2020 Fiscal Year Final Research Report
Chemeicalbiological studies on proanthocyanidins which supress metastasis and invasion of cancer
Project/Area Number |
18K05454
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Multi-year Fund |
Section | 一般 |
Review Section |
Basic Section 38040:Bioorganic chemistry-related
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Research Institution | Shinshu University |
Principal Investigator |
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Co-Investigator(Kenkyū-buntansha) |
梅澤 公二 信州大学, 総合理工学研究科, 助教 (00609258)
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Project Period (FY) |
2018-04-01 – 2021-03-31
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Keywords | プロアントシアニジン / 抗腫瘍 |
Outline of Final Research Achievements |
Syntheses of epigallocatechin tetramer and pentamer were achieved. The key condensation was accomplished using a dimeric epigallocatechin electrophile and dimeric or trimeric epigallocatechin nucleophile in the presence of zinc triflate or TMSOTf. The condensed products were successfully converted to epigallocatechin tetramer and pentamer. These compounds showed significant antitumor activity against prostate PC-3 cell lines. Synthesis of fluorescent probe of epigallocatechin dimer was achieved. Condensation of carboxylic acid and fluorescein amine afforded fluorescent probe of epigallocatechin dimer in a trace yield. The improvement of condensation yield is now underway. Synthesis of epicatechin epicatechin 3,3”-digallate was achieved. The self condensation of epicatechin gallate derivative using ytterbium triflate afforded dimer of epicatechin gallate in 73% yield. The condensed product was successfully converted to epicatechin 3,3”-digallate.
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Free Research Field |
生物有機化学
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Academic Significance and Societal Importance of the Research Achievements |
本研究では,プロアントシアニジン類のうちでピロガロール部分を有するものが癌細胞増殖阻害活性を持ち,エピカテキンを構成単位とした5量体以上のものがガンの転移に関わる遺伝子の発現を抑制することを明らかにした。ガン細胞の増殖阻害のみに焦点を当てた従来の研究より,転移を抑制する点で優位性がある。また,プロアントシアニジン類は農産物の可食部以外に含まれているので未利用農産物の有効利用に繋がる研究成果である。
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