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Antiproliferative and antioxidant activity of xanthohumol acyl derivatives

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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).

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Acknowledgements

This work was financially supported by National Science Center (Grant No.2011/01/B/NZ9/02890), 2011–2014.

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Authors and Affiliations

  1. Department of Chemistry, The Faculty of Food Science, Wrocław University of Environmental and Life Sciences, Norwida 25/27, Wrocław, 50-375, Poland

    Anna K. Żołnierczyk, Bartłomiej Potaniec, Joanna Kozłowska, Małgorzata Grabarczyk, Edyta Woźniak & Mirosław Anioł

  2. Molecular Techniques Unit, Department of Forensic Medicine, Wroclaw Medical University, Wrocław, Poland

    Dagmara Baczyńska

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  1. Anna K. Żołnierczyk
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  2. Dagmara Baczyńska
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Correspondence to Anna K. Żołnierczyk.

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Żołnierczyk, A.K., Baczyńska, D., Potaniec, B. et al. Antiproliferative and antioxidant activity of xanthohumol acyl derivatives. Med Chem Res 26, 1764–1771 (2017). https://doi.org/10.1007/s00044-017-1887-9

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  • DOI: https://doi.org/10.1007/s00044-017-1887-9

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