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Synthesis and structure-activity relationship study of aldose reductase inhibiting marine alkaloid lukianol A and its derivatives
http://hdl.handle.net/10069/00042048
http://hdl.handle.net/10069/00042048120adafc-6216-4288-92eb-88931a1a44b5
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
BBB87_148.pdf (4.5 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2023-02-10 | |||||
| タイトル | ||||||
| タイトル | Synthesis and structure-activity relationship study of aldose reductase inhibiting marine alkaloid lukianol A and its derivatives | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | marine alkaloid | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | lukianol | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | aldose reductase inhibitor | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | total synthesis | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | SAR | |||||
| 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 | |||||
| 著者 |
Ishibashi, Fumito
× Ishibashi, Fumito× Zha, Shijiao× Kondo, Taiyo× Sakamoto, Mayu× Ueno, Mikinori× Fukuda, Tsutomu |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | Lukianol A (1a) and its six derivatives 1b-1g, in which each hydroxyl groups of 1a was individually modified, were synthesized via the common intermediate 7a, which was obtained by condensation of the styryl carbazate 10 with p-hydroxyphenylpyruvic acid and subsequent [3,3]-sigmatropic rearrangement. The synthesized lukianol derivatives were evaluated for their ability to inhibit human aldose reductase. 4′-O-methyl (1b) and 4′-dehydroxy (1g) derivatives showed the same level of inhibitory activity as 1a (IC50 2.2 µM), indicating that the 4′-OH is irrelevant for the activity. In contrast, methylation of the hydroxyl group at the 4″′-position (1d) resulted in the loss of activity at a concentration of 10 µM, and masking the hydroxyl group at the 4″-position (1e) caused a 9-fold decrease in activity compared with that of 1b, suggesting that the 4″-OH is an essential group, and the 4″′-OH is required for higher activity. | |||||
| 書誌情報 |
Bioscience, Biotechnology, and Biochemistry 巻 87, 号 2, p. 148-157, 発行日 2022-12-12 |
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| 出版者 | ||||||
| 出版者 | Oxford University Press | |||||
| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 1347-6947 | |||||
| DOI | ||||||
| 関連タイプ | isVersionOf | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | 10.1093/bbb/zbac193 | |||||
| 権利 | ||||||
| 権利情報 | © The Author(s) 2022. Published by Oxford University Press on behalf of Japan Society for Bioscience, Biotechnology, and Agrochemistry. This article is published and distributed under the terms of the Oxford University Press, Standard Journals Publication Model (https://academic.oup.com/journals/pages/open_access/funder_policies/chorus/standard_publication_model) This is a pre-copyedited, author-produced version of an article accepted for publication in Bioscience, biotechnology, and biochemistry following peer review. The version of record Bioscience, biotechnology, and biochemistry, 87(2), pp.148-157; 2023 is available online at: https://doi.org/10.1093/bbb/zbac193. | |||||
| 著者版フラグ | ||||||
| 出版タイプ | AM | |||||
| 出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||
| 引用 | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | Bioscience, biotechnology, and biochemistry, 87(2), pp.148-157; 2023 | |||||
