ORIGINAL ARTICLES |
|
|
|
|
|
Artemlavanins A and B from Artemisia lavandulaefolia and Their Cytotoxicity Against Hepatic Stellate Cell Line LX2 |
Cheng Shen1,2,3, Xiao-Yan Huang1,2, Chang-An Geng1,2, Tian-Ze Li1,2, Shuang Tang1,2,3, Li-Hua Su1,2,3, Zhen Gao1,2,3, Xue-Mei Zhang1,2, Jing Hu1,2, Ji-Jun Chen1,2,3 |
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China |
|
|
Abstract Two new sesquiterpenoids, artemlavanins A (1) and B (3), together with fifteen known compounds (2 and 4-17) were isolated from the EtOH extract of Artemisia lavandulaefolia. The structures of new compounds were elucidated by extensive spectroscopic analyses (HRESIMS, 1D and 2D NMR) and ECD calculations. Compound 1 was a sesquiterpenoid lactone possessing a rearranged eudesmane skeleton; compounds 2-5, 6-8, 9 and 10-12 belonged to the eudesmane, guaiane, oppositane and farnesane sesquiterpenoids, respectively; compounds 13-17 were the phenyl derivatives with a 4-hydroxy-acetophenone moiety. Twelve compounds (1-3, 5-7, 10-12, 14, 15 and 17) displayed cytotoxicity against hepatic stellate cell line LX2 (HSC-LX2) with IC50 values ranging from 35.1 to 370.3 μM. Compounds 2, 7, 10-12 and 17 exhibited the stronger cytotoxicity than silybin (IC50, 169.6 μM) with IC50 values of 82.1, 35.1, 95.0, 83.8, 81.6 and 90.1 μM. Compound 7 as the most active one showed significant inhibition on the deposition of human collagen type I (Col I), human hyaluronic acid (HA) and human laminin (HL) with IC50 values of 10.7, 24.5 and 13.3 μM.
|
Keywords
Artemisia lavandulaefolia
Sesquiterpenoids
Artemlavanins
Cytotoxicity
HSC-LX2
|
Fund:This work was supported by the Yunnan Wanren Project (YNWR-KJLJ-2019-002), the Program of Yunling Scholarship, the Reserve Talents of Young and Middle-aged Academic and Technical Leaders in Yunnan Province, and the Youth Innovation Promotion Association, CAS (2013252). |
Corresponding Authors:
Ji-Jun Chen
E-mail: chenjj@mail.kib.ac.cn
|
Issue Date: 19 August 2020
|
|
|
1. S.K. Asrani, H. Devarbhavi, J. Eaton, P.S. Kamath, J. Hepatol. 70, 151-171 (2019) 2. L. Chen, D.A. Brenner, T. Kisseleva, Hepatol. Commun. 3, 180-192 (2019) 3. D. Schuppan, M. Ashfaq-Khan, A.T. Yang, Y.O. Kim, Matrix Biol. 68-69, 435-451 (2018) 4. C. Trautwein, S.L. Friedman, D. Schuppan, M. Pinzani, J. Hepatol. 62, S15-S24 (2015) 5. W.D. Zhang, R.F. Wang, H.M. Wu, H. Yang, G.C. Wang, Acta Pharm. Sin. 53, 667-675 (2018) 6. L. Shan, Z.N. Liu, L.L. Ci, C. Shuai, X.W. Lv, J. Li, Int. Immunopharmacol. 75, 105765 (2019) 7. J.M. Han, H.G. Kim, M.K. Choi, J.S. Lee, J.S. Lee, J.H. Wang, H.J. Park, S.W. Son, S.Y. Hwang, C.G. Son, Exp. Toxicol. Pathol. 65, 837-844 (2013) 8. Y. Zhao, C.A. Geng, C.L. Sun, Y.B. Ma, X.Y. Huang, T.W. Cao, K. He, H. Wang, X.M. Zhang, J.J. Chen, Fitoterapia 95, 187-193 (2014) 9. Z.Q. Wang, X.H. Zhang, Y.M. Yu, R.C. Tipton, I. Raskin, D. Ribnicky, W. Johnson, W.T. Cefalu, Metabolism 62, 1239-1249 (2013) 10. H.D. Yuan, G.Z. Jin, G.C. Piao, J. Ethnopharmacol. 127, 528-533 (2010) 11. N. Amat, H. Upur, B. Blažeković, J. Ethnopharmacol. 131, 478-484 (2010) 12. M.L. Corrêa-Ferreira, M.H. Verdan, F.A. dos Reis Lívero, L.F. Galuppo, J.E.Q. Telles, M.