20.500.12556/DKUM-91732 Exploring antioxidative properties of xanthohumol and isoxanthohumol an integrated experimental and computational approach with isoxanthohumol pKa determination This study explores the antioxidative activities of xanthohumol (XN) and isoxanthohumol (IXN), prenylated flavonoids from Humulus lupulus (family Cannabaceae), utilizing the oxygen radical absorption capacity (ORAC) and ferric reducing antioxidant power (FRAP) assays along with computational Density Functional Theory methods. Experimentally, XN demonstrated significantly higher antioxidative capacities than IXN. Moreover, we determined IXN pKa values using the UV/Vis spectrophotometric method for the first time, facilitating its accurate computational modeling under physiological conditions. Through a thermodynamic approach, XN was found to efficiently scavenge HOO• and CH3O• radicals via Hydrogen Atom Transfer (HAT) and Radical Adduct Formation (RAF) mechanisms, while CH3OO• scavenging was feasible only through the HAT pathway. IXN exhibited its best antioxidative activity against CH3O• via both HAT and RAF mechanisms and could also scavenge HOO• through RAF. Both Single Electron Transfer (SET) and Sequential Proton Loss-Electron Transfer (SPLET) mechanisms were thermodynamically unfavorable for all radicals and both compounds. antioxidative activity bio-active membranes xanthohumol isoxanthohumol ORAC and FRAP assays pKa determination density functional theory DFT antioksidanti aktivnosti true false true Elsevier Ltd. Angleški jezik Slovenski jezik https://www.sciencedirect.com/journal/food-chemistry © 2024 The Authors Članek v reviji 2025-01-31 09:55:48 2025-01-31 09:55:49 2026-01-19 07:22:04 0000-00-00 00:00:00 2025 0 0 12 str. part 3, [article no.] 141377 Vol. 463 Jan. 2025 0000-00-00 Zaloznikova Objavljeno NiDoloceno 2024-06-19 2024-09-19 2024-09-29 678.048 211688451 10.1016/j.foodchem.2024.141377 1873-7072 1-s2.0-S0308814624030279-main.pdf 1-s2.0-S0308814624030279-main.pdf 1 27EB29EC0F54E56ED22FB0DB28C84A49 b0433a66722d870887847b2b67add411e77d05ae918a05bd8b7e4ee9bb57a297 9f4ef827-dfb1-11ef-ae92-00155d000105 https://dk.um.si/Dokument.php?lang=slv&id=188357 https://www.sciencedirect.com/science/article/pii/S0308814624030279?via%3Dihub 0 2bfba945-f4ff-11f0-94a4-00155d580e02 https://dk.um.si/Dokument.php?lang=slv&id=202134 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0