Structurally Diverse Sesquiterpenoids with Anti-neuroinflammatory Activity from the Endolichenic Fungus Cryptomarasmius aucubae

doi:10.1007/s13659-021-00299-9

应用天然产物 ›› 2021, Vol. 11 ›› Issue (3): 325-332.DOI: 10.1007/s13659-021-00299-9

• ORIGINAL ARTICLES • 上一篇下一篇

Structurally Diverse Sesquiterpenoids with Anti-neuroinflammatory Activity from the Endolichenic Fungus Cryptomarasmius aucubae

Yi-Jie Zhai, Jian-Nan Li, Yu-Qi Gao, Lin-Lin Gao, Da-Cheng Wang, Wen-Bo Han, Jin-Ming Gao

Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China

收稿日期:2020-12-26 修回日期:2021-01-27 出版日期:2021-06-24 发布日期:2021-06-04
通讯作者: Wen-Bo Han, Jin-Ming Gao
基金资助:
This work was financed by the National Natural Science Foundation of China (Grant Nos. 21702169, 22077102).

Structurally Diverse Sesquiterpenoids with Anti-neuroinflammatory Activity from the Endolichenic Fungus Cryptomarasmius aucubae

Yi-Jie Zhai, Jian-Nan Li, Yu-Qi Gao, Lin-Lin Gao, Da-Cheng Wang, Wen-Bo Han, Jin-Ming Gao

Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China

Received:2020-12-26 Revised:2021-01-27 Online:2021-06-24 Published:2021-06-04
Contact: Wen-Bo Han, Jin-Ming Gao
Supported by:
This work was financed by the National Natural Science Foundation of China (Grant Nos. 21702169, 22077102).

摘要/Abstract

摘要： Two new sterpurane sesquiterpenoids named sterpurol D (1) and sterpurol E (2), and one skeletally new sesquiterpene, cryptomaraone (3), bearing a 5,6-fused bicyclic ring system, along with five known ones, sterpurol A (4), sterpurol B (5), paneolilludinic Acid (6), murolane-2α, 9β-diol-3-ene (7) and (-)-10,11-dihydroxyfarnesol (8) were isolated from an endolichenic fungus Cryptomarasmius aucubae. The structures of the new compounds were elucidated by analysis of NMR spectroscopic spectra and HRESIMS data. The absolute configurations of 1 and 2 were established by spectroscopic data analysis and comparison of specific optical rotation, as well as the biosynthetic consideration. Additionally, compounds 1, 2, 4-6, and 8 showed significant nitric oxide (NO) production inhibition in Lipopolysaccharide (LPS)-induced BV-2 microglial cells with the IC 50 values ranging from 9.06 to 14.81 μM.

关键词: Endolichenic fungus, Cryptomarasmius aucubae, Sesquiterpenes, Anti-neuroinflammatory activity

Abstract: Two new sterpurane sesquiterpenoids named sterpurol D (1) and sterpurol E (2), and one skeletally new sesquiterpene, cryptomaraone (3), bearing a 5,6-fused bicyclic ring system, along with five known ones, sterpurol A (4), sterpurol B (5), paneolilludinic Acid (6), murolane-2α, 9β-diol-3-ene (7) and (-)-10,11-dihydroxyfarnesol (8) were isolated from an endolichenic fungus Cryptomarasmius aucubae. The structures of the new compounds were elucidated by analysis of NMR spectroscopic spectra and HRESIMS data. The absolute configurations of 1 and 2 were established by spectroscopic data analysis and comparison of specific optical rotation, as well as the biosynthetic consideration. Additionally, compounds 1, 2, 4-6, and 8 showed significant nitric oxide (NO) production inhibition in Lipopolysaccharide (LPS)-induced BV-2 microglial cells with the IC 50 values ranging from 9.06 to 14.81 μM.

Key words: Endolichenic fungus, Cryptomarasmius aucubae, Sesquiterpenes, Anti-neuroinflammatory activity

Yi-Jie Zhai, Jian-Nan Li, Yu-Qi Gao, Lin-Lin Gao, Da-Cheng Wang, Wen-Bo Han, Jin-Ming Gao. Structurally Diverse Sesquiterpenoids with Anti-neuroinflammatory Activity from the Endolichenic Fungus Cryptomarasmius aucubae[J]. 应用天然产物, 2021, 11(3): 325-332.

