Synthesis of Caffeic Acid Sulphonamide Derivatives and Preliminary Exploration of Their Biological Applications
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doi: 10.1007/s40242-020-0014-5
Article
Synthesis of Caffeic Acid Sulphonamide Derivatives and Preliminary Exploration of Their Biological Applications PENG Xiaoyu1,5, ZHAO Anran3, HUANG Kelin5, HU Tingju1, LIU Buming4, HUANG Yan4, CHEN Hailan1,2*, CHAI Ling4* and LIN Cuiwu1* 1. School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, P. R. China; 2. School of Animal Science and Technology, Guangxi University, Nanning 530004, P. R. China; 3. Laboratory Medicine Department, First Affiliated Hospital of Guangxi Medical University, Nanning 530021, P. R. China; 4. Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards, Guangxi Institute of Traditional Medical and Pharmaceutical Sciences, Nanning 530022, P. R. China; 5. China Academy of Science and Technology Development Guangxi Branch, Nanning 530022, P. R. China Abstract Structural modification of native compounds is an effective way to develop new drugs with increased pharmacological activities and improved material characteristics. In this study, caffeic acid sulphonamide deriv atives(CSs) were synthesised by conjugating sulphonamides to the backbone of caffeic acid. The structures of these derivatives were elucidated by means of Fourier transform infrared spectroscopy(FTIR), 1H NMR, 13C NMR, and electrospray ionization mass spectroscopy(ESI-MS). A content determination method was established by ultraviolet detection. The lipophilicity, 2,2-diphenyl-1-picrylhydrazy free radical(DPPH) scavenging capacity, anti-coagulant effects, anti-bacterial activity, cytotoxicity, in vitro anti-proliferative activity against tumour cells, and the ability of the compounds to promote the proliferation of chondrocytes were evaluated. The results indicate that CSs exhibit strong DPPH scavenging activity, high lipophilicity, good anti-coagulant activities, wide anti-bacterial activity range, low cytotoxicity, and an excellent ability to promote chondrocyte proliferation. Keywords Caffeic acid; Sulphonamide; Lipophilicity; Anti-oxidant; Cytotoxicity
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Introduction
Blumea riparia DC is a traditional Chinese medicine that is widely distributed in Guangxi, China. It is commonly used for the treatment of gynaecological diseases, and the phenolic acids contained in it are considered as its main effective constituents[1]. In our previous studies, several active phenolic acids, including caffeic acid(CA), chlorogenic acid and gallic acid, were isolated from Blumea riparia DC. Among them, CA, containing two reactive hydroxyl groups in its benzene ring, is also widely found in other plants[2―4]. CA possesses a wide range of biological activities, such as anti-oxidant, antibacterial, anti-cancer, and anti-viral activities, which are mediated by its ability to inhibit the formation of free radicals, prevent the oxidative damage of biological tissues and cells, and interrupt the continuation of free radical reactions[5―8]. CA is also considered a potential natural anti-oxidant that can prevent in vivo oxidative damages closely associated with cancer, d
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