Progress in Chemical Synthesis and Structural Modification of Emodin

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (08): 1324-1333. Previous Articles Next Articles

Reports

大黄素的化学合成及结构修饰研究进展

梁英¹，喻大昭*^,2

(¹ 湖北省农业科学院国家生物农药工程技术研究中心武汉 430064)
(²湖北省农业科学院农作物重大病虫草害防控湖北省重点实验室武汉 430064)

收稿日期:2010-12-31 修回日期:2011-02-17 发布日期:2011-03-16
通讯作者: 梁英 E-mail:ly.liang8@gmail.com

Progress in Chemical Synthesis and Structural Modification of Emodin

Liang Ying¹ Yu Dazhao*^,2

(¹National Biopesticide Engineering Research Center, Hubei Academy of Agricultural Science, Wuhan 430064)
(²Hubei Key Laboratory of Crop Diseases, Insect Pests and Weeds Control, Hubei Academy of Agricultural Science, Wuhan 430064)

Received:2010-12-31 Revised:2011-02-17 Published:2011-03-16
Contact: LIANG Ying E-mail:ly.liang8@gmail.com

Emodin is a widespread hydroxylated anthraquinone and occurs in different Chinese herbs (rhubarb, aloe, polygonum). The pharmacological effects indicated that emodin showed anti-tumor, vasorelaxant, antibacterial, cathartic and diuretic activities and has a promising clinical value. In this paper, recent advances in the chemical synthesis, structural modification and biological activities of natural emodin derivatives are reviewed.

Key words: emodin, chemical synthesis, structural modification, progress

Cite this article

LIANG Ying, YU Da-Zhao. Progress in Chemical Synthesis and Structural Modification of Emodin[J]. Chin. J. Org. Chem., 2011, 31(08): 1324-1333.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

References

1. Zhou, X.; Song, B. A.; Jin, L. H.; Hu, D. Y.; Diao, C. L.; Xu, G. F.; Zou, Z. H.; Yang, S.

Bioorg. Med. Chem. Lett. 2006, 16, 563.

2. Cui, X. R.; Tsutaka, M.; Suzuki, N.; Shimamura, T.; Gao, L.; Koyanagi, J.; Komada, F.; Saito, S.

Eur. J. Med. Chem. 2008, 43, 1206.

3. Noungoue, D. T.; Antheaume, C.; Chaabi, M.; Ndjakou, B. L.; Ngouela, S.; Lobstein, A.; Tsamo, E. Phytochemistry 2008, 69, 1024.

4. Koyama, J.; Takeuchi, A.; Morita, I.; Nishino, Y.; Shimizu, M.; Inoue, M.; Kobayashi, N. Bioorg. Med. Chem. 2009, 17, 7493.

5. Huang, Q.; Lu, G. D.; Shen, H. M.; Chung, M. C. M.; Ong, C. N. Med. Res. Rev. 2007, 27, 609.

6. Kuo, Y. C.; Meng, H. C.; Tsai, W. J. Inflamm. Res. 2001, 50, 73.

7. Lin, M. L.; Lu, Y. C.; Chung, J. G.; Li, Y. C.; Wang, S. G.; NG, S. H.; Wu, C. Y.; Su, H. L.; Chen, S. S. Cancer let. 2010, 291, 46.

8. Chou, T. H.; Liang, C. H. Chem. Res. Toxicol. 2009, 22, 2017.

9. Choi, J. S.; Chung, H. Y.; Jung, H. A.; Park, H. J.; Yokozawa, T. J. Agric. Food Chem. 2000, 48, 6347.

10. Wu, Z. X.; Yu, B. P.; Xia, H.; Xu, L. Eur. J. Pharmacol. 2008, 595, 95.

11. Ding, Y.; Zhao, L.; Mei, H.; Zhang, S. L.; Huang, Z. H.; Duan, Y. Y.; Ye, P. Eur. J. Pharmacol. 2008, 590, 377.

12. Wang, C. G.; Yang, J. Q.; Liu, B. Z.; Jin, D. T.; Wang, C.; Zhong L.; Zhu, D.; Wu, Y. Eur. J. Pharmacol. 2010, 627, 33.

13. Wang, W.; Sun, Y. P.; Huang, X. Z.; He, M.; Chen, Y. Y.; Shi, G. Y.; Li, H.; Yi, J.; Wang, J. Biochem. Pharmaclo. 2010, 79, 1134.

