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

Key words

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

References

• 1 Center J R, Nguyen T V, Schneider D, Sambrook P N, Eisman J A. Mortality after all major types of osteoporotic fracture in men and women: an observational study.  Lancet. 1999;  353 878-82
• 2 Li J X, Kadota S, Li H Y, Miyahara T, Namba T. The effect of traditional medicines on bone resorption induced by parathyroid hormone (PTH) in tissue culture: a detailed study on cimicifugae rhizoma.  J Trad Med. 1996;  13 50-8
• 3 Pharmacopoeia Commission of People's Republic of C hina. Pharmacopoeia of People's Republic of China. Benjing China; Chemical Industry Press 2000: p 54
• 4 Li Z K, Li D D. The immunomodulatory effect of Achyranthes bidentata polysaccharides.  Yao Xue Xue Bao. 1997;  32 881-7
• 5 Deng H B, Cui D P, Jiang J M, Feng Y C, Cai N S, Li D D. Inhibiting effects of Achyranthes bidentata polysaccharide and Lycium barbarum polysaccharide on non-enzyme glycation in d-galactose induced mouse aging model.  Biomed Environ Sci. 2003;  6 267-75
• 6 Meng D L, Li X. The research development of Achyranthes bidentata Bl.  Chinese J Med Chem. 2001;  11 120-4
• 7 Mitaine-Offer A C, Marouf A, Pizza C, Khanh T C, Chauffert B, Lacaille-Dubois M A. Bidentatoside I, a new triterpene saponin from Achyranthes bidentata .  J Nat Prod. 2001;  64 243-5
• 8 Zhang D, Zhang K, Yao Y L, Xia X H, Chen H Y. Multilayer assembly of Prussian blue nanoclusters and enzyme-immobilized poly(toluidine blue) film and its application in glucose biosensor construction.  Langmuir. 2004;  20 7303-7
• 9 Takahashi N, Akatsu T, Udagawa N, Sasaki T, Yamaguchi A, Moseley J M. et al . Osteoblastic cells are involved in osteoclast formation.  Endocrinology,. 1988;  123 2600-2
• 10 Notoya K, Yoshida K, Taketomi S, Yamazaki I, Kumegawa M. Inhibitory effect of ipriflavone on osteoclast-mediated bone resorption and new osteoclast formation in long-term cultures of mouse unfractionated bone cells.  Calcif Tissue Int.. 1993;  53 206-9
• 11 Nie R L, Morita T, Kasai R, Zhou J, Wu C Y, Tanaka O. Saponins from Chinese medicinal plants (I), isolation and structures of hemslosides.  Planta Med. 1984;  50 322-7
• 12 Romussi G, Bignardi G, Falsone G, Wendisch D. Constituents of Cupuliferae 10, triterpene saponins from Fagus silvatica L.  Arch Pharm (Weinheim). 1987;  320 153-8
• 13 Ida Y, Satoh Y, Katsumata M, Nagasao M, Shoji J. Achyranthosides C and D, novel glucuronide saponins from Achyranthes fauriei root.  Chem Pharm Bull. 1995;  43 896-8
• 14 Yoshikawa M, Murakami T, Inazuki M, Hirano K, Yamahara J, Matsuda H. Absolute stereostructure of betavulgarosides III and IV, inhibitor of glucose absorption, from the roots of Beta valgaris L (sugar beet).  Chem Pharm Bull. 1997;  45 561-3
• 15 Murakami T, Matsuda H, Inazuki M, Hirano K, Yoshikawa M. Medicinal foodstuffs XVI. Sugar beet (3): Absolute stereostructure of betavulgarosides I and II, hypoglycemic saponins having a unique substituent, from the roots of Beta valgaris L.  Chem Pharm Bull. 1999;  47 1717-24
• 16 Ida Y, Satoh Y, Katsumata M, Nagasao M, Hirai Y, Kajimoto T. et al . Two novel oleanolic acid saponins having a sialyl Lewis X mimetic structure from Achyranthes fauriei root.  Bioorg Med Chem Lett. 1998;  8 2555-8
• 17 Yoshikawa M, Murakami T, Hirano K, Matsuda H, Ohtani K, Yamasaki K. et al . Absolute stereostructures of spinacosides C and D with a novel acetal type substituent from Spinacia oleracea (spinach) and Basella rubra (Indian spinach).  Heterocycles. 1998;  49 93-6
• 18 Hu M, Xiao P G, Ogawa K, Sashida Y. Triterpenoid glucuronide saponins from root bark of Aralia armata .  Phytochemistry. 1995;  39 179-84
• 19 Kondo N, Marumoto Y, Shoji J. Studies on the constituents of Panacis japonici rhizoma IV, the structure of chikusetsusaponin V.  Chem Pharm Bull. 1971;  19 1103-7
• 20 Iwamoto M. Okabe H, Yamaguchi T. Studies on the constituents of Momordica cochinchinese Spreng II, isolation and characterization of the root saponins, momordins I, II and III.  Chem Pharm Bull. 1985;  33 1-7
• 21 Ida Y, Satoh Y, Katho M, Katsumata M, Nagasao M, Yamaguchi K. et al . Achyranthosides A and B, novel cytotoxic saponins from Achyranthes fauriei root.  Tetrahedron Lett.. 1994;  35 6887-90