| Regular Article |
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Unusual illudin-type sesquiterpenoids from cultures of Agrocybe salicacola |
| Liang-Yan LIUa,b, Ling ZHANGa, Tao FENGa, Zheng-Hui LIa, Ze-Jun DONGa, Xing-Yao LIa,b, Jia SUa,b, Yan LIa, Ji-Kai LIUa |
a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b Graduate University of Chinese Academy of Sciences, Beijing 100039, China |
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Abstract Seven new illudin-type sesquiterpenoids, agrocybins A-G(1-7), along with three known analogues(8-10), have been isolated from the culture broth of the fungus Agrocybe salicacola. Their structures were elucidated on the basis of extensive spectroscopic data analysis and comparison with data reported in the literature. The relative stereoconfigurations of 1 and 6 were elucidated by the X-ray crystallographic diffraction analysis. Compound 1 was highly cyclized containing seven chiral carbons which arranged compactly in six rings.
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| Keywords
Agrocybe salicacola
sesquiterpenoid
agrocybin
stereoconfiguration
X-ray
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| Fund:This project was supported by the National Basic Research Program of China(973 Program, 2009CB522300), the National Natural Sciences Foundation of China(30830113), and MOST(2009ZX09501-029). |
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Issue Date: 24 November 2017
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| [1] |
Diyabalanage, T.; Mulabagal, V.; Mills, G.; DeWitt, D. L.; Nair, M. G. Food Chem. 2008, 108, 97-102.
|
| [2] |
Won-Gon, K.; In-Kyoung, L.; Jong-Pyung, K.; In-Ja, R.; Hiroyuki, K.; Yoo, I. D. J. Nat. Prod. 1997, 60, 721-723.
|
| [3] |
Ngai, P. H. K.; Zhao, Z.; Ng, T. B. Peptides 2005, 26, 191-196.
|
| [4] |
Wang, H. X.; Ng, T. B.; Liu, Q. H. Life Sci. 2002, 70, 877-885.
|
| [5] |
Tadashi, K.; Satoshi, S.; Shigoe, U. Carbohydr. Res. 1994, 251, 81-87.
|
| [6] |
Yang, Z. L.; Zang, M.; Liu, X. X. Acta Bot. Yunn. 1993, 15, 18-20.
|
| [7] |
Zhou, H. M.; Zhao, Y. C.; Chen, W. M.; Chai, H. M.; Li, S. H.; Zhao, J. Acta Bot. Yunn. 2010, 32, 315-322.
|
| [8] |
Zhu, Y. C.; Wang, G.; Yang, X. L.; Luo, D. Q.; Zhu, Q. C.; Peng, T.; Liu, J. K. Tetrahedron Lett. 2010, 51, 3443-3445.
|
| [9] |
Wang, G.; Liu, L. Y.; Zhu, Y. C.; Liu, J. K. J. Asian Nat. Prod. Res. 2011, 13, 430-433.
|
| [10] |
Schobert, R.; Knauer, S.; Seibt, S.; Biersack, B. Curr. Med. Chem. 2011, 18, 790-807.
|
| [11] |
Gonzalez Del Val, A.; Platas, G.; Arenal, F.; Orihuela, J. C.; Garcia, M.; Hernandez, P.; Royo, I.; De Pedro, N.; Silver, L. L.; Young, K.; Vicente, M. F.; Pelaez, F. Mycol. Res. 2003, 107, 1201-1209.
|
| [12] |
Poindessous, V.; Koeppel, F.; Raymond, E.; Cvitkovic, E.; Waters, S. J.; Larsen, A. K. Int. J. Oncol. 2003, 23, 1347-1355.
|
| [13] |
Serova, M.; Calvo, F.; Lokiec, F.; Koeppel, F.; Poindessous, V.; Larsen, A. K.; Van Laar, E. S.; Waters, S. J.; Cvitkovic, E.; Raymond, E. Cancer Chemoth. Pharm. 2006, 57, 491-499.
|
| [14] |
Kelner, M. J.; McMorris, T. C.; Rojas, R. J.; Estes, L. A.; Suthipinjtham, P. Invest. New Drugs 2008, 26, 407-415.
|
| [15] |
Pettit, G. R.; Meng, Y.; Pettit, R. K.; Herald, D. L.; Cichacz, Z. A.; Doubek, D. L.; Richert, L. J. Nat. Prod. 2010, 73, 388-392.
|
| [16] |
Falk, R.; Timm, A.; Olov, S. Tetrahedron 2002, 58, 7785-7789.
|
| [17] |
Alberto A.; Rosanna C.; Gianluca N.; Orso, Vajna de Pava. J. Chem. Soc., Perkin Trans. 1, 1991, 733-737.
|
| [18] |
Kelner, M. J.; McMorris, T. C.; Estes, L. A.; Rutherford, M.; Montoya, M.; Goldstein, J.; Samson, K.; Starr, R.; Taetle, R. Biochem. Pharmcol. 1994, 48, 403-409.
|
| [19] |
Matsuoka, A.; Hirosawa, A.; Natori, S.; Iwasaki, S.; Sofuni, T.; Ishidate, M. J. Mutat. Res. 1989, 215, 179-185;
|
| [20] |
Yamada, K.; Ojika, M.; Kigoshi, H. Nat. Prod. Rep. 2007, 24, 798-813.
|
| [21] |
Reed, L. J.; Muench, H. Am. J. Hyg. 1938, 27, 493-497.
|
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