論文 - 詳細
| RRC ID | 38381 |
|---|---|
| 著者 | Hamada Y, Takano S, Ayano Y, Tokunaga M, Koashi T, Okamoto S, Doi S, Ishida M, Kawasaki T, Hamada M, Nakajima N, Saito A. |
| タイトル | Structure-Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities. |
| ジャーナル | Molecules |
| Abstract |
Proanthocyanidins, which are composed of oligomeric flavan-3-ol units, are contained in various foodstuffs (e.g., fruits, vegetables, and drinks) and are strongly biologically active compounds. We investigated which element of the proanthocyanidin structure is primarily responsible for this functionality. In this study, we elucidate the importance of the upper-unit of 4-8 condensed dimeric flavan-3-ols for antimicrobial activity against Saccharomyces cerevisiae (S. cerevisiae) and cervical epithelioid carcinoma cell line HeLa S3 proliferation inhibitory activity. To clarify the important constituent unit of proanthocyanidin, we synthesized four dimeric compounds, (-)-epigallocatechin-[4,8]-(+)-catechin, (-)-epigallocatechin-[4,8]-(-)-epigallocatechin, (-)-epigallocatechin-[4,8]-(-)-epigallocatechin-3-O-gallate, and (+)-catechin-[4,8]-(-)-epigallocatechin and performed structure-activity relationship (SAR) studies. In addition to antimicrobial activity against S. cerevisiae and proliferation inhibitory activity on HeLa S3 cells, the correlation of 2,2-diphenyl-l-picrylhydrazyl radical scavenging activity with the number of phenolic hydroxyl groups was low. On the basis of the results of our SAR studies, we concluded that B-ring hydroxyl groups of the upper-unit of the dimer are crucially important for strong and effective activity. |
| 巻・号 | 20(10) |
| ページ | 18870-85 |
| 公開日 | 2015-10-16 |
| DOI | 10.3390/molecules201018870 |
| PII | molecules201018870 |
| PMID | 26501251 |
| PMC | PMC6332077 |
| MeSH | Antifungal Agents / chemistry Antifungal Agents / pharmacology Antineoplastic Agents / chemistry Antineoplastic Agents / pharmacology Biphenyl Compounds / chemistry Cell Proliferation / drug effects Drug Screening Assays, Antitumor Flavonoids / chemistry* Flavonoids / pharmacology Free Radical Scavengers / chemistry* Free Radical Scavengers / pharmacology Free Radicals / chemistry HeLa Cells Humans Inhibitory Concentration 50 Microbial Sensitivity Tests Picrates / chemistry Saccharomyces cerevisiae / drug effects Structure-Activity Relationship |
| IF | 3.267 |
| 引用数 | 9 |
| WOS 分野 | CHEMISTRY, ORGANIC |
| オルトメトリクス指標 |
オルトメトリクス指標項目
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| 最多言及媒体 | X(Twitter) |
| 各媒体での言及数の合計 | 2 |
| 過去6か月間でのオルトメトリクス指標の変動値 | 0.0 |
| リソース情報 | |
| ヒト・動物細胞 | HeLa-S3 WI-38 |