Research Progress on Structural Optimization on the Lipid-Soluble Ingredients of Salvia miltiorrhiza

  • Xingjun Li ,
  • Jiang Wang ,
  • Hong Liu
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  • a State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203
    b School of Pharmacy, China Pharmaceutical University, Nanjing 211198
    c Lingang Laboratory, Shanghai 200031
* Corresponding author. E-mail:

Received date: 2022-06-29

  Revised date: 2022-09-14

  Online published: 2022-11-01

Supported by

National Natural Science Foundation of China(82130105)

Abstract

As a traditional Chinese medicine, Salvia miltiorrhiza has been widely applied in the treatment of cardiovascular diseases in clinical. Research on its active components and derivatives has become an issue of great focus both domestically and internationally. The active ingredients of Salvia miltiorrhiza are mainly divided into lipid-soluble and water-soluble ingredients with the lipid-soluble ones performing various pharmacological properties. However, their poor solubility and bioavailability have limited their clinical applications. In order to promote the clinical application of lipid-soluble ingredients of Salvia miltiorrhiza, these components are used as lead compounds to perform structural optimization to improve drug-like properties. In order to generate novel research ideas for the development of novel drugs based on lipid-soluble ingredients of Salvia miltiorrhiza, the research progress of structural optimization and related biological activities of the major lipid-soluble ingredients of Salvia miltiorrhiza in recent years is reviewed, the structural optimization strategy of the drug-like properties of these compounds and the synthetic approaches of their derivatives are summarized, and the effects of different structure modifications on pharmacological activities are described.

Cite this article

Xingjun Li , Jiang Wang , Hong Liu . Research Progress on Structural Optimization on the Lipid-Soluble Ingredients of Salvia miltiorrhiza[J]. Chinese Journal of Organic Chemistry, 2023 , 43(2) : 471 -490 . DOI: 10.6023/cjoc202206054

