Natural Products and Bioprospecting    2019, Vol. 9 Issue (4) : 303-310     DOI: 10.1007/s13659-019-0214-1
ORIGINAL ARTICLES |
Cytotoxic Cycloartane Triterpenoid Saponins from the Rhizomes of Cimicifuga foetida
Jing Lu1,2, Xing-Rong Peng1, Da-Shan Li1, Qiang-Qiang Shi1,2, Ming-Hua Qiu1,2,3
1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences (CAS), Kunming 650204, People's Republic of China;
2 University of Chinese Academy of Sciences, Beijing 100049, China;
3 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, 132 LanHei Road, Kunming 650201, Yunnan, People's Republic of China
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Abstract  To enrich the bioactive cycloartane triterpenoid glycoside named actein and find out more cytotoxic cycloartane triterpenes, a phytochemical study of Cimicifuga foetida was conducted. 113 g (0.17%) actein was purified by recrystallization while eight cycloartane-type triterpenes (1-8) were isolated from the mother liquid. The chemical structures of new compounds (1-4) were elucidated by 1D and 2D NMR and HRESIMS spectroscopic analyses. Moreover, new compounds showed moderate and broad-spectrum cytotoxicity against 5 human cancer cell lines with IC50 values ranging from 4.02 to 15.80 μM.
Keywords Cimicifuga foetida      Cycloartane triterpenoid saponins      Cytotoxic activity     
Fund:This research work was financial supported by Programs of National Natural Science Foundation of China (Nos. 81803396 and U1132604), Autonomous Deployment Project (KIB2017010) of Kunming Institute of Botany, CAS, as well as The Major Program of CAS (No. KSZD-EW-Z-004-01).
Corresponding Authors: Ming-Hua Qiu     E-mail: mhchiu@mail.kib.ac.cn
Issue Date: 09 August 2019
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Jing Lu,Xing-Rong Peng,Da-Shan Li, et al. Cytotoxic Cycloartane Triterpenoid Saponins from the Rhizomes of Cimicifuga foetida[J]. Natural Products and Bioprospecting, 2019, 9(4): 303-310.
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http://npb.kib.ac.cn/EN/10.1007/s13659-019-0214-1     OR     http://npb.kib.ac.cn/EN/Y2019/V9/I4/303
1. Y.Q. Guo, T. Yin, X.M. Wang, F. Zhang, G.X. Pan, H. Lv, X.R. Wang, J.O. Orgaha, Y. Zhua, H.H. Wu, J. Ethnopharmacol. 209, 264-282 (2017)
2. Pharmacopoeia Commission of the People's Republic of China, The Pharmacopoeia of Chinese People's Republic (The Chemical Industry Publishing House, Beijing, 2015), pp. 68-69
3. L.S. Einbond, T. Su, H.A. Wu, R. Friedman, X.M. Wang, A. Ramirez, F. Kronenberg, I.B. Weinstein, Int. J. Cancer 121, 2073-2083 (2007)
4. G.L. Yue, S.D. Xie, K.M. Lee, H.F. Kwok, S. Gao, Y. Nian, X.X. Wu, C.K. Wong, M.H. Qiu, B.S. Lau, Sci. Rep. 6, 35263 (2016)
5. X.X. Wu, G.L. Yue, J.R. Dong, W.K. Lam, C.K. Wong, M.H. Qiu, C.B. Lau, Front Pharmacol. 9, 1466 (2018)
6. R. Xi, L.J. Wang, Biomed. Pharmacother. 88, 242-251 (2017)
7. L.Q. Yuan, Y.M. Chen, C. Sun, Z.Y. Wang, D.L. Wang, Q. Lan, Cancer Biomark. 18, 329-338 (2017)
8. Z. Tian, J. Si, Q. Chang, L. Zhou, S. Chen, P. Xiao, E. Wu, BMC Cancer 7, 237 (2007)
9. Y.S. Fan, Z. Yao, J. Teng, Q. Pan, F.G. Zhang, H.Q. Duan, Chin. Tradit. Herb. Drugs 38, 167-170 (2007)
10. H.J. Chen, J. Liu, Biomed. Pharmacother. 97, 1386-1396 (2018)
11. Z.C. Yang, J. Ma, Biochem. Biophys. Res. Commun. 4, 497 (2016)
12. M.S. Wang, L. Chen, Y.Q. Xiong, J. Xu, J.P. Wang, Z.L. Meng, Int. J. Nanomed. 12, 7627-7651 (2017)
13. Y. Nian, H.Y. Wang, L. Zhou, J. Su, Y. Li, M.H. Qiu, Planta Med. 79, 60-69 (2013)
14. N.Q. Zhu, Y. Jiang, M.F. Wang, C.T. Ho, J. Nat. Prod. 64, 627-629 (2001)
15. G.L. Zhu, Y. Nian, D.F. Zhu, L.S. Wan, N.M. Bao, W.H. Wang, L. Zhou, M.H. Qiu, Phytochem. Lett. 18, 105-112 (2016)
16. S.N. Chen, W.K. Li, D.S. Fabricant, B.D. Santarsiero, A. Mesecar, J.F. Fitzloff, H.S. Fong, N.R. Farnsworth, J. Nat. Prod. 65, 601-605 (2002)
17. S.N. Chen, D.S. Fabricant, Z.Z. Lu, H.S. Fong, N.R. Farnsworth, J. Nat. Prod. 65, 1391-1397 (2002)
18. A. Kusano, M. Shibano, S. Kitagawa, G. Kusano, S. Nozoe, S. Fushiya, J. Nat. Prod. 42, 1940-1943 (1994)
19. H.X. Kuang, Y. Su, B.Y. Yang, Y.G. Xia, Q.H. Wang, Z.B. Wang, Z.F. Yu, Molecules 16, 4348-4357 (2011)
20. G.L. Zhu, D.F. Zhu, L.S. Wan, X.R. Peng, N.M. Bao, Z.R. Zhang, L. Zhou, M.H. Qiu, Nat. Prod. Bioprospect. 4, 187-193 (2016)
21. D.F. Zhu, G.L. Zhu, L.M. Kong, N.M. Bao, L. Zhou, Y. Nian, M.H. Qiu, Nat. Prod. Bioprospect. 5, 61-67 (2015)
22. Y. Nian, X.M. Zhang, Y. Li, Y.Y. Wang, J.C. Chen, L. Lu, L. Zhou, M.H. Qiu, Phytochemistry 72, 1473-1481 (2011)
23. N. Zhu, Y. Jiang, M.F. Wang, C.T. Ho, J. Nat. Prod. 64, 624 (2001)
24. L.J. Reed, H.A. Muench, Am. J. Epidemiol. 27, 493-497 (1938)
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