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. 2016 Jun 8;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

Ling-Na Wang  1   2 , Wei Wang  3 , Masao Hattori  4 , Mohsen Daneshtalab  5 , Chao-Mei Ma  6
Affiliations

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

Ling-Na Wang et al. Molecules. .

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.

Keywords: 3-caffeoylquinic acid amide; anti-HCV; anti-oxidant; cellular oxidative stress; synthesis.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of a chlorogenic acid analogue with an amide bond.
Figure 1
Figure 1
NOE interaction defining the configuration of C-3 in 6a.
Figure 2
Figure 2
Inhibitory effect of chlorogenic acid (CA) and its amide analogue (6b) on reactive species of oxygen (ROS) formation.
See this image and copyright information in PMC

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