References

[1]
Wu, Y.-B.; Ni, Z.-Y.; Shi, Q.-W.; Dong, M.; Kiyota, H.; Gu, Y.-C.; Cong, B. Chem. Rev. 2012, 112, 5967
[2]
(a) Yan, S.-C.; Liang, M.-Q; Khalid, R.; Ting, H.; Ping, Q.-L. Chin. J. Nat. Med. 2015, 13, 0163.
[2]
(b) Guo, Y.-B.; Li, Y.; Xue, L.-M.; Severino, P. R.; Gao, S.-H.; Niu, J.-Z.; Qin, L.-P.; Zhang, D.-W.; Bromme, D. J. Ethnopharmacol. 2014, 155, 1401.
[3]
Li, Z.-M.; Xu, S.-W; Liu, P.-Q. Acta Pharmacol. Sin. 2018, 39, 802.
[4]
(a) Fang, J.; Little, P. J.; Xu, S.-W. Med. Res. Rev. 2018, 38, 201.
[4]
(b) Chen, X.-P.; Guo, J.-J.; Bao, J.-L.; Lu, J.-J.; Wang, Y.-T. Med. Res. Rev. 2014, 34, 768.
[5]
(a) Wang, X.-H.; Bastow, K.F.; Sun, C.-M.; Lin, Y.-L.; Yu, H.-J.; Don, M.-J.; Wu, T.-S.; Nakamura, S.; Lee, K.-H. J. Med. Chem. 2004, 47, 5816.
[5]
(b) Lin, W.-J.; Huang, J.-J.; Liao, X.-L.; Yuan, Z.-W.; Feng, S.-L.; Xie, Y.; Ma, W.-Z. Pharmacol. Res. 2016, 111, 849.
[6]
Zhou, L.-M.; Zuo, Z.; Chow, M. S. S. J. Clin. Pharmacol. 2005, 45, 1345.
[7]
(a) Yuan, L.-M.; Li, Q.-H.; Zhang, Z.-G.; Liu, Q.-L.; Wang, X.-C.; Fan, L.-H. J. Cell. Biochem. 2019, 121, 1400.
[7]
(b) Shang, Q.-H.; Xu, H.; Huang, L. Evidence-Based Complementary Altern. Med. 2012, 2012, 716459.
[7]
(c) Gao, S.; Liu, Z.-P.; Li, H.; Little, P.-J.; Liu, P.-Q.; Xu, S.-W. Atherosclerosis 2012, 220, 3.
[8]
Liu, W.-G.; Zhou, J.-M.; Geng, G.-Y.; Shi, Q.-W.; Sauriol, F.; Wu, J.-H. J. Med. Chem. 2012, 55, 971.
[9]
Bi, Y.-F.; Wang, Y.-Y.; Wu, Z.; Yang, X.-M. CN 106800582, 2017.
[10]
Li, M.-M.; Xia, F.; Li, C.-J.; Xu, G.; Qin, H.-B. Tetrahedron Lett. 2018, 59, 46.
[11]
Xu, D.-F.; Hu, H.; Guan, J.; Da, J.; Xie, Y.-P.; Liu, Y.-L.; Kong, R.; Song, G.-Q. Zhou, H. Chem. Biol. Drug Des. 2019, 94, 1656.
[12]
(a) Bianchini, G.; Balko, J.-M.; Mayer, I.-A.; Sanders, M.-E.; Gianni, L. Nat. Rev. Clin. Oncol. 2016, 13, 674.
[12]
(b) Biffi, G.; Tannahill, D.; Mccafferty, J.; Balasubramanian, S. Nat. Chem. 2013, 5, 182.
[12]
(c) Reed, J.-E.; Arnal, A.-A.; Neidle, S.; Vilar, R. J. Am. Chem. Soc. 2006, 128, 5992.
[12]
(d) Wang, T.; Zou, J.; Wu, Q.; Wang, R.; Yuan, C.-L.; Shun, J.; Zhai, B.-B.; Huang, X.-T.; Liu, N.-Z.; Hua, F.-Y.; Wang, X.-C.; Mei, W.-J. Eur. J. Pharmacol. 2021, 912, 174586.
[12]
(e) Wu, Q.; Zheng, K.-D.; Huang, X.-T.; Li, L.; Mei, W.-J. J. Med. Chem. 2018, 61, 10488.
[12]
(f) Zeng, L.; Wu, Q.; Wang, T.; Li, L.-P.; Zhao, X.-H.; Chen, K.; Qian, J.-Y.; Yuan, L.; Xu, H.; Mei, W.-J. Bioorg. Chem. 2021, 106, 104433.
[13]
Zhou, C.-X.; Gan, L.-D.; Zeng, L.-W.; Zhu, Z.-B. CN 103980341, 2014.
[14]
(a) Kusumi, T.; Kishi, T.; Kakisawa, H. J. Chem. Soc., Perkin Trans. 1 1976, 1716.
[14]
(b) Li, X.-B.; Cheng, X.; Zhang, D.-L.; Wu, H.-Q.; Ye, J.-T.; Du, J.; Huang, Z.-S.; Gu, L.-Q.; An, L.-K. Pharmazie 2014, 69, 163.
[15]
(a) Domagala, J.-M. J. Antimicrob. Chemother. 1994, 33, 685.
[15]
(b) Chen, Y.-L.; Fang, K.-C.; Sheu, J.-Y.; Hsu, S.-L.; Tzeng, C.-C. J. Med. Chem. 2001, 44, 2374.
[15]
(c) Wang, D.-D.; Zhang, W.-X.; Wang, T.-T.; Li, N. Mu, H.-B.; Zhang, J.-W.; Duan, J.-Y. Int. J. Mol. Sci. 2015, 16, 17668.
[16]
Qin, Y.-L.; Jin, Q.; Wu, X.-Z.; Wang, W. CN 106905408, 2017.
[17]
