{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,11]],"date-time":"2026-10-11T11:31:17Z","timestamp":1791718277261,"version":"4.3.4"},"reference-count":38,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2013,3,14]],"date-time":"2013-03-14T00:00:00Z","timestamp":1363219200000},"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>Solanum nudum Dunal steroids have been reported as being antimalarial compounds; however, their concentration in plants is low, meaning that the species could be threatened by over-harvesting for this purpose. Swern oxidation was used for hemisynthesis of diosgenone (one of the most active steroidal sapogenin diosgenin compounds). Eighteen structural analogues were prepared; three of them were found to be more active than diosgenone (IC50 27.9 \u03bcM vs. 10.1 \u03bcM, 2.9 \u03bcM and 11.3 \u03bcM). The presence of a 4-en-3-one grouping in the A-ring of the compounds seems to be indispensable for antiplasmodial activity; progesterone (having the same functional group in the steroid A-ring) has also displayed antiplasmodial activity. Quantitative correlations between molecular structure and bioactivity were thus explored in diosgenone and several derivatives using well-established 3D-QSAR techniques. The models showed that combining electrostatic (70%) and steric (30%) fields can explain most variance regarding compound activity. Malarial parasitemia in mice became reduced by oral administration of two diosgenone derivatives.<\/jats:p>","DOI":"10.3390\/molecules18033356","type":"journal-article","created":{"date-parts":[[2013,3,14]],"date-time":"2013-03-14T12:22:04Z","timestamp":1363263724000},"page":"3356-3378","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Diosgenone Synthesis, Anti-Malarial Activity and QSAR of Analogues of This Natural Product"],"prefix":"10.3390","volume":"18","author":[{"given":"Adriana","family":"Pab\u00f3n","sequence":"first","affiliation":[{"name":"Grupo Malaria, Facultad de Medicina, Universidad de Antioquia, 050010 Medell\u00edn, Colombia"},{"name":"Programa de Biolog\u00eda, Facultad de Ciencias B\u00e1sicas, Universidad del Atl\u00e1ntico,  080001 Barranquilla, Colombia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gustavo","family":"Escobar","sequence":"additional","affiliation":[{"name":"Grupo de Qu\u00edmica Org\u00e1nica de Productos Naturales, Instituto de Qu\u00edmica,  Universidad de Antioquia, 050010 Medell\u00edn, Colombia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Esteban","family":"Vargas","sequence":"additional","affiliation":[{"name":"Grupo de Qu\u00edmica Org\u00e1nica de Productos Naturales, Instituto de Qu\u00edmica,  Universidad de Antioquia, 050010 Medell\u00edn, Colombia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"V\u00edctor","family":"Cruz","sequence":"additional","affiliation":[{"name":"Instituto de Estructura de la Materia, CSIC, 28006 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rafael","family":"Notario","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica-F\u00edsica Rocasolano, CSIC, 28006 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Silvia","family":"Blair","sequence":"additional","affiliation":[{"name":"Grupo Malaria, Facultad de Medicina, Universidad de Antioquia, 050010 Medell\u00edn, Colombia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fernando","family":"Echeverri","sequence":"additional","affiliation":[{"name":"Grupo de Qu\u00edmica Org\u00e1nica de Productos Naturales, Instituto de Qu\u00edmica,  Universidad de Antioquia, 050010 Medell\u00edn, Colombia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2013,3,14]]},"reference":[{"key":"ref_1","unstructured":"WHO (2011). 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