Amyloglucosidase Catalyzed Syntheses of Bakuchiol Glycosides in Supercritical Carbon Dioxide.

Enzymatic syntheses of water soluble Bakuchiol glycosides were carried out in di-isopropyl ether organic media
using amyloglucosidase from Rhizopus mold. The reactions were carried out under conventional reflux conditions
and in supercritical CO2 atmospheric conditions. Out of the eleven carbohydrate molecules employed for the reaction,
D-glucose, D-ribose and D-arabinose gave glycosides in yields of 9.0% to 51.4% under conventional reflux
conditions. Under supercritical CO2 atmosphere (100 bar pressure at 50 oC), bakuchiol formed glycosides with Dglucose,
D-galactose, D-mannose, D-fructose, D-ribose, D-arabinose, D-sorbitol and D-mannitol in yields ranging
from 9% to 46.6%. Out of the bakuchiol glycosides prepared, 6-O-(6-D-fructofruranosyl)bakuchiol showed the best
antioxidant (1.4 mM) and ACE inhibitory activities (0.64 mM).