Isochromophilones from an endophytic fungus Diaporthe sp.

doi:10.1007/s13659-012-0023-2

Natural Products and Bioprospecting ›› 2012, Vol. 2 ›› Issue (3): 117-120.DOI: 10.1007/s13659-012-0023-2

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Isochromophilones from an endophytic fungus Diaporthe sp.

Le-Yun ZANG, Wei WEI, Ting WANG, Ye GUO, Ren-Xiang TAN, Hui-Ming GE

Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Science, Nanjing University, Nanjing 210093, China

Received:2012-03-15 Revised:2012-03-27 Online:2018-02-11 Published:2012-06-24
Supported by:
This work was co-financed by National Natural Science Foundation of China(81121062, 21132004, 90813036, and 81172948), MOE(NCET-10-0477), and Jiangsu Provincial Government(BK2009010).

Isochromophilones from an endophytic fungus Diaporthe sp.

Le-Yun ZANG, Wei WEI, Ting WANG, Ye GUO, Ren-Xiang TAN, Hui-Ming GE

Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Science, Nanjing University, Nanjing 210093, China

通讯作者: Ren-Xiang TAN,E-mail:rxtan@nju.edu.cn;Hui-Ming GE,E-mail:hmge@nju.edu.cn
基金资助:
This work was co-financed by National Natural Science Foundation of China(81121062, 21132004, 90813036, and 81172948), MOE(NCET-10-0477), and Jiangsu Provincial Government(BK2009010).

Abstract

Abstract: Three new azaphilone compounds, isochromophilones X-XII(1-3), together with two known ones sclerotioramine(4) and isochromophilone VI(5) were isolated from the cultures of an endophytic fungus Diaporthe sp. The structures were elucidated by extensive HRESIMS and NMR spectroscopic analyses. All compounds were tested for their cytotoxicities against five human cancer cell lines by MTT method, among which compound 1 showed moderate inhibitory effects on these cell lines. This was the first report of azaphilones isolated from Diaporthe sp.

Key words: azaphilone, endophyte, Diaporthe sp., cytotoxicity

摘要： Three new azaphilone compounds, isochromophilones X-XII(1-3), together with two known ones sclerotioramine(4) and isochromophilone VI(5) were isolated from the cultures of an endophytic fungus Diaporthe sp. The structures were elucidated by extensive HRESIMS and NMR spectroscopic analyses. All compounds were tested for their cytotoxicities against five human cancer cell lines by MTT method, among which compound 1 showed moderate inhibitory effects on these cell lines. This was the first report of azaphilones isolated from Diaporthe sp.

关键词: azaphilone, endophyte, Diaporthe sp., cytotoxicity

Le-Yun ZANG, Wei WEI, Ting WANG, Ye GUO, Ren-Xiang TAN, Hui-Ming GE. Isochromophilones from an endophytic fungus Diaporthe sp.[J]. Natural Products and Bioprospecting, 2012, 2(3): 117-120.

Le-Yun ZANG, Wei WEI, Ting WANG, Ye GUO, Ren-Xiang TAN, Hui-Ming GE. Isochromophilones from an endophytic fungus Diaporthe sp.[J]. 应用天然产物, 2012, 2(3): 117-120.

References

[1] Udagawa, S. I. Chem. Pharm. Bull. 1963, 11, 366-367.
[2] Arai, N.; Shiomi, K.; Tomoda, H.; Tabata, N.; Yang, D. J.; Masuma, R.; Kawakubo, T.; Omura, S. J. Antibiot. 1995, 48, 696-702.
[3] Osmanova, N.; Schultze, W.; Ayoub, N. Phytochem. Rev. 2010, 9, 315-342.
[4] Ge, H. M.; Zhang, W. Y.; Ding, G.; Saparpakorn, P.; Song, Y. C.; Hannongbua, S.; Tan, R. X. Chem. Commun. 2008, 45, 5978-5980.
[5] Laakso, J. A.; Raulli, R.; McElhaney-Feser, G. E.; Actor, P.; Underiner, T. L.; Hotovec, B. J.; Mocek, U.; Cihlar, R. L.; Broedel, S. E. Jr. J. Nat. Prod. 2003, 66, 1041-1046.
[6] Anke, H.; Kemmer, T.; Hofle, G. J. Antibiot. 1981, 34, 923-928.
[7] Quang, D. N.; Hashimoto, T.; Tanaka, M; Stadler, M.; Asakawa, Y. Phytochemistry 2004, 65, 469-473.
[8] Yasukawa, K.; Itabashi, T.; Kawai, K. I.; Takido, M. J. Nat. Med. 2008, 62, 384-386.
[9] Zhang, Y. L.; Zhang, J.; Jiang, N.; Lu, Y. H.; Wang, L.; Xu, S. H.; Wang, W.; Zhang, G. F.; Xu, Q.; Ge, H. M.; Ma, J.; Song, Y. C.; Tan, R. X. J. Am. Chem. Soc. 2011, 133, 5931-5940.
[10] Guo, Z. K.; Yan, T.; Guo, Y.; Song, Y. C.; Jiao, R. H.; Tan, R. X.; Ge, H. M. J. Nat. Prod. 2012, 75, 15-21.
[11] Wang, X.; Sena Filho, J. G.; Hoover, A. R.; King, J. B.; Ellis, T. K.; Powell, D. R.; Cichewicz, R. H. J. Nat. Prod. 2010, 73, 942-948.
[12] Michael, A. P.; Grace, E. J.; Kotiw, M.; Barrow, R. A. Aust. J. Chem. 2003, 56, 13-15.
[13] Lee, S. Y.; Clark, R. C.; Boger D. L. J. Am. Chem. Soc. 2007, 129, 9860-9861.
[14] Clark, R. C.; Lee, S. Y.; Boger D. L. J. Am. Chem. Soc. 2008, 130, 12355-12369.
[15] Matsuzaki, K.; Tanaka, H.; Ōmura, S. J. Antibiot. 1995, 48, 708-713.
[16] Kanokmedhakul, S.; Kanokmedhakul, K.; Nasomjai, P.; Louangsysouphanh, S.; Soytong, K.; Isobe, M.; Kongsaeree, P.; Prabpai, S.; Suksamrarn, A. J. Nat. Prod. 2006, 69, 891-895.
[17] Hajjaj, H.; Klaebe, A.; Loret, M. O.; Goma, G.; Blanc, P. J.; Francois, J. Appl. Environ. Microbiol. 1999, 65, 311-314.

Isochromophilones from an endophytic fungus Diaporthe sp.

Isochromophilones from an endophytic fungus Diaporthe sp.

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