title: Glucosylation of the flavonoid, astragalin by Leuconostoc mesenteroides B-512FMCM dextransucrase acceptor reactions and characterization of the products.
abstract: Astragalin (kaempferol-3-O-β-D-glucopyranoside, Ast) glucosides were synthesized by the acceptor reaction of a dextransucrase produced by Leuconostoc mesenteroides B-512FMCM with astragalin and sucrose. Each glucoside was purified and their structures were assigned as kaempferol-3-O-β-D-glucopyranosyl-(1→3)-O-α-D-glucopyranoside (or kaempferol-3-O-β-D-nigeroside, Ast-G1') and kaempferol-3-O-β-D-glucopyranosyl-(1→6)-O-α-D-glucopyranoside (or kaempferol-3-O-β-D-isomaltoside, Ast-G1) for one glucose transferred, and kaempferol-3-O-β-D-isomaltooligosacharide (Ast-IMO or Ast-Gn; n=2-8). The astragalin glucosides exhibited 8.3-60.6% higher inhibitory effects on matrix metalloproteinase-1 expression, 18.8-20.3% increased antioxidant effects, and 3.8-18.8% increased inhibition activity of melanin synthesis compared to control (without the addition of compound), depending on the number of glucosyl residues linked to astragalin. These novel compounds could be used to further expand the industrial applications of astragalin glucosides, in particular in the cosmetics industry.
authors: Interdisciplinary Program of Graduate School for Bioenergy and Biomaterials, Chonnam National University, Gwangju, 500-757 Republic of Korea.
authors: Go-Eun
authors: GE
authors: Kim
authors: Hee-Kyoung
authors: HK
authors: Kang
authors: Eun-Seong
authors: ES
authors: Seo
authors: Sun-Hwa
authors: SH
authors: Jung
authors: Jun-Seong
authors: JS
authors: Park
authors: Duck-Hee
authors: DH
authors: Kim
authors: Do-Won
authors: DW
authors: Kim
authors: Sul-Ah
authors: SA
authors: Ahn
authors: Changshin
authors: C
authors: Sunwoo
authors: Doman
authors: D
authors: Kim
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology; D001426:Bacterial Proteins / Q000235:genetics / Q000378:metabolism; D001709:Biotechnology; D005960:Glucosides / Q000096:biosynthesis / Q000737:chemistry / Q000494:pharmacology; D005964:Glucosyltransferases / Q000235:genetics / Q000378:metabolism*; D006031:Glycosylation; D044949:Kaempferols / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D007934:Leuconostoc / Q000201:enzymology* / Q000235:genetics; D020781:Matrix Metalloproteinase 1 / Q000096:biosynthesis; D008543:Melanins / Q000096:biosynthesis
chemical_list: D000975:Antioxidants; D001426:Bacterial Proteins; D005960:Glucosides; D044949:Kaempferols; D008543:Melanins; C001579:astragalin; D005964:Glucosyltransferases; C020025:dextransucrase; D020781:Matrix Metalloproteinase 1