Planta Med 2005; 71(7): 673-679
DOI: 10.1055/s-2005-871275
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

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

Jian-Xin Li1 , Toru Hareyama2 , Yasuhiro Tezuka2 , Yuan Zhang1 , Tatsuro Miyahara3 , Shigetoshi Kadota2
  • 1Key Lab of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, P. R. China
  • 2Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
  • 3Faculty of Pharmaceutical Science, Toyama Medical and Pharmaceutical University, Toyama, Japan
Further Information

Publication History

Received: September 30, 2004

Accepted: April 2, 2005

Publication Date:
18 July 2005 (online)

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

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Prof. Jian-Xin Li

Key Lab of Analytical Chemistry for Life Science

School of Chemistry and Chemical Engineering

Nanjing University

Nanjing 210093

P. R. China

Phone: +86-25-8368-6419

Fax: +86-25-8331-7761

Email: lijxnju@nju.edu.cn