller BL (2001a) Resistance to an herbivore through engineered cyanogenic glucoside synthesis. Science 293:1826\u20131828. https:\/\/doi.org\/10.1126\/science.1062249","journal-title":"Science"},{"issue":"5536","key":"3774_CR88","doi-asserted-by":"publisher","first-page":"1826","DOI":"10.1126\/science.1062249","volume":"293","author":"DB Tattersall","year":"2001","unstructured":"Tattersall DB, Bak S, Jones PR, Olsen CE, Nielsen JK, Hansen ML, Hoj PB, M\u00f8ller BL (2001b) Resistance to an herbivore through engineered cyanogenic glucoside synthesis. Science 293(5536):1826\u20131828. https:\/\/doi.org\/10.1126\/science.1062249","journal-title":"Science"},{"key":"3774_CR89","doi-asserted-by":"crossref","first-page":"617","DOI":"10.1104\/pp.67.4.617","volume":"67","author":"SS Thayer","year":"1981","unstructured":"Thayer SS, Conn EE (1981) Subcellular localisation of dhurrin \u03b2-glucosidase and hydroxynitrilelayse in the mesophyll cells of Sorghum leaf blades. Plant Physiol 67:617\u2013622","journal-title":"Plant Physiol"},{"issue":"2","key":"3774_CR90","doi-asserted-by":"crossref","first-page":"664","DOI":"10.1104\/pp.105.063842","volume":"139","author":"KS Thors\u00f8e","year":"2005","unstructured":"Thors\u00f8e KS, Bak S, Olsen CE, Imberty A, Breton C, M\u00f8ller BL (2005) Determination of catalytic key amino acids and UDP sugar donor specificity of the cyanohydrin glycosyltransferase UGT85B1 from Sorghum bicolor molecular modeling substantiated by site-specific mutagenesis and biochemical analyses. Plant Physiol 139(2):664\u2013673","journal-title":"Plant Physiol"},{"key":"3774_CR91","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1071\/PP01116","volume":"29","author":"I Woodrow","year":"2002","unstructured":"Woodrow I, Slocum D, Gleadow R (2002) Influence of water stress on cyanogenic capacity in Eucalyptus cladocalyx. Funct Plant Biol 29:103\u2013110","journal-title":"Funct Plant Biol"},{"key":"3774_CR92","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1111\/2041-210X.12628","volume":"8","author":"G Yu","year":"2017","unstructured":"Yu G, Smith D, Zhu H, Guan Y, Lam T (2017) ggtree: an R package for visualization and annotation of phylogenetic trees with their covariates and other associated data. Methods Ecol Evol 8:28\u201336","journal-title":"Methods Ecol Evol"}],"container-title":["Planta"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s00425-021-03774-2.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/article\/10.1007\/s00425-021-03774-2\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s00425-021-03774-2.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,11,30]],"date-time":"2021-11-30T20:57:31Z","timestamp":1638305851000},"score":1,"resource":{"primary":{"URL":"https:\/\/link.springer.com\/10.1007\/s00425-021-03774-2"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,11,11]]},"references-count":93,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2021,12]]}},"alternative-id":["3774"],"URL":"https:\/\/doi.org\/10.1007\/s00425-021-03774-2","relation":{},"ISSN":["0032-0935","1432-2048"],"issn-type":[{"value":"0032-0935","type":"print"},{"value":"1432-2048","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,11,11]]},"assertion":[{"value":"30 June 2021","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"28 October 2021","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"11 November 2021","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}}],"article-number":"119"}}