Skip to main content
SpringerLink
Log in

Two New Chromones from Cassia auriculata and Their Antiviral Activity

  • Published:
Chemistry of Natural Compounds Aims and scope

Two new chromones, 2-(2-(furan-2-yl)-2-oxoethyl)-6-methoxy-8-(2-oxopropyl)-chromone (1) and 2-(2-(furan-2-yl)-2-oxoethyl)-5-methoxy-8-(2-oxopropyl)-chromone (2), along with four known ones (3–6) were isolated from the stem bark of Cassia auriculata. The new compounds were elucidated by means of spectroscopic methods, whereas the known compounds were identified by comparison with the data in the literature. Compounds 1 and 2 were tested for their anti-tobacco mosaic virus (anti-TMV) activities. The results revealed that 1 and 2 exhibited potential anti-TMV activities with inhibition rates of 28.2 and 30.5% respectively, and these rates are close to that of the positive control. Compounds 1 and 2 were also tested for their anti-rotavirus activities, and compounds 1 and 2 showed potential activity with therapeutic index (TI) values of 14.8 and 15.9 respectively. These values are lower than that of the positive control.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.

Similar content being viewed by others

References

  1. A. A. H. Abdel-Rahman, A. K. Shaban, I. F. Nassar, D. S. El-Kady, N. S. Ismail, S. F. Mahmoud, H. M. Awad, and W. A. El-Sayed, Molecules, 26 (13), 3923 (2021).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. E. W. Matthew, A. S. Scott, and R. S. Brent, Curr. Opin. Chem. Biol., 14, 347 (2010).

    Article  Google Scholar 

  3. Y. Amen, M. Elsbaey, A. Othman, M. Sallam, and K. Shimizu, Molecules, 26 (24), 7646 (2021).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. N. A. ul Mohsin, M. Irfan, S. ul Hassan, and U. Saleem, Pharm. Chem. J., 54, 241 (2020).

  5. A. T. Benny, S. D. Arikkatt, C. G. Vazhappilly, S. Kannadasan, R. Thomas, M. S. Leelabaiamma, E. K. Radhakrishnan, and P. Shanmugam, Mini-Rev. Med. Chem., 22 (7), 1030 (2022).

    Article  CAS  PubMed  Google Scholar 

  6. D. L. Wu, Flora of China, Vol. 39, Chinese Science Press, Beijing, 1988, p. 123.

  7. J. Cai, J. Q. He, X. M. Wang, X. Shu, and L. Wu, Chin. J. Agric. Sci. Bull., 27, 142 (2011).

    Google Scholar 

  8. B. Kumar, V. Bajpai, V. Gond, S. Pal, and N. Chattopadhyay, Phytochemistry of Plants of Genus Cassia, CRC Press, 2021.

  9. Y. D. Duan, Y. Y. Jiang, F. X. Guo, L. X. Chen, L. L. Xu, W. Zhang, and B. Liu, Fitoterapia, 135, 114 (2019).

    Article  CAS  PubMed  Google Scholar 

  10. M. Zhou, K. Zhou, X. M. Gao, Z. Y. Jiang, J. J. Lv, Z. H. Liu, G. Y. Yang, M. M. Miao, C. T. Che, and Q. F. Hu, Org. Lett., 17 (11), 2638 (2015).

    Article  CAS  PubMed  Google Scholar 

  11. P. S. Yang, J. M. Dai, X. J. Gu, W. Xiong, D. Q. Huang, S. Y. Qiu, J. N. Zheng, Y. Li, F. X. Yang, and M. Zhou, Molecules, 27, 3129 (2022).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. L. M. Liao, Y. Q. Sun, J. Li, W. S. Kong, X. Liu, Y. Xu, H. T. Huang, W. L. Zeng, Q. L. Mi, G. Y. Yang, Q. F. Hu, and Y. K. Li, Chem. Nat. Compd., 56, 58 (2020).

    Article  CAS  Google Scholar 

  13. J. R. Jiang, J. D. Zhang, G. Y. Yin, J. Q. Shi, B. B. Cai, W. W. Yang, L. L. Deng, L. Xu, T. Zhou, Q. F. Hu, M. Zhou, and W. S. Kong, Chem. Nat. Compd., 58, 414 (2022).

    Article  Google Scholar 

  14. Q. L. Mi, W. S. Kong, Y. K. Li, X. Liu, W. L. Zeng, H. Y. Xiang, M. Dongiao, G. Y. Yang, Q. F. Hu, W. G. Wang, Q. Gao, and M. Zhou, Chem. Nat. Compd., 57, 432 (2021).

    Article  CAS  Google Scholar 

  15. Z. Zhang, S. W. Ni, X. Xu, W. Z. Huang, S. S. Wang, H. Zhu, and X. M. Gao, China J. Chin. Mater. Med., 46 (15), 3873 (2021).

