{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T18:49:33Z","timestamp":1790621373825,"version":"4.1.0"},"reference-count":111,"publisher":"Springer Science and Business Media LLC","issue":"4","license":[{"start":{"date-parts":[[2023,12,12]],"date-time":"2023-12-12T00:00:00Z","timestamp":1702339200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.springernature.com\/gp\/researchers\/text-and-data-mining"},{"start":{"date-parts":[[2023,12,12]],"date-time":"2023-12-12T00:00:00Z","timestamp":1702339200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/www.springernature.com\/gp\/researchers\/text-and-data-mining"}],"funder":[{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["R35 GM150908"],"award-info":[{"award-number":["R35 GM150908"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Phytochem Rev"],"published-print":{"date-parts":[[2025,8]]},"DOI":"10.1007\/s11101-023-09901-z","type":"journal-article","created":{"date-parts":[[2023,12,12]],"date-time":"2023-12-12T09:02:11Z","timestamp":1702371731000},"page":"2463-2484","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Emerging functions within the enzyme families of plant alkaloid biosynthesis"],"prefix":"10.1007","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8256-4771","authenticated-orcid":false,"given":"Fabiola","family":"Muro-Villanueva","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2537-7010","authenticated-orcid":false,"given":"Ryan S.","family":"Nett","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2023,12,12]]},"reference":[{"key":"9901_CR1","doi-asserted-by":"publisher","first-page":"5619","DOI":"10.1021\/acs.chemrev.6b00571","volume":"117","author":"V Agarwal","year":"2017","unstructured":"Agarwal V, Miles ZD, Winter JM et al (2017) Enzymatic halogenation and dehalogenation reactions: pervasive and mechanistically diverse. Chem Rev 117:5619\u20135674. https:\/\/doi.org\/10.1021\/acs.chemrev.6b00571","journal-title":"Chem Rev"},{"key":"9901_CR2","doi-asserted-by":"publisher","first-page":"51","DOI":"10.1016\/j.pbi.2014.03.007","volume":"19","author":"G Anarat-Cappillino","year":"2014","unstructured":"Anarat-Cappillino G, Sattely ES (2014) The chemical logic of plant natural product biosynthesis. Curr Opin Plant Biol 19:51\u201358. https:\/\/doi.org\/10.1016\/j.pbi.2014.03.007","journal-title":"Curr Opin Plant Biol"},{"key":"9901_CR3","doi-asserted-by":"publisher","first-page":"1191","DOI":"10.1104\/pp.113.228593","volume":"164","author":"S Araji","year":"2014","unstructured":"Araji S, Grammer TA, Gertzen R et al (2014) Novel roles for the polyphenol oxidase enzyme in secondary metabolism and the regulation of cell death in walnut. Plant Physiol 164:1191\u20131203. https:\/\/doi.org\/10.1104\/pp.113.228593","journal-title":"Plant Physiol"},{"key":"9901_CR4","doi-asserted-by":"publisher","first-page":"79","DOI":"10.1039\/b100917f","volume":"20","author":"MB Austin","year":"2003","unstructured":"Austin MB, Noel JP (2003) The chalcone synthase superfamily of type III polyketide synthases. Nat Prod Rep 20:79\u2013110. https:\/\/doi.org\/10.1039\/b100917f","journal-title":"Nat Prod Rep"},{"key":"9901_CR5","doi-asserted-by":"publisher","first-page":"937","DOI":"10.1016\/0968-0896(96)00102-2","volume":"4","author":"AR Battersby","year":"1996","unstructured":"Battersby AR (1996) The marvels of biosynthesis: tracking nature\u2019s pathways. Bioorg Med Chem 4:937\u2013964. https:\/\/doi.org\/10.1016\/0968-0896(96)00102-2","journal-title":"Bioorg Med Chem"},{"key":"9901_CR6","doi-asserted-by":"publisher","first-page":"5281","DOI":"10.1038\/s41467-018-07671-3","volume":"9","author":"MA Bedewitz","year":"2018","unstructured":"Bedewitz MA, Jones AD, D\u2019Auria JC, Barry CS (2018) Tropinone synthesis via an atypical polyketide synthase and P450-mediated cyclization. Nat Commun 9:5281. https:\/\/doi.org\/10.1038\/s41467-018-07671-3","journal-title":"Nat Commun"},{"key":"9901_CR7","doi-asserted-by":"publisher","first-page":"155","DOI":"10.1002\/med.20097","volume":"28","author":"B Bhattacharyya","year":"2008","unstructured":"Bhattacharyya B, Panda D, Gupta S, Banerjee M (2008) Anti-mitotic activity of colchicine and the structural basis for its interaction with tubulin. Med Res Rev 28:155\u2013183. https:\/\/doi.org\/10.1002\/med.20097","journal-title":"Med Res Rev"},{"key":"9901_CR8","doi-asserted-by":"publisher","first-page":"695","DOI":"10.1111\/nph.13498","volume":"208","author":"T Bontpart","year":"2015","unstructured":"Bontpart T, Cheynier V, Ageorges A, Terrier N (2015) BAHD or SCPL acyltransferase? What a dilemma for acylation in the world of plant phenolic compounds. New Phytol 208:695\u2013707. https:\/\/doi.org\/10.1111\/nph.13498","journal-title":"New Phytol"},{"key":"9901_CR9","doi-asserted-by":"publisher","first-page":"18524","DOI":"10.1074\/jbc.M112.343681","volume":"287","author":"S Bulling","year":"2012","unstructured":"Bulling S, Schicker K, Zhang YW et al (2012) The mechanistic basis for noncompetitive ibogaine inhibition of serotonin and dopamine transporters. J Biol Chem 287:18524\u201318534. https:\/\/doi.org\/10.1074\/jbc.M112.343681","journal-title":"J Biol Chem"},{"key":"9901_CR11","doi-asserted-by":"publisher","first-page":"1202","DOI":"10.1105\/tpc.112.095885","volume":"24","author":"S Bunsupa","year":"2012","unstructured":"Bunsupa S, Katayama K, Ikeura E et al (2012) Lysine decarboxylase catalyzes the first step of quinolizidine alkaloid biosynthesis and coevolved with alkaloid production in Leguminosae. Plant Cell 24:1202\u20131216. https:\/\/doi.org\/10.1105\/tpc.112.095885","journal-title":"Plant Cell"},{"key":"9901_CR10","doi-asserted-by":"publisher","first-page":"2432","DOI":"10.1104\/pp.16.00639","volume":"171","author":"S Bunsupa","year":"2016","unstructured":"Bunsupa S, Hanada K, Maruyama A et al (2016) Molecular evolution and functional characterization of a bifunctional decarboxylase involved in Lycopodium alkaloid