| ORIGINAL ARTICLES |
|
|
|
|
|
Cytochalasins from Xylaria sp. CFL5, an Endophytic Fungus of Cephalotaxus fortunei |
| Kai-Liang Ma, Shi-Hui Dong, Hang-Ying Li, Wen-Jun Wei, Yong-Qiang Tu, Kun Gao |
| State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China |
|
|
|
|
Abstract Three previously undescribed cytochalasins, named xylariasins A-C (1-3), together with six known ones (4-9) were isolated from Xylaria sp. CFL5, an endophytic fungus of Cephalotaxus fortunei. The chemical structures of all new compounds were elucidated on the basis of extensive spectroscopic data analyses and electronic circular dichroism calculation, as well as optical rotation calculation. Biological activities of compounds 1, 4-9 were evaluated, including cytotoxic, LAG3/MHC Ⅱ binding inhibition and LAG3/FGL1 binding inhibition activities. Compounds 6 and 9 possessed cytotoxicity against AGS cells at 5 μM, with inhibition rates of 94% and 64%, respectively. In addition, all tested isolates, except compound 6, exhibited obvious inhibitory activity against the interaction of both LAG3/MHC Ⅱ and LAG3/FGL1. Compounds 1, 5, 7, and 8 inhibited LAG3/MHC Ⅱ with IC50 values ranging from 2.37 to 4.74 μM. Meanwhile, the IC50 values of compounds 1, 7, and 8 against LAG3/FGL1 were 11.78, 4.39, and 7.45 μM, respectively.
|
| Keywords
Cytochalasin
Xylaria sp.
Cephalotaxus fortunei
LAG3/MHC II binding inhibition
LAG3/FGL1 binding inhibition
|
| Fund:This project was supported financially by the National Natural Science Foundation of China (No. 21778027) and the Natural Science Foundation of Gansu Province (No. 18JR4RA003). |
|
Corresponding Authors:
Kun Gao
E-mail: npchem@lzu.edu.cn
|
|
Issue Date: 11 March 2021
|
|
|
1. K. Scherlach, D. Boettger, N. Remme, C. Hertweck, Nat. Prod. Rep. 27, 869-886 (2010)
2. E. Skellam, Nat. Prod. Rep. 34, 1252-1263 (2017)
3. W.B. Han, Y.J. Zhai, Y. Gao, H.Y. Zhou, J. Xiao, G. Pescitelli, J.M. Gao, J. Agric. Food Chem. 67, 3643-3650 (2019)
4. Z. Shang, R. Raju, A.A. Salim, Z.G. Khalil, R.J. Capon, J. Org. Chem. 82, 9704-9709 (2017)
5. Z.M. Chen, H.P. Chen, Y. Li, T. Feng, J.K. Liu, J. Antibiot. 68, 23-26 (2015)
6. J.F. Wang, Z. Wang, Z.R. Ju, J.T. Wan, S.R. Liao, X.P. Lin, T.Y. Zhang, X.F. Zhou, H. Chen, Z.C. Tu, Y.H. Liu, Planta Med. 81, 160-166 (2015)
7. X.Q. Xin, Y. Chen, H. Zhang, Y. Li, M.H. Yang, L.Y. Kong, Fitoterapia 132, 53-59 (2019)
8. X. Pang, J.Y. Zhao, X.M. Fang, T. Zhang, D.W. Zhang, H.Y. Liu, J. Su, S. Cen, L.Y. Yu, J. Nat. Prod. 80, 2595-2601 (2017)
9. X.S. Huang, D.X. Zhou, Y. Liang, X.B. Liu, F. Cao, Y.Y. Qin, T.X. Mo, Z.L. Xu, J. Li, R.Y. Yang, Nat. Prod. Res. 1-8 (2019)
10. Y. Xu, B.P. Bashyal, M.X. Liu, P. Espinosaartiles, J.M. Uren, A.E. Arnold, A. Gunatilaka, Nat. Prod. Commun. 10, 1655-1658 (2015)
