{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T18:03:22Z","timestamp":1790532202528,"version":"4.1.0"},"reference-count":92,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2020,5,16]],"date-time":"2020-05-16T00:00:00Z","timestamp":1589587200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100007397","name":"Univerzita Karlova v Praze","doi-asserted-by":"publisher","award":["SVV UK 260 548; Progres\/UK Q40-01 and Q42"],"award-info":[{"award-number":["SVV UK 260 548; Progres\/UK Q40-01 and Q42"]}],"id":[{"id":"10.13039\/100007397","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000780","name":"European Union","doi-asserted-by":"publisher","award":["CZ.02.1.01\/0.0\/0.0\/18_069\/0010046"],"award-info":[{"award-number":["CZ.02.1.01\/0.0\/0.0\/18_069\/0010046"]}],"id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Plants of the Amaryllidaceae family are promising therapeutic tools for human diseases and have been used as alternative medicines. The specific secondary metabolites of this plant family, called Amaryllidaceae alkaloids (AA), have attracted considerable attention due to their interesting pharmacological activities. One of them, galantamine, is already used in the therapy of Alzheimer\u2019s disease as a long acting, selective, reversible inhibitor of acetylcholinesterase. One group of AA is the montanine-type, such as montanine, pancracine and others, which share a 5,11-methanomorphanthridine core. So far, only 14 montanine-type alkaloids have been isolated. Compared with other structural-types of AA, montanine-type alkaloids are predominantly present in plants in low concentrations, but some of them display promising biological properties, especially in vitro cytotoxic activity against different cancerous cell lines. The present review aims to summarize comprehensively the research that has been published on the Amaryllidaceae alkaloids of montanine-type.<\/jats:p>","DOI":"10.3390\/molecules25102337","type":"journal-article","created":{"date-parts":[[2020,5,20]],"date-time":"2020-05-20T10:37:38Z","timestamp":1589971058000},"page":"2337","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":29,"title":["Chemical and Biological Aspects of Montanine-Type Alkaloids Isolated from Plants of the Amaryllidaceae Family"],"prefix":"10.3390","volume":"25","author":[{"given":"Darja","family":"Koutov\u00e1","sequence":"first","affiliation":[{"name":"Department of Medical Biochemistry, Faculty of Medicine in Hradec Kr\u00e1lov\u00e9, Charles University, \u0160imkova 870, 500 03 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4227-7855","authenticated-orcid":false,"given":"Negar","family":"Maafi","sequence":"additional","affiliation":[{"name":"ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0528-1334","authenticated-orcid":false,"given":"Radim","family":"Havelek","sequence":"additional","affiliation":[{"name":"Department of Medical Biochemistry, Faculty of Medicine in Hradec Kr\u00e1lov\u00e9, Charles University, \u0160imkova 870, 500 03 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lubom\u00edr","family":"Opletal","sequence":"additional","affiliation":[{"name":"ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gerald","family":"Blunden","sequence":"additional","affiliation":[{"name":"School of Pharmacy and Biomedical Sciences, University of Portsmouth, Portsmouth, Hampshire P01 2DT, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5370-2290","authenticated-orcid":false,"given":"Martina","family":"\u0158ez\u00e1\u010dov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Medical Biochemistry, Faculty of Medicine in Hradec Kr\u00e1lov\u00e9, Charles University, \u0160imkova 870, 500 03 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1555-8870","authenticated-orcid":false,"given":"Lucie","family":"Cahl\u00edkov\u00e1","sequence":"additional","affiliation":[{"name":"ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,5,16]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Dahlgren, R.M.T., Clifford, H.T., and Yeo, P.F. (1985). The Families of the Monocotyledons. Structure, Evolution and Taxonomy, Springer. [1st ed.].","DOI":"10.1007\/978-3-642-61663-1"},{"key":"ref_2","first-page":"151","article-title":"Bioactivity and bioactive compounds from African Amaryllidaceae","volume":"Volume 1021","author":"Juliani","year":"2009","journal-title":"African Natural Plant Products: New Discoveries and Challenges in Chemistry and Quality"},{"key":"ref_3","first-page":"121","article-title":"In vivo cytotoxicity studies of Amaryllidaceae alkaloids","volume":"11","author":"Nair","year":"2016","journal-title":"Nat. Prod. Commun."