biosynthesis. Plant Physiol 171:2432\u20132444. https:\/\/doi.org\/10.1104\/pp.16.00639","journal-title":"Plant Physiol"},{"key":"9901_CR12","doi-asserted-by":"publisher","first-page":"1002","DOI":"10.2174\/1389557516666160506151213","volume":"17","author":"S Bunsupa","year":"2017","unstructured":"Bunsupa S, Yamazaki M, Saito K (2017) Lysine-derived alkaloids: overview and update on biosynthesis and medicinal applications with emphasis on quinolizidine alkaloids. Mini-Rev Med Chem 17:1002\u20131012. https:\/\/doi.org\/10.2174\/1389557516666160506151213","journal-title":"Mini-Rev Med Chem"},{"key":"9901_CR14","doi-asserted-by":"publisher","first-page":"1235","DOI":"10.1126\/science.aat4100","volume":"360","author":"L Caputi","year":"2018","unstructured":"Caputi L, Franke J, Farrow SC et al (2018) Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle. Science 360:1235\u20131239. https:\/\/doi.org\/10.1126\/science.aat4100","journal-title":"Science"},{"key":"9901_CR13","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1038\/s41589-019-0460-x","volume":"16","author":"L Caputi","year":"2020","unstructured":"Caputi L, Franke J, Bussey K et al (2020) Structural basis of cycloaddition in biosynthesis of iboga and aspidosperma alkaloids. Nat Chem Biol 16:383\u2013386.\u00a0https:\/\/doi.org\/10.1038\/s41589-019-0460-x","journal-title":"Nat Chem Biol"},{"key":"9901_CR15","doi-asserted-by":"publisher","first-page":"1140","DOI":"10.1126\/science.1248000","volume":"343","author":"WC Chang","year":"2014","unstructured":"Chang WC, Guo Y, Wang C et al (2014) Mechanism of the C5 stereoinversion reaction in the biosynthesis of carbapenem antibiotics. Science 343:1140\u20131144. https:\/\/doi.org\/10.1126\/science.1248000","journal-title":"Science"},{"key":"9901_CR16","doi-asserted-by":"publisher","first-page":"e2215372119","DOI":"10.1073\/pnas.2215372119","volume":"119","author":"BG Chavez","year":"2022","unstructured":"Chavez BG, Srinivasan P, Glockzin K et al (2022) Elucidation of tropane alkaloid biosynthesis in Erythroxylum coca using a microbial pathway discovery platform. Proc Natl Acad Sci USA 119:e2215372119. https:\/\/doi.org\/10.1073\/pnas.2215372119","journal-title":"Proc Natl Acad Sci USA"},{"key":"9901_CR17","doi-asserted-by":"publisher","first-page":"738","DOI":"10.1038\/s41589-018-0059-7","volume":"14","author":"X Chen","year":"2018","unstructured":"Chen X, Hagel JM, Chang L et al (2018a) A pathogenesis-related 10 protein catalyzes the final step in thebaine biosynthesis. Nat Chem Biol 14:738\u2013743. https:\/\/doi.org\/10.1038\/s41589-018-0059-7","journal-title":"Nat Chem Biol"},{"key":"9901_CR18","doi-asserted-by":"publisher","first-page":"E4920","DOI":"10.1073\/pnas.1805291115","volume":"115","author":"YC Chen","year":"2018","unstructured":"Chen YC, Holmes EC, Rajniak J et al (2018b) N-Hydroxy-pipecolic acid is a mobile metabolite that induces systemic disease resistance in Arabidopsis. Proc Natl Acad Sci USA 115:E4920\u2013E4929. https:\/\/doi.org\/10.1073\/pnas.1805291115","journal-title":"Proc Natl Acad Sci USA"},{"key":"9901_CR19","doi-asserted-by":"publisher","first-page":"80","DOI":"10.1016\/j.tplants.2005.12.009","volume":"11","author":"A Cona","year":"2006","unstructured":"Cona A, Rea G, Angelini R et al (2006) Functions of amine oxidases in plant development and defence. Trends Plant Sci 11:80\u201388. https:\/\/doi.org\/10.1016\/j.tplants.2005.12.009","journal-title":"Trends Plant Sci"},{"key":"9901_CR20","doi-asserted-by":"publisher","first-page":"2145","DOI":"10.1039\/d0np00092b","volume":"38","author":"V Courdavault","year":"2021","unstructured":"Courdavault V, O\u2019Connor SE, Jensen MK, Papon N (2021) Metabolic engineering for plant natural products biosynthesis: New procedures, concrete achievements and remaining limits. Nat Prod Rep 38:2145\u20132153. https:\/\/doi.org\/10.1039\/d0np00092b","journal-title":"Nat Prod Rep"},{"key":"9901_CR22","doi-asserted-by":"publisher","first-page":"331","DOI":"10.1016\/j.pbi.2006.03.016","volume":"9","author":"JC D\u2019Auria","year":"2006","unstructured":"D\u2019Auria JC (2006) Acyltransferases in plants: a good time to be BAHD. Curr Opin Plant Biol 9:331\u2013340. https:\/\/doi.org\/10.1016\/j.pbi.2006.03.016","journal-title":"Curr Opin Plant Biol"},{"key":"9901_CR21","doi-asserted-by":"publisher","first-page":"384","DOI":"10.1038\/s41589-019-0247-0","volume":"15","author":"M Dastmalchi","year":"2019","unstructured":"Dastmalchi M, Chen X, Hagel JM et al (2019) Neopinone isomerase is involved in codeine and morphine biosynthesis in opium poppy. Nat Chem Biol 15:384\u2013390. https:\/\/doi.org\/10.1038\/s41589-019-0247-0","journal-title":"Nat Chem Biol"},{"key":"9901_CR23","doi-asserted-by":"publisher","first-page":"361","DOI":"10.1126\/science.adf1017","volume":"379","author":"R De La Pe\u00f1a","year":"2023","unstructured":"De La Pe\u00f1a R, Hodgson H, Liu JC-T et al (2023) Complex scaffold remodeling in plant triterpene biosynthesis. Science 379:361\u2013368. https:\/\/doi.org\/10.1126\/science.adf1017","journal-title":"Science"},{"key":"9901_CR24","doi-asserted-by":"publisher","first-page":"311","DOI":"10.1002\/9780470742761.ch6","volume-title":"Medicinal natural products medicinal natural products: a biosynthetic approach","author":"PM Dewick","year":"2009","unstructured":"Dewick PM (2009) Alkaloids. Medicinal natural products medicinal natural products: a biosynthetic approach, 3rd edn. Wiley, Chichester, pp 311\u2013417","edition":"3"},{"key":"9901_CR25","doi-asserted-by":"publisher","first-page":"949","DOI":"10.1038\/s42003-022-03904-w","volume":"5","author":"QM Dudley","year":"2022","unstructured":"Dudley QM, Jo S, Guerrero DAS et al (2022) Reconstitution of monoterpene indole alkaloid biosynthesis in genome engineered Nicotiana benthamiana. Commun Biol 5:949. https:\/\/doi.org\/10.1038\/s42003-022-03904-w","journal-title":"Commun