Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters
The antifungal activities of 5-O-caffeoyl quinic acid (5-CQA) and of methyl, butyl, octyl, and dodecyl esters or 5-CQA, were tested on five toxigenic moulds from the Aspergillus genus (Aspergillus flavus, Aspergillus nomius, Aspergillus ochraceus, Aspergillus parasiticus, Aspergillus westerdijkiae). These mycotoxin producers' moulds may contaminate many types of food crops throughout the food chain posing serious health hazard to animals and humans. The use of chemical methods to decrease mycotoxin producer moulds contamination on food crops in the field, during storage, and/or during processing, has been proved to be efficient. In this work, the antifungal effect of 5-CQA and a homologous series of 5-CQA esters (methyl, butyl, octyl, dodecyl), was investigated using the microdilution method and the minimum inhibitory concentrations (MIC50 and MIC80). All molecules presented antifungal activity, and two esters showed a MIC for all fungi: octyl (MIC50 _ 0.5e0.75 mg/mL, MIC80 ¼ 1.0e1.5 mg/mL) and dodecyl (MIC50 ¼ 0.75e1.25 mg/mL) chlorogenates. Dodecyl chlorogenate showed a MIC80 (1.5 mg/mL) only for A. parasiticus. The maximum percent of growth inhibition on aspergillii was observed with octyl (78.4 e92.7%) and dodecyl (54.5e83.7%) chlorogenates, being octyl chlorogenate the most potent antifungal agent. It was thus concluded that lipophilization improved the antifungal properties of 5-CQA, which increased with the ester alkyl chain length, exhibiting a cut-off effect at 8 carbons. As far as we know, it is the first report demonstrating that lipophilization may improve the antifungal activity of 5-CQA on five toxigenic moulds from the Aspergillus genus. Lipophilization would be a novel way to synthesize a new kind of antifungal agents with a good therapeutic value or a potential use as preservative in food or cosmetics.
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dig-cirad-fr-5693742024-01-28T21:27:21Z http://agritrop.cirad.fr/569374/ http://agritrop.cirad.fr/569374/ Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters. Suárez-Quiroz Mirna, Alonso Campos Angelina, Valerio Alfaro Gerardo, Gonzalez-Rios Oscar, Villeneuve Pierre, Figueroa-Espinoza Maria-Cruz. 2013. Microbial Pathogenesis, 61-62 : 51-56.https://doi.org/10.1016/j.micpath.2013.05.005 <https://doi.org/10.1016/j.micpath.2013.05.005> Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters Suárez-Quiroz, Mirna Alonso Campos, Angelina Valerio Alfaro, Gerardo Gonzalez-Rios, Oscar Villeneuve, Pierre Figueroa-Espinoza, Maria-Cruz eng 2013 Microbial Pathogenesis Q03 - Contamination et toxicologie alimentaires Coffea arabica acide chlorogénique extrait d'origine végétale Aspergillus mycotoxine ester antimicrobien agent de conservation produit alimentaire produit non alimentaire Aspergillus flavus Aspergillus ochraceus Aspergillus parasiticus fève de café http://aims.fao.org/aos/agrovoc/c_1721 http://aims.fao.org/aos/agrovoc/c_36179 http://aims.fao.org/aos/agrovoc/c_8166 http://aims.fao.org/aos/agrovoc/c_672 http://aims.fao.org/aos/agrovoc/c_5026 http://aims.fao.org/aos/agrovoc/c_2671 http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_6172 http://aims.fao.org/aos/agrovoc/c_3032 http://aims.fao.org/aos/agrovoc/c_33517 http://aims.fao.org/aos/agrovoc/c_26370 http://aims.fao.org/aos/agrovoc/c_26374 http://aims.fao.org/aos/agrovoc/c_26376 http://aims.fao.org/aos/agrovoc/c_28379 Mexique http://aims.fao.org/aos/agrovoc/c_4792 The antifungal activities of 5-O-caffeoyl quinic acid (5-CQA) and of methyl, butyl, octyl, and dodecyl esters or 5-CQA, were tested on five toxigenic moulds from the Aspergillus genus (Aspergillus flavus, Aspergillus nomius, Aspergillus ochraceus, Aspergillus parasiticus, Aspergillus westerdijkiae). These mycotoxin producers' moulds may contaminate many types of food crops throughout the food chain posing serious health hazard to animals and humans. The use of chemical methods to decrease mycotoxin producer moulds contamination on food crops in the field, during storage, and/or during processing, has been proved to be efficient. In this work, the antifungal effect of 5-CQA and a homologous series of 5-CQA esters (methyl, butyl, octyl, dodecyl), was investigated using the microdilution method and the minimum inhibitory concentrations (MIC50 and MIC80). All molecules presented antifungal activity, and two esters showed a MIC for all