Synthesis of xylooligosaccharides of daidzein and their anti-oxidant and anti-allergic activities.
The biocatalytic synthesis of xylooligosaccharides of daidzein was investigated using cultured cells of Catharanthus roseus and Aspergillus sp. β-xylosidase. The cultured cells of C. roseus converted daidzein into its 4'-O-β-glucoside, 7-O-β-glucoside, and 7-O-β-primeveroside, which was a new compound. The 7-O-β-primeveroside of daidzein was further xylosylated by Aspergillus sp. β-xylosidase to daidzein trisaccharide, i.e., 7-O-[6-O-(4-O-(β-d-xylopyranosyl))-β-d-xylopyranosyl]-β-d-glucopyranoside, which was a new compound. The 4'-O-β-glucoside, 7-O-β-glucoside, and 7-O-β-primeveroside of daidzein exerted DPPH free-radical scavenging and superoxide radical scavenging activity. On the other hand, 7-O-β-glucoside and 7-O-β-primeveroside of daidzein showed inhibitory effects on IgE antibody production.
Department of Chemistry, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan.
Kei
K
Shimoda
Hiroki
H
Hamada
Hatsuyuki
H
Hamada
D018926:Anti-Allergic Agents / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D001230:Aspergillus / Q000201:enzymology; D053898:Biosynthetic Pathways; D001713:Biphenyl Compounds / Q000037:antagonists & inhibitors / Q000737:chemistry / Q000378:metabolism; D030008:Catharanthus / Q000166:cytology / Q000378:metabolism; D002460:Cell Line; D016166:Free Radical Scavengers / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D005965:Glucuronates / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D007529:Isoflavones / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009844:Oligosaccharides / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D010851:Picrates / Q000037:antagonists & inhibitors / Q000737:chemistry / Q000378:metabolism; D012995:Solubility; D013481:Superoxides / Q000037:antagonists & inhibitors / Q000737:chemistry / Q000378:metabolism; D014867:Water / Q000737:chemistry; D014995:Xylosidases / Q000378:metabolism
D018926:Anti-Allergic Agents; D000975:Antioxidants; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D005965:Glucuronates; D007529:Isoflavones; D009844:Oligosaccharides; D010851:Picrates; C570991:xylooligosaccharide; D014867:Water; D013481:Superoxides; C004742:daidzein; C004931:1,1-diphenyl-2-picrylhydrazyl; D014995:Xylosidases; C026579:exo-1,4-beta-D-xylosidase