Three new furostanol saponins from the bulbs of Ipheion uniflorum.
Phytochemical screening of the bulbs of Ipheion uniflorum (Liliaceae) has led to the isolation of three new furostanol saponins (2-4) along with a known phytoecdysteroid, ecdysterone (1). The structures of the new compounds were determined by two-dimensional NMR techniques, 1H-1H correlation spectroscopy (COSY), homonuclear Hartmann-Hahn (HOHAHA), phase-sensitive nuclear Overhauser effect spectroscopy (NOESY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple-bond correlation (HMBC) spectra, and hydrolysis to be 3 beta-hydroxy-22 alpha-methoxy-26-O-beta-D- glucopyranosyloxy-5 alpha-furost-25(27)-en-2-one 3-O-[O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-alpha-L-arabinopyranosyl+ ++- (1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)]- beta-D-galactopyranoside) (2) and its 25(27)-dihydro derivatives (3: 25S; 4: 25R). The inhibitory activity exhibited by compounds 1-4 and the corresponding spirostanol saponins (2a and 3a) of 2 and 3 on cAMP phosphodiesterase was assayed as a primary screening test to identify new compounds with medicinal potential.
Nakamura
O
O
Tokyo College of Pharmacy, Japan.
Mimaki
Y
Y
Sashida
Y
Y
Nikaido
T
T
Ohmoto
T
T
D015105:3',5'-Cyclic-AMP Phosphodiesterases / Q000037:antagonists & inhibitors*; D000818:Animals; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D002852:Chromatography, Ion Exchange; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D010946:Plants, Medicinal; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013057:Spectrum Analysis; D013256:Steroids
D012503:Saponins; D013256:Steroids; C088992:3-hydroxy-22-methoxy-26-glucopyranosyloxy-furostan-2-one-3-O-(O-rhamnopyranosyl-(1-2)-O-(O-arabinopyranosyl-(1-2)-O-(xylopyranosyl-(1-3))-glucopyranosyl-(1-4))galactopyranoside); C088991:3-hydroxy-22-methoxy-26-O-glucopyranosyloxy-furost-25(27)-en-2-one-3-O-(O-rhamnopyranosyl-(1-2)-O-(O-arabinopyranosyl-(1-2)-O-(xylopyranosyl-(1-3))-glucopyranosyl-(1-4))galactopyranoside); D015105:3',5'-Cyclic-AMP Phosphodiesterases