},{"key":"ref_4","first-page":"701","article-title":"Amaryllidaceae family alkaloids as potential drugs for cancer treatment","volume":"107","author":"Havelek","year":"2013","journal-title":"Chem. Listy"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1318","DOI":"10.1039\/C6NP00068A","article-title":"Amaryllidaceae and Sceletium alkaloids","volume":"33","author":"Jin","year":"2016","journal-title":"Nat. Prod. Rep."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/j.cbi.2017.07.018","article-title":"Anticancer potential of Amaryllidaceae alkaloids evaluated by screening with a panel of human cells, real-time cellular analysis and Ehrlich tumor-bearing mice","volume":"275","author":"Havelek","year":"2017","journal-title":"Chem. Biol. Interact."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/S0378-8741(01)00305-1","article-title":"Crinum species in traditional and modern medicine","volume":"78","author":"Fennell","year":"2001","journal-title":"J. Ethnopharmacol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1016\/S0378-8741(00)00341-X","article-title":"Plants used against cancer\u2014An extension of the work of Jonathan Hartwell","volume":"73","author":"Graham","year":"2000","journal-title":"J. Ethnopharmacol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1016\/j.jep.2011.04.004","article-title":"Screening of plants used in Mayan traditional medicine to treat cancer-like symptoms","volume":"135","year":"2011","journal-title":"J. Ethnopharmacol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1055\/s-2001-11495","article-title":"Crinane and lycorane type alkaloids from Zephyranthes citrina","volume":"67","author":"Herrera","year":"2001","journal-title":"Planta Med."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"262","DOI":"10.1016\/j.fct.2013.08.042","article-title":"Pharmacological and toxicological insights to the South African Amaryllidaceae","volume":"62","author":"Nair","year":"2013","journal-title":"Food Chem. Toxicol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1593\/tlo.08100","article-title":"Amaryllidaceae isocarbostyril alkaloids and their derivatives as promising antitumor agents","volume":"1","author":"Ingrassia","year":"2008","journal-title":"Transl. Oncol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1982","DOI":"10.1021\/cr078198u","article-title":"Chemistry, biology, and medicinal potential of narciclasine and its congeners","volume":"108","author":"Kornienko","year":"2008","journal-title":"Chem. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.neuropharm.2013.07.004","article-title":"Therapeutics of Alzheimer\u2019s disease: Past, present and future","volume":"76","author":"Anand","year":"2014","journal-title":"Neuropharmacology"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1007\/s11101-015-9451-z","article-title":"The Amaryllidaceae alkaloids: Biosynthesis and methods for enzyme discovery","volume":"15","author":"Kilgore","year":"2016","journal-title":"Phytochem. Rev."},{"key":"ref_16","first-page":"1","article-title":"Amaryllidaceae alkaloids: Identification and partial characterization of montanine production in Rhodophiala bifida plant","volume":"9","author":"Reis","year":"2019","journal-title":"Sci. Rep."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"114","DOI":"10.14719\/pst.2014.1.3.41","article-title":"Biosynthesis of the Amaryllidaceae alkaloids","volume":"1","author":"Singh","year":"2014","journal-title":"Plant Sci. Today"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1971","DOI":"10.3389\/fpls.2016.01971","article-title":"Transcriptome analysis of secondary metabolism pathway, transcription factors, and transporters in response to methyl jasmonate in Lycoris aurea","volume":"7","author":"Wang","year":"2017","journal-title":"Front. Plant Sci."},{"key":"ref_19","unstructured":"Ferdausi, A. (2017). A Metabolomics and Transcriptomics Comparison of Narcissus pseudonarcissus cv. Carlton Feld and In Vitro Tissues in Relation to Alkaloid Production. [Ph.D. Thesis, University of Liverpool]."