Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

doi:10.1007/s13659-012-0018-z

应用天然产物 ›› 2012, Vol. 2 ›› Issue (2): 70-75.DOI: 10.1007/s13659-012-0018-z

• Regular Article • 上一篇下一篇

Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

Yan LI^a, Chang-Wei LI^a, Cheng-Bin CUI^a, Xing-Zhong LIU^b, Yong-Sheng CHE^,a

a Division of Natural Products Chemistry, Beijing Institute of Pharmacology & Toxicology, Beijing 100850, China;
b State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, China

收稿日期:2012-03-01 修回日期:2012-03-08 出版日期:2012-04-24 发布日期:2018-02-11
通讯作者: Cheng-Bin CUI,E-mail:cuicb@126.com;Yong-Sheng CHE,E-mail:cheys@im.ac.cn
基金资助:
We gratefully acknowledge financial support from the National Natural Science Foundation of China(30925039), the Beijing Natural Science Foundation(5111003), the Ministry of Science and Technology of China(2009CB522300 and 2010ZX09401-403), and the Chinese Academy of Sciences(KSCX2-EW-G-6).

Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

Yan LI^a, Chang-Wei LI^a, Cheng-Bin CUI^a, Xing-Zhong LIU^b, Yong-Sheng CHE^,a

a Division of Natural Products Chemistry, Beijing Institute of Pharmacology & Toxicology, Beijing 100850, China;
b State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, China

Received:2012-03-01 Revised:2012-03-08 Online:2012-04-24 Published:2018-02-11
Supported by:
We gratefully acknowledge financial support from the National Natural Science Foundation of China(30925039), the Beijing Natural Science Foundation(5111003), the Ministry of Science and Technology of China(2009CB522300 and 2010ZX09401-403), and the Chinese Academy of Sciences(KSCX2-EW-G-6).

摘要/Abstract

摘要： Three new caryophyllene sesquiterpenoids, cytosporinols A-C(1-3), have been isolated from solid cultures of Cytospora sp. The structures of 1-3 were elucidated primarily by NMR spectroscopy, and 3 was further confirmed by X-ray crystallography. The absolute configurations of the C-11 secondary alcohol in 1 and the 6, 8-diol moiety in 3 were deduced using the modified Mosher and Snatzke's method, respectively. Compounds 2 and 3 showed moderate cytotoxicity against HeLa cells.

关键词: caryophyllene sesquiterpenoid, cytosporinol, Cytospora sp.

Abstract: Three new caryophyllene sesquiterpenoids, cytosporinols A-C(1-3), have been isolated from solid cultures of Cytospora sp. The structures of 1-3 were elucidated primarily by NMR spectroscopy, and 3 was further confirmed by X-ray crystallography. The absolute configurations of the C-11 secondary alcohol in 1 and the 6, 8-diol moiety in 3 were deduced using the modified Mosher and Snatzke's method, respectively. Compounds 2 and 3 showed moderate cytotoxicity against HeLa cells.

Key words: caryophyllene sesquiterpenoid, cytosporinol, Cytospora sp.

Yan LI, Chang-Wei LI, Cheng-Bin CUI, Xing-Zhong LIU, Yong-Sheng CHE. Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.[J]. 应用天然产物, 2012, 2(2): 70-75.

Yan LI, Chang-Wei LI, Cheng-Bin CUI, Xing-Zhong LIU, Yong-Sheng CHE. Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.[J]. Natural Products and Bioprospecting, 2012, 2(2): 70-75.