11. Y.N. Liu, Q.F. Ruan, S.Q. Jiang, Y. Qu, J.Y. Chen, M. Zhao, B. Yang, Y.X. Liu, Z.X. Zhao, H. Cui, Fitoterapia 137, 104187 (2019)
12. F. Song, S.H. Wu, Y.Z. Zhai, Q.C. Xuan, T. Wang, Chem. Biodivers. 11, 673-694 (2014)
13. S.E. Helaly, B. Thongbai, M. Stadler, Nat. Prod. Rep. 35, 992-1014 (2018)
14. Q. Zhang, J. Xiao, Q.Q. Sun, J.C. Qin, G. Pescitelli, J.M. Gao, J. Agric. Food Chem. 62, 10962-10969 (2014)
15. J.C. Chang, G. Hsiao, R.K. Lin, Y.H. Kuo, Y.M. Ju, T.H. Lee, J. Nat. Prod. 80, 38-44 (2017)
16. Y.M. Zhao, P.M. Gu, H.J. Zhang, Q.W. Zhang, C.A. Fan, Y.Q. Tu, F.M. Zhang, J. Org. Chem. 74, 3211-3213 (2009)
17. Q.W. Zhang, K. Xiang, Y.Q. Tu, S.Y. Zhang, X.M. Zhang, Y.M. Zhao, T.C. Zhang, Chem. Asian J. 7, 894-898 (2012)
18. V. Gandhi, W. Plunkett, J.E. Cortes, Clin. Cancer Res. 20, 1735-1740 (2014)
19. H.C. Puhr, A. Ilhan-Mutlu, ESMO Open 4, e000482 (2019)
20. L. Barrueto, F. Caminero, L. Cash, C. Makris, P. Lamichhane, R.R. Deshmukh, Transl. Oncol. 13, 100738 (2020)
21. E. Ruffo, R.C. Wu, T.C. Bruno, C.J. Workman, D.A. Vignali, Semin. Immunol. 42, 101305 (2019)
22. C.G. Graydon, A.L. Balasko, K.R. Fowke, PLoS Pathog. 15, e1007429 (2019)
23. M. Collin, Expert Opin. Ther. Pat. 26, 555-564 (2016)
24. J. Wang, M.F. Sanmamed, I. Datar, T.T.J. Su, L. Ji, J.W. Sun, L. Chen, Y.S. Chen, G.F. Zhu, W.W. Yin, L.H. Zheng, T. Zhou, T. Badri, S. Yao, S. Zhu, A. Boto, M. Sznol, I. Melero, D.A.A. Vignali, K. Schalper, L.P. Chen, Cell 176, 334-347 (2019)
25. L.P. Andrews, A.E. Marciscano, C.G. Drake, D.A.A. Vignali, Immunol. Rev. 276, 80-96 (2017)
26. C. Solinas, E. Migliori, P.D. Silva, K. Willard-Gallo, Cancers 11, 1213 (2019)
27. W.X. Wang, Z.H. Li, H.L. Ai, J. Li, J. He, Y.S. Zheng, T. Feng, J.K. Liu, Fitoterapia 137, 104253 (2019)
28. W.X. Wang, Z.H. Li, J. He, T. Feng, J. Li, J.K. Liu, Fitoterapia 137, 104278 (2019)
29. H. Minato, T. Katayama, J. Chem. Soc. Perkin. 1, 45-47 (1970)
30. Y.Y. Li, C.H. Lu, Z.Y. Hu, Y.J. Huang, Y.M. Shen, Nat. Prod. Res. 23, 70-76 (2009)
31. H. Xu, W.S. Fang, X.G. Chen, W.Y. He, K.D. Cheng, J. Asian Nat. Prod. Res. 3, 151-155 (2001)
32. Y. Fujii, H. Tani, M. Ichinoe, H. Nakajima, J. Nat. Prod. 63, 132-135 (2000)
33. H. Wei, Y.M. Xu, P. Espinosa-Artiles, M.X. Liu, J.G. Luo, J.M. U'Ren, A. Elizabeth Arnold, A.L. Leslie Gunatilaka, Phytochemistry 118, 102-108 (2015)
34. S. Milhas, B. Raux, S. Betzi, C. Derviaux, P. Roche, A. Restouin, M.J. Basse, E. Rebuffet, A. Lugari, M. Badol, R. Kashyap, J.C. Lissitzky, C. Eydoux, V. Hamon, M.E. Gourdel, S. Combes, P. Zimmermann, M. Aurrand-Lions, T. Roux, C. Rogers, S. Müller, S. Knapp, E. Trinquet, Y. Collette, J.C. Guillemot, X. Morelli, A.C.S. Chem, Biol. 11, 2140-2148 (2016)
35. B. Alpha-Bazin, E. Quéméneur, Anal. Chem. 84, 9963-9970 (2012) |
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
| |
Shared |
|
|
|
|
| |
Discussed |
|
|
|
|
