التفاصيل البيبلوغرافية
| العنوان: |
Synthesis and structure-activity relationship study of aldose reductase inhibiting marine alkaloid lukianol A and its derivatives. |
| المؤلفون: |
Fumito Ishibashi, Shijiao Zha, Taiyo Kondo, Mayu Sakamoto, Mikinori Ueno, Tsutomu Fukuda |
| المصدر: |
Bioscience, Biotechnology & Biochemistry; Feb2023, Vol. 87 Issue 2, p148-157, 10p |
| مصطلحات موضوعية: |
ALDOSE reductase, STRUCTURE-activity relationships, HYDROXYL group, ISOQUINOLINE alkaloids, ALKALOIDS |
| مستخلص: |
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 (IC 50 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. [ABSTRACT FROM AUTHOR] |
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| قاعدة البيانات: |
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