Two-step enzymatic modification of solid-supported bergenin in aqueous and organic media
The natural flavonoid bergenin was directly immobilized onto carboxylic acid-functionalized controlled pore glass (carboxy-CPG) at 95% yield. Immobilized bergenin was brominated via chloroperoxidase in aqueous solution and then transesterified with vinyl butyrate in diisopropyl ether by subtilisin carslberg (SC) extracted into the organic solvent via ion-pairing. Enzymatic cleavage of 7-bromo-4-butyrylbergenin from carboxy-CPG (9.6% final yield) was accomplished using lipase B (LipB) in an aqueous/organic mixture (90/10 v/v of water/acetonitrile), demonstrating the feasibility of solid-phase biocatalysis of a natural product in aqueous and non-aqueous media.
Akbar, Umar,Shin, Dong-Sik,Schneider, Elizabeth,Dordick, Jonathan S.,Clark, Douglas S.
From the stem bark of Mallotus plicatus (Muell.Arg.) Airy Shaw, two new gallic acid glycosides, namely bergenin-8-O-α-L-rhamnoside (1) and seco-bergenin-8-O-α-L-rhamnoside (2) were isolated along with seven known compounds (3-9). The structures of the new
Tannins and related compounds. LXXXVIII.(1)) Isolation and characterization of hydrolyzable tannins from Mallotus japonicus (THUNB.) MUELLER-ARG. And M. Philippinensis (LAM.) MUELLER-ARG.
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Saijo,Nonaka,Nishioka,Chen,Hwang
p. 2940 - 2947
(2007/10/02)
BERGENIN DERIVAVTIVES FROM MALLOTUS JAPONICUS
Three new bergenin derivatives were isolated from the bark of Mallotus japonicus and determined to be 11-O-galloylbergenin, 4-O-galloylbergenin and 11-O-galloyldemethylbergenin.The 13C resonances of bergenin were fully assigned.Key Word Index - Mallotus japonicus; Euphorbiaceae; polyphenols; 11-O-galloylbergenin; 4-O-galloylbergenin; 11-O-galloyldemethylbergenin; geraniin; methylellagic acid; 13C NMR.