Trypanocidal withanolides and withanolide glycosides from Dunalia brachyacantha.
Two new withanolide glycosides, (20R,22R)-O-(3)-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl-1 alpha,12 beta-diacetoxy-20-hydroxywitha-5,24-dienolide (3) and (20R,22R)-O-(3)-beta-D-xylopyranosyl(1-->3)-[beta-D-xylopyranosyl(1-->4)]-beta-D-glucopyranosyl-1 alpha-acetoxy-12 beta,20-dihydroxywitha-5,24-dienolide (4), were isolated from the leaves and root of Dunalia brachyacantha. Their aglycones, (20R,22R)-1 alpha,12 beta-diacetoxy-3 beta,20-dihydroxywitha-5,24-dienolide (or 1 alpha,12 beta-diacetyldunawithagenine) and (20R,22R)-1 alpha-acetoxy-3 beta,12 beta,20-trihydroxywitha-5,24-dienolide (or 1 alpha-acetyl-12 beta-hydroxydunawithagenine), are novel. The known 18-acetoxywithanolide D (1) and 18-acetoxy-5,6-deoxy-5-withenolide D (2) were also isolated from the leaves. These last two compounds were shown to be responsible for the trypanocidal, leishmanicidal, and bactericidal activities manifested by the crude ethanolic extract. The structures were deduced from spectroscopic data and on the basis of chemical evidence.
Bravo B
J A
JA
Laboratorio de Productos Naturales, Instituto de Investigaciones Químicas, CP 303, Universidad Mayor de San Andrés, La Paz, Bolivia.
Sauvain
M
M
Gimenez T
A
A
Balanza
E
E
Serani
L
L
Laprévote
O
O
Massiot
G
G
Lavaud
C
C
D000818:Animals; D001419:Bacteria / Q000187:drug effects; D001838:Bolivia; D004187:Disaccharides / Q000737:chemistry / Q000302:isolation & purification*; D004875:Ergosterol / Q000031:analogs & derivatives*; D006027:Glycosides / Q000302:isolation & purification / Q000494:pharmacology; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification*; D007891:Leishmania / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D018515:Plant Leaves / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D019657:Solanaceae / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D014312:Trisaccharides / Q000737:chemistry / Q000302:isolation & purification*; D014344:Trypanocidal Agents / Q000302:isolation & purification* / Q000494:pharmacology*; D014349:Trypanosoma cruzi / Q000187:drug effects; D054358:Withanolides
C433551:3-rhamnopyranosyl(1-4)-glucopyranosyl-12-diacetoxy-20-hydroxywitha-5,24-dienolide; D004187:Disaccharides; D006027:Glycosides; D007783:Lactones; D014312:Trisaccharides; D014344:Trypanocidal Agents; D054358:Withanolides; C433552:withanolide 2; D004875:Ergosterol