14. Ho, T. Y.; Wu, S. L.; Chen, J. C.; Li, C. C.; Hsiang, C. Y. Antivir. Res. 2007, 74, 92.

15. Yang, Y. C.; Lim, M. Y.; Lee, H. S. J. Agric. Food Chem. 2003, 51, 7629.

16. Yang, X. J.; Yang, L. J.; Wang, S. N.; Yu, D. Z.; Ni, H. W. Pest. Manag. Sci. 2007, 63, 511.

17. Yang, X. J.; Yang, L. J.; Zeng, F. S.; Xiang, L. B.; Wang, S. N.; Yu, D. Z.; Ni, H. W. Plant Dis. 2008, 92, 1451.

18. Yang, X. J.; Yang, L. J.; Ni, H. W.; Yu, D. Z. Can. J. Plant Pathol. 2008, 30, 391.

19. Eder, R.; Widmer, C. Helv. Chim. Acta. 1923, 6, 966.

20. Li, S. S. Total Synthesis of Natural Product. Chemical Industry Press, Beijing, 2005, p. 35(in Chinese). (李绍顺, 天然产物全合成, 化学工业出版社, 北京, 2005, p. 35.)

21. Chen, X.; Wang, K. W. CN 101033178, 2007.

22. Jacobson, R. A.; Adams, R. J. Am. Chem. Soc. 1924, 46, 1312.

23. Ayyangar, N. R. J. Sci. Industr. Res. 1961, 20B, 493.

24. Liang, J. P.; Bai, W. B.; Che, Q. M.; Xing, G. Z.; Sun, Y. CN 1827574, 2006.

25. Savard, J.; Brassard, P. Tetrahedron 1984, 40, 3455.

26. Khan, A. T.; Blessing, B.; Schmidt, R. R. Synthesis 1994, 3, 255.

27. Motoyoshiya, J.; Masue, Y.; Nishi, Y.; Aoyama, H. Nat. Prod. Comm. 2007, 2, 67.

28. Kintsurashvili, L. A.; Sikharulidze, M. L.; Buganov, V. N.; Turabelidze, D. G. Chem. Nat. Comp. 1999, 35, 619.

29. Park, J. H.; Kim, S. W.; Yang, S. D.; Hur, M. G.; Chun, K. S.; Yu, K. H. Bull. Korean. Chem. Soc. 2008, 29, 595.

30. Wang, X. P.; Xu, W. F. Chin. J. Med. Chem. 2005, 15, 321(in Chinese). (王兴坡, 徐文芳, 中国药物化学杂志, 2005, 15, 321).

31. Wang, X. P.; Xu, W. F. Bull. Korean. Chem.Soc. 2005, 26, 1923.

32. Daub, K. S.; Habermann, B.; Habn, T.; Teich, L.; Eger, K. Eur. J. Org. Chem. 2004, 4, 894.

33. Chen, H.; Wang, Y.; Leng, L.; Cheng, M. S.; Yu, P. F.; Zhang, J. Z. Chin. Chem. Lett. 2007, 18, 141.

34. Song, G. P.; Wang, P.; Zhang, Z. H.; Shi, D. K.; Li, Y. X. Chin. J. Chem. 2008, 26, 1715.

35. Song, G. P.; Liu, H. C.; Zhang, W.; Geng, M. Y.; Li, Y. X. Bioorg. Med. Chem. 2010, 18, 5183.

36. Zhang, W.; Ye, M.; Zhan, J. X.; Chen, Y. J.; Guo, D. A. Biotechnol Lett. 2004, 26, 127.

37. Fonteneau, N.; Martin, P.; Mondon, M.; Ficheux, H.; Gesson, J. P. Tetrahedron 2001, 57, 9131.

38. Zhu, X. K.; Ye, X. L.; Yuan, L. J.; Zhu, J. Y.; Ding, Y. P.; Li, X. G. Chin. J. Org. Chem. 2010, 30, 1335(in Chinese). (朱小康, 叶小利, 袁吕江, 朱家颖, 丁阳平, 李学刚, 有机化学, 2010, 30, 1335.)

39. Teich, L.; Daub, K. S.; Krugel, V.; Nissler, L.; Gebhardt, R.; Eger, K. Bioorg. Med. Chem. 2004, 12, 5961.

40. Koyama, M.; Kelly, T. R.; Watanabe, K. A. J. Med. Chem. 1988, 31, 283.

41. Koyama, M.; Takahashi, K.; Chou, T. C.; Darzynkiewicz, Z.; Kapuscinski, J.; Kelly, T. R.; Watanabe, K. A. J. Med. Chem. 1989, 32, 1594.