Su, M.; Wang, W. CN 107663224, 201.
[18]
(a) Li, Q.-N.; Huang, Z.-P.; Gu, Q.-L.; Zhi, Z.-E.; Yang, Y.-H.; He, L.; Chen, K.-L.; Wang, J.-X. Chin. J. Nat. Med. 2018, 16, 113.
[18]
(b) Wang, J.-X.; Huang, Z.-P.; He, L.; He, L.; You, Q.-D.; Li, X.-N. CN 107118254, 2017.
[19]
Sun, Q.-Y.; Zhang, W.-D.; Yuan, H. CN 107540725, 2018.
[20]
Zhang, K.-J.; Wang, K.-Z.; Zhang, X.-Y.; Qian, Z.-L.; Zhang, W.-B.; Zheng, X.; Wang, J.-Y.; Jiang, Y.; Zhang, W.-H.; Lu, Z.-Y.; Hao, H.-P.; Jiang, S. J. Med. Chem. 2022, 65, 7746.
[21]
Ding, C.-Y; Chen, H.-J.; Liang, B.; Jiao, M.-K.; Liang, G.; Zhang, A. Chem. Sci. 2019, 10, 4667.
[22]
Liu, J.-X.; Ren, J.; Yang, K.; Chen, S.; Yang, X.-N.; Zhao, Q.-S. Eur. J. Med. Chem. 2022, 235, 114294.
[23]
Huang, H.; Yao, Y.-F; Hou, G.-D.; Zhao, C.; Qin, J.-L.; Zhang, Y.-X.; Duan, Y.-T.; Song, C.-J.; Chang, J.-B. Eur. J. Med. Chem. 2021, 224, 113708.
[24]
Zheng, L.-H.; Zhang, Y.; Liu, G.-J.; Cheng, S.; Zhang, G.; An, C.; Sun, S.-P.; Wang, J.; Pang, B.; Li, S.-H. Anticancer Drugs 2020, 31, 601.
[25]
Jin, H.; Li, H.; Mao, S.-J.; Ma, W.-C.; Chen, Y.-T.; Liu, S.-Y. CN 102702302, 2012.
[26]
Liu, X.-W.; Chen, Z.-Y.; Wang, G.-L.; Ma, X.-T.; Gong, Y.; Liu, X.-L; Feng, T.-T.; Zhou, Y. Synth. Commun. 2017, 47, 2378.
[27]
(a) Ding, C.-Y.; Song, S.-S.; Jiao, M.-K.; Wang, Y.-Q.; Liao, Z.-H.; Zhang, A. CN 105622709, 2016,
[27]
(b) Xu, W.-Q.; Jiang, C.-F.; Yang, F.-J.; Shen, X.; Li, R.-F.; Xue, D. CN 103288916, 2013.
[28]
Wang, D.-D.; Lu, C.-B; Sun, F.-F.; Cui, M.-X.; Mu, H.-B.; Duan, J.-Y.; Geng, H.-L. Res. Microbiol. 2017, 168, 46.
[29]
Ding, C.-Y.; Tian, Q.-T.; Li, J.; Jiao, M.-K.; Song, S.-S.; Wang, Y.-Q.; Miao, Z.-M.; Zhang, A. J. Med. Chem. 2018, 61, 760.
[30]
Zhao, Q.-S.; Leng, Y.; Deng, X.; Zhao, Y.; Shen, Y.; Luo, X.-X. CN 102603861, 2012.
[31]
(a) Xu, D.-F.; Zhang, C.-X.; Ji, Y.-J. CN 102127037, 2011.
[31]
(b) Xu, D.-F. CN 106699771, 2017.
[32]
(a) Dong, Y.-Z.; Shi, Q.; Pai, H.-C.; Peng, C.-Y.; Pan, S.-L.; Teng, C.-M.; Nakagawa-Goto, N.; Yu, D.-L.; Liu, Y.-N.; Wu, P.-C.; Bastow, K.-F.; Morris-Natschke, S. L.; Brossi, A.; Lang, J.-Y.; Hsu, J. L.; Huang, M.-C.; Lee, E. Y. H. P.; Lee, K.-H. J. Med. Chem. 2010, 53, 2299.
[32]
(b) Wang, X.; Bastow, K.-F.; Sun, C.-M.; Lin, Y.-L.; Yu, H.-J.; Don, M.-J.; Wu, T.-S.; Nakamura, S.; Lee, K.-H. J. Med. Chem. 2004, 47, 5816.
[33]
Dong, Y.-Z.; Shi, Q.; Liu, Y.-N.; Wang, X.; Bastow, K.-F.; Lee, K.-H. J. Med. Chem. 2009, 52, 3586.
[34]
Dong, Y.-Z.; Shi, Q.; Nakagawa-Goto, K.; Wu, P.-C.; Morris-Natschke, S. L.; Brossi, A.; Bastow, K.-F.; Lang, J.-Y.; Huang, M.-C.; Lee, K.-H. Bioorg. Med. Chem. 2010, 18, 803.
[35]
Dong, Y.-Z.; Shi, Q.; Nakagawa-Goto, K.; Lai, C.-Y.; Morris-Natschke, S. L.; Bastow, K.-F.; Lee, K.-H. Bioorg. Med. Chem. Lett. 2010, 20, 4085.
[36]
Banerji, B.; Killi, S. K.; Katarkar, A.; Chatterjee, S.; Tangella, Y.; Prodhan, C.; Chaudhuri, K. Bioorg. Med. Chem. 2017, 25, 202.
[37]
Saquib, M.; Baig, M. H.; Khan, M. F.; Azmi, S.; Khatoon, S.; Rawat, A. K.; Dong, J. J.; Asad, M.; Arshad, M.; Hussain, M. K. ChemistrySelect 2021, 6, 8754.
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