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"17356","DOI":"10.1038\/s41598-017-17724-0","article-title":"Transcriptome and metabolome profiling of Narcissus pseudonarcissus \u2018King Alfred\u2019 reveal components of Amaryllidaceae alkaloid metabolism","volume":"7","author":"Singh","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"430","DOI":"10.1039\/c39730000430","article-title":"Stereochemistry of hydrogen removal \u03b2 to nitrogen in the biological conversion of O-methylnorbelladine into the montanine-type alkaloids","volume":"13","author":"Fuganti","year":"1973","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1039\/c39760000551","article-title":"Biosynthesis of montanine","volume":"14","author":"Wildman","year":"1976","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2447","DOI":"10.1021\/jo00876a020","article-title":"Biosynthetic oxidation and rearrangement of vittatine and its derivatives","volume":"41","author":"Feinstein","year":"1976","journal-title":"J. Org. Chem."},{"key":"ref_24","unstructured":"Pavlov, A., and Bley, T. (2016). Amaryllidaceae alkaloid accumulation by plant in vitro system. Bioprocessing of Plant In Vitro Systems, Reference Series in Phytochemistry, Springer International Publishing."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"886","DOI":"10.1039\/b502163b","article-title":"Amaryllidaceae and Sceletium alkaloids","volume":"24","author":"Jin","year":"2007","journal-title":"Nat. Prod. Rep."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1248","DOI":"10.1021\/ja01610a045","article-title":"Alkaloids of the Amaryllidaceae. III. Isolation of five new alkaloids from Haemanthus species1","volume":"77","author":"Wildman","year":"1955","journal-title":"J. Am. Chem. Soc."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1021\/np800459d","article-title":"Pancratium canariense as an important source of Amaryllidaceae alkaloids","volume":"72","author":"Oberti","year":"2009","journal-title":"J. Nat. Prod."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1016\/0031-9422(95)00191-9","article-title":"Alkaloids from Boophane flava","volume":"40","author":"Viladomat","year":"1995","journal-title":"Phytochemistry"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"3812","DOI":"10.1039\/c2ob25374g","article-title":"Flexible synthesis of montanine-like alkaloids: Revisiting the structure of montabuphine","volume":"10","author":"Guan","year":"2012","journal-title":"Org. Biomol. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"4693","DOI":"10.1021\/ol801815k","article-title":"A chemoenzymatic total synthesis of the structure assigned to the alkaloid (+)-montabuphine","volume":"10","author":"Matveenko","year":"2008","journal-title":"Org. Lett."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1016\/j.ejphar.2017.02.013","article-title":"Disease modifying anti-rheumatic activity of the alkaloid montanine on experimental arthritis and fibroblast-like synoviocytes","volume":"799","author":"Farinon","year":"2017","journal-title":"Eur. J. Pharmacol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"6439","DOI":"10.1021\/ja01025a036","article-title":"Mass spectra of 5,11-methanomorphanthridine alkaloids. The structure of pancracine","volume":"90","author":"Wildman","year":"1968","journal-title":"J. Am. Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"277","DOI":"10.1016\/j.sajb.2019.01.036","article-title":"Alkaloids isolated from Haemanthus humilis Jacq., an indigenous South African Amaryllidaceae: Anticancer activity of coccinine and montanine","volume":"126","author":"Masi","year":"2019","journal-title":"S. Afr. J. Bot."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1016\/j.sajb.2013.06.002","article-title":"Serotonin transporter protein (SERT) and P-glycoprotein (P-gp) binding activity of montanine and coccinine from three species of Haemanthus L.(Amaryllidaceae)","volume":"88","author":"Stafford","year":"2013","journal-title":"S. Afr. J. Bot."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"882","DOI":"10.1016\/j.phymed.2007.12.001","article-title":"Screening for cytotoxic activity of extracts and isolated alkaloids from bulbs of Hippeastrum vittatum","volume":"15","author":"Silva","year":"2008","journal-title":"Phytomedicine"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1241","DOI":"10.1021\/acs.jnatprod.5b00785","article-title":"Alkaloids from Hippeastrum argentinum and their cholinesterase-inhibitory activities: An in vitro and in silico study","volume":"79","author":"Ortiz","year":"2016","journal-title":"J. Nat. Prod."