Diterpenoids from the Roots of Salvia yunnanensis

doi:10.1007/s13659-015-0080-4

应用天然产物 ›› 2015, Vol. 5 ›› Issue (6): 307-312.DOI: 10.1007/s13659-015-0080-4

• Original article • 上一篇

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

收稿日期:2015-11-04 修回日期:2015-11-04 出版日期:2015-12-24 发布日期:2018-02-11
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.

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:2015-12-24 Published:2018-02-11
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.

摘要/Abstract

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

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

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.

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.

参考文献

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)

[1]	Pengkun Li, Qin Li, Aimin Fu, Yang Xiao, Chunmei Chen, Hucheng Zhu, Changxing Qi, Wei Wei, Yuan Zhou, Yonghui Zhang. Emestrin-type epipolythiodioxopiperazines from Aspergillus nidulans with cytotoxic activities by regulating PI3K/AKT and mitochondrial apoptotic pathways[J]. 应用天然产物, 2025, 15(2): 17-17.
[2]	Dong-Yang Wang, Ming-Xing Li, Yan-Chao Xu, Peng Fu, Wei-Ming Zhu, Li-Ping Wang. Dibohemamines I-O from Streptomyces sp. GZWMJZ-662, an endophytic actinomycete from the medicinal and edible plant Houttuynia cordata Thunb.[J]. 应用天然产物, 2025, 15(1): 9-9.
[3]	Yue-Mei Chen, Nan-Kai Cao, Si-Si Zhu, Meng Ding, Hai-Zhen Liang, Ming-Bo Zhao, Ke-Wu Zeng, Peng-Fei Tu, Yong Jiang. Euchrestifolines A-O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia[J]. 应用天然产物, 2025, 15(1): 5-5.
[4]	Alica Fischle, Mika Lutsch, Florian Hübner, Linda Sch?ker-Hübner, Lina Schürmann, Finn K. Hansen, Svetlana A. Kalinina. Micro-scale screening of genetically modified Fusarium fujikuroi strain extends the apicidin family[J]. 应用天然产物, 2024, 14(6): 51-51.
[5]	Phanruethai Pailee, Paratchata Batsomboon, Wiriya Yaosanit, Theerawat Thananthaisong, Chulabhorn Mahidol, Poonsakdi Ploypradith, Nanthawan Reuk-ngam, Panita Khlaychan, Supanna Techasakul, Somsak Ruchirawat, Vilailak Prachyawarakorn. Grewiifopenes A-K, bioactive clerodane diterpenoids from Casearia grewiifolia Vent.[J]. 应用天然产物, 2024, 14(6): 54-54.
[6]	Qi-Xiu Hai, Kun Hu, Su-Ping Chen, Yang-Yang Fu, Xiao-Nian Li, Han-Dong Sun, Hong-Ping He, Pema-Tenzin Puno. Silvaticusins A-D: ent-kaurane diterpenoids and a cyclobutane-containing ent-kaurane dimer from Isodon silvaticus[J]. 应用天然产物, 2024, 14(5): 45-45.
[7]	Orawan Jongsomjainuk, Jutatip Boonsombat, Sanit Thongnest, Hunsa Prawat, Paratchata Batsomboon, Sitthivut Charoensutthivarakul, Saroj Ruchisansakun, Kittipong Chainok, Jitnapa Sirirak, Chulabhorn Mahidol, Somsak Ruchirawat. Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis[J]. 应用天然产物, 2023, 13(6): 55-55.
[8]	Yang Yu, Yang Wang, Gui-Chun Wang, Cheng-Yong Tan, Yi Wang, Jin-Song Liu, Guo-Kai Wang. Andropanilides A-C, the novel labdane-type diterpenoids from Andrographis paniculata and their anti-inflammation activity[J]. 应用天然产物, 2023, 13(5): 31-31.
[9]	Xun Wei, Jia-Luo Huang, Hua-Hua Gao, Fang-Yu Yuan, Gui-Hua Tang, Sheng Yin. New halimane and clerodane diterpenoids from Croton cnidophyllus[J]. 应用天然产物, 2023, 13(3): 21-21.
[10]	Shuyuan Mo, Ziming Zhao, Zi Ye, Zhihong Huang, Yaxin Zhang, Wanqi Yang, Jianping Wang, Zhengxi Hu, Yonghui Zhang. New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti[J]. 应用天然产物, 2023, 13(3): 17-17.
[11]	Li Hou, Cui-Xuan Mei, Chun-Mao Yuan, Gui-Hua Tang, Duo-Zhi Chen, Qing Zhao, Hong-Ping He, Ming-Ming Cao, Xiao-Jiang Hao. Five new limonoids isolated from Walsura robusta[J]. 应用天然产物, 2023, 13(2): 7-7.
[12]	Jingwen Niu, Jianzhao Qi, Pengchao Wang, Chengwei Liu, and Jin, ming Gao, Abstract. The chemical structures and biological activities of indole diterpenoids[J]. 应用天然产物, 2023, 13(1): 3-3.
[13]	Ya-Li Hu, Xing-Ren Li, Gang Xu. Carascynol A, a hybrid of caryophyllane-type terpenoid and a C₆ unit degraded by polyprenylated acylphloroglucinols from Hypericum ascyron[J]. 应用天然产物, 2022, 12(6): 38-38.
[14]	Xin Zhang, Yun-Bao Ma, Xiao-Feng He, Tian-Ze Li, Chang-An Geng, Li-Hua Su, Shuang Tang, Zhen Gao, Ji-Jun Chen. Artemyrianosins A–J, cytotoxic germacrane-type sesquiterpene lactones from Artemisia myriantha[J]. 应用天然产物, 2022, 12(3): 16-16.
[15]	Natividad Herrera Cano, Sebastian A. Andujar, Cristina Theoduloz, Daniel A. Wunderlin, Ana N. Santiago, Guillermo Schmeda-Hirschmann, Ricardo D. Enriz, Gabriela E. Feresin. Arylated analogues of cypronazole: fungicidal effect and activity on human fibroblasts. Docking analysis and molecular dynamics simulations[J]. 应用天然产物, 2022, 12(2): 9-9.

Diterpenoids from the Roots of Salvia yunnanensis

Diterpenoids from the Roots of Salvia yunnanensis

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价