Biol"},{"key":"9901_CR26","doi-asserted-by":"publisher","first-page":"299","DOI":"10.1038\/s41592-019-0344-8","volume":"16","author":"K D\u00fchrkop","year":"2019","unstructured":"D\u00fchrkop K, Fleischauer M, Ludwig M et al (2019) SIRIUS 4: a rapid tool for turning tandem mass spectra into metabolite structure information. Nat Methods 16:299\u2013302. https:\/\/doi.org\/10.1038\/s41592-019-0344-8","journal-title":"Nat Methods"},{"key":"9901_CR27","doi-asserted-by":"publisher","first-page":"112822","DOI":"10.1016\/j.phytochem.2021.112822","volume":"189","author":"R Eggers","year":"2021","unstructured":"Eggers R, Jammer A, Jha S et al (2021) The scope of flavin-dependent reactions and processes in the model plant Arabidopsis thaliana. Phytochemistry 189:112822. https:\/\/doi.org\/10.1016\/j.phytochem.2021.112822","journal-title":"Phytochemistry"},{"key":"9901_CR28","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1146\/annurev.biochem.73.011303.074021","volume":"73","author":"AC Eliot","year":"2004","unstructured":"Eliot AC, Kirsch JF (2004) Pyridoxal phosphate enzymes: mechanistic, structural, and evolutionary considerations. Annu Rev Biochem 73:383\u2013415. https:\/\/doi.org\/10.1146\/annurev.biochem.73.011303.074021","journal-title":"Annu Rev Biochem"},{"key":"9901_CR29","doi-asserted-by":"publisher","first-page":"3335","DOI":"10.1038\/s41467-022-31100-1","volume":"13","author":"JGM Eng","year":"2022","unstructured":"Eng JGM, Shahsavarani M, Smith DP et al (2022) A Catharanthus roseus Fe(II)\/\u03b1-ketoglutarate-dependent dioxygenase catalyzes a redox-neutral reaction responsible for vindolinine biosynthesis. Nat Commun 13:3335. https:\/\/doi.org\/10.1038\/s41467-022-31100-1","journal-title":"Nat Commun"},{"key":"9901_CR30","doi-asserted-by":"publisher","first-page":"1058","DOI":"10.3389\/fpls.2019.01058","volume":"10","author":"PJ Facchini","year":"2019","unstructured":"Facchini PJ, Morris JS (2019) Molecular origins of functional diversity in benzylisoquinoline alkaloid methyltransferases. Front Plant Sci 10:1058. https:\/\/doi.org\/10.3389\/fpls.2019.01058","journal-title":"Front Plant Sci"},{"key":"9901_CR31","doi-asserted-by":"publisher","first-page":"133","DOI":"10.1186\/s12859-023-05254-8","volume":"24","author":"TR Fallon","year":"2023","unstructured":"Fallon TR, \u010calounov\u00e1 T, Mokrej\u0161 M et al (2023) transXpress: a Snakemake pipeline for streamlined de novo transcriptome assembly and annotation. BMC Bioinform 24:133. https:\/\/doi.org\/10.1186\/s12859-023-05254-8","journal-title":"BMC Bioinform"},{"key":"9901_CR32","doi-asserted-by":"publisher","first-page":"524","DOI":"10.3389\/fpls.2014.00524","volume":"5","author":"SC Farrow","year":"2014","unstructured":"Farrow SC, Facchini PJ (2014) Functional diversity of 2-oxoglutarate\/Fe(II)-dependent dioxygenases in plant metabolism. Front Plant Sci 5:524. https:\/\/doi.org\/10.3389\/fpls.2014.00524","journal-title":"Front Plant Sci"},{"key":"9901_CR33","doi-asserted-by":"publisher","first-page":"728","DOI":"10.1038\/nchembio.1879","volume":"11","author":"SC Farrow","year":"2015","unstructured":"Farrow SC, Hagel JM, Beaudoin GAW et al (2015) Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy. Nat Chem Biol 11:728\u2013732. https:\/\/doi.org\/10.1038\/nchembio.1879","journal-title":"Nat Chem Biol"},{"key":"9901_CR34","doi-asserted-by":"publisher","first-page":"12979","DOI":"10.1021\/jacs.9b05999","volume":"141","author":"SC Farrow","year":"2019","unstructured":"Farrow SC, Kamileen MO, Caputi L et al (2019) Biosynthesis of an anti-addiction agent from the iboga plant. J Am Chem Soc 141:12979\u201312983. https:\/\/doi.org\/10.1021\/jacs.9b05999","journal-title":"J Am Chem Soc"},{"key":"9901_CR35","doi-asserted-by":"publisher","first-page":"4802","DOI":"10.1002\/anie.201107204","volume":"51","author":"JM Finefield","year":"2012","unstructured":"Finefield JM, Sherman DH, Kreitman M, Williams RM (2012) Enantiomeric natural products: occurrence and biogenesis. Angew Chem Int Ed 51:4802\u20134836. https:\/\/doi.org\/10.1002\/anie.201107204","journal-title":"Angew Chem Int Ed"},{"key":"9901_CR36","doi-asserted-by":"publisher","first-page":"e2307981120","DOI":"10.1073\/pnas.2307981120","volume":"120","author":"M Florean","year":"2023","unstructured":"Florean M, Luck K, Hong B et al (2023) Reinventing metabolic pathways: independent evolution of benzoxazinoids in flowering plants. Proc Natl Acad Sci USA 120:e2307981120. https:\/\/doi.org\/10.1073\/pnas.2307981120","journal-title":"Proc Natl Acad Sci USA"},{"key":"9901_CR37","doi-asserted-by":"publisher","first-page":"1095","DOI":"10.1126\/science.aac9373","volume":"349","author":"S Galanie","year":"2015","unstructured":"Galanie S, Thodey K, Trenchard IJ et al (2015) Complete biosynthesis of opioids in yeast. Science 349:1095\u20131100. https:\/\/doi.org\/10.1126\/science.aac9373","journal-title":"Science"},{"key":"9901_CR38","doi-asserted-by":"publisher","first-page":"620","DOI":"10.1038\/s41557-020-0467-7","volume":"12","author":"L Gao","year":"2020","unstructured":"Gao L, Su C, Du X et al (2020) FAD-dependent enzyme-catalysed intermolecular [4+2] cycloaddition in natural product biosynthesis. Nat Chem 12:620\u2013628. https:\/\/doi.org\/10.1038\/s41557-020-0467-7","journal-title":"Nat Chem"},{"key":"9901_CR39","doi-asserted-by":"publisher","first-page":"5703","DOI":"10.1016\/S0040-4039(00)73838-X","volume":"34","author":"J Gollwitzer","year":"1993","unstructured":"Gollwitzer J, Lenz R, Hampp N, Zenk MH (1993) The transformation of neopinone to codeinone in morphine biosynthesis proceeds non-enzymatically. Tetrahedron Lett 34:5703\u20135706. https:\/\/doi.org\/10.1016\/S0040-4039(00)73838-X","journal-title":"Tetrahedron Lett"},{"key":"9901_CR40","doi-asserted-by":"publisher","first-page":"289","DOI":"10.1016\/S0045-6535(03)00207-8","volume":"52","author":"GW Gribble","year":"2003","unstructured":"Gribble GW (2003) The diversity of naturally produced organohalogens. Chemosphere 