Creating a Water-Soluble Resveratrol-Based Antioxidant by Site-Selective Enzymatic Glucosylation

Alexander Lepak, Alexander Gutmann, Sandra Tanja Kulmer, Bernd Nidetzky

Research output: Contribution to journalArticleResearchpeer-review

Abstract

The phytochemical resveratrol (trans-3,5,4′-trihydroxystilbene) has drawn great interest as health-promoting food ingredient and potential therapeutic agent. However, resveratrol shows vanishingly low water solubility; this limits its uptake and complicates the development of effective therapeutic forms. Glycosylation should be useful to enhance resveratrol solubility, with the caveat that unselective attachment of sugars could destroy the molecule's antioxidant activity. UGT71A15 (a uridine 5′-diphosphate α-D-glucose-dependent glucosyltransferase from apple) was used to synthesize resveratrol 3,5-β-D-diglucoside; this was about 1700-fold more water-soluble than the unglucosylated molecule (∼0.18 mM), yet retained most of the antioxidant activity. Resveratrol 3-β-D-glucoside, which is the naturally abundant form of resveratrol, was a practical substrate for perfect site-selective conversion into the target diglucoside in quantitative yield (g L−1 concentration).
LanguageEnglish
Pages1870-1874
JournalChemBioChem
Volume16
Issue number13
DOIs
StatusPublished - 2015

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Antioxidants
Water
Solubility
Glycosylation
Glucosyltransferases
Molecules
Uridine Diphosphate
Diphosphates
Uridine
Glucosides
Phytochemicals
Malus
resveratrol
Sugars
Health
Glucose
Food
Substrates
Therapeutics

Fields of Expertise

  • Human- & Biotechnology

Cite this

Creating a Water-Soluble Resveratrol-Based Antioxidant by Site-Selective Enzymatic Glucosylation. / Lepak, Alexander; Gutmann, Alexander; Kulmer, Sandra Tanja; Nidetzky, Bernd.

In: ChemBioChem, Vol. 16, No. 13, 2015, p. 1870-1874.

Research output: Contribution to journalArticleResearchpeer-review

Lepak, Alexander ; Gutmann, Alexander ; Kulmer, Sandra Tanja ; Nidetzky, Bernd. / Creating a Water-Soluble Resveratrol-Based Antioxidant by Site-Selective Enzymatic Glucosylation. In: ChemBioChem. 2015 ; Vol. 16, No. 13. pp. 1870-1874
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