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Synthesis and evaluation of bibenzyl glycosides as potent tyrosinase inhibitors |
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| Authors: | Tajima Reiko Oozeki Hiromi Muraoka Seiichi Tanaka Saori Motegi Yukari Nihei Hiroyuki Yamada Yoichi Masuoka Noriyoshi Nihei Ken-ichi |
| Affiliation: | a Department of Applied Biochemistry, Faculty of Agriculture, Utsunomiya University, Utsunomiya, Tochigi 321-0943, Japan b Department of Chemistry, Faculty of Education, Utsunomiya University, Utsunomiya, Tochigi 321-0943, Japan c Department of Life Science, Okayama University of Science, Okayama 700-0005, Japan |
| Abstract: | Bibenzyl glycosides 1-6 were synthesized from 2,4-dihydoxybenzaldehyde and xylose, glucose, cellobiose or maltose. The key steps in the synthesis were the Wittig reaction and trichloroacetimidate glycosylation. Tests for tyrosinase inhibitory activity showed that all were significantly active, indicating that they are unique hydrophilic tyrosinase inhibitors. Bibenzyl xyloside 2 is a particularly potent inhibitor (IC50 = 0.43 μM, 17 times higher than that of kojic acid). These results suggest that the hydrophilic cavity of tyrosinase might accommodate the bulky carbohydrate on the bibenzyl scaffold. |
| Keywords: | Tyrosinase inhibitor Bibenzyl glycoside Wittig reaction Glycosylation |
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