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Chemical Study on Protective Effect Against Hydroxyl‐induced DNA Damage and Antioxidant Mechanism of Myricitrin
Author(s) -
Li Xican,
Mai Wenqiong,
Chen Dongfeng
Publication year - 2014
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201300396
Subject(s) - chemistry , radical , antioxidant , reactive oxygen species , dna damage , hydroxyl radical , abts , deoxyribose , oxidative damage , oxidative stress , dpph , biochemistry , dna
Excessive reactive oxygen species (ROS) can oxidatively damage DNA to cause severe biological consequences. In the study, a natural flavonoid, myricitrin (myricetin‐3‐O‐α‐L‐rhamnopyranoside), was found to have a protective effect against hydroxyl‐induced DNA damage (IC 50 159.86 ± 54.24 μg/mL). To investigate the mechanism, it was determined by various antioxidant assays. The results revealed that myricitrin could effectively scavenge ·OH, ·O 2 − , DPPH· (1,1‐diphenyl‐2‐picrylhydrazyl radical), and ABTS + · (2,2′‐Azino‐bis(3‐ethylbenzothiazoline‐6‐sulfonic acid) radicals (IC 50 values were respectively 69.71 ± 5.93, 69.71 ± 5.93, 25.34 ± 2.14, and 1.71 ± 0.09 μg/mL), and bind Cu 2+ (IC 50 27.33 ± 2.36 μg/mL). Based on the mechanistic analysis, it can be concluded that: ( i ) myricitrin can effectively protect against hydroxyl‐induced DNA oxidative damage via ROS scavenging and deoxynucleotide radicals repairing approaches. Both approaches can be attributed to its antioxidant. From a structure‐activity relationship viewpoint, its antioxidant ability can be attributed to the ortho ‐dihydroxyl moiety, and ultimately to the stability of its oxidized form ortho ‐benzoquinone; ( ii ) its ROS scavenging is mediated via metal‐chelating, and direct radical‐scavenging which is through donating hydrogen (H·) and electron ( e ); and ( iii ) its protective effect against DNA oxidative damage may be primarily responsible for the pharmacological effects, and offers promise as a new therapeutic reagent for diseases from DNA oxidative damage.