参考文献

1. A.E. Arnold, Fungal. Biol. Rev. 21, 51-66 (2007)
2. J.J. Kellogg, H.A. Raja, Phytochem. Rev. 16, 271-293 (2017)
3. B.N. Singh, D.K. Upreti, V.K. Gupta, X.F. Dai, Y. Jiang, Trends Biotechnol. 35, 808-813 (2017)
4. X.B. Li, L. Li, R.X. Zhu, W. Li, W.Q. Chang, L.L. Zhang, X.N. Wang, Z.T. Zhao, H.X. Lou, J. Nat. Prod. 78, 2155-2160 (2015)
5. M.H. Chen, R.Z. Wang, W.L. Zhao, L.Y. Yu, C.R. Zhang, S.S. Chang, Y. Li, T. Zhang, J.G. Xing, M.L. Gan, F. Feng, S.Y. Si, Org. Lett. 21, 1530-1533 (2019)
6. Y.L. Li, R.X. Zhu, J.Z. Zhang, F. Xie, X.N. Wang, K. Xu, Y.N. Qiao, Z.T. Zhao, H.X. Lou, ACS Omega 3, 176-180 (2018)
7. K. Xu, Y. Gao, Y.L. Li, F. Xie, Z.T. Zhao, H.X. Lou, J. Nat. Prod. 81, 2041-2049 (2018)
8. Y.H. Zhou, X.B. Li, J.Z. Zhang, L. Li, M. Zhang, W.Q. Chang, X.N. Wang, H.X. Lou, J. Asian Nat. Prod. Res. 18, 409-414 (2016)
9. Y.H. Wu, G.D. Chen, C.X. Wang, D. Hu, X.X. Li, Y.Y. Lian, F. Lin, L.D. Guo, H. Gao, J. Asian Nat. Prod. Res. 17, 671-675 (2015)
10. S. Padhi, M. Masi, A. Cimmino, A. Tuzi, S. Jena, K. Tayung, A. Evidente, Phytochemistry 157, 175-183 (2019)
11. F. Xie, X.Y. Luan, Y. Gao, K. Xu, H.X. Lou, J. Nat. Prod. 83, 1623-1633 (2020)
12. S. Lee, G. Tamayo-Castillo, C. Pang, J. Clardy, S. Cao, K.H. Kim, Bioorg. Med. Chem. Lett. 26, 2438-2441 (2016)
13. W. Wu, H.Q. Dai, L. Bao, B. Ren, J.C. Lu, Y.M. Luo, L.D. Guo, L.X. Zhang, H.W. Liu, J. Nat. Prod. 74, 1303-1308 (2011)
14. S.X. Cai, S.W. Sun, H.N. Zhou, X.L. Kong, T.J. Zhu, D.H. Li, Q.Q. Gu, J. Nat. Prod. 74, 1106-1110 (2011)
15. K. Ma, J.J. Han, L. Bao, T.Z. Wei, H.W. Liu, J. Nat. Prod. 77, 942-947 (2014)
16. G.S. Kim, W. Ko, J.W. Kim, M.H. Jeong, S.K. Ko, J.S. Hur, H. Oh, J.H. Jang, J.S. Ahn, J. Nat. Prod. 81, 1084-1088 (2018)
17. B.M. Fraga, Nat. Prod. Rep. 30, 1226-1264 (2013)
18. W.A. Ayer, M.H. Saeedi-Ghomi, D. Van Engen, B. Tagle, J. Clardy, Tetrahedron 37, 379-385 (1981)
19. O. Sterner, T. Anke, W.S. Sheldrick, W. Steglich, Tetrahedron 46, 2389-2400 (1990)
20. M. Jonassohn, H. Anke, O. Sterner, C. Svensson, Tetrahedron Lett. 35, 1593-1596 (1994)
21. A. Schuffler, B. Wollinsky, T. Anke, J.C. Liermann, Opatz T. J. Nat. Prod. 75, 1405-1408 (2012)
22. Y.B. Zheng, Y.M. Shen, Org. Lett. 11, 109-112 (2009)
23. Y.Q. Wang, L. Bao, D.L. Liu, X.L. Yang, S.F. Li, H. Gao, X.S. Yao, H.A. Wen, H.W. Liu, Tetahedron 68, 3012-3018 (2012)
24. F. Rasser, T. Anke, O. Sterner, Phytochemistry 54, 511-516 (2000)
25. G. Cimino, A.D. Giulio, S.D. Rosa, S.D. Stefano, Tetrahedron 45, 6479-6484 (1989)
26. W.B. Han, G.Y. Wang, J.J. Tang, W.J. Wang, H. Liu, R.R. Gil, N.V. Armando, X.X. Lei, J.M. Gao, Org. Lett. 22, 405-409 (2020)
27. Y.J. Zhai, G.M. Huo, Q. Zhang, D. Li, D.C. Wang, J.Z. Qi, W.B. Han, J.M. Gao, J. Nat. Prod. 83, 1592-1597 (2020)
28. W.B. Han, Y.J. Zhai, Y.-Q. Gao, H.Y. Zhou, J. Xiao, G. Pescitelli, J.M. Gao, J. Agric. Food Chem. 67, 3643-3650 (2019)
29. B.B. Gu, F.R. Jiao, W. Wu, W.H. Jiao, L. Li, F. Sun, S.P. Wang, F. Yang, H.W. Lin, J. Nat. Prod. 81, 2275-2281 (2018)
30. Y.Q. Wang, L. Bao, X.L. Yang, L. Li, S.F. Li, H. Gao, XSh. Yao, H.A. Wen, H.W. Liu, Food Chem. 132, 1346-1353 (2012)
31. W.Z. Ma, Y.C. Huang, L.D. Lin, X.F. Zhu, Y.Z. Chen, H.H. Xu, X.Y. Wei, J. Antibiot. 57, 721-725 (2004)
32. Y.H. Kuo, Y.S. Cheng, Y.T. Lin, Tetrahedron Lett. 28, 2375-2377 (1969)
33. Y. Suzuki, K. Imai, S. Marumo, J. Am. Chem. Soc. 96, 3703-3705 (1974)
34. D. Tang, Y.Z. Xu, W.W. Wang, Z. Yang, B. Liu, M. Stadler, L.L. Liu, J.M. Gao, J. Nat. Prod. 82, 1599-1608 (2019)
35. W.J. Dan, Q. Zhang, F. Zhang, W.W. Wang, J.M. Gao, J. Enzym. Inhib. Med. Chem. 34, 937-945 (2019)
36. J. Wei, X.Y. Zhang, S. Deng, L. Cao, Q.H. Xue, J.M. Gao, Nat. Prod. Res. 31, 2062-2066 (2017)
37. W.J. Dan, H.L. Geng, J.W. Qiao, R. Guo, S.P. Wei, L.B. Li, W.J. Wu, J.W. Zhang, Molecules 21, 96 (2016)

