title: Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters.
abstract: 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 ≤ 0.5-0.75 mg/mL, MIC80 = 1.0-1.5 mg/mL) and dodecyl (MIC50 = 0.75-1.25 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 (78.4-92.7%) and dodecyl (54.5-83.7%) 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.
authors.affiliation: Instituto Tecnológico de Veracruz, Unidad de Investigación y Desarrollo en Alimentos, Miguel Angel de Quevedo No. 2779, 91860 Veracruz, Mexico.
authors.forename: M L
authors.initials: ML
authors.lastname: Suárez-Quiroz
authors.forename: A
authors.initials: A
authors.lastname: Alonso Campos
authors.forename: G
authors.initials: G
authors.lastname: Valerio Alfaro
authors.forename: O
authors.initials: O
authors.lastname: González-Ríos
authors.forename: P
authors.initials: P
authors.lastname: Villeneuve
authors.forename: M C
authors.initials: MC
authors.lastname: Figueroa-Espinoza
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology*; D001230:Aspergillus / Q000145:classification* / Q000187:drug effects*; D001231:Aspergillus flavus / Q000187:drug effects; D001235:Aspergillus ochraceus / Q000187:drug effects; D002726:Chlorogenic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D003069:Coffee / Q000737:chemistry*; D004952:Esters / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests / Q000592:standards; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000935:Antifungal Agents; D002726:Chlorogenic Acid; D003069:Coffee; D004952:Esters; D011801:Quinic Acid; C473200:5-caffeoylquinic acid
keywords: 5-O-Caffeoyl quinic acid; Alkyl chlorogenate; Antifungal agent; Aspergillus; Cut-off effect; Lipophilization; MIC