Constituents from Ranunculus sieboldii Miq.

Aim To investigate the chemical composition of Ranunculus sieboldii Miq.. Methods Repeated column chromatography over silica gel, polyamide and RP-18 followed by gel filtration on sephadex LH-20 were used to isolate chemical constituents, and their structures were elucidated by extensive spectroscopic methods (UV, IR, MS, 1H NMR, 13C NMR) including 2D NMR (COSY, HMQC, HMBC, NOESY) techniques and by direct comparing spectral data with those reported in literature. Results Five flavonoid glycosides named apigenin-4′-O-α-L-rhamnopyranoside (1), apigenin-7-O-β-D-glucopyranosyl-4′-O-α-L-rhamnopyranoside (2), apigenin-8-C-α-L-arabinopyranoside (3), apigenin-8-C-β-D-galactopyranoside (4), tricin-7-O-β-D-glucopyranoside (5), together with tricin (6), luteolin (7), scopoletin (8), esculetin (9), scoparone (10), ferulic acid (11), protocatechuic acid (12), and ternatolide (13) were isolated from the 95% ethanolic extract of its whole plant, and their cytotoxic activities were preliminarily tested. Conclusion Compounds 1-12 were obtained from this genus and compound 13 from this species for the first time. Furthermore, compound 1 was for the first time isolated from nature while the 13C NMR data of compounds 2 and 3 are reported for the first time. The bioassay revealed that compound 1 was active against BEL-7407 and A549 cell lines (IC 50 43, 77 μg·mL -1), 8 and 10 showed inhibitory activities on KB cell lines (IC 50 78, 44 μg·mL -1) and HL-60 cell lines (IC 50 85, 85 μg·mL -1), while 7 exerted moderate cytotoxic activities on KB, BEL-7407, A549 and HL-60 cell lines with their IC 50 being 51, 55, 44 and 10 μg·mL -1, respectively.