請用此 Handle URI 來引用此文件: http://hdl.handle.net/11455/96330
標題: Synthetic study of Lithospermic acid and its possible role as a precursor in Salvianolic acid B synthesis
紫草酸之合成研究及其為丹參酚酸B的前驅物之可能性
作者: Wei-Yi Li
李韋毅
關鍵字: 紫草酸
丹參酚酸B合成
Lithospermic acid and Salvianolic acid B synthesis
引用: 文獻資料 1. X. Pan, G. Niu and H. Liu, J. Chromatogr. A. 2001, 922, 371-375 2. L. Zhou, Z. Zuo and M. S. S. Chow, J Clin Pharmacol, 2005, 45, 1345-1359 3. T. O. Cheng, International journal of cardiology 2007, 121, 9-22 4. K. Y. Hur, H. J. Seo, E. S. Kang, S. H. Kim, S. Song, E. H. Kim, S. Lim, C. Choi, J. H. Heo and K. C. Hwang, European journal of pharmacology 2008, 586, 226-233 5. B.-Q. Wang, J. Med. Plant. Res. 2010, 4, 2813-2820 6. B. H. Zhi and A. Alfermann, Phytochemistry 1993, 32, 699-703 7. B. Clebsch, The new book of salvias: sages for every garden, Portland, Or.: Timber Press 344p.-illus., col. illus.. ISBN, 2003 8. B.-Q. Wang, J. Med. Plant. Res. 2010, 4, 2813-2820 9. K. De-Yun, Chinese Journal of Pharmaceuticals 1989, 6, 014 10. G. Zheng and H. Kakisawa, Zhongguo Yaoxue Zazhi 1989, 24, 6-10 11. X. Pan, G. Niu and H. Liu, J. Chromatogr. A. 2001, 922, 371-375 12. L. Zhou, Z. Zuo and M. S. S. Chow, J Clin Pharmacol, 2005, 45, 1345-1359 13. 黎莲娘, 中国药学: 英文版 1997, 3-10 14. W. Schönfeld, J. Weiland, C. Lindig, M. Masnyk, M. M. Kabat, A. Kurek, J. Wicha and K. R. Repke, Naunyn-Schmiedeberg's archives of pharmacology 1985, 329, 414-426 15. I. Prassas and E. P. Diamandis, Nature reviews Drug discovery 2008, 7, 926-935 16. A. Goto, K. Yamada, M. Ishii and T. Sugimoto, The American journal of medicine 1990, 89, 420-426 17. L. J. Feldman, D. Himbert, J.-M. Juliard, G. J. Karrillon, H. Benamer, P. Aubry, O. Boudvillain, P. Seknadji, M. Faraggi and P. G. Steg, Journal of the American College of Cardiology 2000, 35, 1162-1169 18. Y. L. Chen, S. P. Yang, M. S. Shiao, J. W. Chen and S. J. Lin, Journal of Cellular Biochemistry 2001, 83, 484-493 19. D. C. Gadsby, J. Kimura and A. Noma, 1985, 63-65 20. P. L. Jorgensen, K. O. Håkansson and S. J. Karlish, Annual review of physiology 2003, 65, 817-849 21. J. H. Kaplan, Annual review of biochemistry 2002, 71, 511-535 22. W. Schoner, The FEBS Journal 2002, 269, 2440-2448 23. W. Schoner and G. Scheiner-Bobis, American journal of cardiovascular drugs 2007, 7, 173-189 24. W. Schoner and G. Scheiner-Bobis, American Journal of Physiology-Cell Physiology 2007, 293, C509-C536 25. Y.-c. Chen, T.-r. JInn, T.-y. ChUnG, F.-y. Li, R.-j. FAn and J. T. Tzen, Acta Pharmacologica Sinica 2010, 31, 923-929 26. R. M. Jacobson and R. A. Raths, The Journal of Organic Chemistry 1979, 44, 4013-4014 27. S. J. O'Malley, K. L. Tan, A. Watzke, R. G. Bergman and J. A. Ellman, Journal of the American Chemical Society 2005, 127, 13496-13497 28. N. Mase and T. Horibe, Organic letters 2013, 15, 1854-1857 29. D.-H. Wang and J.-Q. Yu, Journal of the American Chemical Society 2011, 133, 5767-5769 30. T. G. Varadaraju and J. R. Hwu, Organic & biomolecular chemistry 2012, 10, 5456-5465 31. K. Heuzé, D. Méry, D. Gauss, J. C. Blais and D. Astruc, Chemistry–A European Journal 2004, 10, 3936-3944 32. R. Chinchilla and C. Nájera, Chemical Society Reviews 2011, 40, 5084-5121 33. Y. Nan, H. Miao and Z. Yang, Organic letters 2000, 2, 297-299 34. J. Fischer, G. P. Savage and M. J. Coster, Organic letters 2011, 13, 3376-3379 35. D. Mujahidin and S. Doye, European journal of organic chemistry 2005, 2005, 2689-2693. 36. J. Hacon, A. Morris, M. J. Johnston, S. E. Shanahan, M. D. Barker, G. G. Inglis and S. J. Macdonald, Chemical Communications 2007, 625-627 37. S. Sengmany, C. Ceballos, R. Belhadj, C. Cachet,Vivier, E. L. Gall, B. Brissault, J. Penelle and E. Léonel, Journal of Polymer Science Part A: Polymer Chemistry 2012, 50, 900-911.
摘要: Salvia miltiorrhiza is a famous traditional Chinese medicinal plant, the root of this plant called Danshen[6]. It is commonly used in traditional Chinese medicine for promoting blood circulation to remove blood stasis, relieving vexation, nourishing blood, tranquilizing the mind, cooling the blood to relieve carbuncles, clearing away heat[7-8]. However, Magnesium lithospermate B (MLB) is the main ingredient in the water-soluble extracts of danshen and it has been considered as a potential replacement of the traditional cardiac medicine for increasing cardiac contractility and as an effective free radical scavenger at the same time. For this reason, we want to study this compound as our target molecule. The MLB precursor is Salvianolic acid B (SAB) and then we divide it into two parts by retrosynthetic analysis. We try to use lithospermic acid as a synthetic template. Finally, we have successfully completed the synthesis of the derivative of lithospermic acid and Salvianolic acid B .
丹參,其根部為中國傳統長用之草藥,用以治療冠心病、腦血管疾病、肝炎、慢性腎衰竭、經痛及失眠等。自1930年丹參的化學成分已經有許多的研究,而早年的研究主要集中在疏水性化合物,像是丹參酮。而近年來的研究主要以親水性化合物為主,至少有50種以上的化合物被分離及鑑定[1-5]。 在上述研究中發現丹參酚酸B鎂鹽(Magnesium lithospermate B,MLB)為丹參中水溶性成分含量最高之物種,故由其結構及含量即可推論相較於其他丹參水溶性化學成分在藥理活性上其有較好之效果。而在結構中能夠發現紫草酸及丹參酚酸B之結構相近,故以紫草酸之核心架構作出發點著手進行。在合成進行發現由紫草酸合成作為模板來建立丹參酚酸B之結構並非一、兩步可以完成,但我們成功將中心核及側支鏈完成並將其接合,後以水解方式將其完成紫草酸及丹參酚酸B之前驅物。
URI: http://hdl.handle.net/11455/96330
文章公開時間: 2020-08-17
顯示於類別:化學系所

文件中的檔案:
檔案 大小格式 
nchu-106-7104051105-1.pdf8.15 MBAdobe PDF 請求副本


在 DSpace 系統中的文件,除了特別指名其著作權條款之外,均受到著作權保護,並且保留所有的權利。