Total of eighteen steroidal saponins were isolated from the rhizomes of Hosta sieboldii, one of which appeared to be the first isolation from a plant source and six to be new compounds. The structures of the new saponins were determined by spectral data and a few chemical transformations to be (25R)-2 alpha,3 beta-dihydroxy-5 alpha-spirostan-12-one (manogenin) 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(l-->4)-beta-D-galacltopyranoside}, (25R)-2 alpha,3 beta-dihydroxy-5 alpha-spirost-9-en-12-one (9,11-dehydromanogenin) 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside}, 9,11-dehydromanogenin 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-[O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside}, (25R)-2 alpha,3 beta-dihydroxy-26-beta-D-glucopyranosyloxy-22-methoxy-5 alpha-furostan-12-one 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside}, (25R)-2 alpha,3 beta-dihydroxy-26-beta-D-glucopyranosyloxy-22-methoxy-5 alpha-furost-9-en-12-one 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} and (25R)-5 alpha-spirostan-2 alpha,3 beta,12 beta-triol 3-O-(O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranoside), respectively. Cytostatic activity of the isolated saponins on leukaemia HL-60 cells was examined.
steroidal saponins, Liliaceae, cytostatic activity, furostanol saponins, spirostanol saponins, rhizomes, HL-60 cells, Hosta sieboldii
NCBI PubMed ID: 9720315Publication DOI: 10.1016/s0031-9422(98)00157-5Journal NLM ID: 0151434Publisher: Elsevier
Institutions: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Tokyo, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, enzymatic hydrolysis, acid hydrolysis, UV, optical rotation measurement, CC, COSY, MTT, extraciton
Found