Cycloartane-type Triterpene Glycosides from the Rhizomes of Cimicifuga heracleifolia and Their Anticomplementary Activity

Abstract

Seven known triterpene glycosides, 23-O-acetylshengmanol 3-O-α-L-arabinopyranoside (1), 23-O-acetylshengmanol 3-O-β-D-xylopyranoside (2), 24-epi-24-O-acetylhydroshengmanol 3-O-β-D-xylopyranoside (3), cimiaceroside B (4), (23R,24S)-cimigenol 3-O-β-D-xylopyranoside (5), (23R,24R)-25-O-acetylcimigenol 3-O-β-D-xylopyranoside (6) and (23R,24S)-25-O-anhydrocimigenol 3-O-β-D-xylopyranoside (7) were isolated from the rhizomes of Cimicifuga heracleifolia. Their chemical structures were determined on the basis of spectroscopic analyses including 2D NMR. All isolates were investigated for their inhibitory effects on the classical pathway of the complement system. Among them, compound 6 showed strong inhibitory activity with an IC₅₀ value of 7.7 µM while compound 3 was moderately active with an IC₅₀ value of 195.6 µM.

Key words

Cimicifuga heracleifolia - Ranunculaceae - cycloartane glycoside - anticomplement activity

^* These authors contributed equally to this work.

• References

• 1 Kirschfink M. Controlling the complement system in inflammation. Immunopharmacology 1997; 38: 51-62
• 2 Ember JA, Hugli TE. Complement factors and their receptors. Immunopharmacology 1997; 38: 3-15
• 3 Kuby J. Complement in immunology. 2nd. edition. New York: WH Freeman Company; 1994: 336-355
• 4 Shibata M, Yamatake Y, Amagaya Y, Fukushima M. Pharmacological studies on the Chinese crude drug “Shoma” I. Acute toxicity and anti-inflammatory action of Cimicifuga rhizoma, Cimicifuga dahurica Maxim. Yakugaku Zasshi 1994; 95: 539-546
• 5 Takahara M, Kusano A, Shibano M, Kusano G, Koizumi K, Suzuki R, Kim HS, Wataya Y. Antimalarial activity and nucleoside transport inhibitory activity of the triterpenic constituents of Cimicifuga spp. Biol Pharm Bull 1998; 21: 823-828
• 6 Noguchi M, Nagai M, Koeda M, Nakayama S, Sakurai N, Takahira M, Kusano G. Vasoactive effects of cimicifugic acids C and D, and fukinolic acid in Cimicifuga rhizome. Biol Pharm Bull 1998; 21: 1163-1168
• 7 Huh JE, Shin YJ, Baek YH, Lee JD, Choi DY, Park DS. Combined prescription (OAH19 T) of Aralia cordata Thunb and Cimicifuga heracleifolia Komar and its major compounds inhibit matrix proteinases and vascular endothelial growth factor through the regulation of mitogen-activated protein kinase pathway. J Ethnopharmacol 2011; 135: 414-421
• 8 Shao Y, Harris A, Wang M, Zhang H, Cordell G, Bowman M, Lemmo E. Triterpene glycoside from Cimicifuga racemosa. J Nat Prod 2000; 63: 905-910
• 9 Kadota S, Li JX, Namba T. Constituents of Cimicifuga rhizoma. II. Isolation and structures of new cycloartane triterpenoids and related compounds from Cimicifuga foetida . Tetrahedron 1995; 51: 1143-1166
• 10 Kusano A, Shibano M, Kusano G. Studies on the constituents of Cimicifuga species. XXVII. Malonyl cyclolanostanol glycosides from the underground parts of Cimicifuga simplex WORMSK. Chem Pharm Bull 1999; 47: 1175-1179
• 11 Kusano A, Shibano M, Kusano G. Studies on the constituents of Cimicifuga species. XVIII. Four new xylosides from the aerial parts of Cimicifuga simplex WORMSK. Chem Pharm Bull 1996; 44: 167-172
• 12 Kusano A, Shibano M, Kusano G. Studies on the constituents of Cimicifuga species. XVII. Four new glycosides from the aerial parts of Cimicifuga simplex WORMSK. Chem Pharm Bull 1995; 43: 1167-1170
• 13 Li JX, Kadota S, Hattori M, Yoshimachi S, Shiro M, Oogami N, Mizuno H, Namba T. Constituents of Cimicifugae rhizoma. I. Isolation and characterization of ten new cycloartenol triterpens from Cimiciguga heracleifolia KOMAROZ. Chem Pharm Bull 1993; 41: 832-841
• 14 Tian Z, Pan LR, Si JY, Xiao PG. Cytotoxicity of cycloartane triterpenoids from the aerial part of Cimicifuga foetida . Fitoterapia 2006; 77: 39-42
• 15 Min BS, Lee SY, Kim JH, Lee JK, Kim TJ, Kim DH, Kim YH, Joung H, Lee HK, Nakamura N, Miyashiro H, Hattori M. Anticomplement activity of constituents from the stem-bark of Juglans mandshurica. Biol Pharm Bull 2003; 26: 1042-1044
• 16 Qui MH, Kim JH, Lee HK, Min BS. Anticomplement activity of cycloartane glycosides from the rhizome of Cimicifuga foetida . Phytother Res 2006; 20: 945-948
• 17 Min BS, Lee IS, Chang MJ, Yoo JK, Na MK, Hung TM, Thuong PT, Lee J, Kim JH, Kim JC, Woo MH, Choi JS, Lee HK, Bae KH. Anticomplementary activity of triterpenoids from the whole plant of Aceriphyllum rossii against the classical pathway. Planta Med 2008; 74: 726-729
• 18 Kabat EA, Mayer MM. Experimental immunochemistry. 2nd. edition. Springfield, Ill.: Charles C Thomas Publisher; 1961: 133-240
• 19 Klerx JPAMC, Beukelman CJ, Dijk HV, Willers JMN. Microassay for colorimetric estimation of complement activity in guinea pig, human and mouse serum. J Immunol Methods 1983; 63: 215-220
• 20 Yamada H, Ohtani K, Kiyohara H, Cyong JC, Otsuka Y, Ueno Y, Omura S. Purification and chemical properties of anti-complementary polysaccharide from the leaves of Artemisia princeps . Planta Med 1985; 51: 121-125
• 21 Oh SR, Kinjo J, Shii Y, Ikeda T, Nohara T, Ahn KS, Kim JH, Lee HK. Effects of triterpenoids from Pueraria lobata on immunohemolysis: beta-D-glucuronic acid plays an active role in anti-complementary activity in vitro . Planta Med 2000; 66: 506-510