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Open AccessArticle

Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin

1
School of Basic Medical Science, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
2
The Research Center of Basic Integrative Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
3
School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China
*
Authors to whom correspondence should be addressed.
Molecules 2020, 25(3), 674; https://doi.org/10.3390/molecules25030674
Received: 16 January 2020 / Revised: 4 February 2020 / Accepted: 4 February 2020 / Published: 5 February 2020
(This article belongs to the Special Issue Properties and Activity of Molecules of Nutritional Interest)
To elucidate the mechanism of anti-ferroptosis and examine structural optimization in natural phenolics, cellular and chemical assays were performed with 2′-hydroxy chalcone butein and dihydroflavone (S)-butin. C11-BODIPY staining and flow cytometric assays suggest that butein more effectively inhibits ferroptosis in erastin-treated bone marrow-derived mesenchymal stem cells than (S)-butin. Butein also exhibited higher antioxidant percentages than (S)-butin in five antioxidant assays: linoleic acid emulsion assay, Fe3+-reducing antioxidant power assay, Cu2+-reducing antioxidant power assay, 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO)-trapping assay, and α,α-diphenyl-β-picrylhydrazyl radical (DPPH)-trapping assay. Their reaction products with DPPH were further analyzed using ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS). Butein and (S)-butin produced a butein 5,5-dimer (m/z 542, 271, 253, 225, 135, and 91) and a (S)-butin 5′,5′-dimer (m/z 542, 389, 269, 253, and 151), respectively. Interestingly, butein forms a cross dimer with (S)-butin (m/z 542, 523, 433, 419, 415, 406, and 375). Therefore, we conclude that butein and (S)-butin exert anti-ferroptotic action via an antioxidant pathway (especially the hydrogen atom transfer pathway). Following this pathway, butein and (S)-butin yield both self-dimers and cross dimers. Butein displays superior antioxidant or anti-ferroptosis action to (S)-butin. This can be attributed the decrease in π-π conjugation in butein due to saturation of its α,β-double bond and loss of its 2′-hydroxy group upon biocatalytical isomerization. View Full-Text
Keywords: butein; (S)-butin; anti-ferroptosis; antioxidant; 2′-hydroxy chalcone; isomerization butein; (S)-butin; anti-ferroptosis; antioxidant; 2′-hydroxy chalcone; isomerization
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MDPI and ACS Style

Liu, J.; Li, X.; Cai, R.; Ren, Z.; Zhang, A.; Deng, F.; Chen, D. Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin. Molecules 2020, 25, 674. https://doi.org/10.3390/molecules25030674

AMA Style

Liu J, Li X, Cai R, Ren Z, Zhang A, Deng F, Chen D. Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin. Molecules. 2020; 25(3):674. https://doi.org/10.3390/molecules25030674

Chicago/Turabian Style

Liu, Jie; Li, Xican; Cai, Rongxin; Ren, Ziwei; Zhang, Aizhen; Deng, Fangdan; Chen, Dongfeng. 2020. "Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin" Molecules 25, no. 3: 674. https://doi.org/10.3390/molecules25030674

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