2010 Fiscal Year Final Research Report
Synthesis and structure-activity relationship of catechin derivatives having DNA polymerase inhibitory activity
| Project/Area Number |
20590106
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Drug development chemistry
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| Research Institution | Toyama Prefectural University |
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Principal Investigator |
NAKAJIMA Noriyuki Toyama Prefectural University, 工学部, 教授 (40188959)
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| Project Period (FY) |
2008 – 2010
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| Keywords | カテキン類 / プロシアニジン類 / 3-アシルカテキン / 3-アシルエピカテキン / γ-butyrolactone |
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| Research Abstract |
3-Acylcatechins and 3-acylepicatechins having TBS-protecting group were chemically synthesized and their DNA polymerase inhibitory activity and the structure-activity relationship was studied. We also developed a simple and versatile method of synthesizing procyanidin oligomers. This method is applicable to the synthesis of [4-8]-condensed (-)-epicatechin series procyanidin tetramers and pentamers. Catechin and epi-catechin conjugated with longer fatty acid (acyl-catechin) strongly inhibited DNA polymerase activity. Procyanidin tetramers and pentamers also inhibited the DNA polymerase much higher than monomeric and dimmeric oligomers. Catechins and epicatechins afford many metabolites including through metabolic pathways in the human body. We interested in the activity of catechin metabolites and synthesized these g-butyrolactones metabolites as the optically pure authentic standards. The study of DNA polymerase inhibitory activity of g-butyrolactones is on going project.
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