Chain length affects antioxidant properties of chlorogenate esters in emulsion: The cutoff theory behind the polar paradox

Laguerre Mickaël, Lopez Giraldo Luis Javier, Lecomte Jérôme, Figueroa-Espinoza Maria-Cruz, Baréa Bruno, Weiss Jochen, Decker Eric Andrew, Villeneuve Pierre. 2009. Chain length affects antioxidant properties of chlorogenate esters in emulsion: The cutoff theory behind the polar paradox. Journal of Agricultural and Food Chemistry, 57 (23) : pp. 11335-11342.

Journal article ; Article de revue à facteur d'impact
[img] Published version - Anglais
Access restricted to CIRAD agents
Use under authorization by the author or CIRAD.

Télécharger (927kB)

Quartile : Outlier, Sujet : AGRICULTURE, MULTIDISCIPLINARY / Quartile : Q1, Sujet : FOOD SCIENCE & TECHNOLOGY / Quartile : Q1, Sujet : CHEMISTRY, APPLIED

Abstract : Twenty years ago, Porter et al. (J. Agric. Food Chem. 1989, 37, 615-624) put forward the polar paradox stating among others that apolar antioxidants are more active in emulsified media than their polar homologues. However, some recent results showing that not all antioxidants behave in the manner proposed by this hypothesis led us to investigate the relationship between antioxidant property and hydrophobicity. With a complete homologous series of chlorogenic acid esters (methyl, butyl, octyl, dodecyl, hexadecyl, octadecyl, and eicosyl), we observed in emulsified medium that antioxidant capacity increases as the alkyl chain is lengthened, with a threshold for the dodecyl chain, after which further chain extension leads to a drastic decrease in antioxidant capacity. The antioxidant capacity evaluation in emulsion was possible using a newly developed conjugated autoxidizable triene (CAT) assay, which allows the assessment of both hydrophilic and lipophilic antioxidants. The nonlinear behavior was mainly explained in terms of antioxidant location since it was found from partition analysis that the dodecyl ester presented the lowest concentration in the aqueous phase and also that the quantity of emulsifier drastically changes the partition of antioxidant. In addition, this nonlinear influence was connected to the so-called cutoff effect largely observed in studies using cultured cells. Taken together, these different results allow one to make the proposal of a new scenario of the behavior of phenolic compounds in emulsified systems with special emphasis on the micellization process. Finally, in the CAT system, the polar paradox appeared to be the particular case of a far more global nonlinear effect that was observed here. (Résumé d'auteur)

Mots-clés Agrovoc : Antioxydant, Acide chlorogénique, Estérase, Huile de tournesol, Composé phénolique, Émulsion, Lipase

Mots-clés complémentaires : Ester gras

Classification Agris : Q02 - Food processing and preservation
Q04 - Food composition

Champ stratégique Cirad : Axe 3 (2005-2013) - Alimentation accessible et de qualité

Auteurs et affiliations

  • Laguerre Mickaël, University of Massachusetts (USA)
  • Lopez Giraldo Luis Javier, CIRAD-PERSYST-UMR IATE (FRA)
  • Lecomte Jérôme, CIRAD-PERSYST-UMR IATE (FRA)
  • Figueroa-Espinoza Maria-Cruz, CIRAD-PERSYST-UMR IATE (FRA)
  • Weiss Jochen, University of Massachusetts (USA)
  • Decker Eric Andrew, University of Massachusetts (USA)
  • Villeneuve Pierre, CIRAD-PERSYST-UMR IATE (FRA) ORCID: 0000-0003-1685-1494

Autres liens de la publication

Source : Cirad - Agritrop (

View Item (staff only) View Item (staff only)

[ Page générée et mise en cache le 2020-10-06 ]