Unusual illudin-type sesquiterpenoids from cultures of Agrocybe salicacola

doi:10.1007/s13659-011-0018-4

应用天然产物 ›› 2011, Vol. 1 ›› Issue (2): 87-92.DOI: 10.1007/s13659-011-0018-4

Unusual illudin-type sesquiterpenoids from cultures of Agrocybe salicacola

Liang-Yan LIU^a,b, Ling ZHANG^a, Tao FENG^a, Zheng-Hui LI^a, Ze-Jun DONG^a, Xing-Yao LI^a,b, Jia SU^a,b, Yan LI^a, Ji-Kai LIU^a

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

收稿日期:2011-09-19 修回日期:2011-10-26 出版日期:2011-04-24 发布日期:2017-11-24
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 Basic Research Program of China(973 Program, 2009CB522300), the National Natural Sciences Foundation of China(30830113), and MOST(2009ZX09501-029).

Unusual illudin-type sesquiterpenoids from cultures of Agrocybe salicacola

Liang-Yan LIU^a,b, Ling ZHANG^a, Tao FENG^a, Zheng-Hui LI^a, Ze-Jun DONG^a, Xing-Yao LI^a,b, Jia SU^a,b, Yan LI^a, Ji-Kai LIU^a

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

Received:2011-09-19 Revised:2011-10-26 Online:2011-04-24 Published:2017-11-24
Supported by:
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).

摘要/Abstract

摘要： 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.

关键词: Agrocybe salicacola, sesquiterpenoid, agrocybin, stereoconfiguration, X-ray

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.

Key words: Agrocybe salicacola, sesquiterpenoid, agrocybin, stereoconfiguration, X-ray

Liang-Yan LIU, Ling ZHANG, Tao FENG, Zheng-Hui LI, Ze-Jun DONG, Xing-Yao LI, Jia SU, Yan LI, Ji-Kai LIU. Unusual illudin-type sesquiterpenoids from cultures of Agrocybe salicacola[J]. 应用天然产物, 2011, 1(2): 87-92.

参考文献

[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.

Unusual illudin-type sesquiterpenoids from cultures of Agrocybe salicacola

Unusual illudin-type sesquiterpenoids from cultures of Agrocybe salicacola

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