Syntheses of prodelphinidin B1, B2, and B4 and their antitumor activities against human PC-3 prostate cancer cell lines

Tetrahedron Letters

Volumn 54, Issue 52, 2013, Pages 7188-7192

  Fujii, Wataru ^a   Toda, Kazuya ^a   Matsumoto, Kiriko ^a   Kawaguchi, Koichiro ^a   Kawahara, Sei Ichi ^b   Hattori, Yasunao ^c   Fujii, Hiroshi ^a   Makabe, Hidefumi ^a  

^a SHINSHU UNIVERSITY   (Japan)

^b St Cousair Co Ltd   (Japan)

^c KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Anticancer agents; Natural product; Polyphenols; Synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; EPIGALLOCATECHIN; EPIGALLOCATECHIN GALLATE; FLAVONOID; GALLOCATECHIN; LEWIS ACID; NUCLEOPHILE; PRODELPHINIDIN B1; PRODELPHINIDIN B2; PRODELPHINIDIN B3; PRODELPHINIDIN B4; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CANCER CELL CULTURE; CELL PROLIFERATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; ELECTROPHILICITY; HUMAN; HUMAN CELL; IC 50; MEDIATOR; POLYMERIZATION; PROSTATE CANCER;

EID: 84888129269     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.10.113     Document Type: Article

References (42)

