{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,9]],"date-time":"2025-11-09T07:38:21Z","timestamp":1762673901052,"version":"build-2065373602"},"reference-count":25,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2012,11,13]],"date-time":"2012-11-13T00:00:00Z","timestamp":1352764800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The Amaryllidaceae family is well known for its pharmacologically active alkaloids. An important approach to treat Alzheimer\u2019s disease involves the inhibition of the enzyme acetylcholinesterase (AChE). Galanthamine, an Amaryllidaceae alkaloid, is an effective, selective, reversible, and competitive AchE inhibitor. This work was aimed at studying the alkaloid composition of four wild Argentinian Amarillydaceae species for the first time, as well as analyzing their inhibitory activity on acetylcholinesterase. Alkaloid content was characterized by means of GC-MS analysis. Chloroform basic extracts from Habranthus jamesonii, Phycella herbertiana, Rhodophiala mendocina and Zephyranthes filifolia collected in the Argentinian Andean region all contained galanthamine, and showed a strong AChE inhibitory activity (IC50 between 1.2 and 2 \u00b5g\/mL). To our knowledge, no previous reports on alkaloid profiles and AChEIs activity of wild Argentinian Amarillydaceae species have been publisihed. The demand for renewable sources of industrial products like galanthamine and the need to protect plant biodiversity creates an opportunity for Argentinian farmers to produce such crops.<\/jats:p>","DOI":"10.3390\/molecules171113473","type":"journal-article","created":{"date-parts":[[2012,11,13]],"date-time":"2012-11-13T11:17:36Z","timestamp":1352805456000},"page":"13473-13482","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":38,"title":["Wild Argentinian Amaryllidaceae, a New Renewable Source of the Acetylcholinesterase Inhibitor Galanthamine and Other Alkaloids"],"prefix":"10.3390","volume":"17","author":[{"given":"Javier","family":"Ortiz","sequence":"first","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas, Universidad Nacional de San Juan, Av. Libertador General San Mart\u00edn 1109 (O), CP 5400, San Juan, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Strahil","family":"Berkov","sequence":"additional","affiliation":[{"name":"Departament de Productes Naturals, Biologia Vegetal i Edafologia, Facultat de Farm\u00e0cia, Universitat de Barcelona, Avda. Joan XXIII s\/n, 08028 Barcelona, Catalunya, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Natalia","family":"Pigni","sequence":"additional","affiliation":[{"name":"Departament de Productes Naturals, Biologia Vegetal i Edafologia, Facultat de Farm\u00e0cia, Universitat de Barcelona, Avda. Joan XXIII s\/n, 08028 Barcelona, Catalunya, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cristina","family":"Theoduloz","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias de la Salud, Universidad de Talca, Casilla 747, Talca, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"German","family":"Roitman","sequence":"additional","affiliation":[{"name":"Facultad de Agronom\u00eda, Universidad de Buenos Aires, Av. San Mart\u00edn 4453, 1417, Buenos Aires, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alejandro","family":"Tapia","sequence":"additional","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas, Universidad Nacional de San Juan, Av. Libertador General San Mart\u00edn 1109 (O), CP 5400, San Juan, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jaume","family":"Bastida","sequence":"additional","affiliation":[{"name":"Departament de Productes Naturals, Biologia Vegetal i Edafologia, Facultat de Farm\u00e0cia, Universitat de Barcelona, Avda. Joan XXIII s\/n, 08028 Barcelona, Catalunya, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4076-3999","authenticated-orcid":false,"given":"Gabriela","family":"Feresin","sequence":"additional","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas, Universidad Nacional de San Juan, Av. Libertador General San Mart\u00edn 1109 (O), CP 5400, San Juan, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2012,11,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1016\/j.indcrop.2011.01.019","article-title":"Review Cultivation of medicinal and aromatic plants for specialty industrial materials","volume":"34","author":"Lubbe","year":"2011","journal-title":"Ind. Crops Prod."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1021\/ed078p175","article-title":"Old yet new-pharmaceuticals from plants","volume":"78","author":"Houghton","year":"2001","journal-title":"J. Chem. Educ."},{"key":"ref_3","first-page":"87","article-title":"Chemical and biological aspects of Narcissus alkaloids","volume":"63","author":"Cordell","year":"2006","journal-title":"The Alkaloids"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1016\/j.jep.2004.02.012","article-title":"Galanthamine from snowdrop-the development of a modern drug against Alzheimer\u2019s disease from local Caucasian knowledge","volume":"92","author":"Heinrich","year":"2004","journal-title":"J. Ethnopharmacol."