Five New Guanacastane-Type Diterpenes from Cultures of the Fungus Psathyrella candolleana

doi:10.1007/s13659-014-0020-8

Natural Products and Bioprospecting ›› 2014, Vol. 4 ›› Issue (3): 149-155.DOI: 10.1007/s13659-014-0020-8

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Five New Guanacastane-Type Diterpenes from Cultures of the Fungus Psathyrella candolleana

Xia Yin^1,2, Tao Feng¹, Zheng-Hui Li¹, Ying Leng³, Ji-Kai Liu¹

1. 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;
2. University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3. Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China

Received:2014-04-03 Revised:2014-04-03 Online:2018-02-11 Published:2014-06-24
Supported by:
This project was supported by the National Natural Sciences Foundation of China(U1132607, 81373289).

Five New Guanacastane-Type Diterpenes from Cultures of the Fungus Psathyrella candolleana

Xia Yin^1,2, Tao Feng¹, Zheng-Hui Li¹, Ying Leng³, Ji-Kai Liu¹

1. 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;
2. University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3. Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China

通讯作者: Ji-Kai Liu,e-mail:jkliu@mail.kib.ac.cn
基金资助:
This project was supported by the National Natural Sciences Foundation of China(U1132607, 81373289).

Abstract

Abstract: Five new guanacastane-type diterpenes, named guanacastepenes P-T(1-5), were isolated from cultures of the fungus Psathyrella candolleana. Their structures were elucidated on the basis of extensive spectroscopic methods. All of the compounds were tested for their 11β-hydroxysteroid dehydrogenase(11β-HSD1) inhibitory activity. Compound 3 exhibited inhibitory activity against both human and mouse isozymes of 11β-HSD1 with IC₅₀ values of 6.2 and 13.9 μM, respectively.

Key words: Psathyrella candolleana, Psathyrellaceae diterpenes, Guanacastepenes P-T, 11β-HSD1

摘要： Five new guanacastane-type diterpenes, named guanacastepenes P-T(1-5), were isolated from cultures of the fungus Psathyrella candolleana. Their structures were elucidated on the basis of extensive spectroscopic methods. All of the compounds were tested for their 11β-hydroxysteroid dehydrogenase(11β-HSD1) inhibitory activity. Compound 3 exhibited inhibitory activity against both human and mouse isozymes of 11β-HSD1 with IC₅₀ values of 6.2 and 13.9 μM, respectively.

关键词: Psathyrella candolleana, Psathyrellaceae diterpenes, Guanacastepenes P-T, 11β-HSD1

Xia Yin, Tao Feng, Zheng-Hui Li, Ying Leng, Ji-Kai Liu. Five New Guanacastane-Type Diterpenes from Cultures of the Fungus Psathyrella candolleana[J]. Natural Products and Bioprospecting, 2014, 4(3): 149-155.

Xia Yin, Tao Feng, Zheng-Hui Li, Ying Leng, Ji-Kai Liu. Five New Guanacastane-Type Diterpenes from Cultures of the Fungus Psathyrella candolleana[J]. 应用天然产物, 2014, 4(3): 149-155.

References

1. S.F. Brady, M.P. Singh, J.E. Janso, J. Clardy, J. Am. Chem. Soc. 122, 2116-2117 (2000)
2. S.F. Brady, S.M. Bondi, J. Clardy, J. Am. Chem. Soc. 123, 9900-9901 (2001)
3. M. Kettering, C. Valdivia, O. Sterner, H. Anke, E. Thines, J. Antibiot. 58, 390-396 (2005)
4. C. Valdivia, M. Kettering, H. Anke, E. Thines, O. Sterner, Tetrahedron 61, 9527-9532 (2005)
5. Y.X. Qu, Y.Y. Li, X.M. Qian, Y.M. Shen, Phytochemistry 78, 190-196 (2012)
6. M.A. Battiste, P.M. Pelphrey, D.L. Wright, Chemistry 12, 3438-3447 (2006)
7. K.M. Brummond, D. Gao, Org. Lett. 5, 3491-3494 (2003)
8. X.H. Du, H.V. Chu, O. Kwon, Org. Lett. 5, 1923-1926 (2003)
9. G.B. Dudley, D.S. Tan, G. Kim, J.M. Tanski, S.J. Danishefsky, Tetrahedron Lett. 42, 6789-6791 (2001)
10. G.B. Dudley, S.J. Danishefsky, Org. Lett. 3, 2399-2402 (2001)
11. C.M. Gampe, E.M. Carreira, Angew. Chem. Int. Ed. 50, 2962-2965 (2011)
12. C.C. Hughes, J.J. Kennedy-Smith, D. Trauner, Org. Lett. 5, 4113-4115 (2003)
13. C.C. Hughes, A.K. Miller, D. Trauner, Org. Lett. 7, 3425-3428 (2005)
14. C.C. Li, C.H. Wang, B. Liang, X.H. Zhang, L.J. Deng, S. Liang, J.H. Chen, Y.D. Wu, Z. Yang, J. Org. Chem. 71, 6892-6897 (2006)
15. S.N. Lin, G.B. Dudley, D.S. Tan, S.J. Danishefsky, Angew. Chem. Int. Ed. 41, 2188-2191 (2002)
16. C.A. McGowan, A.K. Schmieder, L. Roberts, M.F. Greaney, Org. Biomol. Chem. 5, 1522-1524 (2007)
17. G. Mehta, J.D. Umarye, Org. Lett. 4, 1063-1066 (2002)
18. Y. Oonishi, A. Taniuchi, Y. Sato, Synthesis 28, 84-2892 (2010)
19. S. Iimura, L.E. Overman, R. Paulini, A. Zakarian, J. Am. Chem. Soc. 128, 13095-13101 (2006)
20. M.P. Singh, J.E. Janso, S.W. Luckman, S.F. Brady, J. Clardy, M. Greenstein, W.M.J. Maiese, J. Antibiot. 53, 256-261 (2000)
21. T. Mosmann, J. Immunol. Methods 65, 55-63 (1983)
22. L.J. Reed, H. Muench, Am. J. Hyg. 27, 493-497 (1938)
23. Q.C. Zhu, Y. Wang, T. Peng, J. Biomol. Screen. 15, 1016-1020 (2010)
24. H.Y. Yang, W. Dou, J. Lou, Y. Leng, J.H. Shen, J Bioorg. Med. Chem. Lett. 18, 1340-1345 (2008)
25. H.Y. Yang, Y. Shen, J.H. Chen, Q.F. Jiang, Y. Leng, J.H. Shen, Eur. J. Med. Chem. 44, 1167-1171 (2009)

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Five New Guanacastane-Type Diterpenes from Cultures of the Fungus Psathyrella candolleana

Five New Guanacastane-Type Diterpenes from Cultures of the Fungus Psathyrella candolleana

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