52:289\u2013297. https:\/\/doi.org\/10.1016\/S0045-6535(03)00207-8","journal-title":"Chemosphere"},{"key":"9901_CR41","doi-asserted-by":"publisher","first-page":"1494","DOI":"10.1038\/nprot.2013.084","volume":"8","author":"BJ Haas","year":"2013","unstructured":"Haas BJ, Papanicolaou A, Yassour M et al (2013) De novo transcript sequence reconstruction from RNA-seq using the Trinity platform for reference generation and analysis. Nat Protoc 8:1494\u20131512. https:\/\/doi.org\/10.1038\/nprot.2013.084","journal-title":"Nat Protoc"},{"key":"9901_CR42","doi-asserted-by":"publisher","first-page":"721","DOI":"10.1039\/c7np00060j","volume":"35","author":"JM Hagel","year":"2018","unstructured":"Hagel JM, Facchini PJ (2018) Expanding the roles for 2-oxoglutarate-dependent oxygenases in plant metabolism. Nat Prod Rep 35:721\u2013734. https:\/\/doi.org\/10.1039\/c7np00060j","journal-title":"Nat Prod Rep"},{"key":"9901_CR43","doi-asserted-by":"publisher","first-page":"1244","DOI":"10.1016\/j.molp.2021.06.028","volume":"14","author":"CC Hansen","year":"2021","unstructured":"Hansen CC, Nelson DR, M\u00f8ller BL, Werck-Reichhart D (2021) Plant cytochrome P450 plasticity and evolution. Mol Plant 14:1244\u20131265. https:\/\/doi.org\/10.1016\/j.molp.2021.06.028","journal-title":"Mol Plant"},{"key":"9901_CR44","doi-asserted-by":"publisher","first-page":"456","DOI":"10.1016\/j.cell.2018.02.049","volume":"173","author":"M Hartmann","year":"2018","unstructured":"Hartmann M, Zeier T, Bernsdorff F et al (2018) Flavin monooxygenase-generated N-hydroxypipecolic acid is a critical element of plant systemic immunity. Cell 173:456-469.e16. https:\/\/doi.org\/10.1016\/j.cell.2018.02.049","journal-title":"Cell"},{"key":"9901_CR45","doi-asserted-by":"publisher","first-page":"7119","DOI":"10.1016\/S0040-4020(01)87895-9","volume":"46","author":"RB Herbert","year":"1990","unstructured":"Herbert RB, Kattah AE, Knagg E (1990) The biosynthesis of the phenethylisoquinoline alkaloid colchicine.\u00a0Early and intermediate stages.\u00a0Tetrahedron 46:7119\u20137138. https:\/\/doi.org\/10.1016\/S0040-4020(01)87895-9","journal-title":"Tetrahedron"},{"key":"9901_CR46","doi-asserted-by":"publisher","first-page":"617","DOI":"10.1038\/s41586-022-04950-4","volume":"607","author":"B Hong","year":"2022","unstructured":"Hong B, Grzech D, Caputi L et al (2022) Biosynthesis of strychnine. Nature 607:617\u2013622. https:\/\/doi.org\/10.1038\/s41586-022-04950-4","journal-title":"Nature"},{"key":"9901_CR47","doi-asserted-by":"publisher","first-page":"4036","DOI":"10.1038\/s41467-019-11987-z","volume":"10","author":"J-P Huang","year":"2019","unstructured":"Huang J-P, Fang C, Ma X et al (2019) Tropane alkaloids biosynthesis involves an unusual type III polyketide synthase and non-enzymatic condensation. Nat Commun 10:4036. https:\/\/doi.org\/10.1038\/s41467-019-11987-z","journal-title":"Nat Commun"},{"key":"9901_CR48","doi-asserted-by":"publisher","first-page":"1634","DOI":"10.1039\/d0np00076k","volume":"38","author":"JP Huang","year":"2021","unstructured":"Huang JP, Wang YJ, Tian T et al (2021) Tropane alkaloid biosynthesis: a centennial review. Nat Prod Rep 38:1634\u20131658. https:\/\/doi.org\/10.1039\/d0np00076k","journal-title":"Nat Prod Rep"},{"key":"9901_CR49","doi-asserted-by":"publisher","first-page":"631","DOI":"10.1146\/annurev-arplant-081519-035634","volume":"71","author":"JR Jacobowitz","year":"2020","unstructured":"Jacobowitz JR, Weng JK (2020) Exploring uncharted territories of plant specialized metabolism in the postgenomic era. Annu Rev Plant Biol 71:631\u2013658. https:\/\/doi.org\/10.1146\/annurev-arplant-081519-035634","journal-title":"Annu Rev Plant Biol"},{"key":"9901_CR50","doi-asserted-by":"publisher","first-page":"19673","DOI":"10.1021\/jacs.2c08107","volume":"144","author":"MO Kamileen","year":"2022","unstructured":"Kamileen MO, Demars MD, Hong B et al (2022) Recycling upstream redox enzymes expands the regioselectivity of cycloaddition in pseudo-aspidosperma alkaloid biosynthesis. J Am Chem Soc 144:19673\u201319679. https:\/\/doi.org\/10.1021\/jacs.2c08107","journal-title":"J Am Chem Soc"},{"key":"9901_CR51","doi-asserted-by":"publisher","first-page":"550","DOI":"10.1093\/pcp\/pcm018","volume":"48","author":"A Katoh","year":"2007","unstructured":"Katoh A, Shoji T, Hashimoto T (2007) Molecular cloning of N-methylputrescine oxidase from tobacco. Plant Cell Physiol 48:550\u2013554. https:\/\/doi.org\/10.1093\/pcp\/pcm018","journal-title":"Plant Cell Physiol"},{"key":"9901_CR52","doi-asserted-by":"publisher","first-page":"328","DOI":"10.1111\/tpj.12479","volume":"78","author":"Y Kawai","year":"2014","unstructured":"Kawai Y, Ono E, Mizutani M (2014) Evolution and diversity of the 2-oxoglutarate-dependent dioxygenase superfamily in plants. Plant J 78:328\u2013343. https:\/\/doi.org\/10.1111\/tpj.12479","journal-title":"Plant J"},{"key":"9901_CR53","doi-asserted-by":"publisher","first-page":"1867","DOI":"10.1038\/s41467-020-15777-w","volume":"11","author":"CY Kim","year":"2020","unstructured":"Kim CY, Mitchell AJ, Glinkerman CM et al (2020) The chloroalkaloid (\u2212)-acutumine is biosynthesized via a Fe(II)- and 2-oxoglutarate-dependent halogenase in Menispermaceae plants. Nat Commun 11:1867. https:\/\/doi.org\/10.1038\/s41467-020-15777-w","journal-title":"Nat Commun"},{"key":"9901_CR54","doi-asserted-by":"publisher","first-page":"936","DOI":"10.1039\/b813006j","volume":"26","author":"J Kobayashi","year":"2009","unstructured":"Kobayashi J, Kubota T (2009) The Daphniphyllum alkaloids. Nat Prod Rep 26:936\u2013962","journal-title":"Nat Prod Rep"},{"key":"9901_CR55","doi-asserted-by":"publisher","first-page":"433","DOI":"10.1016\/j.plantsci.2006.10.013","volume":"172","author":"A Kulma","year":"2007","unstructured":"Kulma A, Szopa J (2007) Catecholamines are active compounds in plants. Plant Sci 172:433\u2013440. https:\/\/doi.org\/10.1016\/j.plantsci.2006.10.013","journal-title":"Plant