6,7-<i>seco</i>-<i>ent</i>-Kaurane diterpenoids from Isodon <i>sculponeatus</i> and their bioactivity

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6,7-seco-ent-Kaurane diterpenoids from Isodon sculponeatus and their bioactivity

Hua-Yi Jiang , Wei-Guang Wang , Min Zhou , Hai-Yan Wu , Rui Zhan , Xue Du , Jian-Xin Pu , Han-Dong Sun

Citation: Hua-Yi Jiang, Wei-Guang Wang, Min Zhou, Hai-Yan Wu, Rui Zhan, Xue Du, Jian-Xin Pu, Han-Dong Sun. 6,7-seco-ent-Kaurane diterpenoids from Isodon sculponeatus and their bioactivity[J]. Chinese Chemical Letters, 2014, 25(4): 541-544. doi: 10.1016/j.cclet.2014.01.041 shu

shu

6,7-seco-ent-Kaurane diterpenoids from Isodon sculponeatus and their bioactivity

通讯作者: Jian-Xin Pu,
Han-Dong Sun,

摘要: One new 6,7-seco-ent-kaurane diterpenoid, sculponin T (1), was isolated from the aerial parts of Isodon sculponeatus, along with four known analogs, sculponeatin J (2), sculponeatin K (3), sculponeatin C (4), and sculponeatin Q (5). Their structures were elucidated by extensive spectroscopic analysis and by comparison with data reported in the literature. Significant cytotoxic activity was observed for compound 2 against five human tumor cell lines with IC₅₀ values ranging from 1.8 μmol/L to 3.3 μmol/L, and it also inhibited NO production in LPS-stimulated RAW264.7 cells, with IC₅₀ value of 3.3 μmol/L.

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English

6,7-seco-ent-Kaurane diterpenoids from Isodon sculponeatus and their bioactivity

1.
a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2.
b University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Jian-Xin Pu, Han-Dong Sun,

Received Date: 06 November 2013
Available Online: 31 January 2014

Abstract: One new 6,7-seco-ent-kaurane diterpenoid, sculponin T (1), was isolated from the aerial parts of Isodon sculponeatus, along with four known analogs, sculponeatin J (2), sculponeatin K (3), sculponeatin C (4), and sculponeatin Q (5). Their structures were elucidated by extensive spectroscopic analysis and by comparison with data reported in the literature. Significant cytotoxic activity was observed for compound 2 against five human tumor cell lines with IC₅₀ values ranging from 1.8 μmol/L to 3.3 μmol/L, and it also inhibited NO production in LPS-stimulated RAW264.7 cells, with IC₅₀ value of 3.3 μmol/L.

Key words:

