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.
Highlights
Despite its 60-year history, naturally occurring 2-phenyl-benzofuran is not a well-known type of stilbene
The process by which this occurs is commonly called “antioxidation”; essentially, this process consists of reactions which inhibit reactive oxygen species (ROS) or reactive nitrogen species (RNS) accumulation. O2 − is a significant form of ROS
Both moracin C and iso-moracin C displayed higher percentages of O2 − inhibition compared to Trolox, a standard antioxidant
Summary
Despite its 60-year history, naturally occurring 2-phenyl-benzofuran is not a well-known type of stilbene. Morus alba [3,4], Artocarpus champeden [5], Erythrina addisoniae [6], and Calpocalyx dinklagei [7] All these compounds contain a scaffold of 2-phenyl substituted benzo[b]furan-fused-ring (Figure 1). This scaffold is usually called 2-phenyl-benzofuran, somestudies refer to it as “2-arylbenzofuran” or “aryl benzofuran” [6,7,8]. While this name can be used to deduce its chemical structure, it does not comply with IUPAC terminology; i.e., the numbering does not start from the O-atom of the furan ring This nomenclature is different from that of the first reported natural 2-phenyl-benzofuran derivative [i.e., 2-(6-hydroxy-2-methoxy-3,4-methylenedioxy phenyl)-benzofuran] [1] and other analogous derivatives such as 2-[20 ,40 -dihydroxy-30 -(3-methlbut-. It will provide new information about the effect of the double bond position on the antioxidant properties of phytophenols—especially phenolic 2-phenyl-benzofurans
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