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Radiolytic Cyclization Products of Phloridzin as Potent Anti‐Glycation Agents
Author(s) -
Jeong Gyeong Han,
Kim Tae Hoon
Publication year - 2020
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202000305
Subject(s) - chemistry , glycation , radiolysis , circular dichroism , dpph , mass spectrometry , antioxidant , irradiation , scavenging , stereochemistry , biochemistry , radical , chromatography , physics , receptor , nuclear physics
The current research examined for radiolytic structure modification and improved bioefficacy of phloridzin by γ ‐ray, subsequent to a 50 kGy irradiation dose. Structures of the unusual degraded products phlorocyclin, isophlorocyclin, and radiophlorisin were determined spectroscopically, by detailed nuclear magnetic resonance (NMR) and mass spectrometry (MS). Additionally, absolute configuration of the novel cyclized phlorocyclin and isophlorocyclin were proposed by circular dichroism (CD) spectrum analysis. Among the compounds tested, phlorocyclin and isophlorocyclin exhibit potent antidiabetic complication capacities toward advanced glycation end products (AGEs) formation inhibition assay, with IC 50 values of 9.1±0.5 and 13.8±0.7 μM, respectively. Furthermore, the predominantly formed products phlorocyclin and isophlorocyclin exerted significantly enhanced DPPH radical scavenging activity compared to the parent phloridzin. These results indicate that γ ‐ray mediated cyclization of phloridzin exerts a positive influence on the bioactivity.