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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 35, Number 6
BKCSDE 35(6)
June 20, 2014 

Protective Effect Against Hydroxyl Radical-induced DNA Damage and Antioxidant Mechanism of [6]-gingerol: A Chemical Study
Jing Lin, Xican Li,a*, Li Chen, Weizhao Lu, Xianwen Chen, Lu Han, Dongfeng Chen*
[6]-Gingerol, Hydrogen atom transfer, Sequential electron proton transfer, Antioxidant mechanism, Hydroxyl radical
[6]-Gingerol is known as the major bioactive constituent of ginger. In the study, it was observed to effectively protect against •OH-induced DNA damage (IC50 328.60 ± 24.41 μM). Antioxidant assays indicated that [6]- gingerol could efficiently scavenge various free radicals, including •OH radical (IC50 70.39 ± 1.23 μM), •O2 − radical (IC50 228.40 ± 9.20 μM), DPPH• radical (IC50 27.35 ± 1.44 μM), and ABTS+• radical (IC50 2.53 ± 0.070 μM), and reduce Cu2+ ion (IC50 11.97 ± 0.68 μM). In order to investigate the possible mechanism, the reaction product of [6]-gingerol and DPPH• radical was further measured using HPLC combined mass spectrometry. The product showed a molecular ion peak at m/z 316 [M+Na]+, and diagnostic fragment loss (m/z 28) for quinone. On this basis, it can be concluded that: (i) [6]-gingerol can effectively protect against •OH-induced DNA damage; (ii) a possible mechanism for [6]-gingerol to protect against oxidative damage is •OH radical scavenging; (iii) [6]-gingerol scavenges •OH radical through hydrogen atom (H•) transfer (HAT) and sequential electron (e) proton transfer (SEPT) mechanisms; and (iv) both mechanisms make [6]-gingerol be oxidized to semi-quinone or quinone forms.
1633 - 1638
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