fungi: octyl (MIC50 _ 0.5e0.75 mg/mL, MIC80 ¼ 1.0e1.5 mg/mL) and dodecyl (MIC50 ¼ 0.75e1.25 mg/mL) chlorogenates. Dodecyl chlorogenate showed a MIC80 (1.5 mg/mL) only for A. parasiticus. The maximum percent of growth inhibition on aspergillii was observed with octyl (78.4 e92.7%) and dodecyl (54.5e83.7%) chlorogenates, being octyl chlorogenate the most potent antifungal agent. It was thus concluded that lipophilization improved the antifungal properties of 5-CQA, which increased with the ester alkyl chain length, exhibiting a cut-off effect at 8 carbons. As far as we know, it is the first report demonstrating that lipophilization may improve the antifungal activity of 5-CQA on five toxigenic moulds from the Aspergillus genus. Lipophilization would be a novel way to synthesize a new kind of antifungal agents with a good therapeutic value or a potential use as preservative in food or cosmetics. article info:eu-repo/semantics/article Journal Article info:eu-repo/semantics/publishedVersion http://agritrop.cirad.fr/569374/1/document_569374.pdf application/pdf Cirad license info:eu-repo/semantics/restrictedAccess https://agritrop.cirad.fr/mention_legale.html https://doi.org/10.1016/j.micpath.2013.05.005 10.1016/j.micpath.2013.05.005 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.micpath.2013.05.005 info:eu-repo/semantics/altIdentifier/purl/https://doi.org/10.1016/j.micpath.2013.05.005 |
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Q03 - Contamination et toxicologie alimentaires Coffea arabica acide chlorogénique extrait d'origine végétale Aspergillus mycotoxine ester antimicrobien agent de conservation produit alimentaire produit non alimentaire Aspergillus flavus Aspergillus ochraceus Aspergillus parasiticus fève de café http://aims.fao.org/aos/agrovoc/c_1721 http://aims.fao.org/aos/agrovoc/c_36179 http://aims.fao.org/aos/agrovoc/c_8166 http://aims.fao.org/aos/agrovoc/c_672 http://aims.fao.org/aos/agrovoc/c_5026 http://aims.fao.org/aos/agrovoc/c_2671 http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_6172 http://aims.fao.org/aos/agrovoc/c_3032 http://aims.fao.org/aos/agrovoc/c_33517 http://aims.fao.org/aos/agrovoc/c_26370 http://aims.fao.org/aos/agrovoc/c_26374 http://aims.fao.org/aos/agrovoc/c_26376 http://aims.fao.org/aos/agrovoc/c_28379 http://aims.fao.org/aos/agrovoc/c_4792 Q03 - Contamination et toxicologie alimentaires Coffea arabica acide chlorogénique extrait d'origine végétale Aspergillus mycotoxine ester antimicrobien agent de conservation produit alimentaire produit non alimentaire Aspergillus flavus Aspergillus ochraceus Aspergillus parasiticus fève de café http://aims.fao.org/aos/agrovoc/c_1721 http://aims.fao.org/aos/agrovoc/c_36179 http://aims.fao.org/aos/agrovoc/c_8166 http://aims.fao.org/aos/agrovoc/c_672 http://aims.fao.org/aos/agrovoc/c_5026 http://aims.fao.org/aos/agrovoc/c_2671 http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_6172 http://aims.fao.org/aos/agrovoc/c_3032 http://aims.fao.org/aos/agrovoc/c_33517 http://aims.fao.org/aos/agrovoc/c_26370 http://aims.fao.org/aos/agrovoc/c_26374 http://aims.fao.org/aos/agrovoc/c_26376 http://aims.fao.org/aos/agrovoc/c_28379 http://aims.fao.org/aos/agrovoc/c_4792 |
spellingShingle |
Q03 - Contamination et toxicologie alimentaires Coffea arabica acide chlorogénique extrait d'origine végétale Aspergillus mycotoxine ester antimicrobien agent de conservation produit alimentaire produit non alimentaire Aspergillus flavus Aspergillus ochraceus Aspergillus parasiticus fève de café http://aims.fao.org/aos/agrovoc/c_1721 http://aims.fao.org/aos/agrovoc/c_36179 http://aims.fao.org/aos/agrovoc/c_8166 http://aims.fao.org/aos/agrovoc/c_672 http://aims.fao.org/aos/agrovoc/c_5026 http://aims.fao.org/aos/agrovoc/c_2671 http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_6172 http://aims.fao.org/aos/agrovoc/c_3032 http://aims.fao.org/aos/agrovoc/c_33517 http://aims.fao.org/aos/agrovoc/c_26370 http://aims.fao.org/aos/agrovoc/c_26374 http://aims.fao.org/aos/agrovoc/c_26376 http://aims.fao.org/aos/agrovoc/c_28379 http://aims.fao.org/aos/agrovoc/c_4792 Q03 - Contamination et toxicologie alimentaires Coffea arabica acide chlorogénique extrait d'origine végétale Aspergillus mycotoxine ester antimicrobien agent de conservation produit alimentaire produit non alimentaire Aspergillus flavus Aspergillus ochraceus Aspergillus parasiticus fève de café http://aims.fao.org/aos/agrovoc/c_1721 