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Dibenzocyclooctadiene lignans from Artemisia sieversiana and their anti-inflammatory activities

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Abstract

Abstract

Two previously undescribed dibenzocyclooctadiene lignans, named sieverlignans D–E (12), as well as eight known ones (310), were isolated from the aerial parts of Artemisia sieversiana. Their structures were elucidated from extensive spectroscopic analysis, including HRMS, NMR and electronic circular dichroism (ECD) experiments. This study is the first to report dibenzocyclooctadiene lignans in the genus Artemisia and this plant. All the compounds were evaluated for their anti-neuroinflammatory activities on the lipopolysaccharides (LPS)-induced nitric oxide production in BV-2 murine microglial cells. Compounds 1 and 6 exhibited the moderate activities with their IC50 values of 47.7 and 21.9 μM, compared to a positive control quercetin with the IC50 value of 16.0 μM.

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References

  1. Jiangsu College of New Medicine (1977) A Comprehensive Dictionary of Traditional Chinese Medicine, Shanghai Scientific & Technical Publishers, Shanghai, pp 627–629

  2. Chang W-T, Wu S-N (2020) Inhibitory effectiveness of gomisin A, a dibenzocyclooctadiene lignan isolated from Schizandra chinensis, on the amplitude and gating of voltage-gated Na+ current. Int J Mol Sci 21:8816

    Article  CAS  Google Scholar 

  3. Park W-S, Koo K-A, Bae J-Y, Kim H-J, Kang D-M, Kwo J-M, Paek S-M, Lee M-K, Kim C-Y, Ahn M-J (2021) Dibenzocyclooctadiene lignans in plant parts and fermented beverages of Schisandra chinensis. Plants 10:361

    Article  CAS  Google Scholar 

  4. Choi S-K, Lee Y-G, Wang R-B, Kim H-G, Yoon D, Lee D-Y, Kim Y-J, Baek N-I (2020) Dibenzocyclooctadiene lignans from the fruits of Schisandra chinensis and their cytotoxicity on human cancer cell lines. Applied Biological Chemistry 63:39

    Article  CAS  Google Scholar 

  5. Tan R-X, Tang H-Q, Hu J, Shuai B (1998) Lignans and sesquiterpene lactones from Artemisia sieversiana and Inula racemosa. Phytochemistry 49:157–161

    Article  CAS  Google Scholar 

  6. Tang H-Q, Hu J, Yang L, Tan R-X (2000) Terpenoids and flavonoids from Artemisia species. Planta Med 66:391–393

    Article  CAS  Google Scholar 

  7. Zhang Q, Guo G-N, Miao R-D, Chen N-Y, Wang Q (2004) Studies on the chemical constituents of Artemisia sieversiana and their anticancer activities. J Lanzhou Univ (Nat Sci) 40:68–71

    CAS  Google Scholar 

  8. Zhou X-D, Chai X-Y, Zeng K-W, Zhao M-B, Jiang Y, Tu P-F (2015) Artesin A, a new cage-shaped dimeric guaianolide from Artemisia sieversiana. Tetrahedron Lett 56:1141–1143

    Article  CAS  Google Scholar 

  9. Zhou X-D, Zhang C, He S, Zheng B, Zeng K-W, Zhao M-B, Jiang Y, Tu P-F (2017) New terpenoids and thiophene derivatives from the aerial parts of Artemisia sieversiana. Bioorg Med Chem Lett 27:5441–5445

    Article  CAS  Google Scholar 

  10. Chen M, Kilgore N, Lee K-H, Chen D-F (2006) Rubrisandrins A and B, lignans and related anti-HIV compounds from Schisandra rubriflora. J Nat Prod 69:1697–1701

    Article  CAS  Google Scholar 

  11. Piao L-Z, Lee Y-J, Phamp-hu T-T, Shin J-K (2005) Dibenzocyclooctene lignan compounds isolated from the fruits of Schisandra chinensis Bail. Nat Prod Sci 11:248–252

    CAS  Google Scholar 

  12. Zhao X-M, Guo F-J, Li Y-M, Zhu D-Y (2012) Two new lignans from Celastrus flagellaris Rupr. J Asian Nat Prod Res 14:159–164

