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- Title
Synthesis and structure-activity relationship study of aldose reductase inhibiting marine alkaloid lukianol A and its derivatives.
- Authors
Fumito Ishibashi; Shijiao Zha; Taiyo Kondo; Mayu Sakamoto; Mikinori Ueno; Tsutomu Fukuda
- Abstract
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.
- Subjects
ALDOSE reductase; STRUCTURE-activity relationships; HYDROXYL group; ISOQUINOLINE alkaloids; ALKALOIDS
- Publication
Bioscience, Biotechnology & Biochemistry, 2023, Vol 87, Issue 2, p148
- ISSN
0916-8451
- Publication type
Article
- DOI
10.1093/bbb/zbac193