Angiotensin-converting enzyme inhibitory and antioxidant activities of enzymatically synthesized phenolic and vitamin glycosides.
Amyloglucosidase from Rhizopus mould and beta-glucosidase from sweet almond were employed for the preparation of phenolic and vitamin glycosides of vanillin, N-vanillylnonanamide, DL-dopa, dopamine, curcumin, alpha-tocopherol (vitamin E), pyridoxine (vitamin B(6)), ergocalciferol (vitamin D(2)), thiamin (vitamin B(1)) and riboflavin (vitamin B(2)). Approx. 20 enzymatically prepared phenolic and vitamin glycosides were subjected to ACE (angiotensin-converting enzyme) inhibition activity measurements, and 14 glycosides were tested for antioxidant activities. Both phenolic and vitamin glycosides exhibited IC(50) values for ACE inhibition in the 0.52+/-0.03-3.33+/-0.17 mM range and antioxidant activities ranging from 0.8+/-0.04 to 1.18+/-0.06 mM. Comparable ACE inhibition values were observed between free phenols and vitamin glycosides. However, antioxidant activities of glycosides were, in general, lesser than those of free phenols. Best IC(50) value for ACE inhibition were observed for 11-O-(D-fructofuranosyl)thiamin (0.52+/-0.03 mM), 3-hydroxy-4-O-(6-D-sorbitol)phenylalanine (0.56+/-0.03 mM), 4-O-(beta-D-glucopyranosyl)vanillin (0.61+/-0.03 mM), 4-O-(D-galactopyranosyl)vanillin (0.61+/-0.03 mM) and pyridoxine-D-glucoside (0.84+/-0.04 mM). Similarly, best IC(50) values for antioxidant activity were observed for 1,7-O-(bis-beta-D-glucopyranosyl)curcumin (0.8+/-0.04 mM), 4-O-(beta-D-glucopyranosyl)vanillin (0.9+/-0.05 mM), 3-hydroxy-4-O-(beta-D-galactopyranosyl-(1'-->4)beta-D-glucopyranosyl)phenylalanine (0.9+/-0.05 mM), 20-O-(D-glucopyranosyl)ergocalciferol (0.9+/-0.05 mM) and dopamine-D-galactoside (0.93+/-0.05 mM).
Charles
Rajachristu Einstein
RE
Fermentation Technology and Bioengineering, Central Food Technological Research Institute, Council of Scientific and Industrial Research, Mysore 570 020, India.
Ponrasu
Thangavel
T
Sivakumar
Ramaiah
R
Divakar
Soundar
S
D000806:Angiotensin-Converting Enzyme Inhibitors / Q000378:metabolism*; D000975:Antioxidants / Q000378:metabolism*; D005087:Glucan 1,4-alpha-Glucosidase / Q000378:metabolism; D006027:Glycosides / Q000378:metabolism*; D020128:Inhibitory Concentration 50; D007700:Kinetics; D008958:Models, Molecular; D019906:Nuclear Magnetic Resonance, Biomolecular; D007703:Peptidyl-Dipeptidase A / Q000378:metabolism; D010636:Phenols / Q000378:metabolism*; D027861:Prunus / Q000737:chemistry; D012233:Rhizopus / Q000201:enzymology; D014815:Vitamins / Q000378:metabolism*; D001617:beta-Glucosidase / Q000378:metabolism
D000806:Angiotensin-Converting Enzyme Inhibitors; D000975:Antioxidants; D006027:Glycosides; D010636:Phenols; D014815:Vitamins; D001617:beta-Glucosidase; D005087:Glucan 1,4-alpha-Glucosidase; D007703:Peptidyl-Dipeptidase A