    Article  CAS  Google Scholar 

  13. Li R-T, Han Q-B, Zheng Y-T, Wang R-R, Yang L-M, Peng L-Y, Xiao W-L, Sun H-D (2005) Anti-HIV lignans from Schisandra micrantha. Chin J Nat Med 3:208–212

    CAS  Google Scholar 

  14. Yang L-B, Huang S-X, Pu J-X, Li L-M, Zhao Y (2012) Lignans from Schisandra elongate (BI.) Baill. Chinese Tradit Pat Med 34:2365–2368

    CAS  Google Scholar 

  15. Jiang S-J, Wang Y-H, Chen D-F (2005) Sphenanlignan, a new lignan from the seeds of Schisandra sphenanthera. Chin J Nat Med 3:78–82

    CAS  Google Scholar 

  16. Chen H-Y, Zhou C-X, Yao W, Wang L-W, Dou H, Dong X-W, Zhao Y (2005) An NMR study of two lignans isolated from Schisandra Chinensis. Chinese J Magn Reson 22:43–54

    Google Scholar 

  17. Chen M, Xu X-M, Xu B, Yang P-P, Liao Z-H, Morris-Natschke S-L, Lee K-H, Chen D-F (2013) Neglschisandrins E-F: two new lignans and related cytotoxic lignans from Schisandra neglecta. Molecules 18:2297–2306

    Article  CAS  Google Scholar 

  18. Shen Y-C, Lin Y-C, Cheng Y-B, Chiang M-Y, Liou S-S (2009) Dibenzocyclooctadiene lignans from Kadsura philippinensis. Phytochemistry 70:114–120

    Article  CAS  Google Scholar 

  19. Ikeya Y, Taguchi H, Sasaki H, Nakajima K, Yosioka I (1980) The constituents of Schizandra chinensis Baill VI 13C nuclear magnetic resonance spectroscopy of dibenzocyclooctadiene lignans. Chem Pharm Bull 28:2414–2421

    Article  CAS  Google Scholar 

  20. Wu H-H, Li Z-F, Zhang Q-H, Pei Y-H (2010) Application of CD in study of the absolute configuration of lignans. J Shenyang Pharm Univ 27:587–594

    CAS  Google Scholar 

  21. Ikeya Y, Taguchi H, Yosioka I (1978) The constituents of Schizandra chinensis BAILL. The structures of three new lignans, angeloylgomisin H, tigloylgomisin H and benzoylgomisin H, and the absolute structure of schizandrin. Chem Pharm Bull 26:328–331

    Article  CAS  Google Scholar 

  22. Ikeya Y, Taguchi H, Yosioka I, Kobayashi H (1979) The constituents of Schizandra chinensis Baill. I. Isolation and structure determination of five new lignans, gomisin A, B, C, F and G, and the absolute structure of schizandrin. Chem Pharm Bull 27:1383–1394

    Article  CAS  Google Scholar 

  23. Zhang C, Wang S, Zeng K-W, Cui F-X, Jin H-W, Guo X-Y, Jiang Y, Tu P-F (2014) Bioorg Med Chem Lett 24:4318–4322

    Article  Google Scholar 

  24. Hu D, Yang Z-Y, Yao X-C, Wang H, Han N, Liu Z-H, Wang Y, Yang J-Y, Yin J (2014) Dibenzocyclooctadiene lignans from Schisandra chinensis and their inhibitory activity on NO production in lipopolysaccharide-activated microglia cells. Phytochemistry 104:72–78

    Article  CAS  Google Scholar 

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Acknowledgements

The authors express thanks to the analytical center of Peking University Health Science Center for measurements of MS and NMR. This work is financially supported by grants from the National Natural Science Foundation of China (Nos. 81903514 and 81473106) and the key research and Development Projects of Hunan Science Technology Department (No.2016NK2133).

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Correspondence to Wei Wang or Peng-Fei Tu.

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Zhou, XD., Chen, CX., Zheng, XK. et al. Dibenzocyclooctadiene lignans from Artemisia sieversiana and their anti-inflammatory activities. J Nat Med 75, 1014–1020 (2021). https://doi.org/10.1007/s11418-021-01532-y

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