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Molecules 2018, 23(4), 754; https://doi.org/10.3390/molecules23040754

Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C

1,2,†,* , 1,2,†
,
1
and
3,4,*
1
School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China
2
Innovative Research & Development Laboratory of TCM, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China;
3
School of Basic Medical Science, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China;
4
The Research Center of Basic Integrative Medicine, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 9 February 2018 / Revised: 16 March 2018 / Accepted: 22 March 2018 / Published: 24 March 2018
(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products)
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Abstract

Two 2-phenyl-benzofurans, moracin C {2-[3′,5′-dihydroxy-4′-(3-methlbut-2-enyl)phenyl]-6-hydroxybenzofuran} and its isomer iso-moracin C{2-[3′,5′-dihydroxy-4′-(3-methlbut-1-enyl)phenyl]-6-hydroxybenzofuran}, were comparatively studied using redox-related antioxidant assays and non-redox antioxidant assays. Moracin C always resulted in higher IC50 values than iso-moracin C in the redox-related antioxidant assays, including •O2-inhibition, Cu2+-reducing power, DPPH•-inhibition, and ABTS+•-inhibition assays. In the non-redox antioxidant assay, moracin C and iso-moracin C underwent similar radical-adduct-formation (RAF), evidenced by the peaks at m/z 704 and m/z 618 in HPLC-MS spectra. In conclusion, both moracin C and iso-moracin C can act as 2-phenyl-benzofuran antioxidants; their antioxidant mechanisms may include redox-related ET and H+-transfer, and non-redox RAF. A double bond at the conjugation position can enhance the redox-related antioxidant potential, but hardly affects the RAF potential. View Full-Text
Keywords: 2-phenyl-benzofuran; antioxidant; moracin; double bond; positional isomeric effect 2-phenyl-benzofuran; antioxidant; moracin; double bond; positional isomeric effect
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Li, X.; Xie, H.; Zhan, R.; Chen, D. Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C. Molecules 2018, 23, 754.

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