DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer
Autori
Cvijetić, IlijaBigović, Miljan
Ristivojević, Petar
Vitorović-Todorović, Maja D.
Zloh, Mire
Milojković-Opsenica, Dušanka
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Structure-antioxidant activity relationship / Density functional theory / Prenylated flavonoids / Bond dissociation enthalpy / HopIzvor:
Structural Chemistry, 2021, 32, 2051-2059Izdavač:
- Springer
Finansiranje / projekti:
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200168 (Univerzitet u Beogradu, Hemijski fakultet) (RS-MESTD-inst-2020-200168)
DOI: 10.1007/s11224-021-01780-4
ISSN: 1040-0400
WoS: 000642014900001
Scopus: 2-s2.0-85104973766
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Cvijetić, Ilija AU - Bigović, Miljan AU - Ristivojević, Petar AU - Vitorović-Todorović, Maja D. AU - Zloh, Mire AU - Milojković-Opsenica, Dušanka PY - 2021 UR - https://cherry.chem.bg.ac.rs/handle/123456789/4534 AB - 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. PB - Springer T2 - Structural Chemistry T1 - DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer VL - 32 SP - 2051 EP - 2059 DO - 10.1007/s11224-021-01780-4 ER -
@article{ author = "Cvijetić, Ilija and Bigović, Miljan and Ristivojević, Petar and Vitorović-Todorović, Maja D. and Zloh, Mire and Milojković-Opsenica, Dušanka", year = "2021", 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.", publisher = "Springer", journal = "Structural Chemistry", title = "DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer", volume = "32", pages = "2051-2059", doi = "10.1007/s11224-021-01780-4" }
Cvijetić, I., Bigović, M., Ristivojević, P., Vitorović-Todorović, M. D., Zloh, M.,& Milojković-Opsenica, D.. (2021). DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer. in Structural Chemistry Springer., 32, 2051-2059. https://doi.org/10.1007/s11224-021-01780-4
Cvijetić I, Bigović M, Ristivojević P, Vitorović-Todorović MD, Zloh M, Milojković-Opsenica D. DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer. in Structural Chemistry. 2021;32:2051-2059. doi:10.1007/s11224-021-01780-4 .
Cvijetić, Ilija, Bigović, Miljan, Ristivojević, Petar, Vitorović-Todorović, Maja D., Zloh, Mire, Milojković-Opsenica, Dušanka, "DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer" in Structural Chemistry, 32 (2021):2051-2059, https://doi.org/10.1007/s11224-021-01780-4 . .