http://aims.fao.org/aos/agrovoc/c_36179 http://aims.fao.org/aos/agrovoc/c_8166 http://aims.fao.org/aos/agrovoc/c_672 http://aims.fao.org/aos/agrovoc/c_5026 http://aims.fao.org/aos/agrovoc/c_2671 http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_6172 http://aims.fao.org/aos/agrovoc/c_3032 http://aims.fao.org/aos/agrovoc/c_33517 http://aims.fao.org/aos/agrovoc/c_26370 http://aims.fao.org/aos/agrovoc/c_26374 http://aims.fao.org/aos/agrovoc/c_26376 http://aims.fao.org/aos/agrovoc/c_28379 http://aims.fao.org/aos/agrovoc/c_4792 Suárez-Quiroz, Mirna Alonso Campos, Angelina Valerio Alfaro, Gerardo Gonzalez-Rios, Oscar Villeneuve, Pierre Figueroa-Espinoza, Maria-Cruz Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters |
description |
The antifungal activities of 5-O-caffeoyl quinic acid (5-CQA) and of methyl, butyl, octyl, and dodecyl esters or 5-CQA, were tested on five toxigenic moulds from the Aspergillus genus (Aspergillus flavus, Aspergillus nomius, Aspergillus ochraceus, Aspergillus parasiticus, Aspergillus westerdijkiae). These mycotoxin producers' moulds may contaminate many types of food crops throughout the food chain posing serious health hazard to animals and humans. The use of chemical methods to decrease mycotoxin producer moulds contamination on food crops in the field, during storage, and/or during processing, has been proved to be efficient. In this work, the antifungal effect of 5-CQA and a homologous series of 5-CQA esters (methyl, butyl, octyl, dodecyl), was investigated using the microdilution method and the minimum inhibitory concentrations (MIC50 and MIC80). All molecules presented antifungal activity, and two esters showed a MIC for all fungi: octyl (MIC50 _ 0.5e0.75 mg/mL, MIC80 ¼ 1.0e1.5 mg/mL) and dodecyl (MIC50 ¼ 0.75e1.25 mg/mL) chlorogenates. Dodecyl chlorogenate showed a MIC80 (1.5 mg/mL) only for A. parasiticus. The maximum percent of growth inhibition on aspergillii was observed with octyl (78.4 e92.7%) and dodecyl (54.5e83.7%) chlorogenates, being octyl chlorogenate the most potent antifungal agent. It was thus concluded that lipophilization improved the antifungal properties of 5-CQA, which increased with the ester alkyl chain length, exhibiting a cut-off effect at 8 carbons. As far as we know, it is the first report demonstrating that lipophilization may improve the antifungal activity of 5-CQA on five toxigenic moulds from the Aspergillus genus. Lipophilization would be a novel way to synthesize a new kind of antifungal agents with a good therapeutic value or a potential use as preservative in food or cosmetics. |
format |
article |
topic_facet |
Q03 - Contamination et toxicologie alimentaires Coffea arabica acide chlorogénique extrait d'origine végétale Aspergillus mycotoxine ester antimicrobien agent de conservation produit alimentaire produit non alimentaire Aspergillus flavus Aspergillus ochraceus Aspergillus parasiticus fève de café http://aims.fao.org/aos/agrovoc/c_1721 http://aims.fao.org/aos/agrovoc/c_36179 http://aims.fao.org/aos/agrovoc/c_8166 http://aims.fao.org/aos/agrovoc/c_672 http://aims.fao.org/aos/agrovoc/c_5026 http://aims.fao.org/aos/agrovoc/c_2671 http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_6172 http://aims.fao.org/aos/agrovoc/c_3032 http://aims.fao.org/aos/agrovoc/c_33517 http://aims.fao.org/aos/agrovoc/c_26370 http://aims.fao.org/aos/agrovoc/c_26374 http://aims.fao.org/aos/agrovoc/c_26376 http://aims.fao.org/aos/agrovoc/c_28379 http://aims.fao.org/aos/agrovoc/c_4792 |
author |
Suárez-Quiroz, Mirna Alonso Campos, Angelina Valerio Alfaro, Gerardo Gonzalez-Rios, Oscar Villeneuve, Pierre Figueroa-Espinoza, Maria-Cruz |
author_facet |
Suárez-Quiroz, Mirna Alonso Campos, Angelina Valerio Alfaro, Gerardo Gonzalez-Rios, Oscar Villeneuve, Pierre Figueroa-Espinoza, Maria-Cruz |
author_sort |
Suárez-Quiroz, Mirna |
title |
Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters |
title_short |
Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters |
title_full |
Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters |
title_fullStr |
Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters |
title_full_unstemmed |
Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters |
title_sort |
anti-aspergillus activity of green coffee 5-o-caffeoyl quinic acid and its alkyl esters |
url |
http://agritrop.cirad.fr/569374/ http://agritrop.cirad.fr/569374/1/document_569374.pdf |
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