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1. (Article ID: 11394)
 
Deng SJ, Yu B, Hui YZ
A facile synthetic approach to a group of structurally typical diosgenyl saponins
Tetrahedron Letters 39(36) (1998) 6511-6514
 

Five new steroids, the cholest-4-ene-3,22-diones : tumacone A (1), tumacone B (2), tumacoside A (3), tumacoside B (4), and a furostenone: tumaquenone (5), besides diosgenone (6), were isolated from the aerial parts of Solanum nudum. Their structures were determined by 2D NMR, MS analyses and chemical correlations. Steroid 3 and 5 displayed in vitro antimalarial activity against a Plasmodium falciparum chloroquine-resistant FCB-1 strain (IC50 27 and 16 mu M). The observed stereodependent cyclization into spiroketals of two 16-O isomers is discussed.

antimalarial, steroids, Solanum nudum, cholest-4-en-3, 22-dione, tumacones A and B, tumacosides A and B, tumaquenone, stereodependent cyclization

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