Structural elucidation and synthesis of vialinin C, a new inhibitor of TNF-α production

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 8, 2014, Pages 2442-2446

  Ye, Yue Qi ^a,b   Negishi, Chiemi ^b   Hongo, Yayoi ^a   Koshino, Hiroyuki ^a   Onose, Jun Ichi ^b   Abe, Naoki ^b   Takahashi, Shunya ^a  

^a RIKEN   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE   (Japan)

Author keywords

TNF ; Vialinin A; Vialinin B; Vialinin C

Indexed keywords

GANBAJUNIN B; NATURAL PRODUCT; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; VIALININ A; VIALININ B; VIALININ C; 4 HYDROXYBENZOIC ACID ESTER; BENZOFURAN DERIVATIVE; TERPHENYL DERIVATIVE;

ARTICLE; CYTOKINE PRODUCTION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FRUITING BODY; IC 50; PROTEIN SYNTHESIS INHIBITION; THELEPHORA VIALIS; THELEPHORALES; AGARICALES; ANTAGONISTS AND INHIBITORS; CHEMISTRY; CONFORMATION; ISOLATION AND PURIFICATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

BASIDIOMYCOTA; THELEPHORA VIALIS;

AGARICALES; BENZOFURANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PARABENS; TERPHENYL COMPOUNDS; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84897975993     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.02.058     Document Type: Article

References (27)

1. C. Xie, H. Koshino, Y. Esumi, S. Takahashi, K. Yoshikawa, and N. Abe Biosci. Biotechnol. Biochem. 69 2005 2326
2. C. Xie, H. Koshino, Y. Esumi, J. Onose, K. Yoshikawa, and N. Abe Bioorg. Med. Chem. Lett. 16 2006 5424
3. L. Hu, J.M. Gao, and J.K. Liu Helv. Chim. Acta 84 2001 3342
4. E. Jagers, E. Hillen-Maske, and W. Steglich Z. Naturforsch. 42b 1987 1349
5. J. Onose, C. Xie, Y.-Q. Ye, S. Takahashi, H. Koshino, K. Yasunaga, N. Abe, and K. Yoshikawa Biol. Pharm. Bull. 31 2008 831
6. P. Vassalli Annu. Rev. Immunol. 10 1992 411
7. J. Sieper, and J. Braun Expert Opin. Emerg. Drugs 2 2002 235
8. S.T. Holgate Cytokine 28 2004 152
9. Y.-Q. Ye, J. Onose, N. Abe, H. Koshino, and S. Takahashi Bioorg. Med. Chem. Lett. 22 2012 2385
10. J. Onose, Y. Yoshioka, Y.-Q. Ye, K. Sugaya, A. Yajima, K. Taniguchi, K. Okada, S. Yajima, S. Takahashi, H. Koshino, and N. Abe Cell. Immunol. 279 2012 140
11. K. Okada, Y.-Q. Ye, K. Taniguchi, A. Yoshida, T. Akiyama, Y. Yoshioka, J. Onose, H. Koshino, S. Takahashi, A. Yajima, N. Abe, and S. Yajima Bioorg. Med. Chem. Lett. 23 2013 4328
12. Y. Yoshioka, Y.-Q. Ye, K. Okada, K. Taniguchi, A. Yoshida, K. Sugaya, J. Onose, H. Koshino, S. Takahashi, A. Yajima, S. Yajima, and N. Abe PLoS ONE 8 2013 e80931
13. N. Radulović, D.N. Quang, T. Hashimoto, M. Nukada, and Y. Asakawa Phytochemistry 66 2005 1052
14. T. Norikura, K. Fujiwara, T. Narita, S. Yamaguchi, Y. Morinaga, K. Iwai, and H. Matsue J. Agric. Food Chem. 59 2011 6974
15. Y.-Q. Ye, H. Koshino, J. Onose, C. Negishi, K. Yoshikawa, N. Abe, and S. Takahashi J. Org. Chem. 74 2009 4642
16. Y.-Q. Ye, H. Koshino, J. Onose, K. Yoshikawa, N. Abe, and S. Takahashi Org. Lett. 11 2009 5074
17. K. Stott, J. Stonehouse, J. Keeler, T.-L. Hwang, and A.J. Shaka J. Am. Chem. Soc. 117 1995 4199
18. K. Stott, J. Keeler, Q.N. Van, and A.J. Shaka J. Magn. Reson. 125 1997 302
19. J.-K. Liu Chem. Rev. 106 2006 2209
20. K. Kaniwa, T. Ohtsuki, Y. Yamamoto, and M. Ishibashi Tetrahedron Lett. 47 2006 1505
21. A. Kaneko, M. Tsukada, M. Fukai, T. Suzuki, K. Nishio, K. Miki, K. Kinoshita, K. Takahashi, and K. Koyama J. Nat. Prod. 73 2010 1002
22. H. Huang, X. Feng, Z. Xiao, L. Liu, H. Li, L. Ma, Y. Lu, J. Ju, Z. She, and Y. Lin J. Nat. Prod. 74 2011 997
23. S.W. Wossa, A.M. Beekman, P. Ma, O. Kevo, and R.A. Barrow Asian J. Org. Chem. 2 2013 565
24. Y.-Q. Ye, H. Koshino, J. Onose, K. Yoshikawa, N. Abe, and S. Takahashi Org. Lett. 9 2007 4131
25. Y.-Q. Ye, H. Koshino, N. Abe, T. Nakamura, D. Hasizume, and S. Takahashi Biosci. Biotech. Biochem. 74 2010 2342
26. L. Hu, and J.K. Liu Z. Naturforsch. 58c 2003 452 454
27. C.J. Cavallito, and J.S. Buck J. Am. Chem. Soc. 65 1943 2140