Antiproliferative and antioxidant activity of xanthohumol acyl derivatives

Abstract

A series of mono- and diacyl- xanthohumol (1) derivatives was synthesized with yields of 10–30%. All the compounds were tested against the antiproliferative activity of human cancer cell line of colon adenocarcinoma (HT-29) using SRB assay. The most active (IC50 values < 12 μM) were three compounds: 4-O-acetylxanthohumol (2) (IC50 = 11.84 μM), 4,4′-Di-O-acetylxanthohumol (3) (IC50 = 11.75 μM) and 4-Odecanoylxanthohumol (4) (IC50 = 10.04 μM). For the starting compound xanthohumol (1) IC50 = 9.74 μM. The antioxidant activity was determined by the method of 2.2-diphenyl-1-picrylhydrazyl radical and 2,2′-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid and expressed as μM of Trolox equivalent antioxidant capacity per gram. Only one compound 4-O-acetylxanthohumol (2) (15 μM Trolox equivalent antioxidant capacity for 2,2-diphenyl-1-picrylhydrazyl radical and 160 μM Trolox equivalent antioxidant capacity for 2,2′-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid methods) showed a lower antioxidant activity compared to xanthohumol (1) (38 μM Trolox equivalent antioxidant capacity for 2,2-diphenyl-1-picrylhydrazyl radical and 19 μM Trolox equivalent antioxidant capacity for 2,2′-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid methods). Other tested compounds showed comparable or higher antioxidant activity as xanthohumol (1).