Hepatoprotective aliphatic glycosides from three Goodyera species.
Hepatoprotective aliphatic glycosides 3-(S)-3-beta-D-glucopyranosyloxybutanolide (1) and its congener, 3-(S)-3-beta-D-glucopyranosyloxy-4-hydroxybutanoic acid (2) were isolated as major constituents from the whole plants of three Goodyera species, G. schlechtendaliana Reichb. fil., G. matsumurana Schltr. and G. discolor Ker-Gawl. The structures of 1 and 2 have been determined by NMR, MS spectroscopic and chemical means. Compound 1 was converted into its methyl ester form (5) during the purification step, when the lactone ring was cleaved by catalysis of silica gel with the CHCl3-MeOH-H2O as a solvent. On the other hand, 1 was obtained in a high yield by the same purification procedure without MeOH. Based on this fact, a simple and economic method for the purification of 1 was confirmed. Compounds 1 and 2 were found to have a hepatoprotective effect on liver injury induced by carbon tetrachloride in primary cultured rat hepatocytes.
Du
X M
XM
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
Sun
N Y
NY
Chen
Y
Y
Irino
N
N
Shoyama
Y
Y
D000818:Animals; D002478:Cells, Cultured; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008099:Liver / Q000166:cytology / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal / Q000737:chemistry*; D051381:Rats; D016339:Spectrometry, Mass, Fast Atom Bombardment
D006027:Glycosides