title: Synthesis of quercetin-3-O-glucoside from rutin by Penicillium decumbens naringinase.
abstract: 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.
  
  
  CONCLUSIONS
  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.
authors: Department of Food and Nutrition, Brain Korea 21 Project, Yonsei University, Seoul, Republic of Korea.
authors: Young-Su
authors: YS
authors: Lee
authors: Ji-Young
authors: JY
authors: Huh
authors: So-Hyun
authors: SH
authors: Nam
authors: Doman
authors: D
authors: Kim
authors: Soo-Bok
authors: SB
authors: Lee
mesh_terms: D001682:Biological Availability; D005419:Flavonoids / Q000096:biosynthesis* / Q000494:pharmacology; D005960:Glucosides; D065089:Glycoside Hydrolase Inhibitors; D006801:Humans; D006863:Hydrogen-Ion Concentration; D006903:Hydroxymethylglutaryl CoA Reductases / Q000096:biosynthesis; D009097:Multienzyme Complexes / Q000378:metabolism*; D010407:Penicillium / Q000378:metabolism*; D011794:Quercetin / Q000031:analogs & derivatives; D012210:Rhamnose / Q000378:metabolism; D012431:Rutin / Q000737:chemistry*; D012995:Solubility; D001617:beta-Glucosidase / Q000378:metabolism*
chemical_list: D005419:Flavonoids; D005960:Glucosides; D065089:Glycoside Hydrolase Inhibitors; D009097:Multienzyme Complexes; C532085:quercetin 3'-O-glucoside; D012431:Rutin; D011794:Quercetin; D006903:Hydroxymethylglutaryl CoA Reductases; C039827:naringinase; D001617:beta-Glucosidase; D012210:Rhamnose