Triterpene saponins from Chenopodium quinoa Willd.

Twenty triterpene saponins (1–20) have been isolated from different parts of Chenopodium quinoa (flowers, fruits, seed coats, and seeds) and their structures have been elucidated by analysis of chemical and spectroscopic data including 1D- and 2D-NMR. Four compounds (1–4) were identified: 3β-[(O-β-d-glucopyranosyl-(1 → 3)-α-l-arabinopyranosyl)oxy]-23-oxo-olean-12-en-28-oic acid β-d-glucopyranoside (1), 3β-[(O-β-d-glucopyranosyl-(1 → 3)-α-l-arabinopyranosyl)oxy]-27-oxo-olean-12-en-28-oic acid β-d-glucopyranoside (2), 3-O-α-l-arabinopyranosyl serjanic acid 28-O-β-d-glucopyranosyl ester (3), and 3-O-β-d-glucuronopyranosyl serjanic acid 28-O-β-d-glucopyranosyl ester (4). The following known compounds have not previously been reported as saponin constituents from the flowers and the fruits of this plant: two bidesmosides of serjanic acid (5, 6), four bidesmosides of oleanolic acid (7–10), five bidesmosides of phytolaccagenic acid (11–15), four bidesmosides of hederagenin (16–19), and one bidesmoside of 3β,23,30-trihydroxy olean-12-en-28-oic acid (20). The cytotoxicity of these saponins and their aglycones was tested in HeLa cells. Induction of apoptosis in Caco-2 cells by bidesmosidic saponins 1–4 and their aglycones I–III was determined by flow cytometric DNA analysis. The saponins with an aldehyde group were most active. The relationships between structure and cytotoxic activity of saponins and their aglycones are discussed.