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Chemistry of Natural Compounds

, Volume 55, Issue 6, pp 1002–1006 | Cite as

A New Lignanamide Derivative and Bioactive Constituents of Lycium chinense

  • Hui-Chu Huang
  • Li-Chai Chen
  • Tsung-Hsien Chang
  • Tong-Fei Zhu
  • Chun-Lin Chen
  • Ming-Jen Cheng
  • Jih-Jung ChenEmail author
Article
  • 16 Downloads

A new lignanamide derivative, lycichinenamide (1), has been isolated from the root barks of Lycium chinense together with nine known compounds, lyciumamide H (2), 5,2′-dihydroxy-6,7,8,6′-tetramethoxyflavone (3), 7α,8β-3′-O-methylcedrusin (4), smiglabrol (5), trans-N-caffeoyltyramine (6), vanillic acid (7), syringic acid (8), 2,6-dimethoxy-1,4-benzoquinone (9), and 1,5-dihydroxy-2-isoprenyl-3-methoxyxanthone (10). The structure of the new compound 1 was determined through spectroscopic and MS analyses. Among the isolates, lycichinenamide (1), lyciumamide H (2), smiglabrol (5), and trans-N-caffeoyltyramine (6) showed potent inhibition with IC50 values of 18.5 ± 2.1, 21.8 ± 1.8, 12.4 ± 0.3, and 24.6 ± 2.0 μM, respectively, against LPS-induced NO generation. In addition, 1,5-dihydroxy-2-isoprenyl-3-methoxyxanthone (10) exhibited anti-Dengue virus activity with IC50 value of 22.4 ± 1.6 μM against Dengue virus serotype 2 strain PL046.

Keywords

Lycium chinense Solanaceae root barks lignanamide anti-inflammatory activity anti-Dengue virus activity 

Notes

Acknowledgment

This research was supported by a grant from the Ministry of Science and Technology, Taiwan (MOST 106-2320-B-010-033-MY3) awarded to Prof. J.-J. Chen. This work was also supported by a grant from the Zuoying Branch of Kaohsiung Armed Forces General Hospital (ZBH 107-27). Hui-Chu Huang, Li-Chai Chen, Tsung-Hsien Chang, and Tong-Fei Zhu have contributed equally to this paper.

References

  1. 1.
    H. Chen, Y. J. Li, Y. J. Sun, J. H. Gong, K. Du, Y. L. Zhang, C. F. Su, Q. Q. Han, X. K. Zheng, and W. S. Feng, Fitoterapia, 122, 119 (2017).CrossRefGoogle Scholar
  2. 2.
    I. M. Chung, N. Praveen, S. J. Kim, and A. Ahmad, Asian J. Chem., 24, 885 (2012).Google Scholar
  3. 3.
    K. Jung, Y. W. Chin, Y. C. Kim, and J. Kim, Arch. Pharm. Res., 28, 1381 (2005).CrossRefGoogle Scholar
  4. 4.
    M. Terauchi, H. Kanamori, M. Nobuso, S. Fukuda, S. Yahara, and K. Yamasaki, J. Food Hyg. Soc. Jpn., 39, 399 (1998).CrossRefGoogle Scholar
  5. 5.
    M. Fan, L. Jiang, R. Yu, J. Zhao, X. Yuan, W. Wang, and L. Mei, Chem. Nat. Compd., 54, 1154 (2018).CrossRefGoogle Scholar
  6. 6.
    P. J. Tsai, W. C. Huang, M. C. Hsieh, P. J. Sung, Y. H. Kuo, and W. H. Wu, Molecules, 21, E15 (2015).CrossRefGoogle Scholar
  7. 7.
    Y. C. Shen, P. W. Hsieh, and Y. H. Kuo, Phytochemistry, 48, 719 (1998).CrossRefGoogle Scholar
  8. 8.
    S. Xu, M. Y. Shang, G. X. Liu, F. Xu, X. Wang, C. C. Shou, and S. Q. Cai, Molecules, 18, 5265 (2013).CrossRefGoogle Scholar
  9. 9.
    S. H. Han, H. H. Lee, I. S. Lee, Y. H. Moon, and E. R. Woo, Arch. Pharm. Res., 25, 433 (2002).CrossRefGoogle Scholar
  10. 10.
    S. L. Wang, T. L. Hwang, M. I. Chung, P. J. Sung, C. W. Shu, M. J. Cheng, and J. J. Chen, Molecules, 20, 20912 (2015).CrossRefGoogle Scholar
  11. 11.
    J. J. Chen, R. W. Lin, C. Y. Duh, H. Y. Huang, and I. S. Chen, J. Chin. Chem. Soc., 51, 665 (2004).CrossRefGoogle Scholar
  12. 12.
    C. Y. Chen, F. R. Chang, C. M. Teng, and Y. C. Wu, J. Chin. Chem. Soc., 46, 77 (1999).CrossRefGoogle Scholar
  13. 13.
    M. Iinuma, H. Tosa, T. Tanaka, F. Asai, Y. Kobayashi, R. Shimano, and K. Miyauchi, J. Pharm. Pharmacol., 48, 861 (1996).CrossRefGoogle Scholar
  14. 14.
    M. Johansson, B. Kopcke, H. Anke, and O. Sterner, J. Antibiot., 55, 104 (2002).CrossRefGoogle Scholar
  15. 15.
    Y. L. Lin, C. L. Liao, L. K. Chen, C. T. Yeh, C. I. Liu, S. H. Ma, Y. Y. Huang, Y. L. Huang, C. L. Kao, and C. C. King, J. Virol., 72, 9729 (1998).PubMedPubMedCentralGoogle Scholar
  16. 16.
    S. F. Wu, C. J. Lee, C. L. Liao, R. A. Dwek, N. Zitzmann, and Y. L. Lin, J. Virol., 76, 3596 (2002).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Hui-Chu Huang
    • 1
  • Li-Chai Chen
    • 2
  • Tsung-Hsien Chang
    • 3
  • Tong-Fei Zhu
    • 4
  • Chun-Lin Chen
    • 5
  • Ming-Jen Cheng
    • 6
  • Jih-Jung Chen
    • 7
    • 8
    Email author
  1. 1.Department of Respiratory CareZuoying Branch of Kaohsiung Armed Forces General HospitalKaohsiungTaiwan
  2. 2.Department of PharmacyTajen UniversityPingtungTaiwan
  3. 3.Department of Medical Education and ResearchKaohsiung Veterans General HospitalKaohsiungTaiwan
  4. 4.Chongqing Medical and Pharmaceutical CollegeChongqingP. R. China
  5. 5.Department of Biological SciencesNational Sun Yat-Sen UniversityKaohsiungTaiwan
  6. 6.Bioresource Collection and Research Center (BCRC)Food Industry Research and Development Institute (FIRDI)HsinchuTaiwan
  7. 7.Faculty of Pharmacy, School of Pharmaceutical SciencesNational Yang-Ming UniversityTaipeiTaiwan
  8. 8.Department of Medical ResearchChina Medical University HospitalTaichungTaiwan

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