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 †

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...

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Detalles Bibliográficos
Autores principales: Wang, Ling-Na, Wang, Wei, Hattori, Masao, Daneshtalab, Mohsen, Ma, Chao-Mei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273953/
https://www.ncbi.nlm.nih.gov/pubmed/27338318
http://dx.doi.org/10.3390/molecules21060737
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author Wang, Ling-Na
Wang, Wei
Hattori, Masao
Daneshtalab, Mohsen
Ma, Chao-Mei
author_facet Wang, Ling-Na
Wang, Wei
Hattori, Masao
Daneshtalab, Mohsen
Ma, Chao-Mei
author_sort Wang, Ling-Na
collection PubMed
description 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.
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spelling pubmed-62739532018-12-28 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 † Wang, Ling-Na Wang, Wei Hattori, Masao Daneshtalab, Mohsen Ma, Chao-Mei Molecules Article 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. MDPI 2016-06-08 /pmc/articles/PMC6273953/ /pubmed/27338318 http://dx.doi.org/10.3390/molecules21060737 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wang, Ling-Na
Wang, Wei
Hattori, Masao
Daneshtalab, Mohsen
Ma, Chao-Mei
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 †
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 †
title_full 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 †
title_fullStr 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 †
title_full_unstemmed 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 †
title_short 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 †
title_sort 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 †
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273953/
https://www.ncbi.nlm.nih.gov/pubmed/27338318
http://dx.doi.org/10.3390/molecules21060737
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