Triterpenoid saponins from the buds of Lonicera similis

Abstract

Four new lupane triterpenoid saponins, along with one known lupane and eight hederagenin saponins, were isolated from the EtOH extract of the buds of Lonicera similis Hemsl. The structures of the new compounds were established as 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl 23-hydroxybetulinic acid 28-O-β-D-glucopyranosyl ester (lonisimilioside A, 1), 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl 23-hydroxybetulinic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (lonisimilioside B, 2), 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl betulinic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (lonisimilioside C, 3) and 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl betulinic acid 28-O-β-D-glucopyranosyl ester (lonisimilioside D, 4), respectively. The cytotoxic activities of the isolates against human cancer cell lines HepG2, MCF-7 and A-549 were evaluated. Only the monodesmosidic saponin with a free carboxyl group at C-28 (12) exhibited significant cytotoxicities against HepG2, MCF-7 and A-549 cell lines with the IC₅₀ values of 8.98 ± 0.19, 12.48 ± 0.45 and 11.62 ± 0.54 μM, respectively. Furthermore, Hoechst fluorescence 33342 staining was used to demonstrate that 12 could induce HepG2 and A-549 cells apoptosis significantly.

Keywords:

• Lonicera similis
• triterpenoid saponins
• lupane
• oleanane
• cytotoxic activity
• apoptosis