Phytochemicals and biological activities of Ligularia species

doi:10.1007/s13659-011-0003-y

应用天然产物 ›› 2011, Vol. 1 ›› Issue (1): 1-24.DOI: 10.1007/s13659-011-0003-y

• Review • 下一篇

Phytochemicals and biological activities of Ligularia species

Jun-Li YANG^a, Rui WANG^b, Yan-Ping SHI^a,b

a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China;
b Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China

收稿日期:2011-06-23 修回日期:2011-07-25 出版日期:2011-01-29 发布日期:2017-11-10
通讯作者: Yan-Ping SHI,E-mail:shiyp@licp.cas.cn
基金资助:
This work was supported by the Important Directional Project of the Chinese Academy of Sciences(No. KSCX2-EW-R-15) and the National Natural Science Foundation of China(No. 21075127).

Phytochemicals and biological activities of Ligularia species

Jun-Li YANG^a, Rui WANG^b, Yan-Ping SHI^a,b

a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China;
b Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China

Received:2011-06-23 Revised:2011-07-25 Online:2011-01-29 Published:2017-11-10
Supported by:
This work was supported by the Important Directional Project of the Chinese Academy of Sciences(No. KSCX2-EW-R-15) and the National Natural Science Foundation of China(No. 21075127).

摘要/Abstract

摘要： Ligularia, an important genus of the Compositae family, has captured the interest of natural product chemists for years. Phytochemical investigations on the title genus have led to isolation of hundreds of secondary metabolites with various skeletons. Herein, we summarized the chemical constituents of this genus and their biological activities over the past few decades.

Jun-Li YANG, Rui WANG, Yan-Ping SHI. Phytochemicals and biological activities of Ligularia species[J]. 应用天然产物, 2011, 1(1): 1-24.

Jun-Li YANG, Rui WANG, Yan-Ping SHI. Phytochemicals and biological activities of Ligularia species[J]. Natural Products and Bioprospecting, 2011, 1(1): 1-24.

