Cycloartane Glycosides from the Roots of Cimicifuga foetida with Wnt Signaling Pathway Inhibitory Activity

doi:10.1007/s13659-015-0053-7

Natural Products and Bioprospecting ›› 2015, Vol. 5 ›› Issue (2): 61-67.DOI: 10.1007/s13659-015-0053-7

• Original article • Next Articles

Cycloartane Glycosides from the Roots of Cimicifuga foetida with Wnt Signaling Pathway Inhibitory Activity

Di-Fan Zhu, Guo-Lei Zhu, Ling-Mei Kong, Ni-Man Bao, Lin Zhou, Yin Nian, Ming-Hua Qiu

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China

Received:2015-01-14 Revised:2015-01-26 Online:2018-02-11 Published:2015-04-24
Supported by:
This project was supported by Program for National Natural Science Foundation of China(Nos. U1132604 and 81302670), The Major Deployment Program of the CAS(No. KSZDEW-Z-004-01), and Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China(P2008-ZZ05).

Cycloartane Glycosides from the Roots of Cimicifuga foetida with Wnt Signaling Pathway Inhibitory Activity

Di-Fan Zhu, Guo-Lei Zhu, Ling-Mei Kong, Ni-Man Bao, Lin Zhou, Yin Nian, Ming-Hua Qiu

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China

基金资助:
This project was supported by Program for National Natural Science Foundation of China(Nos. U1132604 and 81302670), The Major Deployment Program of the CAS(No. KSZDEW-Z-004-01), and Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China(P2008-ZZ05).

Abstract

Abstract: Four new 9, 19-cycloartane triterpenoids, cimilactone E(1), cimilactone F(2), 20-O-(E)-butenoyl-23-epi-26-deoxyactein(3), and 20, 12β-O-diacetylcimiracemonol-3-O-β-D-xylopyranoside(4), together with four known constituents(5-8) were isolated from the roots of Cimicifuga foetida. The new structures were elucidated by extensive spectroscopic analysis. In addition, compounds 7 and 8 showed significant Wnt signaling pathway inhibitory activity, with IC₅₀ values of 3.33 and 13.34 μM, respectively, using the luciferase reporter gene assay.

Key words: Cimicifuga foetida, 9, 19-Cycloartane triterpenoids, Cimilactone-type, Wnt signal pathway, Luciferase activity

摘要： Four new 9, 19-cycloartane triterpenoids, cimilactone E(1), cimilactone F(2), 20-O-(E)-butenoyl-23-epi-26-deoxyactein(3), and 20, 12β-O-diacetylcimiracemonol-3-O-β-D-xylopyranoside(4), together with four known constituents(5-8) were isolated from the roots of Cimicifuga foetida. The new structures were elucidated by extensive spectroscopic analysis. In addition, compounds 7 and 8 showed significant Wnt signaling pathway inhibitory activity, with IC₅₀ values of 3.33 and 13.34 μM, respectively, using the luciferase reporter gene assay.

关键词: Cimicifuga foetida, 9, 19-Cycloartane triterpenoids, Cimilactone-type, Wnt signal pathway, Luciferase activity

Di-Fan Zhu, Guo-Lei Zhu, Ling-Mei Kong, Ni-Man Bao, Lin Zhou, Yin Nian, Ming-Hua Qiu. Cycloartane Glycosides from the Roots of Cimicifuga foetida with Wnt Signaling Pathway Inhibitory Activity[J]. Natural Products and Bioprospecting, 2015, 5(2): 61-67.

