Citation: Wu Jie-Wei, Tang Chun-Ping, Cai Yao-Yao, Ke Chang-Qiang, Lin Li-Gen, Yao Sheng, Ye Yang. Cytotoxic germacrane-type sesquiterpene lactones from the whole plant of Inula cappa[J]. Chinese Chemical Letters, ;2017, 28(5): 927-930. doi: 10.1016/j.cclet.2016.11.011 shu

Cytotoxic germacrane-type sesquiterpene lactones from the whole plant of Inula cappa

Wu Jie-Wei ^a,b ,
Tang Chun-Ping ^a ,
Cai Yao-Yao ^c ,
Ke Chang-Qiang ^a ,
Lin Li-Gen ^d ,
Yao Sheng ^a,, ,
Ye Yang ^a,e,,

a.
State Key Laboratory of Drug Research, and Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
Department of NMR Technology Services, Public Technical Service Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
d.
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macao 999078, China
e.
School of Life Science and Technology, ShanghaiTech University, Shanghai 201203, China

Corresponding author: Yao Sheng, yaosheng@simm.ac.cn Ye Yang, yye@simm.ac.cn
Received Date: 25 July 2016
Revised Date: 15 October 2016
Accepted Date: 30 October 2016
Available Online: 18 May 2016

Figures(3)

Phytochemical investigation on the whole plant of Inula cappa led to the isolation of two new germacrane-type sesquiterpene lactones, ineupatolides D and E (1 and 2), together with three known analogs. The structures of the new compounds were established by extensive analysis of 1D and 2D NMR spectra, as well as MS data. Their absolute configurations were determined by CD spectra. All compounds showed moderate inhibitory effects on A431, A549, BGC-823, HL-60, HT-29, and MCF-7 cancer cell lines with IC₅₀ values ranging from 2.1 to 36.3 μM.
- Inula cappa,
- Germacrane,
- Sesquiterpene lactones,
- Ineupatolide D,
- Ineupatolide E
1. [1]
  Editorial Committee of the Administration Bureau of Chinese Plant Medicine, Chinese Flora, Science Press, Beijing, 1979, pp. 248(in Chinese).
2. [2]
  Guo Q.L., Yang J.S.. Sesquiterpenes in Inula L. plants and their pharmacological activities[J]. Nat. Prod. Res. Dev., 2005(17):804-809.
3. [3]
  Editorial Committee of the Administration Bureau of Chinese Plant Medicine, Chinese Flora, Science Press, Beijing, 1979, pp. 271(in Chinese).
4. [4]
  Xie H.G., Chen H., Cao B., Zhang H.W., Zou Z.M.. Cytotoxic germacranolide sesquiterpene from Inula cappa[J]. Chem. Pharm. Bull., 2007(55):1258-1260.
5. [5]
  Wang F.Y., Li X.Q., Sun Q.. Sesquiterpene lactones from Inula cappa[J]. Phytochem. Lett., 2012(5):639-642.
6. [6]
  Bohlmann F., Ahmed M., Jakupovic J.. Inositol angelates from Inula cappa[J]. Phytochemistry, 1982(21):780-782.
7. [7]
  Zou Z.M., Xie H.G., Zhang H.W., Xu L.. Inositol angelates from the whole herb of Inula cappa[J]. Fitoterapia, 2008(79):393-394.
8. [8]
  Wu J.W., Tang C.P., Yao S.. Anti-inflammatory inositol derivatives from the whole plant of Inula cappa[J]. J. Nat. Prod., 2015(78):2332-2338.
9. [9]
  Baruah N.C., Sharma R.P., Thyagarajan G., Herz W., Govindan S.V.. New flavonoids from Inula cappa[J]. Phytochemistry, 1979(18):2003-2006.
10. [10]
  Wang Y.L., Li Y.J., Wang A.M.. Two new phenolic glycosides from Inula cappa[J]. J. Asian Nat. Prod. Res., 2010(12):765-769.
11. [11]
  Wu Z.J., Shen Y.H., Zhang W.D.. Two new phenolic glycosides from Inula cappa DC[J]. Nat. Prod. Res., 2013(27):719-722.
12. [12]
  Kim D.K., Baek N.I., Choi S.U.. Four new cytotoxic germacranolides from Carpesium divaricatum[J]. J. Nat. Prod., 1997(60):1199-1202.
13. [13]
  Kim M.R., Hwang B.Y., Jeong E.S.. Cytotoxic germacranolide sesquiterpene lactones from Carpesium triste var. manshuricum[J]. Arch. Pharm. Res., 2007(30):556-560.
14. [14]
  Heilmann J., Wasescha M.R., Schmidt T.J.. The influence of glutathione and cysteine levels on the cytotoxicity of helenanolide type sesquiterpene lactones against KB cells[J]. Bioorg. Med. Chem., 2001(9):2189-2194.
15. [15]
  Stöchlin W., Waddell T.G., Geissman T.A.. Circular dichroism and optical rotatory dispersion of sesquiterpene lactones[J]. Tetrahedron, 1970(29):2397-2409.
16. [16]
  Youssef D., Frahm A.W.. Circular dichroism of C-7, C-6 trans-fused guaianolides of Centaurea scoparia[J]. Phytochemistry, 1996(41):1107-1111.
17. [17]
  Baruah R.N., Sharma R.P., Thyagarajan G.. Unusual germacranolides from Inula eupatorioides[J]. J. Org. Chem., 1980(45):4838-4843.
18. [18]
  Lin Y.L., Ou J.C., Kuo Y.H.. four new sesquiterpene lactones from Carpesium nepalense[J]. J. Nat. Prod., 1996(59):991-993.
19. [19]
  Skehan P.A., Storeng R., Scudiero D.. New colorimetric cytotoxicity assay for anticancer-drug screening[J]. J. Natl. Cancer Inst., 1990(82):1107-1112.
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