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"41","DOI":"10.2165\/00003495-200161010-00005","article-title":"Cholinesterase inhibitors for Alzheimer\u2019s disease (Review)","volume":"61","author":"Grutzendler","year":"2001","journal-title":"Drugs"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"105","DOI":"10.2174\/157488906775245246","article-title":"Galanthamine, a natural product for the treatment of Alzheimer\u2019s disease","volume":"1","author":"Marco","year":"2006","journal-title":"Recent Pat. CNS Drug Discov."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"886","DOI":"10.1039\/b502163b","article-title":"Amaryllidaceae and Sceletium alkaloids","volume":"24","author":"Zhong","year":"2007","journal-title":"Nat. Prod. Rep."},{"key":"ref_8","first-page":"575","article-title":"Chemical synthesis of galantamine, an acetylcholinesterase inhibitor for treatment of Alzheimer\u2019s disease","volume":"15","author":"Contelles","year":"2005","journal-title":"Inform Healthc."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"116","DOI":"10.1021\/cr040415t","article-title":"Synthesis and pharmacology of galantamine","volume":"106","author":"Contelles","year":"2006","journal-title":"Chem. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"254","DOI":"10.1039\/b705909b","article-title":"Recent advances in biomimetic natural product synthesis","volume":"25","author":"Bulger","year":"2008","journal-title":"Nat. Prod. Rep."},{"key":"ref_11","unstructured":"Zuloaga, F.O., and Morrone, O. (1996). Catalogo de las Plantas Vasculares de la Republica Argentina I, Missouri Botanical Garden."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/0006-2952(61)90145-9","article-title":"A new and rapid colorimetric determination of acetylcholinesterase activity","volume":"7","author":"Ellman","year":"1961","journal-title":"Biochem. Pharmacol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"2521","DOI":"10.1016\/S0024-3205(02)02034-9","article-title":"Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts","volume":"71","author":"Bastida","year":"2002","journal-title":"Life Sci."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1002\/cbdv.200900380","article-title":"Alkaloid Diversity in Galanthus elwesii and Galanthus nivalis","volume":"8","author":"Berkov","year":"2011","journal-title":"Chem. Biodivers."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"182","DOI":"10.1002\/1097-0134(20010201)42:2<182::AID-PROT50>3.0.CO;2-1","article-title":"Three-dimensional structure of a complex of galanthamine (Nivalin\u00ae) with acetylcholinesterase from Torpedo californica: Implications for the design of new anti-Alzheimer drugs","volume":"42","author":"Bartolucci","year":"2001","journal-title":"Proteins"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1153","DOI":"10.1248\/cpb.57.1153","article-title":"Chemical constituents of the bulbs of Habranthus brachyandrus and their cytotoxic activities","volume":"57","author":"Jitsuno","year":"2009","journal-title":"Chem. Pharm. Bull."},{"key":"ref_17","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_18","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_19","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1039\/b508966m","article-title":"Acetylcholinesterase inhibitors from plants and fungi","volume":"23","author":"Houghton","year":"2006","journal-title":"Nat. Prod. Rep."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1068","DOI":"10.1016\/j.phytochem.2007.01.006","article-title":"Selective apoptosis-inducing activity of crinum-type Amaryllidaceae alkaloids","volume":"68","author":"McNulty","year":"2007","journal-title":"Phytochemistry"},{"key":"ref_21","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_22","doi-asserted-by":"crossref","first-page":"913","DOI":"10.1016\/j.phytochem.2009.04.012","article-title":"Structure-activity studies on the lycorine pharmacophore: A potent inducer of apoptosis in human leukemia cells","volume":"70","author":"McNulty","year":"2009","journal-title":"Phytochemistry"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1002\/(SICI)1099-1573(199805)12:3<205::AID-PTR203>3.0.CO;2-7","article-title":"Antiinflammatory effects of lycorine and haemanthidine","volume":"12","author":"Citoglu","year":"1998","journal-title":"Phytother. Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1016\/j.canlet.2008.08.029","article-title":"Lycorine induces apoptosis and down-regulation of Mcl-1 in human leukemia cells","volume":"274","author":"Liu","year":"2009","journal-title":"Cancer Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1055\/s-2006-958007","article-title":"Cytotoxic activity of Amaryllidaceae alkaloids","volume":"61","author":"Weniger","year":"1995","journal-title":"Planta Med."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/17\/11\/13473\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:53:33Z","timestamp":1760219613000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/17\/11\/13473"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,11,13]]},"references-count":25,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2012,11]]}},"alternative-id":["molecules171113473"],"URL":"https:\/\/doi.org\/10.3390\/molecules171113473","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2012,11,13]]}}}