参考文献

[1] Liu, X.; Wu, Q. X.; Wei, X. N.; Shi, Y. P. Helv. Chim. Acta 2007, 90, 1802-1810.
[2] Li, P. L.; Zhang, Z. X.; Jia, Z. J. Chem. Lett. 2008, 37, 308-309.
[3] Xie, W. D.; Weng, C. W.; Li, X.; Row, K. H. Helv. Chim. Acta 2010, 93, 1983-1989.
[4] Liu, Q.; Shen, L.; Wang, T. T.; Chen, C. J.; Qi, W. Y.; Gao, K. Food Chem. 2010, 122, 55-59.
[5] Fei, D. Q.; Li, S. G.; Liu, C. M.; Wu, G.; Gao, K. J. Nat.l Prod. 2007, 70, 241-245.
[6] Wang, C. F.; Zhao, Y.; Shi, S. Y.; Li, J. P.; Zhang, Z. Z.; Liu, Y. Z. Chem. Nat. Comp. 2010, 46, 184-186.
[7] Wu, Q. X.; Shi, Y. P,; Jia, Z. J. Nat.Prod. Rep. 2006, 63, 699-734.
[8] Yang, J. L.; Liu, L. L.; Shi, Y. P. Tetrahedron Lett. 2009, 50, 6315-6317.
[9] Wu, Q. X.; Shi, Y. P.; Yang, L. Org. Lett. 2004, 6, 2313-2316.
[10] Yang, J. L.; Liu, L. L.; Shi, Y. P. Planta Med. 2011, 77, 271-276.
[11] Yang, J. L.; Wang, R.; Liu, L. L.; Shi, Y. P. Planta Med. 2011, 77, 362-367.
[12] Yang, J. L.; Liu, L. L.; Wang, B. G.; Shi, Y. P. Biochem. Syst. Ecol. 2010, 38, 850-852.
[13] Liu, J. X.; Wei, X. N.; Shi, Y. P.; Lu, R. H. Chin. Chem. Lett. 2005, 16, 1618-1620.
[14] Zhang, W. J.; Li, X. H.; Shi, Y. P. J. Nat. Prod. 2010, 73, 143-146.
[15] Wu, Q. H.; Liu, C. M.; Chen, Y. J.; Gao, K. Helv. Chim. Acta 2006, 89, 915-922.
[16] Xu, J. Q.; Hu, L. H. Helv. Chim. Acta 2009, 92, 357-361.
[17] Zhang, Z. X.; Fei, D. Q.; Jia, Z. J. Helv. Chim. Acta, 2008, 91, 1045-1052.
[18] Jia, Z. J.; Zhao, Y.; Tan, R. X. J. Nat. Prod. 1993, 56, 494-499.
[19] Li, L.; Xu, L. W.; Jiang, Y. F.; Xi, C. J.; Wang, H. Q.; Suo, Y. R. Z. Naturforsch. 2004, 59b, 921-924.
[20] Wang, W. S.; Dai, X.; Hong, L. Y.; Lu, P.; Feng, J. C.; Jiao, Y. G. Helv. Chim. Acta 2008, 91, 1118-1123.
[21] Zhao, Y.; Jia, Z. J.; Peng, H. R. J. Nat. Prod. 1995, 58, 1358-1364.
[22] Li, L.; Xu, L. W.; Wang, H. Q. Helv. Chim. Acta 2004, 87, 1125-1129.
[23] Deng, M. C.; Dong, W. W.; Jiao, W.; Lu, R. H. Helv. Chim. Acta 2009, 92, 495-501.
[24] Tori, M.; Watanabe, A.; Matsuo, S.; Okamoto, Y.; Tachikawa, K.; Takaoka, S.; Gong, X.; Kuroda, C.; Hanai, R. Tetrahedron, 2008, 64, 4486-4495.
[25] Park, H. J.; Kwon, S. H.; Yoo, K. O.; Sohn, I. C.; Lee, K. T.; Lee, H. K. Planta Med. 2000, 66,783-784.
[26] Li, X. Q.; Gao, K.; Jia, Z. J. Planta Med. 2003, 69, 356-360.
[27] Jia, Z. J.; Zhao, Y.; Tan, R. X.; Yang, L. Phytochemistry 1992, 31, 199-201.
[28] Zhao, Y.; Jia, Z. J. Chin. Chem. Lett. 1993, 4, 323-326.
[29] Jia, Z. J.; Zhao, Y.; Tan, R. X. Planta Med. 1992, 58, 365-367.
[30] Liu, J. X.; Wei, X. N.; Shi, Y. P. Planta Med. 2006, 72, 175-179.
[31] Wu, Q. X.; Yang, A. M.; Shi, Y. P. Tetrahedron 2005, 61, 10529-10535.
[32] Nakatani, M.; Maeda, S.; Higashi, K.; Kurawaki, J.; Okamura, H.; Iwagawa, T. Heterocycles 2003, 60, 373-378.
[33] Zhao, Y.; Jia, Z. J.; Tan, R. X.; Yang, L. Phytochemistry 1992, 31, 2785-2787.
[34] Tori, M.; Okamoto, Y.; Tachikawa, K.; Mihara, K.; Watanabe, A.; Sakaoku, M.; Takaoka, S.; Tanaka, M.; Gong, X.; Kuroda, C.; Hattori, M.; Hanai, R. Tetrahedron 2008, 64, 9136-9142.