},{"key":"ref_37","first-page":"1255","article-title":"GC\/MS analysis of three Amaryllidaceae species and their cholinesterase activity","volume":"6","author":"Opletal","year":"2011","journal-title":"Nat. Prod. Commun."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4902","DOI":"10.1021\/ja00949a038","article-title":"Mass spectrometry in structural and stereochemical problems. LXXXII. 1 A study of the fragmentation of some Amaryllidaceae alkaloids2","volume":"87","author":"Duffield","year":"1965","journal-title":"J. Am. Chem. Soc."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"7285","DOI":"10.1021\/jo00052a051","article-title":"Total synthesis of montanine-type Amaryllidaceae alkaloids, which possess a 5, 11-methanomorphanthridine ring system, through cyclization with sodium bis (2-methoxyethoxy) aluminum hydride (SMEAH): The first stereoselective total syntheses of (\u00b1)-montanine, (\u00b1)-coccinine, (\u00b1)-O-acetylmontanine, (\u00b1)-pancracine, and (\u00b1)-brunsvigine","volume":"57","author":"Ishizaki","year":"1992","journal-title":"J. Org. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"14167","DOI":"10.1002\/anie.201307324","article-title":"Bioinspired total synthesis of montanine-type Amaryllidaceae alkaloids","volume":"52","author":"Bao","year":"2013","journal-title":"Angew. Chem. Int. Edit."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1016\/S0254-6299(15)30148-4","article-title":"Alkaloids from three ethnomedicinal Haemanthus species: H. albiflos, H. deformis and H. pauculifolius (Amaryllidaceae)","volume":"71","author":"Crouch","year":"2005","journal-title":"S. Afr. J. Bot."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1016\/j.pbb.2006.07.027","article-title":"Anxiolytic-, antidepressant- and anticonvulsant-like effects of the alkaloid montanine isolated from Hippeastrum vittatum","volume":"85","author":"Bevilaqua","year":"2006","journal-title":"Pharmacol. Biochem. Behav."},{"key":"ref_43","first-page":"154","article-title":"Alkaloid profiling of Hippeastrum cultivars by GC-MS, isolation of Amaryllidaceae alkaloids and evaluation of their cytotoxicity","volume":"14","author":"Havelek","year":"2020","journal-title":"Rec. Nat. Prod."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1515\/znc-2004-1-214","article-title":"Alkaloids in Bulgarian Pancratium maritimum L.","volume":"59","author":"Berkov","year":"2004","journal-title":"Zeitschrift f\u00fcr Naturforschung C"},{"key":"ref_45","first-page":"1","article-title":"Chemical composition and enzyme inhibitory activities of Turkish Pancratium maritimum bulbs","volume":"14","author":"Bozkurt","year":"2019","journal-title":"Nat. Prod. Commun."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"847","DOI":"10.1016\/S0031-9422(02)00154-1","article-title":"Alkaloids from Narcissus angustifolius subsp","volume":"60","author":"Machocho","year":"2002","journal-title":"transcarpathicus. Phytochemistry"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"13854","DOI":"10.3390\/molecules200813854","article-title":"Antiproliferative and structure activity relationships of Amaryllidaceae alkaloids","volume":"20","author":"Ravelo","year":"2015","journal-title":"Molecules"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1016\/j.fitote.2013.05.006","article-title":"Neuroprotective compounds from the bulbs of Lycoris radiata","volume":"88","author":"Li","year":"2013","journal-title":"Fitoterapia"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"7580","DOI":"10.1021\/jo801089y","article-title":"An expedient route to montanine-type Amaryllidaceae alkaloids: Total syntheses of (\u2212)-brunsvigine and (\u2212)-manthine","volume":"73","author":"Hong","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2153","DOI":"10.1021\/jo01082a019","article-title":"Structures of montanine, coccinine, and manthine","volume":"25","author":"Inubushi","year":"1960","journal-title":"J. Org. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1855","DOI":"10.1016\/0040-4020(75)87041-4","article-title":"Alkaloids of the Amaryllidaceae: Brunsvigine: NMR, ORD\/CD and mass spectrometry, degradation and interconversion studies","volume":"31","author":"Clark","year":"1975","journal-title":"Tetrahedron"},{"key":"ref_52","doi-asserted-by":"crossref","unstructured":"Dry, L.J., Poynton, M., Thompson, M.E., and Warren, F.L. (1958). The alkaloids of the Amaryllidaceae. Part IV. The alkaloids of Brunsvigia cooperi Baker. J. Chem. Soc., 4701\u20134704.","DOI":"10.1039\/jr9580004701"},{"key":"ref_53","first-page":"725","article-title":"Alkaloids from Rhodophiala bifida, Crinum erubescens and Sprekelia formisissima","volume":"22","author":"Wildman","year":"1967","journal-title":"Pharmazie"},{"key":"ref_54","first-page":"1677","article-title":"Cytotoxic agents of the crinane series of Amaryllidaceae alkaloids","volume":"7","author":"Nair","year":"2012","journal-title":"Nat. Prod. Comm."