Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii

doi:10.1007/s13659-014-0009-3

应用天然产物 ›› 2014, Vol. 4 ›› Issue (2): 91-100.DOI: 10.1007/s13659-014-0009-3

Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii

Chun-Shuai Huang^1,2, Shi-Hong Luo¹, Yao-Lan Li³, Chun-Huan Li¹, Juan Hua¹, Yan Liu¹, Shu-Xi Jing¹, Ying Wang¹, Min-Jie Yang¹, Sheng-Hong Li¹

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2. Graduate University of Chinese Academy of Sciences, Beijing 100049, China;
3. Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou 510632, China

收稿日期:2014-01-20 修回日期:2014-01-20 出版日期:2014-04-24 发布日期:2018-02-11
通讯作者: Sheng-Hong Li,e-mail:shli@mail.kib.ac.cn
基金资助:
This research was supported financially by the National Natural Science Foundation of China(31200263), the Youth Innovation Promotion association of Chinese Academy of Sciences(awarded to Shi-Hong Luo), the''Western Light''Program of Chinese Academy of Sciences(awarded to Shi-Hong Luo), and the''Hundred Talents Program''of Chinese Academy of Sciences(awarded to Sheng-Hong Li).

Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii

Chun-Shuai Huang^1,2, Shi-Hong Luo¹, Yao-Lan Li³, Chun-Huan Li¹, Juan Hua¹, Yan Liu¹, Shu-Xi Jing¹, Ying Wang¹, Min-Jie Yang¹, Sheng-Hong Li¹

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2. Graduate University of Chinese Academy of Sciences, Beijing 100049, China;
3. Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou 510632, China

Received:2014-01-20 Revised:2014-01-20 Online:2014-04-24 Published:2018-02-11
Supported by:
This research was supported financially by the National Natural Science Foundation of China(31200263), the Youth Innovation Promotion association of Chinese Academy of Sciences(awarded to Shi-Hong Luo), the''Western Light''Program of Chinese Academy of Sciences(awarded to Shi-Hong Luo), and the''Hundred Talents Program''of Chinese Academy of Sciences(awarded to Sheng-Hong Li).

摘要/Abstract

摘要： The perennial herbaceous plant Euphorbia jolkinii(Euphorbiaceae) is a noxious weed widely distributed in the grasslands of northwestern Yunnan and has greatly threatened the local biodiversity. Phytochemical investigation on the fresh roots of E. jolkinii afforded six new diterpenoids 1, 2, 4-6, and 8, together with fifteen known diterpenoids. Their structures were elucidated on the basis of 1D and 2D NMR and other spectroscopic methods. Casbane, lathyrane, abietane, and ent-kaurane diterpenoids were reported from this plant for the first time. Selected compounds were evaluated for their antifeedant and anti-RSV(respiratory syncytial virus) activities. Compound 2 and ingenol(3) exhibited moderate antifeedant activity against a generalist insect herbivore, Spodoptera exigua, with EC₅₀ values of 17.88 and 17.71 lg/cm² respectively. Compound 19 showed significant anti-RSV activity, with 50% inhibition(IC₅₀) value of 10.0 μM and selective index of 8.0. Compounds 1 and 2 were less active against RSV virus, both with IC₅₀ value of 25 μM, and with selective indices of 1.0 and 3.2 respectively. These findings provided new evidence for the biological functions and utilization of the diversified diterpenoid metabolites in the roots of this rich but harmful plant.