Sci"},{"key":"9901_CR56","doi-asserted-by":"publisher","DOI":"10.1016\/j.pbi.2022.102330","volume":"71","author":"BD Kwan","year":"2023","unstructured":"Kwan BD, Seligmann B, Nguyen TD et al (2023) Leveraging synthetic biology and metabolic engineering to overcome obstacles in plant pathway elucidation. Curr Opin Plant Biol 71:102330. https:\/\/doi.org\/10.1016\/j.pbi.2022.102330","journal-title":"Curr Opin Plant Biol"},{"key":"9901_CR57","doi-asserted-by":"publisher","first-page":"1224","DOI":"10.1126\/science.aac7202","volume":"349","author":"W Lau","year":"2015","unstructured":"Lau W, Sattely ES (2015) Six enzymes from mayapple that complete the biosynthetic pathway to the etoposide aglycone. Science 349:1224\u20131228. https:\/\/doi.org\/10.1126\/science.aac7202","journal-title":"Science"},{"key":"9901_CR58","doi-asserted-by":"publisher","first-page":"31091","DOI":"10.1074\/jbc.270.52.31091","volume":"270","author":"R Lenz","year":"1995","unstructured":"Lenz R, Zenk MH (1995) Acetyl coenzyme A:salutaridinol-7-O-acetyltransferase from Papaver somniferum plant cell cultures. J Biol Chem 270:31091\u201331096. https:\/\/doi.org\/10.1074\/jbc.270.52.31091","journal-title":"J Biol Chem"},{"key":"9901_CR59","doi-asserted-by":"publisher","first-page":"103","DOI":"10.1039\/d0np00031k","volume":"38","author":"BR Lichman","year":"2021","unstructured":"Lichman BR (2021) The scaffold-forming steps of plant alkaloid biosynthesis. Nat Prod Rep 38:103\u2013129. https:\/\/doi.org\/10.1039\/d0np00031k","journal-title":"Nat Prod Rep"},{"key":"9901_CR60","doi-asserted-by":"publisher","unstructured":"Lichman BR, Godden GT, Hamilton JP et al (2020) The evolutionary origins of the cat attractant nepetalactone in catnip. Sci Adv 6:eaba0721. https:\/\/doi.org\/10.1126\/sciadv.aba0721","DOI":"10.1126\/sciadv.aba0721"},{"key":"9901_CR61","doi-asserted-by":"publisher","first-page":"187","DOI":"10.1016\/j.synbio.2020.06.008","volume":"5","author":"X Liu","year":"2020","unstructured":"Liu X, Zhu X, Wang H et al (2020) Discovery and modification of cytochrome P450 for plant natural products biosynthesis. Synth Syst Biotechnol 5:187\u2013199. https:\/\/doi.org\/10.1016\/j.synbio.2020.06.008","journal-title":"Synth Syst Biotechnol"},{"key":"9901_CR62","doi-asserted-by":"publisher","first-page":"752","DOI":"10.1039\/b409720n","volume":"21","author":"X Ma","year":"2004","unstructured":"Ma X, Gang DR (2004) The Lycopodium alkaloids. Nat Prod Rep 21:752\u2013772. https:\/\/doi.org\/10.1039\/b409720n","journal-title":"Nat Prod Rep"},{"key":"9901_CR63","doi-asserted-by":"publisher","first-page":"1231809","DOI":"10.3389\/fpls.2023.1231809","volume":"14","author":"BB Majhi","year":"2023","unstructured":"Majhi BB, G\u00e9linas SE, M\u00e9rindol N et al (2023) Characterization of norbelladine synthase and noroxomaritidine\/norcraugsodine reductase reveals a novel catalytic route for the biosynthesis of Amaryllidaceae alkaloids including the Alzheimer\u2019s drug galanthamine. Front Plant Sci 14:1231809. https:\/\/doi.org\/10.3389\/fpls.2023.1231809","journal-title":"Front Plant Sci"},{"key":"9901_CR64","doi-asserted-by":"publisher","first-page":"1423","DOI":"10.1039\/d1np00069a","volume":"39","author":"D Mancinotti","year":"2022","unstructured":"Mancinotti D, Frick KM, Geu-Flores F (2022) Biosynthesis of quinolizidine alkaloids in lupins: mechanistic considerations and prospects for pathway elucidation. Nat Prod Rep 39:1423\u20131437. https:\/\/doi.org\/10.1039\/d1np00069a","journal-title":"Nat Prod Rep"},{"key":"9901_CR65","doi-asserted-by":"publisher","first-page":"15326","DOI":"10.1021\/ja508127q","volume":"136","author":"Y Matsuda","year":"2014","unstructured":"Matsuda Y, Wakimoto T, Mori T et al (2014) Complete biosynthetic pathway of anditomin: nature\u2019s sophisticated synthetic route to a complex fungal meroterpenoid. J Am Chem Soc 136:15326\u201315336. https:\/\/doi.org\/10.1021\/ja508127q","journal-title":"J Am Chem Soc"},{"key":"9901_CR66","doi-asserted-by":"publisher","first-page":"257","DOI":"10.1016\/S0031-9422(00)94158-X","volume":"17","author":"BA McGaw","year":"1978","unstructured":"McGaw BA, Woolley JG (1978) Stereochemistry of tropane alkaloid formation in Datura. Phytochemistry 17:257\u2013259. https:\/\/doi.org\/10.1016\/S0031-9422(00)94158-X","journal-title":"Phytochemistry"},{"key":"9901_CR67","doi-asserted-by":"publisher","first-page":"2955","DOI":"10.1038\/s41598-023-29415-0","volume":"13","author":"IM Men\u00e9ndez-Perdomo","year":"2023","unstructured":"Men\u00e9ndez-Perdomo IM, Facchini PJ (2023) Elucidation of the (R)-enantiospecific benzylisoquinoline alkaloid biosynthetic pathways in sacred lotus (Nelumbo nucifera). Sci Rep 13:2955. https:\/\/doi.org\/10.1038\/s41598-023-29415-0","journal-title":"Sci Rep"},{"key":"9901_CR68","doi-asserted-by":"publisher","first-page":"256","DOI":"10.1016\/j.sbi.2016.08.005","volume":"41","author":"JT Mindrebo","year":"2016","unstructured":"Mindrebo JT, Nartey CM, Seto Y et al (2016) Unveiling the functional diversity of the alpha\/beta hydrolase superfamily in the plant kingdom. Curr Opin Struct Biol 41:256\u2013257. https:\/\/doi.org\/10.1016\/j.sbi.2016.08.005","journal-title":"Curr Opin Struct Biol"},{"key":"9901_CR69","doi-asserted-by":"publisher","first-page":"194","DOI":"10.1016\/j.abb.2010.09.026","volume":"507","author":"M Mizutani","year":"2011","unstructured":"Mizutani M, Sato F (2011) Unusual P450 reactions in plant secondary metabolism. Arch Biochem Biophys 507:194\u2013203. https:\/\/doi.org\/10.1016\/j.abb.2010.09.026","journal-title":"Arch Biochem Biophys"},{"key":"9901_CR70","doi-asserted-by":"publisher","first-page":"264","DOI":"10.1002\/cbic.202000354","volume":"22","author":"JS Morris","year":"2021","unstructured":"Morris JS, Caldo KMP, Liang S, Facchini PJ (2021) PR10\/Bet v1-like proteins as novel contributors to plant biochemical diversity. ChemBioChem 