É.A. Stefanello, A. Acco, C.L. de Oliveira Petkowicz, Phytomedicine 24, 68-76 (2017) 13. J.M. Han, H.G. Kim, M.K. Choi, J.S. Lee, H.J. Park, J.H. Wang, J.S. Lee, S.W. Son, S.Y. Hwang, C.G. Son, Food Chem. Toxicol. 50, 3505-3513 (2012) 14. M. Sefi, H. Bouaziz, N. Soudani, T. Boudawara, N. Zeghal, Pestic. Biochem. Physiol. 101, 71-79 (2011) 15. S. Wang, J. Li, J. Sun, K.W. Zeng, J.R. Cui, Y. Jiang, P.F. Tu, Fitoterapia 85, 169-175 (2013) 16. J.D. Cha, Y.H. Kim, J.Y. Kim, Food Sci. Biotechnol. 19, 185-191 (2010) 17. J.D. Cha, M.R. Jeong, H.J. Choi, S.I. Jeong, S.E. Moon, S.I. Yun, Y.H. Kim, B.S. Kil, Y.H. Song, Planta Med. 71, 575-577 (2005) 18. L. Ma, B.H. Wei, L. Hu, J. Guangzhou Univ. Tradit. Chin. Med. 29, 450-453 (2012) 19. L.F. Ding, G.M. Yang, Y.D. Guo, L.D. Song, X.D. Wu, Chin. Tradit. Herb. Drugs 49, 1995-1999 (2018) 20. L.F. Ding, L.Y. Peng, H.F. Zhou, L.D. Song, X.D. Wu, Q.S. Zhao, Tetrahedron Lett. 61, 151872 (2020) 21. J.L. Lv, Z. Li, L.M. Guo, L.B. Zhang, Chem. Biodiversity 15, e1700548 (2018) 22. X.Q. Wang, C.J. Zhou, N. Zhang, G. Wu, M.H. Li, J. Chin. Med. Mater. 34, 234-236 (2011) 23. J.Y. Xie, G.L. Zhang, Z.G. Yu, Chin. J. Pestic. Sci. 21, 383-388 (2019) 24. L. Ma, H.L. Zhou, Y.M. Gong, L. Hu, Q. Duan, Tradit. Chin. Drug Res. Clin. Pharmacol. 23, 555-578 (2012) 25. W.G. Dauben, P.D. Hance, W.K. Hayes, J. Am. Chem. Soc. 77, 4609-4612 (1955) 26. M. Sumi, W.G. Dauben, W.K. Hayes, J. Am. Chem. Soc. 80, 5704-5705 (1958) 27. Y. Peng, J. Xiao, X.B. Xu, S.M. Duan, L. Ren, Y.L. Shao, Y.W. Wang, Org. Lett. 18, 5170-5173 (2016) 28. Y.S. Cai, Z. Wu, X.Q. Zheng, C. Wang, J.R. Wang, X.X. Zhang, G.F. Qiu, K.K. Zhu, S.G. Cao, J.Q. Yu, Org. Chem. Front. 7, 303-309 (2020) 29. T.A. Van Beek, R. Kleis, M.A. Posthumus, A. Van Veldhuizen, Phytochemistry 28, 1909-1911 (1989) 30. X.L. Gao, Z.M. Xiong, G. Zhou, Y.L. Li, Synthesis 1, 37-39 (2001) 31. J. Jakupovic, A. Schuster, F. Bohlmann, M.O. Dillon, Phytochemistry 27, 1113-1120 (1988) 32. T. Ohmoto, K. Ikeda, S. Nomura, M. Shimizu, S. Saito, Chem. Pharm. Bull. 35, 2272-2279 (1987) 33. M.A. Metwally, J. Jakupovic, M.I. Youns, F. Bohlmann, Phytochemistry 24, 1103-1104 (1985) 34. V.E. Sosa, J.C. Oberti, R.R. Gil, E.A. Rúveda, V.L. Goedken, A.B. Gutiérrez, W. Herz, Phytochemistry 28, 1925-1929 (1989) 35. H.F. Wong, G.D. Brown, J. Nat. Prod. 65, 481-486 (2002) 36. A.A. Ahmed, T. Gáti, T.A. Hussein, A.T. Ali, O.A. Tzakou, M.A. Couladis, T.J. Mabry, G. Tóth, Tetrahedron 59, 3729-3735 (2003) 37. L.R. Soares, Quim. Nova. 35, 323-326 (2012) 38. K.K. Wan, C.D. Evans-Klock, B.C. Fielder, D.A. Vosburg, Synthesis 45, 1541-1545 (2013) 39. G. Appendino, P. Gariboldi, G.M. Nano, P. Tétényi, Phytochemistry 23, 2545-2551 (1984) 40. F. Bohlmann, N. Ates, J. Jakupovic, R.M. King, H. Robinson, Phytochemistry 21, 2691-2697 (1982) 41. H.Y. Ding, H.C. Lin, C.M. Teng, Y.C. Wu, J. Chin. Chem. Soc. 47, 381-388 (2000) 42. X.N. Fan, S. Lin, C.G. Zhu, Y. Liu, J.F. Hu, X.G. Chen, W.J. Wang, N.H. Chen, J.G. Shi, China J. Chin. Mater. Med. 36, 48-56 (2011) 43. M.D.R. Cuenca, S. Borkosky, C.A.N. Catalan, V.L. Goedken, J.G. Diáz, W. Herz, Phytochemistry 32, 1509-1513 (1993) 44. F. Bohlmann, N. Rao, Chem. Ber. 106, 3035-3038 (1973) 45. A. Zana, Z. Hajdú, N. Jedlinszki, I. Máthé, G. Dombi, J. Hohmann, Tetrahedron 71, 4817-4820 (2015) |
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|