关键词: Euphorbia jolkinii, Diterpenoids, Antifeedant activity, Antiviral activity

Abstract: The perennial herbaceous plant Euphorbia jolkinii(Euphorbiaceae) is a noxious weed widely distributed in the grasslands of northwestern Yunnan and has greatly threatened the local biodiversity. Phytochemical investigation on the fresh roots of E. jolkinii afforded six new diterpenoids 1, 2, 4-6, and 8, together with fifteen known diterpenoids. Their structures were elucidated on the basis of 1D and 2D NMR and other spectroscopic methods. Casbane, lathyrane, abietane, and ent-kaurane diterpenoids were reported from this plant for the first time. Selected compounds were evaluated for their antifeedant and anti-RSV(respiratory syncytial virus) activities. Compound 2 and ingenol(3) exhibited moderate antifeedant activity against a generalist insect herbivore, Spodoptera exigua, with EC₅₀ values of 17.88 and 17.71 lg/cm² respectively. Compound 19 showed significant anti-RSV activity, with 50% inhibition(IC₅₀) value of 10.0 μM and selective index of 8.0. Compounds 1 and 2 were less active against RSV virus, both with IC₅₀ value of 25 μM, and with selective indices of 1.0 and 3.2 respectively. These findings provided new evidence for the biological functions and utilization of the diversified diterpenoid metabolites in the roots of this rich but harmful plant.

Key words: Euphorbia jolkinii, Diterpenoids, Antifeedant activity, Antiviral activity

Chun-Shuai Huang, Shi-Hong Luo, Yao-Lan Li, Chun-Huan Li, Juan Hua, Yan Liu, Shu-Xi Jing, Ying Wang, Min-Jie Yang, Sheng-Hong Li. Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii[J]. 应用天然产物, 2014, 4(2): 91-100.

参考文献

1. A.R. Jassbi, Phytochemistry 67, 1977-1984 (2006)
2. J.R. Hanson, Nat. Prod. Rep. 20, 70-78 (2003)
3. Q.W. Shi, X.H. Su, H. Kiyota, Chem. Rev. 108, 4295-4327 (2008)
4. J.R. Hanson, Nat. Prod. Rep. 29, 890-898 (2012)
5. B.B. Zhang, X.L. Han, Q. Jiang, Z.X. Liao, C. Liu, Y.B. Qu, Fitoterapia 83, 1242-1247 (2012)
6. D. Cao, Y.L. Su, J.S. Yang, Acta Pharm. Sin. 27, 445-451 (1992)
7. D.G. Wu, B. Sorg, W. Adolf, E.H. Seip, E. Hecker, Phytother. Res. 6, 237-240 (1992)
8. F. He, J.X. Pu, S.X. Huang, W.L. Xiao, L.B. Yang, X.N. Li, Y. Zhao, J. Ding, C.H. Xu, H.D. Sun, HeIv. Chim. Acta 91, 2139-2147 (2008)
9. L.Y. Wang, N.L. Wang, X.S. Yao, S. Miyata, S. Kitanaka, J. Nat. Prod. 65, 1246-1251 (2002)
10. D.S. Yang, W.B. Peng, Z.L. Li, X. Wang, J.G. Wei, K.C. Liu, Y.P. Yang, X.L. Li, Nat. Prod. Bioprospect. 3, 112-116 (2013)
11. A.R. Lal, R.C. Cambie, P.S. Rutledge, P.D. Woodgate, Phytochemistry 29, 1925-1935 (1990)
12. Z. Jia, Y. Ding, Planta Med. 57, 569-571 (1991)
13. D. Uemura, Y. Hirata, Chem. Lett. 7, 819-822 (1974)
14. N. Crespi-Perellino, L. Garofano, E. Arlandini, V. Pinciroli, A. Minghetti, F.F. Vincieri, B. Danieli, J. Nat. Prod. 59, 773-776 (1996)
15. F. Jeske, J. Jakupovic, W. Berendsohn, Phytochemistry 40, 1743-1750 (1995)
16. Q.L. Liang, C.C. Dai, J.H. Jiang, Y.P. Tang, J.A. Duan, Fitoterapia 80, 514-516 (2009)
17. F.G. Shao, R. Bu, C. Zhang, C.J. Chen, J. Huang, J.H. Wang, J. Asian Nat. Prod. Res. 13, 805-810 (2011)
18. W.W. Tao, J.A. Duan, Y.P. Tang, N.Y. Yang, J.P. Li, Y.F. Qian, Phytochemistry 94, 249-253 (2013)
19. R.M. Dawson, P.R. Jefferies, J.R. Knox, Phytochemistry 14, 2593-2597 (1975)
20. C. Valente, M. Pedro, J.R. Ascenso, P.M. Abreu, M.S. Nascimento, M.J.U. Ferreira, Planta Med. 70, 244-249 (2004)
21. H. Wang, X.F. Zhang, Y. Zhou, S.L. Peng, D.W. Zhou, L.S. Ding, Fitoterapia 79, 262-266 (2008)
22. S.H. Luo, Q. Luo, X.M. Niu, M.J. Xie, X. Zhao, B. Schneider, J. Gershenzon, S.H. Li, Angew. Chem. Int. Ed. 49, 4471-4475 (2010)
23. S.H. Luo, L.H. Weng, M.J. Xie, X.N. Li, J. Hua, X. Zhao, S.H. Li, Org. Lett. 13, 1864-1867 (2011)
24. Y.L. Li, P.P. But, V.E. Ooi, Antivir. Res. 68, 1-9 (2005)
25. Y.L. Li, L.S. Ooi, H. Wang, P.P. But, V.E. Ooi, Phytother. Res. 18, 718-722 (2004)
26. A. Kujumgiev, I. Tsvetkova, Y. Serkedjieva, V. Bankova, R. Christov, S. Popov, J. Ethnopharmacol. 64, 235-240 (1999)

