A methanol extract of Anemone raddeana Regel (Ranunculaceae) was studied chemically with a view to isolate saponin constituents. As a result of this study, six compounds were purified and identified. These compounds are triterpene saponins composed of either oleanolic acid or 27-hydroxyoleanolic acid as the aglycone. The identification of these compounds was accomplished by a combination of spectroscopic methods, especially 2-D NMR spectroscopy and FAB mass spectrometry. The structures of the isolated compounds were established as 3-0-[α-L- rhamnopyranosyl-( 1 → 2)-α-L-arabinopyranosyl]-27-hydroxyoleanolic acid (Saponin A, novel structure), 3-0-α-L-rhamnopyranosyl-(1 → 2)-α-L- arabinopyranosyl-oleanolic acid (Saponin B, known as β-Hederin), 3-0-{α-L-rhamnopyranosyl- (1 → 2)-[β-D-glucopy...[ Read more ]

A methanol extract of Anemone raddeana Regel (Ranunculaceae) was studied chemically with a view to isolate saponin constituents. As a result of this study, six compounds were purified and identified. These compounds are triterpene saponins composed of either oleanolic acid or 27-hydroxyoleanolic acid as the aglycone. The identification of these compounds was accomplished by a combination of spectroscopic methods, especially 2-D NMR spectroscopy and FAB mass spectrometry. The structures of the isolated compounds were established as 3-0-[α-L- rhamnopyranosyl-( 1 → 2)-α-L-arabinopyranosyl]-27-hydroxyoleanolic acid (Saponin A, novel structure), 3-0-α-L-rhamnopyranosyl-(1 → 2)-α-L- arabinopyranosyl-oleanolic acid (Saponin B, known as β-Hederin), 3-0-{α-L-rhamnopyranosyl- (1 → 2)-[β-D-glucopyranosyl-( 1 → 4)]-α-L-arabinopyranosyl} -27- hydroxyoleanolic acid (Saponin C, novel structure), 3-0-{α-L-rhamnopyranosyl- (1 → 2)-[β-D-glucopyranosyl-( 1 → 4)]-α-L-arabinopyranosyl}-oleanolic acid (Saponin D, known compound), 3-0-[α-L-rhamnopyranosyl-( 1 → 2)-β-D- glucopyranosyl-(1 → 2)-α-L-arabinopyranosyl]-27-hydroxyoleanolic acid 28-0-α-L- rhamnopyranosyl-(l→ 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (Saponin E, known as Raddeanoside 9), 3-0-[α-L-rhamnopyranosyl-(1 → 2)-β-D- glucopyranosyl-(1 → 2)-α-L-arabinopyranosyl]-oleanolic acid 28-0-α-L- rhamnopyranosyl-(1→ 4)-β-D-glucopyranosyl-(1→ 6)-β-D-glucopyranosyl ester (Saponin F, known as Raddeanoside 8).

It is notable that the technique of counter-current chromatography was successfully employed to purify some of these saponins.

The isolated compounds were subjected to human cancer cell culture bioassays to assess their in vitro cytotoxic effects. Saponin D and Saponin E were found to be modestly active in a few cell lines.