title: Synthesis, Anti-HCV, Antioxidant and Reduction of Intracellular Reactive Oxygen Species Generation of a Chlorogenic Acid Analogue with an Amide Bond Replacing the Ester Bond.
abstract: Chlorogenic acid is a well known natural product with important bioactivities. It contains an ester bond formed between the COOH of caffeic acid and the 3-OH of quinic acid. We synthesized a chlorogenic acid analogue, 3α-caffeoylquinic acid amide, using caffeic and quinic acids as starting materials. The caffeoylquinc acid amide was found to be much more stable than chlorogenic acid and showed anti-Hepatitis C virus (anti-HCV) activity with a potency similar to chlorogenic acid. The caffeoylquinc acid amide potently protected HepG2 cells against oxidative stress induced by tert-butyl hydroperoxide.
authors.affiliation: College of Life Sciences, Inner Mongolia University, Huhhot 010021, China. shxywln@163.com.|College of Biochemical Engineering, Huhhot Vocational College, Huhhot 010058, China. shxywln@163.com.
authors.forename: Ling-Na
authors.initials: LN
authors.lastname: Wang
authors.affiliation: Department of Chemistry, School of Pharmaceutical Sciences, Kunming Medical University, Kunming 650500, China. wangwei.kmu@hotmail.com.
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan. mhattori@po4.canet.ne.jp.
authors.forename: Masao
authors.initials: M
authors.lastname: Hattori
authors.affiliation: School of Pharmacy, Memorial University of Newfoundland, St. John's, NL A1B 3V6, Canada.
authors.forename: Mohsen
authors.initials: M
authors.lastname: Daneshtalab
authors.affiliation: College of Life Sciences, Inner Mongolia University, Huhhot 010021, China. cmma@imu.edu.cn.
authors.forename: Chao-Mei
authors.initials: CM
authors.lastname: Ma
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D002109:Caffeic Acids / Q000737:chemistry; D002726:Chlorogenic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000627:therapeutic use*; D004952:Esters / Q000737:chemistry; D006526:Hepatitis C / Q000188:drug therapy / Q000821:virology; D006801:Humans; D018384:Oxidative Stress / Q000187:drug effects*; D011801:Quinic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D017382:Reactive Oxygen Species / Q000737:chemistry / Q000378:metabolism; D020122:tert-Butylhydroperoxide / Q000737:chemistry
chemical_list: D000577:Amides; D000975:Antioxidants; D002109:Caffeic Acids; D004952:Esters; D017382:Reactive Oxygen Species; C472707:caffeoylquinic acid; D011801:Quinic Acid; D002726:Chlorogenic Acid; D020122:tert-Butylhydroperoxide; C040048:caffeic acid
keywords: 3-caffeoylquinic acid amide; anti-HCV; anti-oxidant; cellular oxidative stress; synthesis