Antiproliferative and antioxidant activity of xanthohumol acyl derivatives

• Published in: Medicinal chemistry research Vol. 26; no. 8; pp. 1764 - 1771
• Main Authors: Żołnierczyk, Anna K., Baczyńska, Dagmara, Potaniec, Bartłomiej, Kozłowska, Joanna, Grabarczyk, Małgorzata, Woźniak, Edyta, Anioł, Mirosław
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.08.2017; Springer Nature B.V
• Subjects: Adenocarcinoma; Antioxidants; Antiproliferatives; Assaying; Biochemistry; Biomedical and Life Sciences; Biomedicine; Cancer; Cell Biology; Cocoa; Colon; Colon cancer; Derivatives; Equivalence; Original Research; Pharmacology/Toxicology; Series (mathematics); Vitamin E; Xanthohumol; Xanthohumol; Hop flavonoids; Antiproliferative activity; Antioxidant activity
• ISSN: 1054-2523; 1554-8120
• DOI: 10.1007/s00044-017-1887-9

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 ).