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DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer
dc.creator | Cvijetić, Ilija | |
dc.creator | Bigović, Miljan | |
dc.creator | Ristivojević, Petar | |
dc.creator | Vitorović-Todorović, Maja D. | |
dc.creator | Zloh, Mire | |
dc.creator | Milojković-Opsenica, Dušanka | |
dc.date.accessioned | 2021-08-27T11:30:57Z | |
dc.date.available | 2021-08-27T11:30:57Z | |
dc.date.issued | 2021 | |
dc.identifier.issn | 1040-0400 | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/4534 | |
dc.description.abstract | Humulones and iso-humulones are potent natural antioxidants found in beer. In this study, density functional theory (DFT) method was applied for elucidating the structure-antioxidant activity relationship and molecular mechanism of antioxidant activity of eight bioactive humulones previously identified in different beer samples: isoxanthohumol, (R)- and (S)-adhumulone, cis- and trans-iso-adhumulone, cis- and trans-iso-n-humulone, and desdimethyl-octahydro-iso-cohumulone. The calculated bond dissociation enthalpies (BDEs) suggest that desdimethyl-octahydro-iso-cohumulone was the most potent compound with BDEs 5.1 and 23.9 kJ/mol lower compared to the values for resveratrol in gas phase and water, respectively. The enolic –OH is the most reactive site for hydrogen atom transfer (HAT). The presence of β-keto group with respect to enolic –OH diminishes the HAT potency via the formation of a strong intramolecular hydrogen bond. Another common antioxidant mechanism, single electron transfer followed by proton transfer (SET-PT), is only feasible for isoxanthohumol. The results of this study indicate a strong correlation between the increased antioxidant activity of beer products and the higher content of reduced iso-α-acids. | |
dc.language | en | |
dc.publisher | Springer | |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200168/RS// | |
dc.rights | openAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | |
dc.source | Structural Chemistry | |
dc.subject | Structure-antioxidant activity relationship | |
dc.subject | Density functional theory | |
dc.subject | Prenylated flavonoids | |
dc.subject | Bond dissociation enthalpy | |
dc.subject | Hop | |
dc.title | DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer | |
dc.type | article | en |
dc.rights.license | BY | |
dcterms.abstract | Милојковић-Опсеница, Душанка; Биговић, Миљан; Виторовић-Тодоровић, Маја Д.; Ристивојевић, Петар; Цвијетић, Илија; Злох, Мире; | |
dc.citation.volume | 32 | |
dc.citation.spage | 2051 | |
dc.citation.epage | 2059 | |
dc.identifier.wos | 000642014900001 | |
dc.identifier.doi | 10.1007/s11224-021-01780-4 | |
dc.citation.rank | M22~ | |
dc.type.version | publishedVersion | |
dc.identifier.scopus | 2-s2.0-85104973766 | |
dc.identifier.fulltext | https://cherry.chem.bg.ac.rs/bitstream/id/27429/DFT_study_pub_2021.pdf |