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Studies on the Chemical Synthesis of Natural Drugs Berberine

  • Xifei Yan ,
  • Jianfeng Zheng ,
  • Wei-Dong Z. Li
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  • a Sichuan Engineering Research Center for Biomimetic Synthesis of Natural Drugs, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031
    b Key Laboratory of Natural Product Chemistry and Application in Xinjiang, Yili Normal University, Yining, Xinjiang 835000
*Corresponding authors.E-mail:;

Received date: 2020-12-31

  Revised date: 2021-01-26

  Online published: 2021-02-26

Supported by

National Natural Science Foundation of China(21901215); National Natural Science Foundation of China(21672030); Fundamental Research Funds for the Central Universities(2682020CX53); Key Program of Natural Science Foundation of Xinjiang Autonomous Region Colleges(XJEDU2018I018)

Abstract

Berberine is an important natural drug and a kind of benzyl isoquinoline alkaloid, which has unique four-ring structure. In recent years, pharmacological research has found berberine is expected to be used in the clinical treatment of cancer, diabetes and other frequently occurring diseases. Based on the Woodward’s biosynthetic hypothesis, a schematic review on the synthetic studies towards berberine is provided.

Cite this article

Xifei Yan , Jianfeng Zheng , Wei-Dong Z. Li . Studies on the Chemical Synthesis of Natural Drugs Berberine[J]. Chinese Journal of Organic Chemistry, 2021 , 41(6) : 2217 -2227 . DOI: 10.6023/cjoc202012053

