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Creating a Water‐Soluble Resveratrol‐Based Antioxidant by Site‐Selective Enzymatic Glucosylation
Author(s) -
Lepak Alexander,
Gutmann Alexander,
Kulmer Sandra T.,
Nidetzky Bernd
Publication year - 2015
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201500284
Subject(s) - resveratrol , chemistry , glucosyltransferase , antioxidant , glucoside , glycosylation , biochemistry , phytochemical , glycoside , functional food , enzyme , solubility , substrate (aquarium) , organic chemistry , food science , biology , medicine , alternative medicine , pathology , ecology
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 m M ), 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).