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KMID : 0043320130360121432
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Archives of Pharmacal Research
2013 Volume.36 No. 12 p.1432 ~ p.1436
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Concise synthesis of licochalcone C and its regioisomer, licochalcone H
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Wang Zengtao
Cao Yongkai
Paudel Suresh
Yoon Goo
Cheon Seung-Hoon
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Abstract
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Licochalone C (7a) is a retrochalcone isolated from Glycyrrhiza inflata, which shows potent antioxidant properties and inhibition of bacterial growth and cellular respiration. Biological studies have suggested that licochalcone C attenuates the lipopolysaccharide and interferon-gamma induced inflammatory response by decreasing the expression and activity of inducible nitric oxide synthase and modulating the antioxidant network activity of superoxide dismutase, catalase, and glutathione peroxidase activity. Licochalcone C also inhibits NADH-cytochrome C reductase in the membrane fraction of Micrococcusluteus. Since pharmacological activity studies of licochalcone C are ongoing and the yield of the compound is poor from natural product, we report a concise four step synthesis of licochalcone C (7a) and its regioisomer, tentatively called licochalcone H (7b), by employing acid-mediated Claisen-Schmidt condensation as a key step with 6 and 20 % overall yield, respectively.
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KEYWORD
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Licochalcone C, Licochalcone H, Acid-mediated Claisen-Schmidt condensation, Total synthesis
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