Synthesis of procyanidin B1, B2, and B4 and their anti-inflammatory activity: The effect of 4-alkoxy group of catechin and/or epicatechin electrophiles for condensation

Letters in Organic Chemistry

Volumn 9, Issue 4, 2012, Pages 233-238

  Katoh, M ^a   Oizumi, Y ^a   Mohri, Y ^a   Hirota, M ^a   Makabe, H ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

Anti inflammatory; Equimolar condensation; Polyphenol; Procyanidin

Indexed keywords

EID: 84860558439     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017812800233697     Document Type: Article

References (11)

1. Ferreira, D.; Li, X.-C. Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Nat. Prod. Rep. 2000, 17, 193-212. (Pubitemid 30220676)
2. Ferreira, D.; Slade, D. Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Nat. Prod. Rep. 2002, 19, 517-541. (Pubitemid 35259017)
3. Mohri, Y.; Sagehashi, M.; Yamada, T.; Hattori, Y.; Morimura, K.; Kamo, T.; Hirota, M.; Makabe, H. An efficient synthesis of procyanidins. Rare earth metal Lewis acid catalyzed equimolar condensation of catechin and epicatechin. Tetrahedron Lett., 2007, 48, 5891-5894. (Pubitemid 47068763)
4. Mohri, Y.; Sagehashi, M.; Yamada, T.; Hattori, Y.; Morimura, K.; Hamauzu, Y.; Kamo, T.; Hirota, M.; Makabe, H. An efficient synthesis of procyanidins using equimolar condensation of catechin and/or epicatechin catalyzed by ytteribium triflate. Heterocycles 2009, 79, 549-563.
5. Oizumi, Y.; Y. Mohri, Y.; Hirota, M.; Makabe, H. Synthesis of procyanidin B3 and its anti-inflammatory activity. The effect of 4- alkoxy group of catechin electrophile in the Yb(OTf)3-catalyzed condensation with catechin nucleophile. J. Org. Chem., 2010, 75, 4884-4886.
6. Kawamoto, H.; Nakatsubo, F.; Murakami, K. Chemical structure of synthetic condensed tannin from benzylated flavan-3,4-diol. Mokuzai Gakkaishi 1991, 37, 488-493.
7. Saito, A.; Nakajima, N.; Matsuura, N.; Tanaka, A.; Ubukata, M. Synthetic studies of procyanidins. Part 2: Stereoselective gram-scale synthesis of procyanidin-B3. Tetrahedron 2002, 58, 7829-7837. (Pubitemid 35253982)
8. Saito, A.; Nakajima, N.; Tanaka, A.; Ubukata, M. Synthetic studies of procyanidins. Part 4: The synthesis of procyanidin B1 and B4: TMSOTf-catalyzed cyclization catechin and epicatechin condensation. Heterocycles 2003, 61, 287-298.
9. Gschwendt, M.; Kittstein, W.; Furstenberger, G.; Marks, F. The mouse ear edema: A quantitatively evaluable assay for tumor promoting compounds and for inhibitors of tumor promotion. Cancer. Lett., 1984, 25, 177-185. (Pubitemid 15195080)
10. Iijima, T.; Mohri, Y.; Hattori, Y.; Kashima, A.; Kamo, T.; Hirota, M.; Kiyota, H.; Makabe, H. Synthesis of (-)-epicatechin 3-(3-Omethylgallate) and (+)-catechin 3-(3-O-methylgallate), and their anti-inflammatory activity. Chem. Biodivers., 2009, 6, 520-526.
11. Mizushina, Y.; Saito, A.; Tanaka, A.; Nakajima, N.; Kuriyama, I.; Takemura, M.; Takeuchi, T.; Sugawara, F.; Yoshida, H. Structural analysis of catechin derivatives as mammalian DNA polymerase inhibitors. Biochem. Biophys. Res. Commun., 2005, 333, 101-109 (Pubitemid 40813452)