Synthesis,characterization, anti-inflammatory and anti-proliferative activity against MCF-7 cells of O-alkyl and O-acyl flavonoid derivatives |
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| Institution: | 1. Department of Integrative Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong, Gwangjin-gu, Seoul 143-701, Republic of Korea;2. Center for Neuro-Medicine, Korea Institute of Science and Technology, 39-1 Hawolgok-dong, Seoungbuk-gu, Seoul 136-791, Republic of Korea;3. Department of Biological Chemistry, Korea University of Science and Technology, Youseong-gu, Daejeon 305-350, Republic of Korea;1. Key Laboratory of Industrial Fermentation Microbiology (Tianjin University of Science and Technology), Ministry of Education, Tianjin 300457, China;2. Tianjin Key Laboratory of Industry Microbiology, and Sino-French Joint Lab of Food Nutrition/Safety and Medicinal Chemistry, College of Biotechnology, Tianjin University of Science and Technology, Tianjin 300457, China;3. School of Pharmacy, Tianjin Medical University, Tianjin 300070, China;4. Université Pierre et Marie Curie-Paris 6, Institut Parisien de Chimie Moléculaire UMR CNRS 8232, 4 place Jussieu, 75005 Paris, France;5. 382 Longvalley Lane, DeKalb, USA;1. State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, People''s Republic of China;2. School of Pharmacuetical Sciences, Guizhou Medical University, Guiyang 550025, People''s Republic of China;3. Key Laboratory of Chemistry for Natural Products of Guizhou Province, Chinese Academy of Sciences, Guiyang 550014, People''s Republic of China;4. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People''s Republic of China;1. Jiangsu Collaborative Innovation Center of Chinese Medicine Resources Industrialization, Jiangsu Key Laboratory for High Technology Research of TCM Formulae, and National and Local Collaborative Engineering Center of Chinese Medicine Resources, Nanjing University of Chinese Medicine, Nanjing 210023, China;2. Department of Organic Chemistry, China Pharmaceutical University, Nanjing, Jiangsu 211198, China;1. Industrial and Applied Organic Chemistry Research Unit, Department of Inorganic and Organic Chemistry (Section of Organic Chemistry), University of Barcelona, c/Martí Franquès 1-11, 08028, Barcelona, Spain;2. Department of Chemistry, University of Bath, Bath, BA2 7AY, UK |
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| Abstract: | A series of O-alkyl and O-acyl flavonoid derivatives was synthesized in high efficiency. Alkylation and acylation of 5-hydroxyflavonoids showed that the low reactivity hydroxyl group, 5-OH, well reacted with strong reagents whereas with weaker reagents, the different products were obtained dependently on structural characteristic of ring C of respective flavonoid. In order to evaluate anti-inflammatory activity, all compounds were tested for in vitro inhibition of bovine serum albumin denaturation and in vivo inhibition of carrageenan-induced mouse paw edema. Among them, the compounds 3, 3b, 4b and 4c demonstrated more effective anti-inflammatory activity than standard drugs (diclofenac sodium and ketoprofen) in both tests. Meanwhile, the flavonoids 2, 2c, 3a and 4b displayed anti-proliferative activity against MCF-7 cell lines. Triacetyl derivative of hesperetin 4b inducing degradation of DNA in MCF-7 cells was observed. |
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| Keywords: | Flavonoid Synthesis Anti-inflammatory Anti-proliferative MCF-7 |
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