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Angiotensin‐converting enzyme inhibitory and antioxidant activities of enzymatically synthesized phenolic and vitamin glycosides
Author(s) -
Charles Rajachristu Einstein,
Ponrasu Thangavel,
Sivakumar Ramaiah,
Divakar Soundar
Publication year - 2009
Publication title -
biotechnology and applied biochemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 70
eISSN - 1470-8744
pISSN - 0885-4513
DOI - 10.1042/ba20080041
Subject(s) - antioxidant , glycoside , enzyme , chemistry , inhibitory postsynaptic potential , biochemistry , angiotensin converting enzyme , enzyme inhibitor , pharmacology , stereochemistry , medicine , endocrinology , blood pressure
Amyloglucosidase from Rhizopus mould and β‐glucosidase from sweet almond were employed for the preparation of phenolic and vitamin glycosides of vanillin, N ‐vanillylnonanamide, DL ‐dopa, dopamine, curcumin, α‐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 ‐(β‐ 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‐β‐ D ‐glucopyranosyl)curcumin (0.8±0.04 mM), 4‐ O ‐(β‐ D ‐glucopyranosyl)vanillin (0.9±0.05 mM), 3‐hydroxy‐4‐ O ‐(β‐ D ‐galactopyranosyl‐(1′→4)β‐ 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).