Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius

Two new cycloartane-type glycosides oleifoliosides A ( 1) and B ( 2) were isolated from the lower stem parts of Astragalus oleifolius and evaluated for in vitro trypanocidal, leishmanicidal and antiplasmodial activities as well as their cytotoxic potential on primary mammalian (L6) cells. Their structures were identified as 3- O-[β-xylopyranosyl-(1 → 2)-α-arabinopyranosyl]-6- O-β-xylopyranosyl-3β,6α,16β,24( S),25-pentahydroxycycloartane and 3- O-[β-xylopyranosyl-(1 → 2)-α-arabinopyranosyl]-6- O-β-glucopyranosyl-3β,6α,16β,24( S),25-pentahydroxycycloartane, respectively, by means of spectroscopic methods (IR, 1D and 2D NMR, ESI-MS). Two new cycloartane-type glycosides oleifoliosides A ( 1) and B ( 2) were isolated from the lower stem parts of Astragalus oleifolius. Their structures were identified as 3- O-[β-xylopyranosyl-(1 → 2)-α-arabinopyranosyl]-6- O–β-xylopyranosyl-3β,6α,16β,24( S),25-pentahydroxycycloartane and 3- O-[β-xylopyranosyl-(1 → 2)-α-arabinopyranosyl]-6- O–β-glucopyranosyl-3β,6α,16β,24( S),25-pentahydroxycycloartane, respectively, by means of spectroscopic methods (IR, 1D and 2D NMR, ESI-MS). Three known cycloartane glycosides cyclocanthoside E ( 3), astragaloside II ( 4) and astragaloside IV ( 5) were also isolated and characterized. All five compounds were evaluated for in vitro trypanocidal, leishmanicidal and antiplasmodial activities as well as their cytotoxic potential on primary mammalian (L6) cells. Except for the compound 5, all compounds showed notable growth inhibitory activity against Leishmania donovani with IC 50 values ranging from 13.2 to 21.3 μg/ml. Only weak activity against Trypanosoma brucei rhodesiense was observed with the known compounds astragaloside II ( 4, IC 50 66.6 μg/ml) and cyclocanthoside E ( 3, IC 50 85.2 μg/ml), while all compounds were inactive against Trypanosoma cruzi and Plasmodium falciparum. None of the compounds were toxic to mammalian cells (IC 50’s > 90 μg/ml). This is the first report of leishmanicidal and trypanocidal activity of cycloartane-type triterpene glycosides.