title: Enzymatic Synthesis of a Novel Kaempferol-3-O-β-d-glucopyranosyl-(1→4)-O-α-d-glucopyranoside Using Cyclodextrin Glucanotransferase and Its Inhibitory Effects on Aldose Reductase, Inflammation, and Oxidative Stress.
abstract: Kaempferol-3-O-β-d-glucopyranoside (astragalin, AS), a major flavonoid that exists in various plants, exerts antioxidant, antitumor, anti-human immunodeficiency virus (HIV), and anti-inflammatory effects. However, the low water solubility of AS limits its use. In this study, we used cyclodextrin glucanotransferase (CGTase) with maltose (G2) as a donor molecule to enzymatically modify AS to improve its water solubility and physiochemical properties. We isolated the glycosylated astragalin (G1-AS) and identified the structure of G1-AS as kaempferol-3-O-β-d-glucopyranosyl-(1→4)-O-α-d-glucopyranoside, where one glucose residue was transferred to AS. G1-AS retained the antioxidative activity of the original AS compound; however, the solubility of G1-AS was 65-fold higher than that of AS. In addition, G1-AS showed enhanced anti-inflammatory effects and aldose reductase inhibitory activity compared to AS when applied to rat lenses.
authors.affiliation: Department of Food Science and Nutrition, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.|Center for Aging and Health Care, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.
authors.forename: Woo-Jae
authors.initials: WJ
authors.lastname: Choung
authors.affiliation: Department of Food Science and Nutrition, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.
authors.forename: Seung Hwan
authors.initials: SH
authors.lastname: Hwang
authors.affiliation: Department of Food Science and Nutrition, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.|Center for Aging and Health Care, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.
authors.forename: Dam-Seul
authors.initials: DS
authors.lastname: Ko
authors.affiliation: Department of Food Science and Nutrition, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.
authors.forename: Set Byeol
authors.initials: SB
authors.lastname: Kim
authors.affiliation: Center for Aging and Health Care, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.|Department of Life Science, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.
authors.forename: Seo Hyun
authors.initials: SH
authors.lastname: Kim
authors.affiliation: Center for Aging and Health Care, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.|Department of Life Science, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.
authors.forename: Sung Ho
authors.initials: SH
authors.lastname: Jeon
authors.affiliation: Division of Strategic Food Research, Korea Food Research Institute , Gyeonggi 13539, South Korea.
authors.forename: Hee-Don
authors.initials: HD
authors.lastname: Choi
authors.affiliation: Department of Food Science and Nutrition, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.
authors.forename: Soon Sung
authors.identifier: http://orcid.org/0000-0003-4548-1285
authors.initials: SS
authors.lastname: Lim
authors.affiliation: Department of Food Science and Nutrition, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.|Center for Aging and Health Care, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.
authors.forename: Jae-Hoon
authors.identifier: http://orcid.org/0000-0002-0230-1769
authors.initials: JH
authors.lastname: Shim
mesh_terms: D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors* / Q000737:chemistry; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology; D055162:Biocatalysis; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D005964:Glucosyltransferases / Q000737:chemistry*; D007249:Inflammation; D044949:Kaempferols / Q000737:chemistry* / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000276:immunology; D051379:Mice; D015394:Molecular Structure; D018384:Oxidative Stress / Q000187:drug effects*; D000067996:RAW 264.7 Cells
chemical_list: D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D004791:Enzyme Inhibitors; D044949:Kaempferols; C006552:kaempferol; C001579:astragalin; D000449:Aldehyde Reductase; D005964:Glucosyltransferases; C019963:cyclomaltodextrin glucanotransferase
keywords: aldose reductase; anti-inflammatory; astragalin; glucanotransferase; solubility; transglycosylation