[1]	Kennedy D. Nyongbela, Fidele Ntie-Kang, Thomas R. Hoye, Simon M. N. Efange. Antiparasitic Sesquiterpenes from the Cameroonian Spice Scleria striatinux and Preliminary In Vitro and In Silico DMPK Assessment[J]. 应用天然产物, 2017, 7(3): 235-247.
[2]	Rong-Hua Yin, Zhen-Zhu Zhao, Xu Ji, Ze-Jun Dong, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Steroids and Sesquiterpenes From Cultures of the Fungus Phellinus igniarius[J]. 应用天然产物, 2015, 5(1): 17-22.
[3]	Can-Bin Ouyang, Xiao-Man Liu, Qi Liu, Jie Bai, Hou-Yong Li, Yuan Li, Qiu-Xia Wang, Dong-Dong Yan, Lian-Gang Mao, Aocheng Cao, Mei-Xia Guo. Toxicity Assessment of Cadinene Sesquiterpenes from Eupatorium adenophorum in Mice[J]. 应用天然产物, 2015, 5(1): 29-36.
[4]	Zi-Ming Chen, Qiong-Ying Fan, Xia Yin, Xiao-Yan Yang, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Three New Humulane Sesquiterpenes from Cultures of the Fungus Antrodiella albocinnamomea[J]. 应用天然产物, 2014, 4(4): 207-211.
[5]	Xia YIN, Tao FENG, Zheng-Hui LI, Jia SU, Yan LI, Ning-Hua TAN, Ji-Kai LIU. Chemical investigation on the cultures of the fungus Xylaria carpophila[J]. 应用天然产物, 2011, 1(2): 75-80.

Structurally Diverse Sesquiterpenoids with Anti-neuroinflammatory Activity from the Endolichenic Fungus Cryptomarasmius aucubae

Structurally Diverse Sesquiterpenoids with Anti-neuroinflammatory Activity from the Endolichenic Fungus Cryptomarasmius aucubae

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 5

编辑推荐

Metrics

本文评价