[35] Zhang, Z. X.; Lin, C. J.; Li, P. L.; Jia, Z. J. Planta Med. 2007, 73, 585-590.
[36] Li, W. X.; Lei, M.; Fei, D. Q.; Gao, K. Planta Med. 2009, 75, 635-640.
[37] Xu, Y. J.; Nan, Z. D.; Li, W. H.; Huang, H. L.; Yuan, C. S. Helv. Chim. Acta 2009, 92, 209-216.
[38] Liu, J. Q.; Zhang, M.; Zhang, C. F.; Qi, H. Y.; Bashall, A.; Bligh, S. W. A.; Wang, Z. T. Phytochemistry 2008, 69, 2231-2236.
[39] Li, E. W.; Gao, K.; Jia, Z. J. Chin. Chem. Lett. 2004, 15, 194-196.
[40] Li, P. L.; Jia, J. Z. Helv. Chim. Acta 2008, 91, 1717-1727.
[41] Xu, J. Q.; Hu, L. H. Helv. Chim. Acta 2008, 91, 951-957.
[42] Tori, M.; Honda, K.; Nakamizo, H.; Okamoto, Y.; Sakaoku, M.; Takaoka, S.; Gong, X.; Shen, Y. M.; Kuroda, C.; Hanai, R. Tetrahedron 2006, 62, 4988-4995.
[43] Wu, Q. X.; Shi, Y. P.; Yang, L. Chin. Chem. Lett. 2004, 15, 1441-1444.
[44] Chen, H. M.; Jia, Z. J. Chin. Chem. Lett. 1991, 2, 849-852.
[45] Wu, Q. X.; Shi, Y. P.; Yang, L. Planta Med. 2004, 70, 479-482.
[46] Tori, M.; Nakamizo, H.; Mihara, K.; Sato, M.; Okamoto, Y.; Nakashima, K.; Tanaka, M.; Saito, Y.; Sono, M.; Gong, X.; Shen, Y. M.; Hanai, R.; Kuroda, C. Phytochemistry, 2008, 69, 1158-1165
[47] Han, Y. F.; Pan, J.; Gao, K.; Jia, Z. J. Chem. Pharm. Bull. 2005, 53, 1338-1341.
[48] Li, Y. S.; Wang, Z. T.; Zhang, M.; Zhou, H.; Chen, J. J.; Luo, S. D. Planta Med. 2004, 70, 239-243.
[49] Chen, H. M.; Cai, M. S.; Jia, Z. J. Phytochemistry 1997, 45, 1441-1444.
[50] Chen, H. M.; Zhang, K. Q.; Cai, M. S.; Jia, Z. J. Indian J. Chem. 1998, 37b, 720-722.
[51] Shi, S. Y.; Wu, D. Y.; Gong, X.; Peng, H.; Zhang, R. P.; Zhou, X.; Hao, X. J.; Jia, Z. J.; StOckigt, J.; Zhao, Y. Chin. Chem. Lett. 2007, 18, 59-61.
[52] Nagano, H.; Iwazaki, Y.; Matsushima, M.; Sato, M.; Gong, X.; Shen, Y. M.; Hirota, H.; Kuroda, C.; Hanai, R. Chem. Biodiv. 2007, 4, 2874-2888.
[53] Fu, B.; Zhu, Q. X.; Yang, X. P.; Jia, Z. J. Pharmazie 2002, 57, 275-278.
[54] Zhang, W. J.; Qi, H. Y.; Shi, Y. P. Planta Med. 2010, 76, 159-164.
[55] Jia, Z. J.; Zhao, Y. J. Nat. Prod. 1994, 57, 146-150.
[56] Zhang, M.; Zhang, Z. F.; Wang, Z. T. Acta Pharm. Sin. 2005, 40, 529-532.
[57] Jun, Z.; Wu, H.; Huang, K. X.; Shi, S. Y.; Peng, H.; Sun, X. F.; Chen, L. R.; Zhang, Q. X.; Zhang, Q. J.; Hao, X. J.; StOckigt, J.; Li, X. K.; Zhao, Y.; Qu, J. Chin. Chem. Lett. 2008, 19, 1319-1322.
[58] Wang, Q.; Mu, Q.; Shibano, M.; Morris-Natschke, S. L.; Lee, K. H.; Chen, D. F. J. Nat. Prod. 2007, 70, 1259-1262.
[59] Tori, M.; Tanio, Y.; Okamoto, Y.; Saito, Y.; Gong, X.; Kuroda, C.; Hanai, R. Heterocycles 2008, 75, 2029-2034.
[60] Nagano, H.; Matsushima, M.; Yamada, H.; Hanai, R.; Gong, X.; Kuroda, C. Nat. Prod. Comm. 2010, 5, 1-4.
[61] Nagano, H.; Kanda, M.; Yamada, H.; Hanai, R.; Gong, X.; Kuroda, C. Helv. Chim. Acta 2010, 93, 1945-1952.
[62] Chen, H. M.; Jia, Z. J.; Yang, L. Phytochemistry 1992, 31, 2146-2147.