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"16562","DOI":"10.1039\/C4RA14666B","article-title":"Biological and pharmacological activities of Amaryllidaceae alkaloids","volume":"5","author":"He","year":"2015","journal-title":"RSC Adv."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1220","DOI":"10.1002\/ptr.1346","article-title":"Antimalarial activity screening of some alkaloids and the plant extracts from Amaryllidaceae","volume":"17","author":"Sener","year":"2003","journal-title":"Phytother. Res."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1016\/j.phytol.2010.06.004","article-title":"In vitro antiprotozoal activity of alkaloids from Phaedranassa dubia (Amaryllidaceae)","volume":"3","author":"Osorio","year":"2010","journal-title":"Phytochem. Lett."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1120","DOI":"10.1002\/cbdv.201200144","article-title":"Alkaloids from Zephyranthes robusta Baker and their acetylcholinesterase and butyrylcholinesterase inhibition activity","volume":"10","author":"Opletal","year":"2013","journal-title":"Chem. Biodivers."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"479","DOI":"10.1016\/j.phymed.2013.09.005","article-title":"The effect of Amaryllidaceae alkaloids Haemanthamine and Haemanthidine on cell cycle progression and apoptosis in p53-negative human leukemic Jurkat cells","volume":"21","author":"Havelek","year":"2014","journal-title":"Phytomedicine"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1016\/B978-0-444-63601-0.00003-X","article-title":"Cytotoxic alkaloids constituents of the Amaryllidaceae","volume":"Volume 49","author":"Rahman","year":"2016","journal-title":"Studies in Natural Products Chemistry"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"1021","DOI":"10.1111\/jcmm.12493","article-title":"Haemanthus coccineus extract and its main bioactive component narciclasine display profound anti-inflammatory activities in vitro and in vivo","volume":"19","author":"Fuchs","year":"2015","journal-title":"J. Cell Mol. Med."},{"key":"ref_62","doi-asserted-by":"crossref","unstructured":"Breiterov\u00e1, K., Koutov\u00e1, D., Ma\u0159\u00edkov\u00e1, J., Havelek, R., Kune\u0161, J., Majoro\u0161ov\u00e1, M., Opletal, L., Ho\u0161\u0165\u00e1lkov\u00e1, A., Jen\u010do, J., and \u0158ez\u00e1\u010dov\u00e1, M. (2020). Amaryllidaceae alkaloids of different structural types from Narcissus L. cv. Professor Einstein and their cytotoxic activity. Plants, 9.","DOI":"10.3390\/plants9020137"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"589","DOI":"10.1016\/j.bmcl.2018.01.041","article-title":"Synthetic analogues of the montanine-type alkaloids with activity against apoptosis-resistant cancer cells","volume":"28","author":"Govindaraju","year":"2018","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"698","DOI":"10.1016\/j.phymed.2009.10.003","article-title":"Effect of isoquinoline alkaloids from two Hippeastrum species on in vitro acetylcholinesterase activity","volume":"17","author":"Pagliosa","year":"2010","journal-title":"Phytomedicine"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"2113","DOI":"10.1016\/j.phytochem.2004.03.020","article-title":"(\u2212)-Amarbellisine, a lycorine-type alkaloid from Amaryllis belladonna L. growing in Egypt","volume":"65","author":"Evidente","year":"2004","journal-title":"Phytochemistry."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"189","DOI":"10.6026\/97320630011189","article-title":"In silico inhibition of GABARAP activity using antiepileptic medicinal derived compounds","volume":"11","author":"Mathew","year":"2015","journal-title":"Bioinformation"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1590\/S0102-695X2007000200013","article-title":"Availacao in vitro das atividades antiinflamatoria, antioxidante e antimicrobiana do alcaloide montanina","volume":"17","author":"Castilhos","year":"2007","journal-title":"Rev. Bras. Pharmacogn."