1. [1] H.D. Sun, S.X. Huang, Q.B. Han, Diterpenoids from Isodon species and their biological activities, Nat. Prod. Rep. 23 (2006) 673-698.[1] H.D. Sun, S.X. Huang, Q.B. Han, Diterpenoids from Isodon species and their biological activities, Nat. Prod. Rep. 23 (2006) 673-698.
2. [2] H.D. Sun, Y.L. Xu, B. Jiang, Diterpenoids from Isodon Species, Science Press, Beijing, 2001, p. 4.[2] H.D. Sun, Y.L. Xu, B. Jiang, Diterpenoids from Isodon Species, Science Press, Beijing, 2001, p. 4.
3. [3] Compiling Groups of Compilation of Countrywide Herbal Medicine of China, Compilation of Countrywide Herbal Medicine of China, People's Medical Publishing House, Beijing, 1996, p. 853.[3] Compiling Groups of Compilation of Countrywide Herbal Medicine of China, Compilation of Countrywide Herbal Medicine of China, People's Medical Publishing House, Beijing, 1996, p. 853.
4. [4] Delectis Florae Reipublicae Popularis Sinicae Agendae Academiae Sinicae Edita, Flora Reipublicae Popularis Sinica, Science Press, Beijing, 1977, p. 504.[4] Delectis Florae Reipublicae Popularis Sinicae Agendae Academiae Sinicae Edita, Flora Reipublicae Popularis Sinica, Science Press, Beijing, 1977, p. 504.
5. [5] X.R. Wang, Z.Q. Wang, J.G. Dong, A new diterpene from Huanghua-xiangchacai (Rabdosia sculponeata), Zhongcaoyao 13 (1982) 11-12.[5] X.R. Wang, Z.Q. Wang, J.G. Dong, A new diterpene from Huanghua-xiangchacai (Rabdosia sculponeata), Zhongcaoyao 13 (1982) 11-12.
6. [6] H.D. Sun, Z.W. Lin, Y.L. Xu, et al., Structures of sculponins A, B and C, three new diterpenoids having unique acetal structures from Rabdosia sculponeata, Heterocycles 24 (1986) 1-4.[6] H.D. Sun, Z.W. Lin, Y.L. Xu, et al., Structures of sculponins A, B and C, three new diterpenoids having unique acetal structures from Rabdosia sculponeata, Heterocycles 24 (1986) 1-4.
7. [7] R.P. Zhang, H.J. Zhang, H.D. Sun, et al., Diterpenoids from Rabdosia sculponeata, Chin. Chem. Lett. 2 (1991) 293-296.[7] R.P. Zhang, H.J. Zhang, H.D. Sun, et al., Diterpenoids from Rabdosia sculponeata, Chin. Chem. Lett. 2 (1991) 293-296.
8. [8] M.H. Yang, Q.S. Zhao, H.D. Sun, et al., Studies on diterpenoids of Isodon sculponeata, Zhongcaoyao 32 (2001) 397-399.[8] M.H. Yang, Q.S. Zhao, H.D. Sun, et al., Studies on diterpenoids of Isodon sculponeata, Zhongcaoyao 32 (2001) 397-399.
9. [9] B. Jiang, H. Yang, H.D. Sun, et al., Two new ent-kauranoids from Isodon sculponeata, Chin. Chem. Lett. 13 (2002) 1083-1086.[9] B. Jiang, H. Yang, H.D. Sun, et al., Two new ent-kauranoids from Isodon sculponeata, Chin. Chem. Lett. 13 (2002) 1083-1086.
10. [10] B. Jiang, S.X. Mei, H.D. Sun, et al., Diterpenoids from Isodon sculponeatus, Chin. J. Chem. 20 (2002) 887-890.[10] B. Jiang, S.X. Mei, H.D. Sun, et al., Diterpenoids from Isodon sculponeatus, Chin. J. Chem. 20 (2002) 887-890.
11. [11] B. Jiang, A.J. Hou, H.D. Sun, et al., Cytotoxic ent-kaurane diterpenoids from Isodon sculponeata, Planta Med. 68 (2002) 921-925.[11] B. Jiang, A.J. Hou, H.D. Sun, et al., Cytotoxic ent-kaurane diterpenoids from Isodon sculponeata, Planta Med. 68 (2002) 921-925.
12. [12] L.M. Li, G.Y. Li, H.D. Sun, et al., Sculponins A-C, three new 6,7-seco-ent-kauranoids from Isodon sculponeatus, Tetrahedron Lett. 48 (2007) 9100-9103.[12] L.M. Li, G.Y. Li, H.D. Sun, et al., Sculponins A-C, three new 6,7-seco-ent-kauranoids from Isodon sculponeatus, Tetrahedron Lett. 48 (2007) 9100-9103.
13. [13] F. Wang, X.M. Li, J.K. Liu, New terpenoids from Isodon sculponeata, Chem. Pharm. Bull. 57 (2009) 525-527.[13] F. Wang, X.M. Li, J.K. Liu, New terpenoids from Isodon sculponeata, Chem. Pharm. Bull. 57 (2009) 525-527.
14. [14] (a) L.M. Li, G.Y. Li, H.D. Sun, et al., Ent-kaurane and cembrane diterpenoids from Isodon sculponeatus and their cytotoxicity, J. Nat. Prod. 72 (2009) 1851-1856; (b) L.M. Li, J.X. Pu, H.D. Sun, et al., A new phenylethanoid glycoside from Isodon sculponeatus, Chin. Chem. Lett. 22 (2011) 961-963.[14] (a) L.M. Li, G.Y. Li, H.D. Sun, et al., Ent-kaurane and cembrane diterpenoids from Isodon sculponeatus and their cytotoxicity, J. Nat. Prod. 72 (2009) 1851-1856; (b) L.M. Li, J.X. Pu, H.D. Sun, et al., A new phenylethanoid glycoside from Isodon sculponeatus, Chin. Chem. Lett. 22 (2011) 961-963.
15. [15] X. Li, J.X. Pu, H.D. Sun, et al., 6,7-seco-ent-Kaurane diterpenoids from Isodon sculponeatus with cytotoxic activity, Chem. Biodivers. 7 (2010) 2888-2896.[15] X. Li, J.X. Pu, H.D. Sun, et al., 6,7-seco-ent-Kaurane diterpenoids from Isodon sculponeatus with cytotoxic activity, Chem. Biodivers. 7 (2010) 2888-2896.
16. [16] H.Y. Jiang, W.G. Wang, H.D. Sun, et al., Enmein-type 6,7-seco-ent-kauranoids from Isodon sculponeatus, J. Nat. Prod. 76 (2013) 2113-2119.[16] H.Y. Jiang, W.G. Wang, H.D. Sun, et al., Enmein-type 6,7-seco-ent-kauranoids from Isodon sculponeatus, J. Nat. Prod. 76 (2013) 2113-2119.
17. [17] A. Monks, D. Scudiero, P. Cronise, et al., Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines, J. Natl. Cancer Inst. 83 (1991) 757-766.[17] A. Monks, D. Scudiero, P. Cronise, et al., Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines, J. Natl. Cancer Inst. 83 (1991) 757-766.
18. [18] L.J. Reed, H. Muench, A simple method of estimating fifty percent endpoints, Am. J. Hyg. 27 (1983) 493-497.[18] L.J. Reed, H. Muench, A simple method of estimating fifty percent endpoints, Am. J. Hyg. 27 (1983) 493-497.
19. [19] J.T. Fan, J. Su, N.H. Tan, et al., Rubiyunnanins C-H, cytotoxic cyclic hexapeptides from Rubia yunnanensis inhibiting nitric oxide production and NF-kB activation, Bioorg. Med. Chem. 18 (2010) 8226-8234.[19] J.T. Fan, J. Su, N.H. Tan, et al., Rubiyunnanins C-H, cytotoxic cyclic hexapeptides from Rubia yunnanensis inhibiting nitric oxide production and NF-kB activation, Bioorg. Med. Chem. 18 (2010) 8226-8234.
20. [20] H.D. Sun, Y.L. Xu, B. Jiang, Diterpenoids from Isodon Species, Science Press, Beijing, 2001, p. 312.[20] H.D. Sun, Y.L. Xu, B. Jiang, Diterpenoids from Isodon Species, Science Press, Beijing, 2001, p. 312.
21. [21] N.L. McCartney-Francis, X. Song, D.E. Mizel, et al., Selective inhibition of inducible nitric oxide synthase exacerbates erosive joint disease, J. Immunol. 166 (2001) 2734.[21] N.L. McCartney-Francis, X. Song, D.E. Mizel, et al., Selective inhibition of inducible nitric oxide synthase exacerbates erosive joint disease, J. Immunol. 166 (2001) 2734.

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