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Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-O-galloyl-β-d-glucopyranose
ACS Medicinal Chemistry Letters ( IF 3.5 ) Pub Date : 2020-10-05 , DOI: 10.1021/acsmedchemlett.0c00359 Xican Li 1 , Jie Liu 2 , Ban Chen 1 , Yingci Chen 1 , Wanjian Dai 1 , Yuling Li 1 , Meiling Zhu 3
ACS Medicinal Chemistry Letters ( IF 3.5 ) Pub Date : 2020-10-05 , DOI: 10.1021/acsmedchemlett.0c00359 Xican Li 1 , Jie Liu 2 , Ban Chen 1 , Yingci Chen 1 , Wanjian Dai 1 , Yuling Li 1 , Meiling Zhu 3
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The ellagitannin corilagin and its analogue 1,3,6-tri-O-galloyl-β-d-glucopyranose (TGG) were found to protect bone marrow-derived mesenchymal stem cells (bmMSCs) against erastin-induced ferroptosis by cellular assays. However, the antiferroptosis bioactivity of corilagin was higher than that of TGG. Corilagin also exhibited higher antioxidant and Fe2+-chelation levels than TGG. Treated with 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, corilagin and TGG yielded a corilagin- and a TGG–DPPH adduct, respectively. The corilagin–DPPH adduct retained the covalent bridge throughout the ultrahigh-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC-ESI-Q-TOF-MS) analysis. The strength of the covalent bridge is attributable to enhancement of its partial π–π conjugation. Thus, the bridge has sufficient strength to twist the chair conformation of the glucopyranosyl ring and to assemble two large aromatic rings, thereby improving the antioxidant (including Fe2+-chelation) reactivities. The bridge can also stabilize the product intermediate via partial π–π conjugation. Hence, corilagin is a superior ferroptosis inhibitor and antioxidant compared to TGG.
中文翻译：
Corilagin 的共价桥接提高抗铁死亡活性：与 1,3,6-Tri-O-galloyl-β-d-吡喃葡萄糖的比较
通过细胞分析发现鞣花鞣质 corilagin及其类似物 1,3,6-三-O-没食子酰-β- d-吡喃葡萄糖(TGG) 可保护骨髓来源的间充质干细胞 (bmMSCs) 免受erastin 诱导的铁死亡。然而，corilagin的抗铁死亡生物活性高于TGG。Corilagin 还表现出更高的抗氧化性和 Fe 2+-螯合水平高于TGG。用 1,1-二苯基-2-苦基肼 (DPPH) 自由基处理后，corilagin 和 TGG 分别产生了 corilagin- 和 TGG-DPPH 加合物。corilagin-DPPH 加合物在整个超高效液相色谱结合电喷雾电离四极杆飞行时间串联质谱 (UHPLC-ESI-Q-TOF-MS) 分析中保留了共价桥。共价桥的强度归因于其部分 π-π 共轭的增强。因此，该桥具有足够的强度来扭曲吡喃葡萄糖基环的椅子构象并组装两个大的芳香环，从而提高抗氧化剂（包括 Fe 2+-螯合）反应性。桥还可以通过部分 π-π 共轭稳定产物中间体。因此，与 TGG 相比，corilagin 是一种优越的铁死亡抑制剂和抗氧化剂。
更新日期：2020-11-12
中文翻译：
Corilagin 的共价桥接提高抗铁死亡活性：与 1,3,6-Tri-O-galloyl-β-d-吡喃葡萄糖的比较
通过细胞分析发现鞣花鞣质 corilagin及其类似物 1,3,6-三-O-没食子酰-β- d-吡喃葡萄糖(TGG) 可保护骨髓来源的间充质干细胞 (bmMSCs) 免受erastin 诱导的铁死亡。然而，corilagin的抗铁死亡生物活性高于TGG。Corilagin 还表现出更高的抗氧化性和 Fe 2+-螯合水平高于TGG。用 1,1-二苯基-2-苦基肼 (DPPH) 自由基处理后，corilagin 和 TGG 分别产生了 corilagin- 和 TGG-DPPH 加合物。corilagin-DPPH 加合物在整个超高效液相色谱结合电喷雾电离四极杆飞行时间串联质谱 (UHPLC-ESI-Q-TOF-MS) 分析中保留了共价桥。共价桥的强度归因于其部分 π-π 共轭的增强。因此，该桥具有足够的强度来扭曲吡喃葡萄糖基环的椅子构象并组装两个大的芳香环，从而提高抗氧化剂（包括 Fe 2+-螯合）反应性。桥还可以通过部分 π-π 共轭稳定产物中间体。因此，与 TGG 相比，corilagin 是一种优越的铁死亡抑制剂和抗氧化剂。
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