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Título

Diosgenone synthesis, anti-malarial activity and QSAR of analogues of this natural product

Autor Pabón, Adriana; Escobar, Gustavo; Vargas, Esteban; Cruz, Víctor L. ; Notario, Rafael ; Blair, Silvia; Echeverri, Fernándo
Palabras clave Steroid
Natural product
Diosgenone
Structural analogue
Animal model
Malaria
Fecha de publicación 2013
EditorMultidisciplinary Digital Publishing Institute
Citación Molecules 18: 3356- 3378 (2013)
ResumenSolanum 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 μM vs. 10.1 μM, 2.9 μM and 11.3 μM). 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.
URI http://hdl.handle.net/10261/103695
DOI10.3390/molecules18033356
Identificadoresdoi: 10.3390/molecules18033356
issn: 1420-3049
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