Diterpenoids from the Roots of Salvia yunnanensis

doi:10.1007/s13659-015-0080-4

Natural Products and Bioprospecting ›› 2015, Vol. 5 ›› Issue (6): 307-312.DOI: 10.1007/s13659-015-0080-4

• Original article • Previous Articles

Diterpenoids from the Roots of Salvia yunnanensis

Fan Xia¹, Chun-Yan Wu², Xing-Wei Yang², Xian Li¹, Gang Xu²

1. School of Pharmaceutical Science and Yunnan Key Laboratory of Pharmacology of Natural Products, Kunming Medical University, Kunming 650500, People's Republic of China;
2. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China

Received:2015-11-04 Revised:2015-11-04 Online:2018-02-11 Published:2015-12-24
Supported by:
The work was financially supported by the National Natural Sciences Foundation of China(81373291), the National Science and Technology Support Program of China(2013BAI11B02), and the foundation from Chinese Academy of Sciences to Dr G. Xu.

Diterpenoids from the Roots of Salvia yunnanensis

Fan Xia¹, Chun-Yan Wu², Xing-Wei Yang², Xian Li¹, Gang Xu²

1. School of Pharmaceutical Science and Yunnan Key Laboratory of Pharmacology of Natural Products, Kunming Medical University, Kunming 650500, People's Republic of China;
2. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China

通讯作者: Xian Li,e-mail:xianlikm@163.com;Gang Xu,e-mail:xugang008@mail.kib.ac.cn
基金资助:
The work was financially supported by the National Natural Sciences Foundation of China(81373291), the National Science and Technology Support Program of China(2013BAI11B02), and the foundation from Chinese Academy of Sciences to Dr G. Xu.

Abstract

Abstract: Two new diterpenoids, salyunnanins I and J(1 and 2), together with ten analogues, were isolated from the roots of Salvia yunnanensis. The structures of the new isolates, possessing different neo-clerodane and seco-abietane diterpenoid skeletons respectively, were elucidated on the basis of comprehensive spectroscopic data. All of the compounds were tested for the inhibitory activities against six human tumor lines in vitro, and several ones showed moderate cytotoxic activities.

Key words: Salvia yunnanensis, Diterpenoid, Cytotoxicity

摘要： Two new diterpenoids, salyunnanins I and J(1 and 2), together with ten analogues, were isolated from the roots of Salvia yunnanensis. The structures of the new isolates, possessing different neo-clerodane and seco-abietane diterpenoid skeletons respectively, were elucidated on the basis of comprehensive spectroscopic data. All of the compounds were tested for the inhibitory activities against six human tumor lines in vitro, and several ones showed moderate cytotoxic activities.

关键词: Salvia yunnanensis, Diterpenoid, Cytotoxicity

Fan Xia,Chun-Yan Wu,Xing-Wei Yang, Xian Li,Gang Xu. Diterpenoids from the Roots of Salvia yunnanensis[J]. Natural Products and Bioprospecting, 2015, 5(6): 307-312.

Fan Xia, Chun-Yan Wu, Xing-Wei Yang, Xian Li, Gang Xu. Diterpenoids from the Roots of Salvia yunnanensis[J]. 应用天然产物, 2015, 5(6): 307-312.