},{"key":"ref_68","unstructured":"De Oliveira, P.G., Pedrazza, G.P.R., Farinon, M., Machado, X.R., Zuanazzi, J.A.S., and Spies, F. (2020). Process for Extracting the Alkaloid Fraction of Rhodophiala bifida (Herb.) Traub and Uses Threof. (2020\/0000798 A1), US Patent."},{"key":"ref_69","doi-asserted-by":"crossref","unstructured":"Kohelov\u00e1, E., Pe\u0159inov\u00e1, R., Maafi, N., Kor\u00e1be\u010dn\u00fd, J., Hulcov\u00e1, D., Ma\u0159\u00edkov\u00e1, J., Ku\u010dera, T., Mart\u00ednez Gonz\u00e1lez, L., Hrabinova, M., and Vor\u010d\u00e1kov\u00e1, K. (2019). Derivatives of the \u03b2-crinane Amaryllidaceae alkaloid haemanthamine as multi-target directed ligands for Alzheimer\u2019s Disease. Molecules, 24.","DOI":"10.3390\/molecules24071307"},{"key":"ref_70","doi-asserted-by":"crossref","unstructured":"Tallini, L.R., Bastida, J., Cortes, N., Osorio, E.H., Theoduloz, C., and Schmeda-Hirschmann, G. (2018). Cholinesterase inhibition activity, alkaloid profiling and molecular docking of Chilean Rhodophiala (Amaryllidaceae). Molecules, 23.","DOI":"10.3390\/molecules23071532"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/j.sajb.2018.09.011","article-title":"Acetylcholinesterase inhibitors from southern African plants: An overview of ethnobotanical, pharmacological potential and phytochemical research including and beyond Alzheimer\u2019s disease treatment","volume":"120","author":"Masondo","year":"2019","journal-title":"S. Afr. J. Bot."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"1189","DOI":"10.1021\/acs.jnatprod.5b00191","article-title":"In vitro inhibitory effects of 8-O-demethylmaritidine and undulatine on acetylcholinesterase and their predicted penetration across the blood\u2013brain barrier","volume":"78","author":"Chlebek","year":"2015","journal-title":"J. Nat. Prod."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"112055","DOI":"10.1016\/j.phytochem.2019.112055","article-title":"Amaryllidaceae alkaloids from Narcissus pseudonarcissus L. cv. Dutch Master as potential drugs in treatment of Alzheimer\u2019s disease","volume":"165","author":"Jun","year":"2019","journal-title":"Phytochemistry"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"7079","DOI":"10.1016\/0040-4039(91)85045-7","article-title":"A first total synthesis of montanine-type Amaryllidaceae alkaloids, (\u00b1)-coccinine, (\u00b1)-montanine, and (\u00b1)-pancracine","volume":"32","author":"Ishizaki","year":"1991","journal-title":"Tetrahedron Lett."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"5005","DOI":"10.1021\/jo00017a002","article-title":"Synthesis applications of cationic aza-Cope rearrangements. 23. First total synthesis of Amaryllidaceae alkaloids of the 5,11-methano morphanthridine type. An efficient total synthesis of (\u00b1)-pancracine","volume":"56","author":"Overman","year":"1991","journal-title":"J. Org. Chem."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1039\/P19930000101","article-title":"Radical-mediated synthesis of the 5,11-methanomorphanthridine ring system: Formal total synthesis of montanine-type Amaryllidaceae alkaloids, (\u00b1)-montanine, (\u00b1)-coccinine and (\u00b1)-pancracine","volume":"1","author":"Ishizaki","year":"1993","journal-title":"J. Chem. Soc. Perkin Trans. 1"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"4662","DOI":"10.1021\/jo00069a032","article-title":"Total synthesis of Amaryllidaceae alkaloids of the 5,11-methanomorphanthridine type. Efficient total synthesis of (-)-pancracine and (\u00b1)-pancracine","volume":"58","author":"Overman","year":"1993","journal-title":"J. Org. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"5773","DOI":"10.1021\/ja970839n","article-title":"Application of a stereospecific intramolecular allenylsilane imino ene reaction to enantioselective total synthesis of the 5,11-methanomorphanthridine class of Amaryllidaceae alkaloids","volume":"119","author":"Jin","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"1724","DOI":"10.1002\/(SICI)1521-3773(19980703)37:12<1724::AID-ANIE1724>3.0.CO;2-8","article-title":"Application of the 2-azaallyl anion cycloaddition method to an enantioselective total synthesis of (+)-coccinine","volume":"37","author":"Pearson","year":"1998","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1949","DOI":"10.1039\/a900467j","article-title":"Stereoselective synthesis of (3R*, 3aS*, 7aS*)-3-aryloctahydroindol-2-ones using radical cyclisation: A formal synthesis of (\u00b1)-pancracine","volume":"14","author":"Ikeda","year":"1999","journal-title":"J. Chem. Soc. Perkin Trans. 