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Title:Exploring antioxidative properties of xanthohumol and isoxanthohumol : an integrated experimental and computational approach with isoxanthohumol pKa determination
Authors:ID Tošović, Jelena (Author)
ID Kolenc, Zala (Author)
ID Hostnik, Gregor (Author)
ID Bren, Urban (Author)
Files:.pdf 1-s2.0-S0308814624030279-main.pdf (2,80 MB)
MD5: 27EB29EC0F54E56ED22FB0DB28C84A49
 
Language:English
Work type:Article
Typology:1.01 - Original Scientific Article
Organization:FKKT - Faculty of Chemistry and Chemical Engineering
Abstract: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.
Keywords:antioxidative activity, bio-active membranes, xanthohumol, isoxanthohumol, ORAC and FRAP assays, pKa determination, density functional theory, DFT
Publication status:Published
Publication version:Version of Record
Submitted for review:06.09.2024
Article acceptance date:19.09.2024
Publication date:19.09.2024
Publisher:Elsevier Ltd.
Year of publishing:2025
Number of pages:12 str.
Numbering:Vol. 463, part 3, [article no.] 141377
PID:20.500.12556/DKUM-91732 New window
UDC:678.048
ISSN on article:1873-7072
COBISS.SI-ID:211688451 New window
DOI:10.1016/j.foodchem.2024.141377 New window
Copyright:© 2024 The Authors
Publication date in DKUM:31.01.2025
Views:0
Downloads:5
Metadata:XML DC-XML DC-RDF
Categories:Misc.
:
TOŠOVIĆ, Jelena, KOLENC, Zala, HOSTNIK, Gregor and BREN, Urban, 2025, Exploring antioxidative properties of xanthohumol and isoxanthohumol : an integrated experimental and computational approach with isoxanthohumol pKa determination. Food Chemistry [online]. 2025. Vol. 463, no. part 3,  141377. [Accessed 21 April 2025]. DOI 10.1016/j.foodchem.2024.141377. Retrieved from: https://dk.um.si/IzpisGradiva.php?lang=eng&id=91732
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Record is a part of a journal

Title:Food Chemistry
Publisher:Elsevier
ISSN:1873-7072
COBISS.SI-ID:23392261 New window

Document is financed by a project

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License:CC BY-NC 4.0, Creative Commons Attribution-NonCommercial 4.0 International
Link:http://creativecommons.org/licenses/by-nc/4.0/
Description:A creative commons license that bans commercial use, but the users don’t have to license their derivative works on the same terms.

Secondary language

Language:Slovenian
Keywords:antioksidanti, aktivnosti


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