Butein Ameliorates Oxidative Stress in H9c2 Cardiomyoblasts through Activation of the NRF2 Signaling Pathway

Tungalag, Tsendsuren; Park, Kye Won; Yang, Dong Kwon

doi:10.3390/antiox11081430

Cited by 6 publications

(3 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We suggest that butein is able to exploit the HOO • radical formed as a side event during the autoxidation of methyl linoleate [45][46][47]. This mechanism is likely of major relevance in biological systems, where O 2 -• /HOO • is produced under both physiologic and pathologic conditions, which lends support to the redox bioactivity reported for butein in previous studies [6,7], complementing other mechanisms such as iron chelation [10] and induction of the NRf2 signaling system [8]. Indeed, catechol-type antioxidants have been shown to possess major potential in handling redox-related pathologies like neurological disorders [53].…”

Section: Discussionsupporting

confidence: 79%

Section: Introductionmentioning

confidence: 99%

“…This has been the subject of different studies, highlighting an indirect antioxidant behavior via the activation of endogenous cellular antioxidant defenses [7]. It was recently demonstrated that a distinct mechanism to explain such antioxidant activity by butein is via the activation of the NRf2 signaling pathway [8]. An early study also indicated that butein has a direct antioxidant action: it can trap peroxyl radicals in water but not in hexane, and it was able to reduce the markers of oxidative damage (TBARS) in metal-catalyzed oxidation of LDL-an activity that was attributed to its ability in chelating transition metal ions, iron, and copper, preventing peroxidation initiated by Fenton reaction [9].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Potent Antioxidant and Anti-Tyrosinase Activity of Butein and Homobutein Probed by Molecular Kinetic and Mechanistic Studies

Pan,

Giovanardi,

Sagynova

et al. 2023

Antioxidants

View full text Add to dashboard Cite

Butein (BU) and homobutein (HB) are bioactive polyhydroxylated chalcones widespread in dietary plants, whose antioxidant properties require mechanistic definition. They were investigated by inhibited autoxidation kinetic studies of methyl linoleate in Triton™ X-100 micelles at pH 7.4, 37 °C. Butein had kinh = (3.0 ± 0.9) × 104 M−1s−1 showing a chain-breaking mechanism with higher antioxidant activity than reference α-tocopherol (kinh = (2.2 ± 0.6) × 104 M−1s−1), particularly concerning the stoichiometry or peroxyl radical trapping n = 3.7 ± 1.1 vs. 2.0 for tocopherol. Homobutein had kinh = (2.8 ± 0.9) × 103 M−1s−1, pairing the relative BDEOH measured by radical equilibration EPR as 78.4 ± 0.2 kcal/mol for BU and estimated as 82.6 kcal/mol for HB. The inhibition of mushroom tyrosinase (mTYR) by HB and BU was also investigated. BU gives a reversible uncompetitive inhibition of monophenolase reaction with KI′ = 9.95 ± 2.69 µM and mixed-type diphenolase inhibition with KI = 3.30 ± 0.75 µM and KI′ = 18.75 ± 5.15 µM, while HB was nearly competitive toward both mono- and diphenolase with respective KI of 2.76 ± 0.70 µM and 2.50 ± 1.56 µM. IC50 values (monophenolase/diphenolase at 1 mM substrate) were 10.88 ± 2.19 µM/15.20 ± 1.25 µM, 14.78 ± 1.05 µM/12.36 ± 2.00 µM, and 33.14 ± 5.03 µM/18.27 ± 3.42 µM, respectively, for BU, HB, and reference kojic acid. Molecular docking studies confirmed the mechanism. Results indicate very potent antioxidant activity for BU and potent anti-tyrosinase activity for both chalcones, which is discussed in relation to bioactivity toward protection from skin disorders and food oxidative spoilage.

show abstract