References

[1]
Schulz, E. R. J. Am. Pharm. Assoc. 1926, 15,33.
[2]
(a) Eckhardt, K.; Zeller, K.-P.; Siehl, H.-U.; Berger, S.; Sicker, D. Chem. Unserer Zeit 2017, 51,344.
[2]
(b) Buchner, J. A.; Herberger, J. E. Repert. Pharm. 1830, 36,1.
[3]
Abadi, B. E. A.; Moss, D. S.; Palmer, R. A. J. Crystallogr. Spectrosc. Res. 1984, 14,269.
[4]
Durairajan, S. S. K.; Liu, L.-F.; Lu, J.-H.; Chen, L.-L.; Yuan, Q J.; Chung, S. K.; Huang, L.; Li, X.-S.; Huang, J.-D.; Li, M. Neurobiol. Aging 2012, 33,2903.
[5]
Hong, Y.; Hui, S.-C.; Chan, T.-Y.; Hou, J.-Y. Am. J. Chin. Med. 2002, 30,589.
[6]
Kong, W. J.; Wei, J.; Abidi, P.; Lin, M.; Inaba, S.; Li, C.; Wang, Y. L.; Wang, Z. Z.; Si, S. Y.; Pan, H. N.; Wang, S. K.; Wu, J. D.; Wang, Y.; Li, Z. R.; Liu, J. W.; Jiang, J.-D. Nat. Med. 2004, 10,1344.
[7]
Lee, H. W.; Suh, J. H.; Kim, H.-N.; Kim, A. Y.; Park, S. Y.; Shin, C. S.; Choi, J.-Y.; Kim, J. B. J. Bone Miner. Res. 2008, 23,1227.
[8]
Xing, J.; He, H. World Latest Med. Inf. 2019, 19,231(in Chinese).
[8]
(邢娟, 何梦静, 世界最新医学信息文摘, 2019, 19,231.)
[9]
Amin, A. H.; Subbaiah, T. V.; Abbasi, K. M. Can. J. Microbiol. 1969, 15,1067.
[10]
Cong, Z. Q. M.S Thesis, Shanghai Institute of Materia Media, Chinese Academy of Sciences, Shanghai, 2019(in Chinese).
[10]
丛湛青, 硕士论文, 中国科学院上海药物研究所,上海, 2019) .
[11]
Liu, Y. Ph.D. Dissertation, East China Normal University, Shanghai, 2019(in Chinese).
[11]
(刘艺, 博士论文, 华东师范大学, 上海, 2019.)
[12]
Sobolova, K.; Hrabinova, M.; Hepnarova, V.; Kucera, T.; Kobrlova, T.; Benkova, M.; Janockova, J.; Dolezal, R.; Prchal, L.; Benek, O.; Mezeiova, E.; Jun, D.; Soukup, O.; Korabecny, J. Eur. J. Med. Chem. 2020, 203,112593.
[13]
Zhang, L.; Shi, M. X.; Liu, J. F.; Han, W. N. J. Int. Pharm. Res. 2018, 45,325(in Chinese).
[13]
(张龙, 史明星, 刘金凤, 韩维娜, 国际药学研究杂志, 2018, 45,325.)
[14]
Jung, H. A.; Min, B.-S.; Yokozawa, T.; Lee, J.-H.; Kim, Y. S.; Choi, J. S. Biol. Pharm. Bull. 2009, 32,1433.
[15]
Li, Y.-H.; Yang, P.; Kong, W.-J.; Wang, Y.-X.; Hu, C.-Q.; Zuo, Z.-Y.; Wang, Y.-M.; Gao, H.; Gao, L.-M.; Feng, Y.-C.; Du, N.-N.; Liu, Y.; Song, D.-Q.; Jiang, J.-D. J. Med. Chem. 2009, 52,492.
[16]
Xu, B. B.; Jiang, X. J.; Xiong, J.; Lan, J.; Tian, Y.; Zhong, L.; Wang, X. Q.; Xu, N.; Cao, H. W.; Zhang, W. Q.; Zhang, H.; Hong, X. T.; Zhan, Y.-Y.; Zhang, Y. D.; Hu, T. H. J. Med. Chem. 2020, 63,5841.
[17]
Gear, J. R.; Spenser, I. D. Can. J. Chem. 1963, 41,783.
[18]
Muller, M. J.; Zenk, M. H. Planta Med. 1992, 58,524.
[19]
Hashimoto, T.; Yamada, Y. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1994, 45,257.
[20]
Menéndez-Perdomo, I. M.; Facchini, P. J. Molecules 2018, 23,2899.
[21]
Beaudoin, G. A. W.; Facchini, P. J. Planta 2014, 240,19.
[22]
Wu, S. W.; Yang, M. Q.; Xiao, Y. L. Chin. J. Org. Chem. 2018, 38,2243(in Chinese).
[22]
(吴世文, 杨盟权, 肖友利, 有机化学, 2018, 38,2243.)
[23]
Woodward, R. B. Nature 1948, 162,155.
[24]
Sato, F.; Yamada, Y. Phytochemistry 1984, 23,281.
[25]
(a) Gao, Y.; Yin, H.; Sun, Y. H.; Zhang, Z. Q.; Cui, Y. J. Fungal Res. 2008, 6,216(in Chinese).
[25]
(高杨, 殷红, 孙宇宏, 张志强, 崔迎, 菌物研究, 2008, 6,216.)
[25]
(b) Gao, Y.; Liu, M. Guangzhou Chem. Ind. 2012, 40,91(in Chinese).
[25]
(高杨, 刘铭, 广州化工, 2012, 40,91.)
[26]
Liu, X. S. Hans J. Chem. Eng. Technol. 2020, 10,306(in Chinese).
[26]
(刘雪松, 化学工程与技术, 2020, 10,306.)
[27]
Dominguez, X. A.; Delgado, J. G.; Reeves, W. P.; Gardner, P. D. Tetrahedron Lett. 1967, 8,2493.
