Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene
| Autor: | Shin-ichi Ozaki, Kei Shimoda, Naoki Nagatani, Hiroki Hamada, Naoji Kubota, Daisuke Uesugi |
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| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Glycosylation Pterostilbene Oxygen radical absorbance capacity Stereochemistry Tyrosinase Chemistry Techniques Synthetic Resveratrol 01 natural sciences Applied Microbiology and Biotechnology Biochemistry Analytical Chemistry 03 medical and health sciences chemistry.chemical_compound Stilbenes Phytolacca americana Organic chemistry Glycosides Enzyme Inhibitors Molecular Biology chemistry.chemical_classification Oxygen Radical Absorbance Capacity biology Monophenol Monooxygenase 010405 organic chemistry Chemistry Organic Chemistry Glycoside General Medicine 0104 chemical sciences 030104 developmental biology Pinostilbene Glucosyltransferases Biocatalysis biology.protein Glucosyltransferase Agaricales Biotechnology |
| Zdroj: | Bioscience, Biotechnology, and Biochemistry. 81:226-230 |
| ISSN: | 1347-6947 0916-8451 |
| Popis: | The stilbene compound resveratrol was glycosylated to give its 4′-O-β-D-glucoside as the major product in addition to its 3-O-β-D-glucoside by a plant glucosyltransferase from Phytolacca americana expressed in recombinant Escherichia coli. This enzyme transformed pterostilbene to its 4′-O-β-D-glucoside, and converted pinostilbene to its 4′-O-β-D-glucoside as a major product and its 3-O-β-D-glucoside as a minor product. An analysis of antioxidant capacity showed that the above stilbene glycosides had lower oxygen radical absorbance capacity (ORAC) values than those of the corresponding stilbene aglycones. The 3-O-β-D-glucoside of resveratrol showed the highest ORAC value among the stilbene glycosides tested, and pinostilbene had the highest value among the stilbene compounds. The tyrosinase inhibitory activities of the stilbene aglycones were improved by glycosylation; the stilbene glycosides had higher activities than the stilbene aglycones. Resveratrol 3-O-β-D-glucoside had the highest tyrosinase inhibitory activity among the stilbene compounds tested. |
| Databáze: | OpenAIRE |
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