22:264\u2013287. https:\/\/doi.org\/10.1002\/cbic.202000354","journal-title":"ChemBioChem"},{"key":"9901_CR71","doi-asserted-by":"publisher","first-page":"345","DOI":"10.1016\/j.bbagen.2006.08.018","volume":"1770","author":"AW Munro","year":"2007","unstructured":"Munro AW, Girvan HM, McLean KJ (2007) Cytochrome P450-redox partner fusion enzymes. Biochim Biophys Acta 1770:345\u2013359. https:\/\/doi.org\/10.1016\/j.bbagen.2006.08.018","journal-title":"Biochim Biophys Acta"},{"key":"9901_CR72","doi-asserted-by":"publisher","first-page":"732","DOI":"10.1016\/S0959-440X(99)00037-8","volume":"9","author":"M Nardini","year":"1999","unstructured":"Nardini M, Dijkstra BW (1999) \u03b1\/\u03b2 Hydrolase fold enzymes: the family keeps growing. Curr Opin Struct Biol 9:732\u2013737. https:\/\/doi.org\/10.1016\/S0959-440X(99)00037-8","journal-title":"Curr Opin Struct Biol"},{"key":"9901_CR73","doi-asserted-by":"publisher","first-page":"194","DOI":"10.1111\/j.1365-313X.2011.04529.x","volume":"66","author":"D Nelson","year":"2011","unstructured":"Nelson D, Werck-Reichhart D (2011) A P450-centric view of plant evolution. Plant J 66:194\u2013211. https:\/\/doi.org\/10.1111\/j.1365-313X.2011.04529.x","journal-title":"Plant J"},{"key":"9901_CR77","doi-asserted-by":"publisher","first-page":"19454","DOI":"10.1021\/jacs.1c08659","volume":"143","author":"RS Nett","year":"2021","unstructured":"Nett RS, Sattely ES (2021) Total biosynthesis of the tubulin-binding alkaloid colchicine. J Am Chem Soc 143:19454\u201319465. https:\/\/doi.org\/10.1021\/jacs.1c08659","journal-title":"J Am Chem Soc"},{"key":"9901_CR75","doi-asserted-by":"publisher","first-page":"148","DOI":"10.1038\/s41586-020-2546-8","volume":"584","author":"RS Nett","year":"2020","unstructured":"Nett RS, Lau W, Sattely ES (2020a) Discovery and engineering of colchicine alkaloid biosynthesis. Nature 584:148\u2013153. https:\/\/doi.org\/10.1038\/s41586-020-2546-8","journal-title":"Nature"},{"key":"9901_CR76","doi-asserted-by":"publisher","unstructured":"Nett RS, Nguyen H, Nagel R et al (2020b) Unraveling a tangled skein: evolutionary analysis of the bacterial gibberellin biosynthetic operon. mSphere 5:e00292-20. https:\/\/doi.org\/10.1128\/msphere.00292-20","DOI":"10.1128\/msphere.00292-20"},{"key":"9901_CR74","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2102949118","volume":"118","author":"RS Nett","year":"2021","unstructured":"Nett RS, Dho Y, Low Y-Y, Sattely ES (2021) A metabolic regulon reveals early and late acting enzymes in neuroactive Lycopodium alkaloid biosynthesis. Proc Natl Acad Sci 118:e2102949118. https:\/\/doi.org\/10.1073\/pnas.2102949118","journal-title":"Proc Natl Acad Sci"},{"key":"9901_CR78","doi-asserted-by":"publisher","first-page":"735","DOI":"10.1016\/S0031-9422(00)91406-7","volume":"13","author":"L Nettleship","year":"1974","unstructured":"Nettleship L, Slaytor M (1974) Limitations of feeding experiments in studying alkaloid biosynthesis in Peganum harmala callus cultures. Phytochemistry 13:735\u2013742. https:\/\/doi.org\/10.1016\/S0031-9422(00)91406-7","journal-title":"Phytochemistry"},{"key":"9901_CR80","doi-asserted-by":"publisher","DOI":"10.3389\/fpls.2021.682181","volume":"12","author":"TD Nguyen","year":"2021","unstructured":"Nguyen TD, Dang TTT (2021) Cytochrome P450 enzymes as key drivers of alkaloid chemical diversification in plants. Front Plant Sci 12:682181. https:\/\/doi.org\/10.3389\/fpls.2021.682181","journal-title":"Front Plant Sci"},{"key":"9901_CR79","doi-asserted-by":"publisher","first-page":"1125158","DOI":"10.3389\/fpls.2023.1125158","volume":"14","author":"TAM Nguyen","year":"2023","unstructured":"Nguyen TAM, Grzech D, Chung K et al (2023) Discovery of a cytochrome P450 enzyme catalyzing the formation of spirooxindole alkaloid scaffold. Front Plant Sci 14:1125158. https:\/\/doi.org\/10.3389\/fpls.2023.1125158","journal-title":"Front Plant Sci"},{"key":"9901_CR81","doi-asserted-by":"publisher","first-page":"71","DOI":"10.1146\/annurev-genet-120213-092053","volume":"49","author":"SE O\u2019Connor","year":"2015","unstructured":"O\u2019Connor SE (2015) Engineering of secondary metabolism. Annu Rev Genet 49:71\u201394. https:\/\/doi.org\/10.1146\/annurev-genet-120213-092053","journal-title":"Annu Rev Genet"},{"key":"9901_CR82","doi-asserted-by":"publisher","first-page":"532","DOI":"10.1039\/b512615k","volume":"23","author":"SE O\u2019Connor","year":"2006","unstructured":"O\u2019Connor SE, Maresh JJ (2006) Chemistry and biology of monoterpene indole alkaloid biosynthesis. Nat Prod Rep 23:532\u2013547. https:\/\/doi.org\/10.1039\/b512615k","journal-title":"Nat Prod Rep"},{"key":"9901_CR83","doi-asserted-by":"crossref","unstructured":"Ortiz de Montellano PR (2015) Substrate Oxidation by Cytochrome P450 Enzymes. In: Ortiz De Montellano PR (ed) Cytochrome P450: structure, mechanism, and biochemistry, Fourth Edi. Springer International Publishing, Switzerland, pp 111\u2013176","DOI":"10.1007\/978-3-319-12108-6_4"},{"key":"9901_CR84","doi-asserted-by":"publisher","first-page":"6768","DOI":"10.1038\/s41467-022-34313-6","volume":"13","author":"N Ozber","year":"2022","unstructured":"Ozber N, Carr SC, Morris JS et al (2022) Alkaloid binding to opium poppy major latex proteins triggers structural modification and functional aggregation. Nat Commun 13:6768. https:\/\/doi.org\/10.1038\/s41467-022-34313-6","journal-title":"Nat Commun"},{"key":"9901_CR85","doi-asserted-by":"publisher","first-page":"1659","DOI":"10.1038\/s41598-020-57671-x","volume":"10","author":"F Panis","year":"2020","unstructured":"Panis F, Kampatsikas I, Bijelic A, Rompel A (2020) Conversion of walnut tyrosinase into a catechol oxidase by site directed mutagenesis. Sci Rep 10:1659. https:\/\/doi.org\/10.1038\/s41598-020-57671-x","journal-title":"Sci Rep"},{"key":"9901_CR86","doi-asserted-by":"publisher","first-page":"107712","DOI":"10.1016\/j.biotechadv.2021.107712","volume":"51","author":"CE Paul","year":"2021","unstructured":"Paul CE, Eggerichs D, Westphal AH et al (2021) Flavoprotein monooxygenases: versatile biocatalysts. Biotechnol Adv 51:107712.