References

1. K.M. Cadigan, R. Nusse, Genes Dev. 11, 3286-3305 (1997)
2. X.Y. Li, Y.Y. Wang, C.G. Yuan, X.J. Hao, Y. Li, Nat. Prod. Bioprospect. 3, 24-28 (2013)
3. A. Gregorieff, H. Clevers, Genes Dev. 2005(19), 877-890 (2005)
4. Pharmacopoeia Commission of the People's Republic of China, The Pharmacopoeia of Chinese People's Republic (The Chemical Industry Publishing House, Beijing, 2010), pp. 68-69
5. Y. Nian, M.X. Zhang, Y. Li, Y.Y. Wang, J.C. Chen, L. Lu, L. Zhou, M.H. Qiu, Phytochemistry 72, 1473-1481 (2011)
6. Y. Nian, H.Y. Wang, J. Su, L. Zhou, M.H. Qiu, Fitoterapia 83, 293-297 (2012)
7. L. Lu, J.C. Chen, Y. Li, C. Qing, Y.Y. Wang, Y. Nian, M.H. Qiu, Chem. Pharm. Bull. 60, 571-577 (2012)
8. D.S. Li, Y. Nian, Y. Sun, M.H. Qiu, Helv. Chim. Acta 94, 632-638 (2011)
9. L.R. Sun, J. Yan, L. Lu, S.J. Pei, Z.R. Li, L. Zhou, X.M. Zhang, M.H. Qiu, Helv. Chim. Acta 90, 1313-1318 (2007)
10. L. Lu, J.C. Chen, H.J. Song, Y. Li, Y. Nian, M.H. Qiu, Chem. Pharm. Bull. 58, 729-733 (2010)
11. D.F. Zhu, Y. Nian, H.Y. Wang, Z.R. Zhang, Y.B. Song, R.T. Li, M.H. Qiu, J. Nat. Med. 12, 0294-0296 (2014)
12. H.Y. Wang, Y. Nian, C.Y. Ma, J.Q. Liu, Y.B. Song, L. Zhou, M.H. Qiu, Chin. J. Chem. 30, 1265-1268 (2012)
13. Y. Nian, H.Y. Wang, L. Zhou, J. Su, Y. Li, M.H. Qiu, Planta Med. 79, 60-69 (2013)
14. Y. Nian, H. Zhu, W.R. Tang, Y. Luo, J. Du, M.H. Qiu, J. Nat. Prod. 76, 896-902 (2013)
15. Y. Liu, D. Chen, J. Si, G. Tu, D. An, J. Nat. Prod. 65, 1486-1488 (2002)
16. Y. Nian, H.Y. Wang, L. Zhou, J. Su, Y. Li, M.H. Qiu, Planta Med. 78, 1-10 (2012)
17. L.R. Sun, C. Qing, Y.L. Zhang, S.Y. Jia, Z.R. Li, S.J. Pei, M.H. Qiu, L.G. Michael, X.Q. Samuel, Beilstein J. Organ. 3(3) (2007)
18. Y.S. Fan, W. Jia, A.H. Zhao, J. Tang, H.Q. Duan, Chin. Chem. Lett. 17, 1477-1480 (2006)
19. S.N. Chen, W. Li, D.S. Fabricant, B.D. Santarsiero, A. Mesecar, J.F. Fitzloff, H.H.S. Fong, N.R. Farnsworth, J. Nat. Prod. 65, 601-605 (2002)
20. Z. Tian, R.L. Pan, J.Y. Si, P.G. Xiao, Fitoterapia 77, 39-42 (2006)
21. J.Y. Chen, P.L. Li, X.L. Tang, X.L. Tang, S.J. Wang, Y.T. Jiang, L. Shen, B.M. Xu, Y.L. Shao, G.Q. Li, J. Nat. Prod. 77, 1997-2005 (2014)
22. Y. Shao, A. Harris, M. Wang, H. Zhang, A.C. Geoffrey, M. Bowman, E. Lemmo, J. Nat. Prod. 63, 905-910 (2000)

[1]	Jing Lu, Xing-Rong Peng, Da-Shan Li, Qiang-Qiang Shi, Ming-Hua Qiu. Cytotoxic Cycloartane Triterpenoid Saponins from the Rhizomes of Cimicifuga foetida [J]. Natural Products and Bioprospecting, 2019, 9(4): 303-310.
[2]	Guo-Lei Zhu, Di-Fan Zhu, Luo-Sheng Wan, Xing-Rong Peng, Ni-Man Bao, Zhi-Run Zhang, Lin Zhou, Ming-Hua Qiu. Six New 9,19-Cycloartane Triterpenoids from Cimicifuga foetida L [J]. Natural Products and Bioprospecting, 2016, 6(4): 187-193.

Cycloartane Glycosides from the Roots of Cimicifuga foetida with Wnt Signaling Pathway Inhibitory Activity

Cycloartane Glycosides from the Roots of Cimicifuga foetida with Wnt Signaling Pathway Inhibitory Activity

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 2

Recommended Articles

Metrics

Comments