References

1. L. Rodriguez-Hahn, B. Esquivel, A.A. Sanchez, J. Cardenas, O.G. Tovar, M. Soriano-Garcia, A. Toscano, J. Org. Chem. 53, 3933-3936 (1988)
2. H.M. Chang, K.P. Cheng, T.F. Choang, H.F. Chow, K.Y. Chui, P.M. Hon, F.W.L. Tan, Y. Yang, Z.P. Zhong, J. Org. Chem. 55, 3537-3543 (1990)
3. Z.H. Pan, G. Xu, Q.S. Zhao, Guang Xi Zhi Wu 30, 781-790 (2010)
4. M. Xue, Y.B. Shi, Y. Chui, B. Zhang, Y.J. Luo, Z.T. Zhou, W.J. Xia, R.C. Zhao, H.Q. Wang, Nat. Prod. Res. Dev. 12, 27-32 (2000)
5. L.H. Meng, J.S. Zhang, J. Ding, J. Biochem. Pharm. 62, 733-741 (2001)
6. X.H. Wang, K.F. Bastow, C.M. Sun, Y.L. Lin, H.J. Yu, M.J. Don, T.S. Wu, S. Nakamura, K.H. Lee, J. Med. Chem. 47, 5816-5819 (2004)
7. Kunming Institute of Botany, Chinese Academy of Sciences, Flora Yunnannica, vol. 1 (Science Press, Beijing, 1997), pp. 656-689
8. M.J. Don, C.C. Shen, Y.L. Lin, W.J. Syu, Y.H. Ding, C.M. Sun, J. Nat. Prod. 68, 1066-1070 (2005)
9. F.W. Lin, A.G. Damu, T.S. Wu, J. Nat. Prod. 69, 93-96 (2006)
10. G. Xu, L.Y. Peng, L. Lu, Z.Y. Weng, Y. Zhao, X.L. Li, Q.S. Zhao, H.D. Sun, Planta Med. 72, 84-86 (2006)
11. D.W. Zhang, X. Liu, D. Xie, R. Chen, X.Y. Tao, J.H. Zou, J. Dai, Chem. Pharm. Bull. 61, 576-580 (2013)
12. H.M. Chang, K.Y. Chui, F.W.L. Tan, Y. Yang, Z.P. Zhong, C.M. Lee, H.L. Sham, H.N.C. Wong, J. Med. Chem. 34, 1675-1692 (1991)
13. C.F. Chyu, Y.M. Chiang, H.C. Lin, Y.H. Kuo, Tetrahedron Lett. 45, 641-643 (2004)
14. E. Wenkert, J. De Paiva Campillo, J.D. McChesney, D.J. Watts, Phytochemistry 13, 2545-2549 (1974)
15. Y.H. Kuo, M.T. Yu, J. Nat. Prod. 60, 648-650 (1997)
16. G. Nagy, G. Gunther, I. Mathe, G. Blunden, M.H. Yang, T.A. Crabb, Phytochemistry 52, 1105-1109 (1999)
17. Y.R. Shi, N. Zaesung, H.K. Sung, W.A. Jong, Planta Med. 63, 44-46 (1997)
18. H. Kakisawa, T. Hayashi, I. Okazaki, M. Ohashi, Tetrahedron Lett. 28, 3231-3234 (1968)
19. W.S. Chen, X.M. Jia, W.D. Zhang, Z.Y. Lou, C.Z. Qiao, Acta Pharm. Sin. 5, 354-357 (2003)
20. A.G. Gonzalez, Z.E. Aguiar, T.A. Grillo, J.G. Luis, Phytochemistry 31, 1691-1695 (1992)
21. G. Xu, F. Zhao, X.W. Yang, J. Zhou, L.X. Yang, X.L. Shen, Y.J. Hu, Q.S. Zhao, Nat. Prod. Bioprospect. 1, 81-86 (2011)
22. M.J. Sexmero Cuadrado, M.C. De la Torre, L.Z. Lin, G.A. Cordell, B. Rodriguez, A. Perales, J. Org. Chem. 57, 4722-4728 (1992)
23. Y.B. Wu, Z.Y. Ni, Q.W. Shi, M. Dong, H. Kiyota, Y.C. Gu, B. Cong, Chem. Rev. 112, 5967-6026 (2012)
24. Y.Z. Dong, S.L. Morris Natschke, K.H. Lee, Nat. Prod. Rep. 28, 529-542 (2011)
25. A.G. Gonzalez, J.R. Herrera, J.G. Luis, A.G. Ravelo, E.A. Ferro, Phytochemistry 27, 1540-1541 (1988)
26. E. Maldonard, M. De los Angeles Flores, B. Salazar, A. Ortega, Phytochemistry 37, 1480-1482 (1994)
27. M.C. Alley, D.A. Scudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H. Shoemaker, M.R. Boyd, Cancer Res. 48, 589-601 (1988)
28. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, J. Nat. Cancer Inst. 83, 757-766 (1991)

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Diterpenoids from the Roots of Salvia yunnanensis

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