Abstract
Three new triterpenoids, 11α-hydroxy-lup-20(29)-ene-3β-palmitate (1), 28-hydroxy-20-oxo-30-norlupane-3β-palmitate (2), and 1β,11α,28-tyrihydroxy oleana-9(11),12-dien-3β-palmitate (3), together with three known compounds were isolated from the 95 % EtOH extract of Saussurea phyllocephala. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR (COSY, HMQC, HMBC and NOESY) analyses. All the triterpenoids were in vitro evaluated for their cytotoxic activities. Compound 1–3 exhibited the significant cytotoxic activities with low IC50 values (IC50 < 4.0 μM) against six tumor cell lines (MCF-7, HeLa, HepG2, SGC-7901, NCI-H460 and BGC-823).
Similar content being viewed by others
References
Chanita, P., and T. Pakakrong. 2005. Lupane-triterpene esters from the leaves of Ceriops decandra (Griff.) Ding Hou. Australian Journal of Chemistry 58: 615–618.
Chaturvedula, V.S., B.N. Zhou, Z. Gao, S.J. Thomas, S.M. Hecht, and D.G. Kingston. 2004. New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase beta. Bioorganic and Medicinal Chemistry 12: 6271–6275.
Chhabra, B.R., S. Gupta, M. Jain, and P.S. Kalsi. 1998. Sesquiterpene lactones from Saussurea lappa. Phytochemistry 49: 801–804.
Chen, J.J., H.C. Hung, P.J. Sung, I.S. Chen, and W.L. Kuo. 2011. Aporphine alkaloids and cytotoxic lignans from the roots of Illigera luzonensis. Phytochemistry 72: 523–532.
Dai, J., C.Y. Zhao, Q. Zhang, Z.L. Liu, R.L. Zheng, and L. Yang. 2001. Taraxastane-type triterpenoids from Saussurea petrovii. Phytochemistry 58: 1107–1111.
De la Torre, M.C., M. Bruno, F. Piozzi, G. Savona, B. Rodriguez, and N. Apostolides Arnold. 1990. Terpenoids from Salvia willeana and S. virgata. Phytochemistry 29: 668–670.
Duan, H.Q., Y. Takaishi, H. Momota, Y. Ohmoto, and T. Taki. 2002. Immunosuppressive constituents from Saussurea medusa. Phytochemistry 59: 85–90.
Faizi, S., and Naz Aneela. 2004. Palmitoleate (_(9Z)-hexadeca-9-enoate) esters of oleanane triterpenoids from the golden flowers of Tagetes erecta: isolation and autoxidation products. Helvetica Chimica Acta 87: 46–56.
Gao, M., B.Z. Song, and C.Z. Liu. 2006. Dynamic microwave-assisted extraction of flavonoids from Saussurea medusa Maxim cultured cells. Biochemical Engineering Journal 32: 79–83.
Li, X.H., J.T. Feng, and Y.P. Shi. 2008. Triterpenoids from Saussurea ussuriensis. Canadian Journal of Chemistry 86: 281–284.
Li, X.W., Z.T. Guo, Y. Zhao, Z. Zhao, and J.F. Hu. 2010. Chemical constituents from Saussurea cordifolia. Phytochemistry 71: 682–687.
Reyes, C.P., M.J. Nunez, I.A. Jimenez, J. Busserolles, M.J. Alcaraz, and I.L. Bazzocchi. 2006. Activity of lupane triterpenoids from Maytenus species as inhibitors of nitric oxide and prostaglandin E2. Bioorganic and Medicinal Chemistry 14: 1573–1579.
Robinson, A., T.V. Kumar, E. Sreedhar, V.G. Naidu, S.R. Krishna, K.S. Babu, P.V. Srinivas, and J.M. Rao. 2008. A new sesquiterpene lactone from the roots of Saussurea lappa: structure–anticancer activity study. Bioorganic & Medicinal Chemistry Letters 18: 4015–4017.
The Editorial Board of Chinese Materia Medica. 1999. Chinese materia medica, vol. 7. Shanghai: Shanghai Science and Technology Publish House.
Wang, H.B., J.P. Zuo, and G.W. Qin. 2010. One new sesquiterpene from Saussurea laniceps. Fitoterapia 81: 937–939.
Zhou, J., C.J. Li, J.Z. Yang, J. Ma, Y. Li, X.Q. Bao, X.G. Chen, D. Zhang, and D.M. Zhang. 2014. Lupane triterpenoids from the Stems of Euonymus carnosus. Journal of Natural Products 77: 276–284.
Acknowledgments
The above research was made possible by the grant from the Scientific Planning Project of the Applied Basic Research of Yunnan Province (S2012FZ0005), the Key Projects of Scientific Research Foundation of the Department of Education of Yunnan Province (2013Z095), and the Developing Key Subject of Ecology of Qujing Normal University.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Jiang Hu and Yan Song have contributed equally to this work.
Rights and permissions
About this article
Cite this article
Hu, J., Song, Y., Yang, B. et al. Cytotoxic triterpenoids from Saussurea phyllocephala . Arch. Pharm. Res. 37, 1515–1521 (2014). https://doi.org/10.1007/s12272-014-0428-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-014-0428-z