Polyphenols from Chilean Propolis and Pinocembrin Reduce MMP-9 Gene Expression and Activity in Activated Macrophages

Figure 1

Chromatogram at 290 nm showing the main components found in the ethanolic extract of Chilean propolis. 1: caffeic acid; 2: p-coumaric acid; 3: ferulic/isoferulic acid; 4: 3,4-dimethylcaffeic acid; 5: pinobanksin-5-methyl ether; 6: p-coumaric methyl ester; 7: quercetin; 8: pinobanksin; 9: quercetin-3-methyl ether; 10: pinocembrin-5-methyl ether; 11: apigenin; 12: luteolin-5-methyl ether; 13: cinnamyliden acetic acid; 14: pinobanksin derivative; 15: isorhamnetin; 16: pinocembrin; 17: caffeic acid benzyl ester; 18: caffeic acid isoprenyl ester; 19: pinobanksin-3-O-acetate; 20: caffeic acid isoprenyl ester; 21: chrysin; 22: caffeic acid phenethyl ester (CAPE); 23: galangin; 24: chrysin methyl ether; 25: p-coumaric benzyl ester; 26: caffeic acid derivative; 27: pinobanksin-3-O-propionate; 28: caffeic acid cinnamyl ester; 29: pinobanksin-3-O-pentenoate; 30: p-coumaric cinnamyl ester; 31: pinobanksin-3-O-butyrate; 32: pinobanksin-3-O-pentanoate/2-methylbutyrate; : unknown.