A pyrroline glucoside ester and steroidal saponins from Lilium martagon

A new phenylpropanoid ester of a pyrroline derivative and two new steroidal saponins were isolated from the fresh bulbs of Lilium martagon, along with several previously known compounds. The structures of the new compounds were determined by spectroscopic data, hydrolysis, and by comparison with spectral data of known compounds to be (-)-5-hydroxy-3-methyl-3-pyrrolin-2-one 5-O-(6-O-p-coumaroyl-beta-D-glucopyranoside), (25S)-spirost-5-ene-3 beta,17 alpha, 27-triol 3-O-(O-beta-D-glucopyranosyl-(1 --> 2)-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucopyranoside) and (25S)-5 alpha-spirostane-3 beta,17 alpha,27-triol 3-O-{O-beta-D-glucopyranosyl-(1 --> 2)-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucopyranoside}, respectively, Lilium martagon crosses well with L. hansonii to produce a valuable garden hybrid lily. In this study, the secondary metabolites of L. martagon were revealed to be closely related to those of L. hansonii, giving a good example of the correlation between the secondary metabolites and cross-compatibility.