\u00a0https:\/\/doi.org\/10.1016\/j.biotechadv.2021.107712","journal-title":"Biotechnol Adv"},{"key":"9901_CR87","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2209339120","volume":"120","author":"F Qiao","year":"2023","unstructured":"Qiao F, He Y, Zhang Y et al (2023) Elucidation of the 1-phenethylisoquinoline pathway from an endemic conifer Cephalotaxus hainanensis. Proc Natl Acad Sci USA 120:e2209339120. https:\/\/doi.org\/10.1073\/pnas.2209339120","journal-title":"Proc Natl Acad Sci USA"},{"key":"9901_CR88","doi-asserted-by":"publisher","first-page":"3180","DOI":"10.1073\/pnas.1719979115","volume":"115","author":"Y Qu","year":"2018","unstructured":"Qu Y, Easson MEAM, Simionescu R et al (2018) Solution of the multistep pathway for assembly of corynanthean, strychnos, iboga, and aspidosperma monoterpenoid indole alkaloids from 19E-geissoschizine. Proc Natl Acad Sci 115:3180\u20133185. https:\/\/doi.org\/10.1073\/pnas.1719979115","journal-title":"Proc Natl Acad Sci"},{"key":"9901_CR89","doi-asserted-by":"publisher","first-page":"1252","DOI":"10.1126\/science.adf3727","volume":"379","author":"J Reed","year":"2023","unstructured":"Reed J, Orme A, El-Demerdash A et al (2023) Elucidation of the pathway for biosynthesis of saponin adjuvants from the soapbark tree. Science 379:1252\u20131264. https:\/\/doi.org\/10.1126\/science.adf3727","journal-title":"Science"},{"key":"9901_CR90","doi-asserted-by":"publisher","first-page":"33878","DOI":"10.1074\/jbc.M203051200","volume":"277","author":"N Samanani","year":"2002","unstructured":"Samanani N, Facchini PJ (2002) Purification and characterization of norcoclaurine synthase: the first committed enzyme in benzylisoquinoline alkaloid biosynthesis in plants. J Biol Chem 277:33878\u201333883. https:\/\/doi.org\/10.1074\/jbc.M203051200","journal-title":"J Biol Chem"},{"key":"9901_CR91","doi-asserted-by":"publisher","first-page":"302","DOI":"10.1111\/j.1365-313X.2004.02210.x","volume":"40","author":"N Samanani","year":"2004","unstructured":"Samanani N, Liscombe DK, Facchini PJ (2004) Molecular cloning and characterization of norcoclaurine synthase, an catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis. Plant J 40:302\u2013314. https:\/\/doi.org\/10.1111\/j.1365-313X.2004.02210.x","journal-title":"Plant J"},{"key":"9901_CR92","doi-asserted-by":"publisher","first-page":"82","DOI":"10.1016\/j.phytochem.2018.02.003","volume":"149","author":"CA Schenck","year":"2018","unstructured":"Schenck CA, Maeda HA (2018) Tyrosine biosynthesis, metabolism, and catabolism in plants. Phytochemistry 149:82\u2013102. https:\/\/doi.org\/10.1016\/j.phytochem.2018.02.003","journal-title":"Phytochemistry"},{"key":"9901_CR93","doi-asserted-by":"publisher","first-page":"338","DOI":"10.1186\/s12870-018-1570-4","volume":"18","author":"A Singh","year":"2018","unstructured":"Singh A, Massicotte MA, Garand A et al (2018) Cloning and characterization of norbelladine synthase catalyzing the first committed reaction in Amaryllidaceae alkaloid biosynthesis. BMC Plant Biol 18:338. https:\/\/doi.org\/10.1186\/s12870-018-1570-4","journal-title":"BMC Plant Biol"},{"key":"9901_CR94","doi-asserted-by":"publisher","first-page":"614","DOI":"10.1038\/s41586-020-2650-9","volume":"585","author":"P Srinivasan","year":"2020","unstructured":"Srinivasan P, Smolke CD (2020) Biosynthesis of medicinal tropane alkaloids in yeast. Nature 585:614\u2013619. https:\/\/doi.org\/10.1038\/s41586-020-2650-9","journal-title":"Nature"},{"key":"9901_CR95","doi-asserted-by":"publisher","first-page":"2642","DOI":"10.1002\/cbic.201200556","volume":"13","author":"AW Struck","year":"2012","unstructured":"Struck AW, Thompson ML, Wong LS, Micklefield J (2012) S-adenosyl-methionine-dependent methyltransferases: highly versatile enzymes in biocatalysis, biosynthesis and other biotechnological applications. ChemBioChem 13:2642\u20132655. https:\/\/doi.org\/10.1002\/cbic.201200556","journal-title":"ChemBioChem"},{"key":"9901_CR96","doi-asserted-by":"publisher","first-page":"783","DOI":"10.3389\/fpls.2014.00783","volume":"5","author":"ML Sullivan","year":"2015","unstructured":"Sullivan ML (2015) Beyond brown: polyphenol oxidases as enzymes of plant specialized metabolism. Front Plant Sci 5:783. https:\/\/doi.org\/10.3389\/fpls.2014.00783","journal-title":"Front Plant Sci"},{"key":"9901_CR97","doi-asserted-by":"publisher","first-page":"5784","DOI":"10.1016\/j.bmcl.2012.07.102","volume":"22","author":"J Sun","year":"2012","unstructured":"Sun J, Morita H, Chen G et al (2012) Molecular cloning and characterization of copper amine oxidase from Huperzia serrata. Bioorg Med Chem Lett 22:5784\u20135790. https:\/\/doi.org\/10.1016\/j.bmcl.2012.07.102","journal-title":"Bioorg Med Chem Lett"},{"key":"9901_CR98","doi-asserted-by":"publisher","first-page":"4994","DOI":"10.1038\/s41467-022-32776-1","volume":"13","author":"T Tian","year":"2022","unstructured":"Tian T, Wang YJ, Huang JP et al (2022) Catalytic innovation underlies independent recruitment of polyketide synthases in cocaine and hyoscyamine biosynthesis. Nat Commun 13:4994. https:\/\/doi.org\/10.1038\/s41467-022-32776-1","journal-title":"Nat Commun"},{"key":"9901_CR100","doi-asserted-by":"publisher","first-page":"205","DOI":"10.1016\/j.molp.2017.12.007","volume":"11","author":"MP Torrens-Spence","year":"2018","unstructured":"Torrens-Spence MP, Pluskal T, Li FS et al (2018) Complete pathway elucidation and heterologous reconstitution of Rhodiola salidroside biosynthesis. Mol Plant 11:205\u2013217. https:\/\/doi.org\/10.1016\/j.molp.2017.12.007","journal-title":"Mol Plant"},{"key":"9901_CR99","doi-asserted-by":"publisher","first-page":"10806","DOI":"10.1073\/pnas.1920097117","volume":"117","author":"MP Torrens-Spence","year":"2020","unstructured":"Torrens-Spence MP, Chiang Y-C, Smith T et al (2020) Structural basis for divergent and convergent evolution of catalytic machineries in plant aromatic amino acid decarboxylase proteins. Proc Natl Acad Sci 117:10806\u201310817. https:\/\/doi.org\/10.1073\/pnas.1920097117","journal-title":"Proc Natl Acad Sci"},{"key":"9901_CR101","doi-asserted-by":"publisher","first-page":"1405","DOI":"10.1038\/s41467-022-28883-8","volume":"13","author":"CJ Vavricka","year":"2022","unstructured":"Vavricka CJ, Takahashi S, Watanabe N et al (2022) Machine learning discovery of missing links that mediate alternative branches to plant alkaloids. Nat Commun 13:1405. https:\/\/doi.org\/10.1038\/s41467-022-28883-8","journal-title":"Nat Commun"},{"key":"9901_CR103","doi-asserted-by":"publisher","first-page":"e6729","DOI":"10.7717\/peerj.6729","volume":"7","author":"R Wang","year":"2019","unstructured":"Wang R, Han X, Xu S et al (2019) Cloning and characterization of a tyrosine decarboxylase involved in the biosynthesis of galanthamine in Lycoris aurea. PeerJ 7:e6729. https:\/\/doi.org\/10.7717\/peerj.6729","journal-title":"PeerJ"},{"key":"9901_CR102","doi-asserted-by":"publisher","first-page":"9725","DOI":"10.1021\/acs.orglett.0c03339","volume":"22","author":"J Wang","year":"2020","unstructured":"Wang J, Zhang Z-K, Jiang F-F et al (2020) Deciphering the biosynthetic mechanism of pelletierine in Lycopodium alkaloid biosynthesis. Org Lett 22:9725\u20138729. https:\/\/doi.org\/10.1021\/acs.orglett.0c03339","journal-title":"Org Lett"},{"key":"9901_CR104","doi-asserted-by":"publisher","first-page":"22000","DOI":"10.1021\/jacs.2c09091","volume":"144","author":"YJ Wang","year":"2022","unstructured":"Wang YJ, Huang JP, Tian T et al (2022) Discovery and engineering of the cocaine biosynthetic pathway. J Am Chem Soc 144:22000\u201322007. https:\/\/doi.org\/10.1021\/jacs.2c09091","journal-title":"J Am Chem Soc"},{"key":"9901_CR105","first-page":"1","volume-title":"Modern alkaloids: structure, isolation, synthesis, and biology","author":"M Wink","year":"2007","unstructured":"Wink M (2007) Ecological Roles of Alkaloids. In: Fattorusso E, Taglialatela-Scafati O (eds) Modern alkaloids: structure, isolation, synthesis, and biology. Wiley, New York, pp 1\u201324"},{"key":"9901_CR106","doi-asserted-by":"publisher","first-page":"309","DOI":"10.1126\/science.aab1852","volume":"349","author":"T Winzer","year":"2015","unstructured":"Winzer T, Kern M, King AJ et al (2015) Morphinan biosynthesis in opium poppy requires a P450-oxidoreductase fusion protein. Science 349:309\u2013312. https:\/\/doi.org\/10.1126\/science.aab1852","journal-title":"Science"},{"key":"9901_CR107","doi-asserted-by":"publisher","first-page":"914","DOI":"10.1111\/j.1467-7652.2009.00453.x","volume":"7","author":"CC Wood","year":"2009","unstructured":"Wood CC, Petrie JR, Shrestha P et al (2009) A leaf-based assay using interchangeable design principles to rapidly assemble multistep recombinant pathways. Plant Biotechnol J 7:914\u2013924. https:\/\/doi.org\/10.1111\/j.1467-7652.2009.00453.x","journal-title":"Plant Biotechnol J"},{"key":"9901_CR108","doi-asserted-by":"publisher","first-page":"5527","DOI":"10.1093\/jxb\/erx362","volume":"68","author":"T Yang","year":"2017","unstructured":"Yang T, Nagy I, Mancinotti D et al (2017) Transcript profiling of a bitter variety of narrow-leafed lupin to discover alkaloid biosynthetic genes. J Exp Bot 68:5527\u20135537. https:\/\/doi.org\/10.1093\/jxb\/erx362","journal-title":"J Exp Bot"},{"key":"9901_CR109","doi-asserted-by":"publisher","first-page":"2364","DOI":"10.1093\/plcell\/koac068","volume":"34","author":"MM Zakaria","year":"2022","unstructured":"Zakaria MM, Stegemann T, Sievert C et al (2022) Insights into polyamine metabolism: homospermidine is double-oxidized in two discrete steps by a single copper-containing amine oxidase in pyrrolizidine alkaloid biosynthesis. Plant Cell 34:2364\u20132382. https:\/\/doi.org\/10.1093\/plcell\/koac068","journal-title":"Plant Cell"},{"key":"9901_CR110","doi-asserted-by":"publisher","first-page":"5","DOI":"10.1016\/j.phytochem.2014.02.010","volume":"101","author":"F Zekiri","year":"2014","unstructured":"Zekiri F, Molitor C, Mauracher SG et al (2014) Purification and characterization of tyrosinase from walnut leaves (Juglans regia). Phytochemistry 101:5\u201315. https:\/\/doi.org\/10.1016\/j.phytochem.2014.02.010","journal-title":"Phytochemistry"},{"key":"9901_CR111","doi-asserted-by":"crossref","unstructured":"Zhang J, Liu YQ, Fang J (2023) The biological activities of quinolizidine alkaloids. In: Alkaloids: chemistry and biology. Academic Press, London, pp 1\u201337","DOI":"10.1016\/bs.alkal.2022.06.001"}],"container-title":["Phytochemistry Reviews"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s11101-023-09901-z.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/article\/10.1007\/s11101-023-09901-z\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s11101-023-09901-z.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,9,5]],"date-time":"2025-09-05T18:20:09Z","timestamp":1757096409000},"score":1,"resource":{"primary":{"URL":"https:\/\/link.springer.com\/10.1007\/s11101-023-09901-z"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,12,12]]},"references-count":111,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2025,8]]}},"alternative-id":["9901"],"URL":"https:\/\/doi.org\/10.1007\/s11101-023-09901-z","relation":{},"ISSN":["1568-7767","1572-980X"],"issn-type":[{"value":"1568-7767","type":"print"},{"value":"1572-980X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,12,12]]},"assertion":[{"value":"7 July 2023","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"8 November 2023","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"12 December 2023","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Declarations"}},{"value":"The authors declare no competing interests.","order":2,"name":"Ethics","group":{"name":"EthicsHeading","label":"Conflict of interest"}}]}}