42. Lu, Y.; Huang, Z. S.; Tan, J. H.; Ding, Y.; Bu, X. Z.; An, L. K.; Ma, L.; Fu, L. W.; Gu, L. Q. Chin. J. Org. Chem. 2005, 25, 944(in Chinese). (陆豫, 黄志纾, 谭嘉恒, 丁岩, 卜宪章, 安林坤, 马林, 符立梧, 古练权, 有机化学, 2005, 25, 944.)

43. Lev-Goldman, V.; Mester, B.; Ben-Aroga, N.; Koch, Y.; Weiner, L.; Fridkin, M. Bioconjugate Chem. 2006, 17, 1008.

44. Salama, T.A.; Lackner, B.; Falk, H. Monatsh. Chem. 2003, 134, 1113.

45. Salama, T.A.; Lackner, B.; Falk, H. Monatsh. Chem. 2004, 135, 735.

46. Waser, M.; Falk, H. Monatsh. Chem. 2005, 136, 609.

47. Lackner, B.; Popova, Y.; Etzlstorfer, C.; Smekerovic, A. A.; Klampfl, C. W.; Falk, H. Monatsh. Chem. 2005, 136, 777.

48. Lackner, B.; Bretterbauer, K. ; Falk, H. Monatsh. Chem. 2005, 136, 1629.

49. Waser, M.; Lacker, B.; Zuschrader, J.; Muler, N.; Falk, H. Tetrahedron Lett, 2005, 46, 2377.

50. Jin, H. S.; Zhao, L. M. Chin. Chem. Lett. 2010, 21, 568.

51. Tan, J. H.; Zhang, Q. X.; Huang, Z. S.; Chen, Y.; Wang, X. D.; Gu, L. Q.; Wu, J. Y. Eur. J. Med. Chem. 2006, 41, 1041.

[1]	Xiaoying Jia, Jiaxia Pu, Lirong Han, Qinghan Li. Research Progress in the Synthesis of Benzo[d]pentamembered Heterocyclic Thioethers Containing Two Heteroatoms [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 18-40.
[2]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[3]	Jiaxia Pu, Xiaoying Jia, Lirong Han, Qinghan Li. Research Progress of Visible Light Promoted C—N Bond Fracture to Construct C—C Bond [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2591-2613.
[4]	Junying Zhang, Xiaojing Zhao, Ganpeng Li, Yonghui He. Electrochemical Synthesis of Masked Organoboronic Acids RB(dan) at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1815-1823.
[5]	Yongzhou Pan, Xiujin Meng, Yingchun Wang, Muxue He. Recent Progress in Electrochemical Fixation of CO₂ to Construct Carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1416-1434.
[6]	Tianyang Wang, Yan-Mei Li. Progress on the Synthesis and Activity of Cyclic Dinucleotides as Stimulator of Interferon Gene (STING) Agonists [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 892-913.
[7]	Zujia Lu, Jian Qin, Jinting Wu, Wenli Cao, Baolong Kuang, Jianguo Zhang. Advances in the Synthesis of Energetic Compounds Based on 1,2,3-Triazoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 526-554.
[8]	Jiawei Huang, Xiaoman Li, Liang Xu, Yu Wei. Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 756-762.
[9]	Peng Liu, Fuming Zhong, Lihao Liao, Weiqiang Tan, Xiaodan Zhao. Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4019-4035.
[10]	Fen Wang, Lanting Wang, Gang Wang, Cheng Qian, Yingxia Zhou, Xin Zheng. Research Progress of Fluorescent Organic Salts [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4147-4156.
[11]	Haiqiong Li, Mengyun Yin, Fenfen Xie, Zhengbing Zhang, Pan Han, Linhai Jing. Synthesis of Nitrile via Electrochemical Appel Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2229-2235.
[12]	Xiang Li, Yifan Zhang, Kailin Lu, Shihui Liu, Yongqiang Zhang. Aminofluorination-Based Structural Modification of Curcumol for the Construction of 3D-Shaped Natural Product Fragment Library [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2124-2133.
[13]	Can Yong, Yun Li, Tao Bi, Guofeng Chen, Dongxia Zheng, Zhouyu Wang, Yuanyuan Zhang. Research Progress on the Synthesis and Activity of D-Galactose Derived Small Galectin Inhibitors [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1307-1325.
[14]	Zhihao Zhang, Xin Jiang, Qinghan Li. Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 945-964.
[15]	Yuqing He, Lin Chen, Ruili He, Keli Zhong, Lijun Tang. Research Progress of Fluorescence Probes Constructed by Cyclodextrin Derivatives and Inclusion Complexes [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 785-795.

大黄素的化学合成及结构修饰研究进展

Progress in Chemical Synthesis and Structural Modification of Emodin

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments