Skip to main content
SpringerLink
Log in

New Benzophenone and Bioactive Constituents from Hypericum nagasawae

  • Published:
Chemistry of Natural Compounds Aims and scope

A new benzophenone derivative, hyperinagasone (1), has been isolated from the aerial part of Hypericum nagasawae together with six known compounds, trichadonic acid (2), norathyriol (3), euxanthone (4), subalatin (5), hyperielliptone D (6), and 1,4-O-diferuloylsecoisolariciresinol (7). The structure of new compound 1 was determined through spectroscopic and MS analyses. Among the isolates, compounds 2, 4, and 7 exhibited cytotoxicities, with IC50 values of 17.25 ± 1.55, 18.14 ± 1.07, and 10.31 ± 0.92 μM, respectively, against the DLD-1 cell line. Compounds 2, 5, and 7 also exhibited cytotoxicities, with IC50 values of 15.10 ± 1.13, 15.89 ± 0.94, and 17.54 ± 1.16 μM, respectively, against the CCRF-CEM cell line. Norathyriol (3) and 7 exhibited cytotoxicities, with IC50 values of 19.62 ± 2.88 and 6.26 ± 0.50 μM, respectively, against HL-60 cell line. Hyperinagasone (1) and 1,4-O-diferuloylsecoisolariciresinol (7) exhibited cytotoxicities, with IC50 values of 16.83 ± 1.55 and 11.38 ± 0.87 μM, respectively, against the IMR-32 cell line. In addition, 3, 4, and 7 showed potent inhibition, with IC50 values of 5.89 ± 0.43, 7.55 ± 0.54, and 8.12 ± 0.91 μM, respectively, against LPS-induced NO generation.

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

Similar content being viewed by others

References

  1. N. K. B. Robson, Guttiferae in Flora of Taiwan, Vol. 2, 2nd Ed., Editorial Committee of the Flora of Taiwan, Taipei, Taiwan, 1996, pp. 694–714.

  2. F. S. Wu, C. J. Hung, C. L. Lin, H. Y. Huang, Y. H. Kuo, T. H. Chang, C. L. Chen, P. J. Sung, M. J. Cheng, C. W. Kuo, and J. J. Chen, Chem. Nat. Compd., 57, 645 (2021).

    Article  CAS  Google Scholar 

  3. D. Hong, F. Yin, L. H. Hu, and P. Lu, Phytochemistry, 65, 2595 (2004).

    Article  CAS  Google Scholar 

  4. C. Y. Huang, T. C. Chang, Y. J. Wu, Y. Chen, and J. J. Chen, Molecules, 25, 4463 (2020).

    Article  CAS  Google Scholar 

  5. Z. Y. Xiao, Y. H. Zeng, Q. Mu, W. K. P. Shiu, and S. Gibbons, Chem. Biodiv., 7, 953 (2010).

    Article  CAS  Google Scholar 

  6. Q. Chen, L. Di, Y. Zhang, and N. Li, J. Ethnopharmacol., 259, 112948 (2020).

    Article  CAS  Google Scholar 

  7. H. Zhu, C. Chen, J. Yang, X. N. Li, J. Liu, B. Sun, S. X. Huang, D. Li, G. Yao, Z. Luo, Y. Li, J. Zhang, Y. Xue, and Y. Zhang, Org. Lett., 16, 6322 (2014).

    Article  CAS  Google Scholar 

  8. P. T. Nedialkov, D. Zheleva-Dimitrova, G. Momekov, K. Karlov, U. Girreser, and G. M. Kitanov, Nat. Prod. Res., 25, 1743 (2011).

    Article  CAS  Google Scholar 

  9. M.-G. F. Guefack, F. Damen, A. T. Mbaveng, S. B. Tankeo, G. T. M. Bitchagno, I. Celik, J. D. S. Mpetga, and V. Kuete, Evid. Based Complement. Alternat. Med., 2020, 4314807 (2020).

    Article  Google Scholar 

  10. C. Cirak, Biochem. Syst. Ecol., 34, 897 (2006).

    Article  CAS  Google Scholar 

  11. T. T. Dao, T. T. Dang, P. H. Nguyen, E. Kim, P. T. Thuong, and W. K. Oh, Bioorg. Med. Chem. Lett., 22, 3688 (2012).

    Article  CAS  Google Scholar 

  12. M.-T. Chen, Heterocycles, 27, 2589 (1988).

    Article  CAS  Google Scholar 

  13. F. Damen, J. D. Simo Mpetga, O. M. F. Demgne, I. Celik, B. E. N. Wamba, L. A. Tapondjou, V. P. Beng, S. Levent, V. Kuete, M. Tene, Nat. Prod. Res., 36, 2071 (2022).

    Article  CAS  Google Scholar 

  14. S.-S. Moon, A. A. Rahman, J.-Y. Kim, and S.-H. Kee, Bioorg. Med. Chem., 16, 7264 (2008).

    Article  CAS  Google Scholar 

  15. T. Mosmann, J. Immunol. Meth., 65, 55 (1983).

    Article  CAS  Google Scholar 

  16. M. Johansson, B. Kopcke, H. Anke, and O. Sterner, J. Antibiot., 55, 104 (2002).

    Article  CAS  Google Scholar 

Download references

Acknowledgment

This research was supported by the grant from the Ministry of Science and Technology, Taiwan (MOST 109-2320-B-010-029-MY3), awarded to Prof. J.-J. Chen. This work was also supported by the grants from Far Eastern Memorial Hospital–National Yang Ming Chiao Tung University Joint Research Program (110DN21), Medical Research Fund (KAFGH-A-110002) of Kaohsiung Armed Forces General Hospital, and Kaohsiung Veterans General Hospital Tainan Branch (VHYK110-07). We gratefully thank Ms. Shou-Ling Huang and Dr. Iren Wang for the assistance in NMR experiments of the Instrumentation Center at NTU, which is supported by the Ministry of Science and Technology, Taiwan. Fu-Sen Wu, I-Chou Wang, Chia-Ching Liaw, and Hsueh-Yang Huang have contributed equally to this manuscript.

Author information

Authors and Affiliations

  1. Department of Pharmacy, Far Eastern Memorial Hospital, 220, New Taipei City, Taiwan

    Fu-Sen Wu

  2. Department of Physical Medicine and Rehabilitation, Kaohsiung Veterans General Hospital Tainan Branch, 710, Tainan City, Taiwan

    I-Chou Wang

  3. Division of Chinese Materia Medica Development, National Research Institute of Chinese Medicine, 112, Taipei, Taiwan

    Chia-Ching Liaw

  4. Department of Pharmacy, Kaohsiung Armed Forces General Hospital, 802, Kaohsiung, Taiwan

    Hsueh-Yang Huang & Chu-Wen Kuo

  5. Institute of Microbiology and Immunology, National Defense Medical Center, 114, Taipei, Taiwan

    Tsung-Hsien Chang

  6. Department of Biological Sciences, National Sun Yat-Sen University, 804, Kaohsiung, Taiwan

    Chun-Lin Chen

  7. National Museum of Marine Biology and Aquarium, 944, Pingtung, Taiwan

    Ping-Jyun Sung

  8. Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), 300, Hsinchu, Taiwan

    Ming-Jen Cheng

  9. Department of Pharmacy, School of Pharmaceutical Sciences, National Yang Ming Chiao Tung University, 112, Taipei, Taiwan

    Jih-Jung Chen

  10. Department of Medical Research, China Medical University Hospital, China Medical University, 404, Taichung, Taiwan

    Jih-Jung Chen

Authors
  1. Fu-Sen Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I-Chou Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chia-Ching Liaw
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hsueh-Yang Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Tsung-Hsien Chang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Chun-Lin Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ping-Jyun Sung
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Ming-Jen Cheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Chu-Wen Kuo
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Jih-Jung Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jih-Jung Chen.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2022, pp. 704–708.

Rights and permissions

Springer Nature or its licensor 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

Wu, FS., Wang, IC., Liaw, CC. et al. New Benzophenone and Bioactive Constituents from Hypericum nagasawae. Chem Nat Compd 58, 833–838 (2022). https://doi.org/10.1007/s10600-022-03810-x

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-022-03810-x

Keywords

Search

Navigation