Cytotoxic triterpenoids from Lysimachia parvifolia

•Eight triterpenoids were isolated from Lysimachia parvifolia for the first time.•Four compounds showed significant cytotoxicities on tested human cancer cell lines.•Cytotoxic activity is directly proportional to the number of sugars.•Hydroxylation of C-16 and hydroxymethylation of Me-23 could improve the cytotoxicity.

Five new oleanane-type triterpenoids, including two aglycones, 13β-28-epoxy-3β,22α,23-trihydroxyolean-16-one (1) and 13β-28-epoxy-22α,23-dihydroxyolean-3,16-dione (2), and three glycosides, anagalligenone-3-O-α-l-arabinopyranoside (3), anagalligenone-3-O-[β-d-glucopyranosyl(1 → 4)-α-l-arabinopyranoside] (4) and anagalligenone-3-O-[β-d-xylopyranosyl(1 → 2)-β-d-glucopyranosyl(1 → 4)-α-l-arabinopyranoside] (5), were isolated from the aerial parts of Lysimachia parvifolia, together with three known oleanane-type triterpenoid glycosides (6–8). The structures of the new compounds were subsequently elucidated by spectroscopic analysis and their cytotoxicities evaluated against six human cancer cell lines. Compounds 5–8 exhibited significant cytotoxicities against all the cell lines tested, with IC50 values lower than 10 μM. The possible mechanism of action of compound 6 was also studied.

Graphical abstractFive new oleanane-type triterpenoids, together with three known oleanane-type triterpenoid glycosides were isolated from “Lysimachia parvifolia” for the first time and some of them showed significant cytotoxicities.Figure optionsDownload full-size imageDownload as PowerPoint slide