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Molecules 2016, 21(6), 737; doi:10.3390/molecules21060737

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

1
College of Life Sciences, Inner Mongolia University, Huhhot 010021, China
2
College of Biochemical Engineering, Huhhot Vocational College, Huhhot 010058, China
3
Department of Chemistry, School of Pharmaceutical Sciences, Kunming Medical University, Kunming 650500, China
4
Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
5
School of Pharmacy, Memorial University of Newfoundland, St. John’s, NL A1B 3V6, Canada
This paper is dedicated to our respected late Professor, Dr. Mohsen Daneshtalab.
*
Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 16 May 2016 / Revised: 28 May 2016 / Accepted: 31 May 2016 / Published: 8 June 2016
(This article belongs to the Section Natural Products)
View Full-Text   |   Download PDF [746 KB, uploaded 8 June 2016]   |  

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. View Full-Text
Keywords: 3-caffeoylquinic acid amide; synthesis; anti-HCV; anti-oxidant; cellular oxidative stress 3-caffeoylquinic acid amide; synthesis; anti-HCV; anti-oxidant; cellular oxidative stress
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Wang, L.-N.; Wang, W.; Hattori, M.; Daneshtalab, M.; Ma, C.-M. 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. Molecules 2016, 21, 737.

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