    Google Scholar 

  16. P. S. Vijayaraj, K. Muthukumar, J. Sabarirajan, and V. Nachiappan, Ind. J. Biochem. Biophys., 48, 54 (2011).

    CAS  Google Scholar 

  17. G. S. Seethapathy, D. Ganesh, J. U. S. Kumar, U. Senthilkumar, S. G. Newmaster, S. Ragupathy, R. U. Shaanker, and G. Ravikanth, Int. J. Legal. Med., 129, 693 (2015).

    Article  PubMed  Google Scholar 

  18. U. Namdaung, N. Aroonrerk, S. Suksamrarn, K. Danwisetkanjana, J. Saenboonrueng, W. Arjchomphu, and A. Suksamrarn, Chem. Pharm. Bull., 54 (10), 1433 (2006).

    Article  CAS  Google Scholar 

  19. Q. F. Hu, B. Zhou, X. M. Gao, L. Y. Yang, L. D. Shu, Y. Q. Shen, G. P. Li, C. T. Che, and G. Y. Yang, J. Nat. Prod., 75, 1909 (2012).

    Article  CAS  PubMed  Google Scholar 

  20. G. Speranza, G. Fontana, S. Zanzola, and A. di Meo, J. Nat. Prod., 60, 692 (1997).

    Article  CAS  Google Scholar 

  21. T. Zhou, F. X. Yang, B. B. Cai, F. Wu, Y. N. Zhu, L. Liu, C. B. Liu, J. Ling, W. S. Kong, G. Y. Yang, Q. F. Hu, and X. Liu, Chem. Nat. Compd., 57, 1019 (2021).

    Article  CAS  Google Scholar 

  22. C. M. Johna, P. Sandrasaigaran, C. K. Tong, A. Adam, and R. Ramasamy, Cell. Immunol., 271, 474 (2011).

    Article  Google Scholar 

  23. K. B. Thorat and V. V. Nimbalkar, World. J. Pharm. Res., 10 (4), 448 (2021).

    CAS  Google Scholar 

  24. W. G. Wang, J. Wang, Y. Xu, H. T. Huang, W. L. Zeng, J. Li, W. S. Kong, X. Liu, G. Qian, G. Y. Yang, Q. F. Hu, and Y. K. Li, Chem. Nat. Compd., 55, 1018 (2019).

    Article  CAS  Google Scholar 

  25. G. H. Kong, Z. Y. Xia, F. Wu, Y. N. Zhu, J. Li, W. S. Kong, M. Zhou, G. Y. Yang, Q. F. Hu, and Y. P. Wu, Heterocycles, 100, 2083 (2020).

    Article  CAS  Google Scholar 

  26. G. Y. Yang, J. M. Dai, Q. L. Mi, Z. J. Li, Xue-Mei Li, J. D. Zhang, J. Wang, Y. K. Li, W. G. Wang, M. Zhou, and Q. F. Hu, Phytochemistry, 198, 113137 (2022).

  27. M. Zhou, M. M. Miao, G. Du, S. Z. Shang, W. Zhao, Z. H. Liu, G. Y. Yang, C. T. Che, Q. F. Hu, and X. M. Gao, Org. Lett., 16, 5016 (2014).

    Article  CAS  PubMed  Google Scholar 

  28. G. Y. Yang, J. M. Dai, Z. J. Li, J. Wang, F. X. Yang, X. Liu, J, Li, Q. Gao, X. M. Li, Y. K. Li, W. G. Wang, M. Zhou, and Q. F. Hu, Arch. Pharm. Res., 45, 572 (2022).

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgment

This project was supported financially by the Foundation of Yunnan Basic Research Program (No. 2019FD119), the National Natural Science Foundation of China (No. 32260111), the Yunnan Applied Basic Research Projects for Excellent Young Scholars (No. 202001AW079992), and the Yunnan Innovative Research Team (2019HC020).

Author information

Authors and Affiliations

  1. Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal, State Ethnic Affairs Commission, Yunnan Minzu University, 650031, Kunming, P. R. China

    Xiao-Shan Liu, Jun-Na Zheng, Si-Yu Shen, Shan-Shan Li, Yin-Ke Li, Min Zhou, Qiu-fen Hu & Dong Miao

  2. Tobacco Research Institute, Chinese Academy of Agricultural Sciences, 266101, Qingdao, P. R. China

    Xiao-Shan Liu, Si-Yu Shen, Shan-Shan Li & Da-Ping Gong

  3. Yunnan Key Laboratory of Tobacco Chemistry, China Tobacco Yunnan Industrial Co., Ltd, 650231, Kunming, P. R. China

    Wen Xiong, Xiao-Wei Ma, Yin-Ke Li & Feng-Mei Zhang

Authors
  1. Xiao-Shan Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jun-Na Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Si-Yu Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wen Xiong
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Shan-Shan Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Xiao-Wei Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yin-Ke Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Min Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Da-Ping Gong
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Qiu-fen Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Dong Miao
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. Feng-Mei Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Dong Miao or Feng-Mei Zhang.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2023, pp. 396–399.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, XS., Zheng, JN., Shen, SY. et al. Two New Chromones from Cassia auriculata and Their Antiviral Activity. Chem Nat Compd 59, 467–471 (2023). https://doi.org/10.1007/s10600-023-04025-4

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-023-04025-4

Keywords

Search

Navigation