@article{oai:nagasaki-u.repo.nii.ac.jp:00027914,
 author = {Ishibashi, Fumito and Zha, Shijiao and Kondo, Taiyo and Sakamoto, Mayu and Ueno, Mikinori and Fukuda, Tsutomu},
 issue = {2},
 journal = {Bioscience, Biotechnology, and Biochemistry},
 month = {Dec},
 note = {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., Bioscience, biotechnology, and biochemistry, 87(2), pp.148-157; 2023},
 pages = {148--157},
 title = {Synthesis and structure-activity relationship study of aldose reductase inhibiting marine alkaloid lukianol A and its derivatives},
 volume = {87},
 year = {2022}
}