[1]	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.
[2]	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.
[3]	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.
[4]	Han Wu, Hui-Xiang Yang, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Psathyrellins A-E, Antibacterial Guanacastane Diterpenoids from Mushroom Psathyrella candolleana[J]. 应用天然产物, 2021, 11(4): 447-452.
[5]	Kai-Yue Han, Xing Wu, Chenglin Jiang, Rong Huang, Zheng-Hui Li, Tao Feng, He-Ping Chen, Ji-Kai Liu. Three New Compounds from the Actinomycete Actinocorallia aurantiaca[J]. 应用天然产物, 2019, 9(5): 351-354.
[6]	Xing Yu, Kai-Ting Duan, Zhen-Xiong Wang, He-Ping Chen, Xiao-Qing Gan, Rong Huang, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Anemhupehins A-C, Podocarpane Diterpenoids from Anemone hupehensis[J]. 应用天然产物, 2018, 8(1): 31-35.
[7]	Rui Chu, Luo-Sheng Wan, Xing-Rong Peng, Mu-Yuan Yu, Zhi-Run Zhang, Lin Zhou, Zhong-Rong Li, Ming-Hua Qiu. Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans[J]. 应用天然产物, 2016, 6(4): 217-223.
[8]	Qiu-Li Xiao, Fan Xia, Xing-Wei Yang, Yang Liao, Li-Xin Yang, Yu-Kun Wei, Xian Li, Gang Xu. New Dimeric and seco-Abietane Diterpenoids from Salvia wardii[J]. 应用天然产物, 2015, 5(2): 77-82.
[9]	Ya-Mei Pan, Yu Zhang, Xiao-Nan Wang, He-Ping Chen, Shun-Lin Li, Ying-Tong Di, Duo-Zhi Chen, Ling-Li Guo, Xiao-Jiang Hao, Hong-Ping He. Chemical Constituents from the Stems of Manihot esculenta[J]. 应用天然产物, 2015, 5(1): 55-59.
[10]	Wei-Ming Zhang, Jie-Qing Liu, Yuan-Yuan Deng, Jian-Jun Xia, Zhi-Run Zhang, Zhong-Rong Li, Ming-Hua Qiu. Diterpenoids and Limonoids from the Leaves and Twigs of Swietenia mahagoni[J]. 应用天然产物, 2014, 4(1): 53-57.
[11]	Bing-Ji Ma, Chun-Nan Wen, Yuan Gao, Fu-Cai Ren, Fei Wang, Ji-Kai Liu. ent-Kaurane diterpenoids from the plant Wedelia trilobata[J]. 应用天然产物, 2013, 3(3): 107-111.
[12]	Gang XU, Fang ZHAO, Xian-Wen YANG, Juan ZHOU, Li-Xin YANG, Xiao-Ling SHEN, Ying-Jie HU, Qin-Shi ZHAO. neo-Clerodane diterpenoids from Salvia dugesii and their bioactive studies[J]. 应用天然产物, 2011, 1(2): 81-86.

Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii

Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 12

编辑推荐

Metrics

本文评价