1"},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1345","DOI":"10.1039\/b102252k","article-title":"An operationally simple and fully regiocontrolled formal total synthesis of the montanine-type Amaryllidaceae alkaloid (\u00b1)-pancracine","volume":"12","author":"Banwell","year":"2001","journal-title":"J. Chem. Soc. Perkin Trans. 1"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"2177","DOI":"10.1021\/ol016022n","article-title":"Synthesis of aza bicyclic enones via anionic cyclization: Application to the total synthesis of (\u2212)-Brunsvigine","volume":"3","author":"Sha","year":"2001","journal-title":"Org. Lett."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"3713","DOI":"10.1021\/ol051321o","article-title":"Stereospecific route to 5,11-methanomorphanthridine alkaloids via intramolecular 1,3-dipolar cycloaddition of nonstabilized azomethine ylide: Formal total synthesis of (\u00b1)-pancracine","volume":"7","author":"Pandey","year":"2005","journal-title":"Org. Lett."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"3503","DOI":"10.1021\/ol071344y","article-title":"Chemoenzymatic approaches to the montanine alkaloids: A total synthesis of (+)-brunsvigine","volume":"9","author":"Banwell","year":"2007","journal-title":"Org. Lett."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"6444","DOI":"10.1016\/j.tet.2008.04.070","article-title":"Chemoenzymatic approaches to the montanine alkaloids: A total synthesis of (+)-nangustine","volume":"64","author":"Kokas","year":"2008","journal-title":"Tetrahedron"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"3069","DOI":"10.1016\/j.tet.2008.10.091","article-title":"Asymmetric formal synthesis of (\u2212)-pancracine via catalytic enantioselective C\u2013H amination process","volume":"65","author":"Anada","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"556","DOI":"10.1021\/ol902761a","article-title":"Stereoselective synthesis of 3-aryloctahydroindoles and application in a formal synthesis of (\u2212)-pancracine","volume":"12","author":"Pansare","year":"2010","journal-title":"Org. Lett."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"4571","DOI":"10.1002\/ejoc.201100601","article-title":"One-step stereospecific strategy for the construction of the core structure of the 5,11-methanomorphanthridine alkaloids in racemic as well as in optically pure form: Synthesis of (\u00b1)-pancracine and (\u00b1)-brunsvigine","volume":"2011","author":"Pandey","year":"2011","journal-title":"Eur. J. Org. Chem."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"1597","DOI":"10.1351\/PAC-CON-11-10-12","article-title":"Stereoselective construction of 5,11-methanomorphanthridine and 5,10b-phenanthridine structural frameworks: Total syntheses of (\u00b1)-pancracine, (\u00b1)-brunsvigine, (\u00b1)-maritidine, and (\u00b1)-crinine","volume":"84","author":"Pandey","year":"2012","journal-title":"Pure Appl. Chem."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"12930","DOI":"10.1002\/chem.201702893","article-title":"Rhodium-catalyzed denitrogenative [3 + 2] cycloaddition: Access to functionalized hydroindolones and the framework of montanine-type Amaryllidaceae alkaloids","volume":"23","author":"Yang","year":"2017","journal-title":"Chem. Eur. J."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"699","DOI":"10.1016\/j.tetlet.2017.01.036","article-title":"Synthesis of biologically active natural products by [3 + 2] cycloaddition of non-stabilized azomethine ylides (AMY): Concepts and realizations","volume":"58","author":"Pandey","year":"2017","journal-title":"Tetrahedron Lett."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"1491","DOI":"10.1021\/ol900065x","article-title":"Bioactive montanine derivatives from halide-induced rearrangements of haemanthamine-type alkaloids. Absolute configuration by VCD","volume":"11","author":"Ravelo","year":"2009","journal-title":"Org. Lett."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/10\/2337\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T09:29:36Z","timestamp":1760174976000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/10\/2337"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,5,16]]},"references-count":92,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2020,5]]}},"alternative-id":["molecules25102337"],"URL":"https:\/\/doi.org\/10.3390\/molecules25102337","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,5,16]]}}}