Synthesis of Guaiacol--D-glucoside and Curcumin-bis--D-glucoside by an Amyloglucosidase from Rhizopus

Authors: R. Vijayakumar, Giriyapura¹; Divakar, Soundar²

Source: Biotechnology Letters, Volume 27, Number 18, September 2005 , pp. 1411-1415(5)

Publisher: Springer

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Abstract:

Guaiacol (2-methoxyphenol) and curcumin [1E,6E-1,7-di(4-hydroxy-3-methoxy-phenyl)-1,6-heptadiene-3,5-dione] were converted into their corresponding glucosides using glucose and an amyloglucosidase from Rhizopus. Guaiacol- alpha

-D-glucoside yields ranged from 3 to 52% with the highest at pH 7.0. Curcumin-bis- alpha

-D-glucoside yields ranged from 3 to 48% with the highest at pH 4.0 with 50% (w/w D-glucose) of enzyme. The phenolic hydroxyl group of guaiacol and both phenolic hydroxyl groups of curcumin were glucosylated at the C1 carbon of alpha

-D-glucose indicating that the enzymatic reaction is stereospecific. Both guaiacol- alpha

-D-glucoside and curcumin-bis- alpha

-D-glucosides had antioxidant activities.

Keywords: amyloglucosidase; curcumin-bis- alpha -D-glucoside; glucosylation; guaiacol- alpha -D-glucoside; phenolic hydroxyl

Document Type: Research article

DOI: http://dx.doi.org/10.1007/s10529-005-3691-8

Affiliations: 1: Fermentation Technology and Bioengineering, Central Food Technological Research Institute, 570020, Mysore, India, 2: Fermentation Technology and Bioengineering, Central Food Technological Research Institute, 570020, Mysore, India, Email: divakar@cscftri.ren.nic.in

Publication date: 2005-09-01