Glycosides and amino acyl esters of carbohydrates as potent inhibitors of angiotensin converting enzyme.

About 12 glycosides prepared through amyloglucosidase catalysis and 23 amino acyl esters of carbohydrates prepared through lipase catalysis in organic solvents showed angiotensin converting enzyme (ACE) inhibition activity. Both amino acyl esters of carbohydrates and glycosides exhibited IC50 values for ACE inhibition in the 0.5 mM to 15.7 mM range. Eugenyl-D-glucoside (IC50: 0.5+/-0.04 mM), L-isoleucyl-D-glucose (IC50: 0.7+/-0.067 mM), vanillyl-D-sorbitol (IC50: 0.8+/-0.09 mM), L-histidyl-D-fructose (IC50: 0.9+/-0.087 mM), L-tryptophanyl-D-fructose (IC50: 0.9+/-0.092 mM), octyl-D-glucoside (IC50: 1.0+/-0.093 mM), vanillyl-D-mannoside (IC50: 1.0+/-0.089 mM), L-valyl-D-mannitol (IC50: 1.0+/-0.092 mM) and L-phenylalanyl-D-glucose (IC50: 1.0+/-0.089 mM) were the compounds, which showed the best ACE inhibitory activities.