1. P.L. Kuo, Y.L. Hsu, T.C. Lin, and C.C. Lin Food Chem. Toxicol. 43 2005 315
2. P.L. Kuo, Y.L. Hsu, T.C. Lin, and C.C. Lin Eur. J. Pharmacol. 501 2004 41
3. D.-X. Hou, D. Luo, S. Tanigawa, F. Hashimoto, T. Uto, S. Masuzaki, M. Fujii, and Y. Sakata Biochem. Pharmacol. 74 2007 742
4. A. Danne, F. Peterreit, and A. Nahrstedt Phytochemistry 34 1993 1129
5. L.Y. Foo, Y. Lu, W.C. McNabb, G. Waghor, and M.J. Ulyatt Phytochemistry 45 1997 1689
6. M. Tits, L. Angenot, P. Poukens, R. Warin, and Y. Dierckxsens Phytochemistry 31 1992 971
7. J.P.F.G. Helsper, H. Kolodziej, J.M. Hoogendijk, and A. Van Norel Phytochemistry 34 1993 1255
8. J.P. De Mello, F. Petereit, and A. Nahrstedt Phytochemistry 41 1996 807
9. Recent review of synthesis of procyanidins: D. Ferreira, and C.M. Coleman Planta Med. 77 2011 1071
10. K.-i. Oyama, K. Yoshida, and T. Kondo Curr. Org. Chem. 15 2011 2567
11. K. Ohmori, and K. Suzuki Curr. Org. Chem. 16 2012 566
12. Recent syntheses of procyanidin dimers: N. Nakajima, K. Horikawa, N. Takekawa, M. Hamada, and T. Kishimoto Heterocycles 84 2012 349
13. M. Katoh, Y. Oizumi, Y. Mohri, M. Hirota, and H. Makabe Lett. Org. Chem. 9 2012 233
14. R.D. Alharthy, and C.J. Hayes Tetrahedron Lett. 51 2010 1193
15. Y. Oizumi, Y. Mohri, M. Hirota, and H. Makabe J. Org. Chem. 75 2010 4884
16. Y. Mohri, M. Sagehashi, T. Yamada, Y. Hattori, K. Morimura, Y. Hamauzu, T. Kamo, M. Hirota, and H. Makabe Heterocycles 79 2009 549
17. K.-i. Oyama, M. Kuwano, M. Ito, K. Yoshida, and T. Kondo Tetrahedron Lett. 49 2008 3176
18. F. Viton, C. Landreau, D. Rustidge, F. Robert, G. Williamson, and G. Barron Eur. J. Org. Chem. 2008 6069
19. Y. Mohri, M. Sagehashi, T. Yamada, Y. Hattori, K. Morimura, T. Kamo, M. Hirota, and H. Makabe Tetrahedron Lett. 48 2007 5891
20. I. Tarascou, K. Barathieu, Y. André, I. Pianet, E.J. Dufourc, and E. Fouquet Eur. J. Org. Chem. 2006 5367
21. A. Saito, N. Nakajima, N. Matsuura, A. Tanaka, and M. Ubukata Heterocycles 62 2004 479
22. A. Saito, N. Nakajima, A. Tanaka, and M. Ubukata Heterocycles 61 2003 287
23. A. Saito, N. Nakajima, A. Tanaka, and M. Ubukata Tetraherdron 58 2002 7829
24. W. Tückmantel, A.P. Kozikowski, and L.J. Romanczyk Jr. J. Am. Chem. Soc. 121 1999 12073
25. Recent syntheses of procyanidin dimers with gallates: M. Suda, M. Katoh, K. Toda, K. Matsumoto, K. Kawaguchi, S.-i. Kawahara, Y. Hattori, H. Fujii, and H. Makabe Bioorg. Med. Chem. Lett. 23 2013 4935
26. H. Sakuda, A. Saito, Y. Mizushina, H. Yoshida, A. Tanaka, and N. Nakajima Heterocycles 67 2006 175
27. A. Saito, Y. Mizushina, H. Ikawa, H. Yoshida, Y. Doi, A. Tanaka, and N. Nakajima Bioorg. Med. Chem. 13 2005 2759
28. A. Saito, M. Emoto, A. Tanaka, Y. Doi, K. Shoji, Y. Mizushina, H. Ikawa, H. Yoshida, N. Matsuura, and N. Nakajima Tetrahedron 60 2004 12043
29. Recent syntheses of procyanidin trimers and related compounds: T. Yano, K. Ohmori, H. Takahashi, T. Kusumi, and K. Suzuki Org. Biomol. Chem. 10 2012 7685
30. Y. Oizumi, M. Katoh, Y. Hattori, K. Toda, K. Kawaguchi, H. Fujii, and H. Makabe Heterocycles 85 2012 2241
31. Y. Oizumi, Y. Mohri, Y. Hattori, and H. Makabe Heterocycles 83 2011 739
32. K. Ohmori, N. Ushimaru, and K. Suzuki Proc. Natl. Acad. Sci. U.S.A. 101 2004 12002
33. A. Saito, Y. Doi, A. Tanaka, N. Matsuura, M. Ubukata, and N. Nakajima Bioorg. Med. Chem. 12 2004 4783
34. A. Saito, A. Tanaka, M. Ubukata, and N. Nakajima Synlett 2004 1069
35. Syntheses of procyanidin oligomers: K. Ohmori, T. Shono, Y. Hatakoshi, T. Yano, and K. Suzuki Angew. Chem., Int. Ed. 50 2011 4862
36. A. Saito, Y. Mizushina, A. Tanaka, and N. Nakajima Tetrahedron 65 2009 7422
37. A.P. Kozikowski, W. Tückmantel, G. Böttcher, and L.J. Romanczyk Jr. J. Org. Chem. 68 2003 1641
38. Synthesis of procyanidin, B6: G. Watanabe, K. Ohmori, and K. Suzuki Chem. Commun. 2013 5210
39. K. Krohn, I. Ahmed, M. John, M.C. Letzel, and D. Kuck Eur. J. Org. Chem. 2010 2544
40. S.B. Wan, Q.P. Dou, and T.H. Chan Tetrahedron 62 2006 5897
41. W. Fujii, K. Toda, K. Kawaguchi, S.-i. Kawahara, Y. Hattori, H. Fujii, and H. Makabe Tetrahedron 69 2013 3543
42. P.J. Steynberg, R.J.J. Nel, H. Van Rensberg, B.C.B. Bezuidenhoudt, and D. Ferreira Tetrahedron 54 1998 8153