Synergistic antioxidative activities of hydroxycinnamoyl-peptides.

Antioxidants have become an important subject of study as an active ingredient for cosmetics and preservatives for food. We synthesized antioxidative peptide conjugates of hydroxycinnamic acids (HCAs) such as ferulic acid (FA), caffeic acid (CA), and sinapic acid (SA) by SPPS method. We measured their potential antioxidant properties by 2, 2-diphenyl-1-picrylhydrazyl radical (DPPH) scavenging test and lipid autoxidation inhibition test. When the antioxidative peptides, such as glutathione analogue (GS(Bzl)H) and carnosine (CAR), were conjugated to HCAs, their antioxidative activities were enhanced significantly. CA-peptides exhibited the highest free radical scavenging activity by the DPPH test, and showed good antioxidative activity in the lipid autoxidation test. FA- and SA-peptides showed excellent antioxidative activity in the lipid autoxidation test. Furthermore, we demonstrated a synergistic antioxidative activity of HCA-peptide conjugates by comparing their antioxidative activity with that of a simple mixture of HCAs and the antioxidant peptides. 2009 European Peptide Society and John Wiley & Sons, Ltd.