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Synthesis of Quercetin‐3‐ O ‐Glucoside from Rutin by Penicillium decumbens Naringinase
Author(s) -
Lee YoungSu,
Huh JiYoung,
Nam SoHyun,
Kim Doman,
Lee SooBok
Publication year - 2013
Publication title -
journal of food science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.772
H-Index - 150
eISSN - 1750-3841
pISSN - 0022-1147
DOI - 10.1111/1750-3841.12056
Subject(s) - rutin , quercetin , chemistry , bioconversion , glucoside , maltase , bioavailability , biochemistry , food science , enzyme , fermentation , biology , antioxidant , pharmacology , medicine , alternative medicine , pathology
Enzymatic bioconversion of rutin to quercetin‐3‐ O ‐glucoside (Q‐3‐G) by Penicillium decumbens naringinase was increased with reaction pH increased approximately to pH 6.0. It resulted in greater than 92% production of Q‐3‐G due to the removal of the terminal rhamnose at the controlled pH 6.0. The enzymatic bioconversion of rutin to Q‐3‐G was repetitively performed, yielding 84% after 5 batches with little quercetin formation. Interestingly, the water solubility of Q‐3‐G was enhanced 69‐ and 328‐fold over those of rutin and quercetin, which may make Q‐3‐G more bioavailable in food. Q‐3‐G was approximately 6‐ and 1.4‐fold more potent than rutin as an inhibitor of human intestinal maltase and human DL‐3‐hydroxy‐3‐methylglutalyl coenzyme A reductase. Q‐3‐G was less potent (16‐ and 1.3‐fold, respectively) than quercetin as an inhibitor of these enzymes. However, the results suggest that Q‐3‐G may be confirmed more effective and bioavailable food component than rutin and even quercetin because of its enhanced solubility and inhibitory properties. Practical Application : Bioconverted intermediate, quercetin‐3‐ O ‐glucoside (Q‐3‐G), was found and confirmed to be largely more soluble than rutin and quercetin in water solution, which might make it more bioavailable as food ingredient. In addition, Q‐3‐G inhibited mildly the intestinal maltase, which might act as antidiabetic substance by modulating the adsorption of glucose in the intestine.