[28]
Pictet, A.; Gams, A. Ber. Dtsch. Chem. Ges. 1911, 44,2480.
[29]
Buck, J. S.; Perkin, W. H. J. Chem. Soc., Trans. 1924, 125,1675.
[30]
Haworth, R. D.; Perkin, W. H.; Rankin, J. J. Chem. Soc., Trans. 1924, 125,1686.
[31]
Buck, J. S.; Perkin, W. H.; Stevens, T. S. J. Chem. Soc., Trans. 1925, 127,1462.
[32]
Buck, J. S.; Davis, R. M. J. Am. Chem. Soc. 1930, 52,660.
[33]
Kametani, T.; Noguchi, I.; Saito, K.; Kaneda, S. J. Chem. Soc. C 1969,2036.
[34]
Cutter, P. S.; Miller, R. B.; Schore, N. E. Tetrahedron 2002, 58,1471.
[35]
Mastranzo, V. M.; Romero, J. L. O.; Yuste, F.; Ortiz, B.; Sánchez-Obregón, R.. García Ruano, J.L. Tetrahedron 2012, 68,1266.
[36]
Makhey, D.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVoie, E. J. Biorg. Med. Chem. 1996, 4,781.
[37]
Szawkalo, J.; Czarnocki, Z. Monatsh. Chem. 2005, 136,1619.
[38]
Miyazawa, M.; Tokuhashi, T.; Horibata, A.; Nakamura, T.; Onozaki, Y.; Kurono, N.; Senboku, H.; Tokuda, M.; Ohkuma, T.; Orito, K. J. Heterocycl. Chem. 2013, 50,E48.
[39]
Matulenko, M. A.; Meyers, A. I. J. Org. Chem. 1996, 61,573.
[40]
Chen, Z. X.; Tao, F.; Xia, Z. J.; Ma, S. M. CN 101245064, 2008.
[41]
Lee, D. Y. W.; Liu, J.; Zhang, S. Z.; Huang, P.; Liu-Chen, L.-Y. Bioorg. Med. Chem. Lett. 2017, 27,1437.
[42]
North-east Pharmaceutical Factory Chin. J. Pharm. 1972, (4),4(in Chinese).
[42]
(东北制药总厂, 中国医药工业杂志, 1972, (4),4.)
[43]
(a) Chen, C.; Luo, Z. M.; Yang, H. J.; Feng, Y. C. Chin. J. Org. Chem. 2016, 36,1426(in Chinese).
[43]
(陈程, 罗卓玛, 杨鸿均, 冯豫川, 有机化学, 2016, 36,1426.)
[43]
(b) Chen, C.; X, M. M.; Zhao, Q.; Liu, C. X.; Yang, H. J.; Feng, Y. C. Chin. J. Org. Chem. 2017, 37,503(in Chinese).
[43]
(陈程, 徐蒙蒙, 赵青, 刘承秀, 杨鸿均, 冯豫川, 有机化学, 2017, 37,503.)
[44]
Guangxi Nanning Pharmaceutical Factory Chin. J. Pharm. 1973, (7),4(in Chinese).
[44]
(广西南宁制药厂, 中国医药工业杂志, 1973, (7),4.)
[45]
Chen, S. Q.; Lin, W. F.; Zang, J. H.; Liu, J. H.; Qi, S. H.; Zhang, L. Q.; Song, G. L. CN 1312250, 2001.
[46]
Tang, C. G. CN 106543171, 2017.
[47]
Feng, X.; Fu, L.; Zhao, C. A. CN 107868072, 2018.
[48]
Yasuda, S.; Hirasawa, T.; Hanaoka, M. Tetrahedron Lett. 1987, 28,2399.
[49]
Nimgirawath, S.; Ponghusabun, O. Aust. J. Chem. 1994, 47,951.
[50]
He, Y.; Zheng, Y.; Hai, L.; Wu, Y. Chin. J. Chem. 2014, 32,1121.
[51]
Garad, D. N.; Mhaske, S. B. Org. Lett. 2016, 18,3862.
[52]
Mori-Quiroz, L. M.; Hedrick, S. L.; De Los Santos, A. R.; Clift, M. D. Org. Lett. 2018, 20,4281.
[53]
Gatland, A. E.; Pilgrim, B. S.; Procopiou, P. A.; Donohoe, T. J. Angew. Chem., Int. Ed. 2014, 53,14555.
[54]
Reddy, V.; Jadhav, A. S.; Anand, R. V. Org. Biomol. Chem. 2015, 13,3732.
[55]
(a) Zhou, S. Q.; Tong, R. B. Chem.-Eur. J. 2016, 22,7084.
[55]
(b) Yu, J. X.; Zhang, Z. H.; Zhou, S. Q.; Zhang, W.; Tong, R. B. Org. Chem. Front. 2018, 5,242.
[56]
Li, K.; Ou, J. J.; Gao, S. H. Angew. Chem., Int. Ed. 2016, 55,14778.
[57]
Jiang, X. J.; Zeng, Z. X.; Hua, Y. H.; Xu, B. B.; Shen, Y.; Xiong, J.; Qiu, H. J.; Wu, Y. F.; Hu, T. H.; Zhang, Y. D. J. Am. Chem. Soc. 2020, 142,15585.
[58]
Li, W.-D.Z.; Yang, H. Tetrahedron 2005, 61,5037.
[59]
Reimann, E.; Grasberger, F.; Polborn, K. Monatsh. Chem. 2003, 134,991.
[60]
Guo, W.-S. Ph.D. Dissertation, Nankai University, Tianjing, 2012(in Chinese).
[60]
(郭维斯, 博士论文, 南开大学, 天津, 2012.)
[61]
Spenser, L. D.; Gear, J. R. J. Am. Chem. Soc. 1962, 84,1059.
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