[63] Wu, Q. H.; Wang, C. M.; Cheng, S. G.; Gao, K. Tetrahedron Lett. 2004, 45, 8855-8858.
[64] Wang, W. S.; Zhu, Q. X.; Gao, K.; Jia, Z. J. J. Chin. Chem. Soc. 2000, 47, 1291-1293.
[65] Tan, A. M.; He, H. P.; Yang, H.; Zhang, M.; Wang, Z. T.; Hao, X. J. Acta Pharm. Sin. 2003, 38, 924-926.
[66] Li, Y.; Shi, Y. P. Hel. Chim. Acta 2006, 89, 870-875.
[67] Wang, C. F.; Zhao,Y.; Liu, Y. Z.; Zhang, Z. Z. Helv. Chim. Acta 2008, 91, 1712-1716.
[68] Zhao, Y.; Peng, H. R.; Jia, Z. J. J. Nat. Prod. 1994, 57, 1626-1630.
[69] Yang, L.; Peng, H. R.; Jia, Z. J. Chin. Chem. Lett. 1995, 6, 875-876.
[70] Li, Y. S.; Wang, Z. T.; Zhang, M.; Chen, J. J.; Luo, S. D. Nat. Prod. Res. 2004, 18, 99-104.
[71] Gao, K.; Jia, Z. J. Phytochemistry 1998, 49, 167-169.
[72] Baba, H.; Yaoita, Y.; Kikuchi, M. J. Tohoku Pharm. Univ. 2007, 54, 53-56.
[73] Gao, K.; Jia, Z. J. J. Lanzhou Univ. 2000, 36, 127-128.
[74] Guo, Z.; Weng, C. W.; Liu, W. X.; Shen, T. J. Chem. Res. 2010, 390-391.
[75] Yoshinori, S.; Masato, H.; Yuko, I.; Yuriko, T.; Kanako, M.;Yoko, S.; Miho, F.; Misato, S.; Anna, S.; Xun, C.; Chiaki, K.; Xun, G.; Ryo, H.; Motoo, T. Tetrahedron 2011, 67, 2220-2231.
[76] Naya, K.; Okayama, T.; Fujiwara, M.; Nakata, M.; Ohtsuka, T.; Kurio, S. Bull. Chem. Soc. Japn. 1990, 63, 2239-2245.
[77] Li, P. L.; Wang, C. M.; Zhang, Z. X.; Jia, Z. J. Tetrahedron 2007, 63, 12665-12670.
[78] Zhao, Y.; Parsons, S.; Smart, B. A.; Tan, R. X.; Jia, Z. J.; Sun, H. D.; Rankin, D. W. H. Tetrahedron 1997, 53, 6195-6208.
[79] Wang, Q.; Chen, T. H.; Bastow, K. F.; Lee, K. H.; Chen, D. F. J. Nat. Prod. 2010, 73, 139-142.
[80] Liu, C. M.; Wang, H. X.; Wei, S. L.; Gao, K. Helv. Chim. Acta 2008, 91, 308-316.
[81] Onuki, H.; Yamazaki, M.; Nakamura, A.; Hanai, R.; Kuroda, C.; Gong, X.; Shen, Y. M.; Hirota, H. J. Nat. Prod. 2008, 71, 520-524.
[82] Liu, C. M.; Fei, D. Q.; Wu, Q. H.; Gao, K. J. Nat. Prod. 2006, 69, 695-699.
[83] Baba, H.; Yaoita, Y.; Kikuchi, M. Helv. Chim. Acta 2007, 90, 1028-1037.
[84] Tan, A. M.; He, H. P.; Zhang, M.; Wang, Z. T.; Hao, X. J. Helv. Chim. Acta 2007, 90, 101-104.
[85] Gao, K.; Yang, L.; Jia, Z. J. Indian J. Chem. 1997, 36b, 715-718.
[86] Baba, H.; Yaoita, Y.; Kikuchi, M. Helv. Chim. Acta 2007, 90, 1302-1312.
[87] Gao, X.; Lin, C. J.; Xie, W. D.; Shen, T.; Jia, Z. J. Helv. Chim. Acta 2006, 89, 1387-1394.
[88] Gao, X.; Xie, W. D.; Jia, Z. J. J. Asian Nat. Prod. Res. 2008, 10,185-192.
[89] Wang, Q.; Chen, D. F. Helv. Chim. Acta 2007, 90, 2432-2437.
[90] Gao, K.; Jia, Z. J. Chem. Res. Chin. Univ. 1999, 15, 70-72.
[91] Jia, Z. J.; Chen, H. M. Phytochemistry 1991, 30, 3132-3134.
[92] Wu, Q. X.; Wei, Q. Y.; Shi, Y. P. Pharmazie 2006, 61, 241-243.
[93] Marco, J. A.; Sanz, J. F.; Yuste, A.; Rustaiyan, A. Liebigs Ann. Chem. 1991, No. 9, 929-931.
[94] Wang, B. G.; Yang, L.; Jia, Z. J.; Chen, H. M. Indian J. Chem. 1998, 37b, 669-671.
[95] Li, Y. S.; Li, S. S.; Wang, Z. T.; Luo, S. D.; Zhu, D. Y. Nat. Prod. Res., Part A 2006, 20, 1241-1245.
[96] Zhang, Z. X.; Fei, D. Q.; Jia, Z. J. Bull. Chem. Soc. Jpn. 2008, 81, 1007-1011.
[97] Sun, X. B.; Xu, Y. J.; Qiu, D. F.; Yuan, C. S. Helv. Chim. Acta 2007, 90, 1705-1711.
[98] Huang, H. L.; Xu, Y. J.; Liu, H. L.; Liu, X. Q.; Shang, J. N.; Han, G. T.; Yao, M. J.; Yuan, C. S. Phytochemistry 2011, 72, 514-517.
[99] Fei, D. Q.; Wu, Q. H.; Li S. G.; Gao, K. Chem. Pharm. Bull. 2010, 58, 467-469.
[100] Lee, K. T.; Koo, S. J.; Jung, S. H.; Choi, J.; Jung, H. J.; Park, H. J. Arch. Pharm. Res. 2002, 25, 820-823.
[101] Fei, D. Q.; Wu, G.; Liu, C. M.; Gao, K. Chem. Pharm. Bull. 2007, 55, 577-579.
[102] Zhu, H.; Tu, P. F. Z. Naturforsch. 2004, 59b, 1063-1066.
[103] Zhao, Y.; Tian, J.; Jia, Z. J.; Sun, H. D. Acta Bot. Yunnan. 1995, 17, 356-358.
[104] Ma, B.; Shi, Y. P.; Jia, Z. J. Planta Med. 1997, 63, 573-574.
[105] Toyoda, K.; Yaoita, Y.; Kikuchi, M. J. Tohoku Pharm. Univ. 2006, 53, 51-55.
[106] Tan, A. M.; Wang, Z. T.; He, H. P.; Zhang, M.; Hao, X. J. Heterocycles 2003, 60, 1195-1198.
[107] Lin, G.; Rose, P.; Chatson, K. B.; Hawes, E. M.; Zhao, X. G.; Wang, Z. T. J. Nat. Prod. 2000, 63, 857-860.
[108] Tan, A. M.; Li, Y. S.; Yang, H.; Wang, Z. T.; He, H. P.; Zhang, M.; Hao, X. J. Chin. Chem. Lett. 2004, 15, 68-70.
[109] Zhang, C. F.; Wang, Q.; Zhang, M. J. Asian Nat.Prod.Res. 2009, 11, 339-344.
[110] Li, Y. S.; Wang, Z. T.; Zhang, M.; Luo, S. D.; Chen, J. J. Nat. Prod. Res. 2005, 19, 125-129.
[111] Gao, X.; Jia, Z. J. Chin. Chem. Lett. 2008, 19, 71-72.
[112] Ma, B.; Gao, K.; Shi, Y. P.; Jia, Z. J. Phytochemistry 1997, 46, 915-919.
[113] Yan, F. L.; Wang, A. X.; Jia, Z. J. J. Chem. Res. 2004, 11, 742-743.
[114] Zhang, M.; Wang, Z. T.; Qin, H. L.; Zhao, X. G.; Xu, G. J.; Li, J. X.; Namba, T. Chin. Chem. Lett. 2002, 13, 620-622.
[115] Shi, S. Y.; Hu, M. H.; Wu, D. Y.; Zhou, C. X.; Mo, J. X.; Xu, J. H.; Chen, L. R.; Dou, H.; Peng, H.; Hao, X. J.; Stockigt. J.; Zhao, Y. Nat. Prod. Res., Part A 2008, 22, 628-632.
[116] Gao, K.; Wang, W. S.; Jia, Z. J. Phytochemistry 1998, 47, 269-272.
[117] Zhao, Y.; Jia, Z. J.; Yang, L.; Wang, J. G. Chin. Chem. Lett. 1993, 4, 895-898.
[118] Yan, F. L.; Wang, A. X.; Jia, Z. J. Pharmazie 2005, 60, 155-159.
[119] Yan, F. L.; Wang, A. X.; Jia, Z. J. J. Chin. Chem. Soc. 2004, 51, 863-868.
[120] Toyoda, K.; Yaoita, Y.; Kikuchi, M. Chem. Pharm. Bull. 2005, 53, 1555-1558.
[121] Li, Y. S.; Wang, Z. T.; Zhang, M.; Tan, A. M.; Chen, L. Chin. Tradit. Herb. Drugs 2005, 36, 335-337.
[122] Choi, J.; Park, J. K.; Lee, K. T.; Park, K. K.; Kim, W. B.; Lee, J. H.; Jung, H. J.; Park, H. J. Nat. Prod. Sci. 2004, 10, 182-189.
[123] Yoon, M. H.; Cho, CW.; Lee, J. W.; Kim, Y. S.; An, G. H.; Lim, C. H. Nat. Prod. Sci. 2008, 14, 62-67.

Phytochemicals and biological activities of Ligularia species

Phytochemicals and biological activities of Ligularia species

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