Enzymatic synthesis of novel phenol acid rutinosides using rutinase and their antiviral activity in vitro.
Novel rutinosides of vanillic acid, sinapic acid, ferulic acid, and caffeic acid were prepared via a rutinase-catalyzed transglycosylation reaction. Reaction mixtures containing rutin, phenolic acid, and rutinase derived from tartary buckwheat ( Fagopyrum tataricum ) seeds were incubated in 20 mM acetate buffer (pH 5.0) at 40 °C. The resulting rutinoside of each phenolic acid was purified by HPLC, and the structure was determined by NMR and FAB-MS analysis. Antiviral activity was determined using feline calicivirus (FCV) strain F9, which is a typical norovirus surrogate. It was found that rutinosylation of the phenolic acids increased their antiviral activity against FCV, with the sinapic acid rutinoside being the most effective. These results will contribute to the development of antiviral agents against noroviruses.
Graduate School of Agriculture, Shinshu University , 8304 minamiminowamura, Ina, Nagano 399-4598, Japan.
Shigeru
S
Katayama
Fumiaki
F
Ohno
Yuki
Y
Yamauchi
Miyuki
M
Kato
Hidefumi
H
Makabe
Soichiro
S
Nakamura
D000818:Animals; D000998:Antiviral Agents / Q000032:analysis*; D017927:Calicivirus, Feline / Q000187:drug effects; D002415:Cats; D002460:Cell Line; D002470:Cell Survival; D002851:Chromatography, High Pressure Liquid; D019612:Fagopyrum / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000494:pharmacology*; D010936:Plant Extracts / Q000494:pharmacology; D012431:Rutin / Q000032:analysis; D012639:Seeds / Q000737:chemistry; D001617:beta-Glucosidase / Q000032:analysis*
D000998:Antiviral Agents; D062385:Hydroxybenzoates; D010936:Plant Extracts; D012431:Rutin; C022559:rutinase; D001617:beta-Glucosidase; C017616:phenolic acid