Five New Oleanolic Acid Glycosides from Achyranthes bidentata with Inhibitory Activity on Osteoclast Formation

Abstract

Bioassay-directed fractionation of a butanol-soluble fraction of methanol extract of the root of Achyranthes bidentata resulted in the isolation of 5 new oleanolic acid glycosides 1 - 5, namely, 18-(β-D-glucopyranosyloxy)-28-oxoolean-12-en-3β-yl 3-O-(β-D-glucopyranosyl)-β-D-glucopyranosiduronic acid methyl ester (1), achyranthoside C dimethyl ester (2), achyranthoside C butyl dimethyl ester (3), achyranthoside E dimethyl ester (4), and achyranthoside E butyl methyl ester (5), together with 10 known compounds. Their structures were established on the basis of spectroscopic interpretation and chemical methods. All the oleanolic acid glycosides inhibited the formation of osteoclast-like multinucleated cells (OCLs) induced by 1α,25(OH)₂D₃ in a co-culture assay system.

Abbreviations

OA:oleanolic acid (OA)

GlcA:glucuronic acid

CC:column chromatography

1α,25(OH)₂D₃:1α,25-dihydroxyvitamin D₃

FBS:fetal bovine serum

α-MEM:minimum essential medium

PTH:parathyroid hormone

OCL:osteoclast-like multinucleated cell

Achyranthes bidentata - Amaranthaceae - oleanolic acid glycosides - osteoclast formation - inhibitory activity

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