Abstract
Two new cyclolanostane diglycosides, cimifoetiside A (1) and cimifoetiside B (2), were isolated from an 80% ethanolic extract of the aerial part of Cimicifuga foetida L. (Ranuculaceae). Using spectral data and chemical analysis, the structures of 1 and 2 were identified as (23R, 24S) cimicigenol 3-O-β-D-glucopyranosyl-(1″→3′)-β-D-xylopyranoside and (23R, 24S) cimicigenol 3-O-β-D-glucopyranosyl-(1″→2′)-β-D-xylopyranoside, respectively. The in vitro immunosuppressive effects of the two new compounds 1 and 2, as well as four other known cyclolanostane saponins 3–6 on T cells were evaluated. All the agents tested effectively inhibited the proliferation of murine splenocytes induced by Concanavalin A (ConA), with IC50 values ranging from 12.7 nM to 33.3 nM.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Cao, P., Pu, X. F., Peng, S. L., Zhang, X. R., and Ding, L. S., Chemical constituents from Cimicifuga foetida. J. Asian Nat. Prod. Res., 7, 145–149 (2005).
Chinese Pharmacopoeial Commission, The Pharmacopoeia of Chinese People’s Republic: Rhizoma Cimicifugae. People’s Health Publishing House & Chemical Industry Publishing House, Beijing, pp. 50 (2005).
Kusano, A., Shibano, M., Kusano, G., and Mivase, T., Studies on the constituents of Cimicifuga Species. XIX. Eight new glycosides from Cimicifuga simplex Wormsk. Chem. Pharm. Bull., 44, 2078–2085 (1996).
Li, C. J., Li, Y. H., Xiao, P. G., Mabry, T. J., Watson, W. H., and Krawiec, M., A unusual cycloartane triterpenoid from Cimicifuga foetida. Phytochemistry. 42, 489–494 (1996).
Pan, R. L., Chen, D. H., Si, J. Y., Zhao, X. H., and Shen, L. G., Studies on glycosides of the aerial part of Cimicifuga foetida. Acta. Pharm. Sin., 37, 117–120 (2002).
Pan, R. L., Chen, D. H., Si, J. Y., Zhao, X. H., and Shen, L. G., Studies on constituents of the aerial parts of Cimicifuga foetida. Acta. Pharm. Sin., 38, 272–276 (2003).
Pan, R. L., Chen, D. H., Si, J. Y., Zhao, X. H., and Shen, L. G., Two new cyclolanostanol glycosides from the aerial parts of Cimicifuga foetida. J. Asian Nat. Prod. Res., 6, 63–67 (2004).
Qiu, M., Kim, J. H., Lee, H. K., and Min, B. S., Anticomplement activity of cycloartane glycosides from the rhizome of Cimicifuga foetida. Phytother. Res., 20, 945–948. (2006).
Sun, L. R., Qing, C., Zhang, Y. L., Jia, S. Y., Li, Z. R., Pei, S. J., Qiu, M. H., Gross, M. L., and Qiu, S. X., Cimicifoetisides A and B, two cytotoxic cycloartane triterpenoid glycosides from the rhizomes of Cimicifuga foetida, inhibit proliferation of cancer cells. Beilstein J. Org. Chem. 3, 3–8 (2007).
Tang, L., Jang, Y., Chang, H. T., Zhao, M. B., Tu, P. F., Cui, J. R., and Wang, R. Q., Triterpene saponins from the leaves of Ilex kudingcha. J. Nat. Prod., 68, 1169–1174 (2005).
Tian, Z., Pan, R. L., Si, j. Y., and Xiao, P. G., Cytotoxicity of cycloartane triterpenoids from aerial part of Cimicifuga foetida. Fitoterapia, 77, 39–42 (2006).
Tian, Z., Pan, R. L., Chang, Q., Xiao, and P. G., Wu, E., Cimicifuga foetida extract inhibits proliferation of hepatocellular cells via induction of cell cycle arrest and apoptosis. J. Ethnopharmacol., 114, 227–233 (2007).
Wagner, U., Burkhardt, E., and Failing, K., Evaluation of canine lymphocyte proliferation: comparison of three different colorimetric methods with the H-thymidin incorporation assay. Vet. Immunol. Immunophathol., 70, 151–159. (1999).
Zhang, Y. N., Xiang, G. Z., Zheng, Z. P., Hu, X. D., Zuo, J. P., and Hu, L. H., Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr. Bioorgan. Med. Chem. 15, 988–996 (2007).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Pan, RL., Chen, DH., Si, JY. et al. Immunosuppressive effects of new cyclolanostane triterpene diglycosides from the aerial part of Cimicifuga foetida . Arch. Pharm. Res. 32, 185–190 (2009). https://doi.org/10.1007/s12272-009-1133-1
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-009-1133-1