Plant polyphenols, including dietary polyphenols such as resveratrol, are important components in the plant antioxidant and defence systems. They are also known to exert beneficial effects on human health through diet. As they are produced, these polyphenols may be subjected to deleterious enzymic oxidation by the plant polyphenol oxidases. They are generally synthesized as glycosides like 5,4′-dihydroxystilbene-3-O-β-d-glucopyranoside, the 3-glucoside of resveratrol. The effects of the glycosylation and methylation of the parent resveratrol on its enzymic oxidation were studied. Methyl and glucosyl derivatives were synthesized using simple one-step methodologies. The kinetics of their enzymic oxidation by tyrosinases were defined. Substitution at the p-hydroxy group, by either glucose or methyl, abolished enzymic oxidation by both mushroom and grape tyrosinases. Substitution at the m-hydroxy group with methyl had a small effect, but substitution with glucose resulted in a much lower affinity of the enzymes for the glycoside. We suggest that glycosylation of polyphenols in nature helps to protect these vital molecules from enzymic oxidation, extending their half-life in the cell and maintaining their beneficial antioxidant capacity and biological properties.
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August 2003
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Research Article|
August 15 2003
Glycosylation of resveratrol protects it from enzymic oxidation
Gilly REGEV-SHOSHANI;
Gilly REGEV-SHOSHANI
∗Institute of Biochemistry, Food Science and Nutrition, The Hebrew University of Jerusalem, P.O. Box 12, Rehovot 76100, Israel
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Oded SHOSEYOV;
Oded SHOSEYOV
†Department of Horticulture, The Faculty of Agricultural, Food and Environmental Quality Sciences, The Hebrew University of Jerusalem, P.O. Box 12, Rehovot 76100, Israel
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Itzhak BILKIS;
Itzhak BILKIS
∗Institute of Biochemistry, Food Science and Nutrition, The Hebrew University of Jerusalem, P.O. Box 12, Rehovot 76100, Israel
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Zohar KEREM
Zohar KEREM
1
∗Institute of Biochemistry, Food Science and Nutrition, The Hebrew University of Jerusalem, P.O. Box 12, Rehovot 76100, Israel
1To whom correspondence should be addressed (e-mail kerem@agri.huji.ac.il).
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Publisher: Portland Press Ltd
Received:
January 20 2003
Revision Received:
April 14 2003
Accepted:
April 16 2003
Accepted Manuscript online:
April 16 2003
Online ISSN: 1470-8728
Print ISSN: 0264-6021
The Biochemical Society, London ©2003
2003
Biochem J (2003) 374 (1): 157–163.
Article history
Received:
January 20 2003
Revision Received:
April 14 2003
Accepted:
April 16 2003
Accepted Manuscript online:
April 16 2003
Citation
Gilly REGEV-SHOSHANI, Oded SHOSEYOV, Itzhak BILKIS, Zohar KEREM; Glycosylation of resveratrol protects it from enzymic oxidation. Biochem J 15 August 2003; 374 (1): 157–163. doi: https://doi.org/10.1042/bj20030141
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