Synthesis of licochalcones and inhibition effects on radical-induced oxidation of DNA
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Med Chem Res (2013) 22:2847–2854 DOI 10.1007/s00044-012-0282-9
ORIGINAL RESEARCH
Synthesis of licochalcones and inhibition effects on radicalinduced oxidation of DNA Jianghua He • Jizhen Li • Zai-Qun Liu
Received: 11 March 2012 / Accepted: 15 October 2012 / Published online: 30 October 2012 Springer Science+Business Media New York 2012
Abstract This study deals with the influence of phenolic hydroxyl groups on the antioxidant capacities of licochalcones. (E)-3-[5-(1,2-Dimethyl-2-propenyl)-4-hydroxy -3-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one (HMP), (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3methoxyphenyl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one (DHM), and (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy -3-methoxyphenyl]-1-(2,4,6-trihydroxyphenyl)-2-propen1-one (HMT) were synthesized via abnormal Claisen rearrangement and Claisen–Schmidt condensation. The antioxidant capacities were evaluated in hydroxyl radical (•OH)-, Cu2?/glutathione (GSH)-, and 2,20 -azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that only HMP possessed weak ability to inhibit •OH-induced oxidation of DNA, and DHM and HMT cannot protect DNA against the oxidation. All the licochalcones employed herein can retard Cu2?/GSHinduced oxidation of DNA, the activity followed the order of HMP [ DHM [ HMT. Hence, more hydroxyl groups did not ameliorate the antioxidant effectiveness in the aforementioned experimental systems. On the other hand, HMT, DHM, and HMP can scavenge 5.61, 2.42, and 1.68 radicals, respectively, when they were applied to protect DNA against AAPH-induced oxidation. This result demonstrated that more hydroxyl groups enhanced the antioxidant capacities of licochalcones in this case. The obtained
J. He J. Li (&) Z.-Q. Liu (&) Department of Organic Chemistry, College of Chemistry, Jilin University, No. 2519 Jiefang Road, Changchun 130021, China e-mail: [email protected] Z.-Q. Liu e-mail: [email protected]
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Keywords Licochalcone Antioxidant Free radical Oxidation of DNA
Introduction Modern medicine also advocates using natural products to treat some diseases (Bhattacharya et al., 2009). After pharmacological functions of traditional herbs have been proved clinically (Udompataikul and Srisatwaja, 2011), active ingredients are isolated in order to test whether these compounds can be applied to treat other diseases (Qiu et al., 2010). The roots and rhizomes of licorice (Glycyrrhiza) species attract much research attention because they exhibit many pharmacological properties such as antiinflammatory, antiviral, antimicrobial, antioxidation, anticancer, immunomodulatory, hepatoprotective, and cardioprotective effects. Licorice species contain some bioactive ingredients such as flavonoids, isoflavones, coumarins, stilbenoids, and miscellaneous compounds. Especially, they involve a series of special chalcones, called licochalcones (Asl and Hosseinzadeh, 2008). Although bioactivities of chalcones have been revealed by
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