参考文献

[1] Pulici, M.; Sugawara, F.; Koshino, H.; Uzawa, J.; Yoshida, S.; Lobkovsky, E.; Clardy, J. J. Org. Chem. 1996, 61, 2122-2124.
[2] Pulici, M.; Sugawara, F.; Koshino, H.; Okada, G.; Esumi, Y.; Uzawa, J. Phytochemistry 1997, 46, 313-319.
[3] Magnani, R. F.; Rodrigues-Fo, E.; Daolio, C.; Ferreira, A. G.; De Souza, A. Q. Z. Naturforsch. 2003, 58C, 319-324.
[4] Deyrup, S. T.; Swenson, D. C.; Gloer, J. B.; Wicklow, D. T. J. Nat. Prod. 2006, 69, 608-611.
[5] Smetanina, O. F.; Kuznetsova, T. A.; Gerasimenko, A. V.; Kalinovsky, A. I.; Pivkin, M. V.; Dmitrenok, P. C.; Elyakov, G. B. Russ. Chem. Bull. 2004, 53, 2643-2646.
[6] Anderson, J. R.; Briant, C. E.; Edwards, R. L.; Mabelis, R. P.; Poyser, J. P.; Spencer, H.; Whalley, A. J. J. Chem. Soc., Chem. Commun. 1984, 405-406.
[7] Anderson, J. R.; Edwards, R. L.; Freer, A. A.; Mabelis, R. P.; Poyser, J. P.; Spencer, H.; Whalley, A. J. J. Chem. Soc., Chem. Commun. 1984, 917-919.
[8] Poyser, J. P.; Edwards, R. L.; Anderson, J. R.; Hursthouse, M. B.; Walker, N. P.; Sheldrick, G. M.; Whalley, A. J. J. Antibiot. 1986, 39, 167-169.
[9] Anderson, J. R.; Edwards, R. L.; Poyser, J. P.; Whalley, A. J. J. Chem. Soc., Perkin Trans. 11988, 823-831.
[10] Edwards, R. L.; Maitland, D. J.; Whalley, A. J. J. Chem. Soc., Perkin Trans. 11989, 57-65.
[11] Edwards, R. L.; Maitland, D. J.; Poyser, J. P.; Whalley, A. J. J. Chem. Soc., Perkin Trans. 11989, 1939-1941.
[12] Frank, M.; Kingston, E.; Jeffery, J. C.; Moss, M. O.; Murray, M.; Simpson, T. J.; Sutherland, A. Tetrahedron Lett. 1999, 40, 133-136.
[13] Yang, S. W.; Chan, T. M.; Terracciano, J.; Boehm, E.; Patel, R.; Chen, G.; Loebenberg, D.; Patel, M.; Gullo, V.; Pramanik, B.; Chu, M. J. Nat. Prod. 2009, 72, 484-487.
[14] (a) Guo, H.; Hu, H.; Liu, S.; Liu, X.; Zhou, Y.; Che, Y. J. Nat. Prod. 2007, 70, 1519-1521. (b) Zhang, Y.; Liu, S.; Che, Y.; Liu, X. J. Nat. Prod. 2007, 70, 1522-1525. (c) Guo, H.; Sun, B.; Gao, H.; Niu, S.; Liu, X.; Yao, X.; Che, Y. Eur. J. Org. Chem. 2009, 5525-5530. (d) Zhang, Y.; Liu, S.; Liu, H.; Liu, X.; Che, Y. J. Nat. Prod. 2009, 72, 1364-1367. (f) Ma, C.; Li, Y.; Niu, S.; Zhang, H.; Liu, X.; Che, Y. J. Nat. Prod. 2011, 74, 32-37.
[15] (a) Lin, J.; Liu, S.; Sun, B.; Niu, S.; Li, E.; Liu, X.; Che, Y. J. Nat. Prod. 2010, 73, 905-910. (b) Zou, X.; Niu, S.; Ren, J.; Li, E.; Liu, X.; Che, Y. J. Nat. Prod. 2011, 74, 1111-1116. (c) Lin, J.; Chen, X.; Cai, X.; Yu, X.; Liu, X.; Cao, Y; Che, Y. J. Nat. Prod. 2011, 74, 1798-1804.
[16] (a) Li, Y.; Niu, S.; Sun, B.; Liu, S.; Liu, X.; Che, Y. Org. Lett. 2010, 12, 3144-3147. (b) Spence, J. T. J.; George, J. H. Org. Lett. 2011, 13, 5318-5311.
[17] (a) Che, Y.; Gloer, J. B.; Scott, J. A.; Malloch, D. Tetrahedron Lett. 2004, 45, 6891-6894. (b) Che, Y.; Araugo, A. R.; Gloer, J. B.; Scott, J. A.; Malloch, D. J. Nat. Prod. 2005, 68, 435-438.
[18] Fleck, M.; Bach, T. Angew. Chem., Int. Ed., 2008, 47, 6189-6191.
[19] Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
[20] Frelek, J.; Snatzke, G.; Szczepek, W. Fresenius J. Anal. Chem. 1993, 345, 683-687.
[21] Frelek, J.; Szczepek, W.; Voelter, W. J. Ptakt. Chem. 1997, 339, 135-139.
[22] Frelek, J.; Perkowska, A.; Snatzke, G.; Tima, M.; Wagner, U.; Wolff, H. P. Spectrosc-Int. J. 1983, 2, 274-295.
[23] Baker, T. M.; Edmonds, D. J.; Hamilton, D.; O'Brien, C. J.; Procter, D. J. Angew. Chem., Int. Ed., 2008, 47, 5631-5633.
[24] Takao, K.-I.; Hayakawa, N.; Yamada, R.; Yamaguchi, T.; Saegusa, H.; Uchida, M.; Samejima, S.; Tadano, K.-I. J. Org. Chem. 2009, 74, 6452-6461.
[25] Crystallographic data for compound 3 have been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC 790902). Copies of the data can be obtained, free of charge, on application to the director, CCDC 12 Union Road, Cambridge CB21EZ, UK (fax:+441223336033 or email:deposit@ccdc.cam.ac.uk).
[26] Sheldrick, G. M. SHELXL-97, Program for X-ray Crystal Structure Solution and Refinement; University of Gottingen:Gottingen, Germany, 1997.
[27] Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Gottingen:Gottingen, Germany, 1999.
[28] Zhang, N.; Chen, Y.; Jiang, R.; Li, E.; Chen, X.; Xi, Z.; Guo, Y.; Liu, X.; Zhou, Y.; Che, Y.; Jiang, X. Autophagy 2011, 7, 598-612.

Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

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