Molecular design of potent, hydrophilic tyrosinase inhibitors based on the natural dihydrooxyresveratrol skeleton
| Autor: | Yuri Tanaka, Ken-ichi Nihei, Marina Suzuki, Yuka Kodachi |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Glycosylation
Stereochemistry Tyrosinase 010402 general chemistry 01 natural sciences Biochemistry Tyrosinase inhibitor Analytical Chemistry Fungal Proteins chemistry.chemical_compound Inhibitory Concentration 50 Structure-Activity Relationship Glucoside Glucosides Enzyme Inhibitors IC50 Molecular Structure 010405 organic chemistry Monophenol Monooxygenase Organic Chemistry General Medicine Resorcinols 0104 chemical sciences chemistry Resveratrol Wittig reaction Kojic acid Agaricales |
| Zdroj: | Carbohydrate research. 472 |
| ISSN: | 1873-426X |
| Popis: | In this study, dihydrooxyresveratrol glucosides 3–6 were synthesized for the first time to the best of our knowledge by the Wittig reaction and Schmidt glycosylation as key steps for the purpose of developing novel hydrophilic tyrosinase inhibitors. Results obtained from inhibitory studies revealed 50% inhibitory concentration (IC50) values of 12.80 μM and 2.63 μM for 4-resorcinol glucosides 3 and 4, respectively. The IC50 value of 4 was approximately 4 times greater than that of kojic acid, which is a typical tyrosinase inhibitor. In contrast, 5-resorcinol glucosides 5 and 6 exhibited tyrosinase-inhibitory activity; however their IC50s were not estimated within 100 μM. These results suggested that the discovering 4-resorcinol structure of dihydrooxyresveratrol glucoside is crucial for inducing potent tyrosinase-inhibitory activity. |
| Databáze: | OpenAIRE |
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