Two new jatropham derivatives and three new steroidal saponins were isolated from the fresh bulbs of Lilium hansonii, along with previously known compounds. The structures of the new compounds were elucidated, on the basis of spectroscopic data and chemical evidence, and by comparing them with those of known compounds, as (−)-5-hydroxy-3-methyl-3-pyrrolin-2-one (jatropham) 5-O-β-d-glucopyranosyl-(1→3)-β-d-glucopyranoside, (2S,4R)-1-(3-methyl-2-oxo-3-pyrrolinyl)-4-methyl-5-oxo-2-pyrrolidinecarboxylic acid, 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-3β,22ξ-diol 3-O-α-l-rhamnopyranosyl-(1→2)-O-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside, (25R)-5α-spirostan-3β,12α-diol 3-O-α-l-rhamnopyranosyl-(1→2)-O-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside and (25R)-spirost-5-en-3β,12α-diol 3-O-α-l-rhamnopyranosyl-(1→2)-O-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside, respectively. The stercostructure of jatropham dimer, the plain structure of which was presented previously, was confirmed by X-ray crystallographic analysis. The inhibitory activity on cyclic AMP phosphodiesterase of the steroidal saponins was evaluated.
steroidal saponins, Liliaceae, bulbs, Lilium hansonii, jatropham derivatives, X-ray analysis, cyclic AMP phosphodiesterase, inhibitory activity
NCBI PubMed ID: 1369389Publication DOI: 10.1016/0031-9422(92)83627-BJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Tokyo College of Pharmacy, Tokyo, Japan, Faculty of Pharmaceutical Sciences, Toho University, Miyama, Funabashi, Chiba, Japan, Central Technical Research Laboratory, Nippon Oil Company Ltd, Yokohama, Kanagawa, Japan
Methods: 13C NMR, 1H NMR, gel filtration, partial acid hydrolysis, X-ray, enzymatic hydrolysis, acid hydrolysis, HPLC, methylation analysis, phosphodiesterase assay
Found