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Synthesis of Methylated Quercetin Analogues for Enhancement of Radical-Scavenging Activity
https://repo.qst.go.jp/records/48085
https://repo.qst.go.jp/records/48085ce393455-b2d8-4433-ab70-f53cb1be64b2
| Item type | 学術雑誌論文 / Journal Article(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2017-07-12 | |||||
| タイトル | ||||||
| タイトル | Synthesis of Methylated Quercetin Analogues for Enhancement of Radical-Scavenging Activity | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| アクセス権 | ||||||
| アクセス権 | metadata only access | |||||
| アクセス権URI | http://purl.org/coar/access_right/c_14cb | |||||
| 著者 |
Imai, Kohei
× Imai, Kohei× Nakanishi, Ikuo× Ohkubo, Kei× Ohba, Yusuke× Arai, Takuya× Mizuno, Mirei× Fukuzumi, Shunichi× Matsumoto, Kenichiro× Fukuhara, Kiyoshi× 今井 耕平× 中西 郁夫× 大久保 敬× 荒井 卓也× 松本 謙一郎 |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | Three quercetin derivatives with enhanced radical-scavenging activity were designed and synthesised. Because the radical-scavenging reaction of quercetin is known to proceed via an electron transfer from quercetin to radicals, producing the corresponding quercetin radical cation intermediate, the introduction of electron-donating groups into the quercetin molecule is expected to enhance its radical-scavenging activity. Thus, methyl groups were introduced into the catechol moiety in the quercetin molecule at either the 2'- or 5'-position, or both. All three quercetin analogues were found to exhibit higher radical-scavenging activity than the parent quercetin. The activity of 5'-methylquercetin is the highest among the three analogues. The optimised structure of 5'-methylquercetin calculated by density functional theory demonstrated a coplanar structure between the 4H-curomen (AC rings) and catechol (B ring) moieties, while dimethylquercetin and 2'-methylquercetin have a twisted structure between the Ac and B rings. These results demonstrate that the highest radical-scavenging activity of 5'-methylquercetin is due to the stabiisation of the radical cation intermediate by the electron-donating effect of the methyl group as well as by the planar structure of the molecule. | |||||
| 書誌情報 |
RSC Advances 巻 7, 号 29, p. 17968-17979, 発行日 2017-03 |
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| 出版者 | ||||||
| 出版者 | Royal Society of Chemistry | |||||
| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 2046-2069 | |||||
| DOI | ||||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | 10.1039/C7RA02329D | |||||
