Three Previously Undescribed Chlorophenyl Glycosides from the Bulbs of Lilium regale

Three previously undescribed chlorophenyl glycosides, (2,4,6-trichloro-3-hydroxy-5-methoxyphenyl)methyl β-D-glucopyranoside (1), (2,4-dichloro-3,5-dimethoxyphenyl)methyl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside (2) and 4-chloro-3-methoxy-5-methylphenyl 6-O-(6-deoxy-β-L-mannopyranosyl)-β-D-glucopyranoside (3) were obtained from Lilium regale. The absolute configurations of these new finds were elucidated by comprehensive analyses of spectroscopic data combined with acid hydrolysis derivatization. (2,4-dichloro-3,5-dimethoxyphenyl)methyl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside (2) can inhibit the proliferation of lung carcinoma A549 cells with an IC₅₀ value of 29 μΜ.