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Synthesis of methylated quercetin analogues for enhancement of radical-scavenging activity
- Synthesis of methylated quercetin analogues for enhancement of radical-scavenging activity
- Imai, Kohei; Nakanishi, Ikuo; Ohkubo, Kei; Ohba, Yusuke; Arai, Takuya; Mizuno, Mirei; Fukuzumi, Shunichi; Matsumoto, Ken-ichiro; Fukuhara, Kiyoshi
- Ewha Authors
- Shunichi Fukuzumi
- SCOPUS Author ID
- Shunichi Fukuzumi
- Issue Date
- Journal Title
- RSC ADVANCES
- vol. 7, no. 29, pp. 17968 - 17979
- ROYAL SOC CHEMISTRY
- SCIE; SCOPUS
- 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 stabilisation of the radical cation intermediate by the electron-donating effect of the methyl group as well as by the planar structure of the molecule.
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