Enzymatic production of highly soluble myricitrin glycosides using beta-galactosidase.
Myricitrin, a botanical flavonol glycoside, could be a useful ingredient of functional foods, cosmetics, and medicines because of its high anti-oxidative activity. However, due to its insolubility in water, it has a limited range of use. To improve this solubility, we glycosylated myricitrin by an enzymatic transglycosylate reaction. Myricitrin was galactosylated by beta-galactosidase from Bacillus circulans using lactose as a sugar donor. The reaction product was 480 times more soluble than myricitrin. Four myricitrin galactosides were isolated from the reaction products by column chromatography, and their molecular structures were identified by using ESI-MS, 1H-NMR, 13C-NMR, 1H-1H COSY, 1H-13C HMQC and 1H-13C HMBC analysis. The solubility of these four myricitrin galactosides was more than 3.9 x 10(3) fold that of myricitrin, and each had similar anti-oxidative activity to that of myricitrin.
Shimizu
Ryosuke
R
Fundamental Research Division, San-Ei Gen F.F.I. Corporation, Sanwacho, Osaka, Japan.
Shimabayashi
Hiroshi
H
Moriwaki
Masamitsu
M
D001407:Bacillus / Q000201:enzymology; D001713:Biphenyl Compounds / Q000737:chemistry / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D005419:Flavonoids / Q000737:chemistry* / Q000378:metabolism*; D005609:Free Radicals / Q000737:chemistry / Q000378:metabolism; D006027:Glycosides / Q000737:chemistry* / Q000378:metabolism* / Q000494:pharmacology; D006834:Hydrazines / Q000737:chemistry / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010851:Picrates; D012995:Solubility; D021241:Spectrometry, Mass, Electrospray Ionization; D014867:Water; D001616:beta-Galactosidase / Q000378:metabolism*
D001713:Biphenyl Compounds; D005419:Flavonoids; D005609:Free Radicals; D006027:Glycosides; D006834:Hydrazines; D010851:Picrates; D014867:Water; C008577:myricitrin; C004931:1,1-diphenyl-2-picrylhydrazyl; D001616:beta-Galactosidase