In this work we studied the effect of polyunsaturated fatty acids (PUFAs) methyl esters on cholesterol photo-induced oxidation. The oxidative routes were modeled with a chemical reaction network (CRN), which represents the first application of CRN to the oxidative degradation of a food-related lipid matrix. Docosahexaenoic acid (DHA, T-I), eicosapentaenoic acid (EPA, T-II) and a mixture of both (T-III) were added to cholesterol using hematoporphyrin as sensitizer, and were exposed to a fluorescent lamp for 48 h. High amounts of Type I cholesterol oxidation products (COPs) were recovered (epimers 7α- and 7β-OH, 7-keto and 25-OH), as well as 5β,6β-epoxy. Fitting the experimental data with the CRN allowed characterizing the associated kinetics. DHA and EPA exerted different effects on the oxidative process. DHA showed a protective effect to 7-hydroxy derivatives, whereas EPA enhanced side-chain oxidation and 7β-OH kinetic rates. The mixture of PUFAs increased the kinetic rates several fold, particularly for 25-OH. With respect to the control, the formation of β-epoxy was reduced, suggesting potential inhibition in the presence of PUFAs.

C. Barnaba, M. T. Rodríguez-Estrada, G. Lercker, H. S. García, I. G. Medina-Meza (2016). Cholesterol photo-oxidation: A chemical reaction network for kinetic modeling. STEROIDS, 116, 52-59 [10.1016/j.steroids.2016.10.004].

Cholesterol photo-oxidation: A chemical reaction network for kinetic modeling

RODRIGUEZ ESTRADA, MARIA TERESA;LERCKER, GIOVANNI;
2016

Abstract

In this work we studied the effect of polyunsaturated fatty acids (PUFAs) methyl esters on cholesterol photo-induced oxidation. The oxidative routes were modeled with a chemical reaction network (CRN), which represents the first application of CRN to the oxidative degradation of a food-related lipid matrix. Docosahexaenoic acid (DHA, T-I), eicosapentaenoic acid (EPA, T-II) and a mixture of both (T-III) were added to cholesterol using hematoporphyrin as sensitizer, and were exposed to a fluorescent lamp for 48 h. High amounts of Type I cholesterol oxidation products (COPs) were recovered (epimers 7α- and 7β-OH, 7-keto and 25-OH), as well as 5β,6β-epoxy. Fitting the experimental data with the CRN allowed characterizing the associated kinetics. DHA and EPA exerted different effects on the oxidative process. DHA showed a protective effect to 7-hydroxy derivatives, whereas EPA enhanced side-chain oxidation and 7β-OH kinetic rates. The mixture of PUFAs increased the kinetic rates several fold, particularly for 25-OH. With respect to the control, the formation of β-epoxy was reduced, suggesting potential inhibition in the presence of PUFAs.
2016
C. Barnaba, M. T. Rodríguez-Estrada, G. Lercker, H. S. García, I. G. Medina-Meza (2016). Cholesterol photo-oxidation: A chemical reaction network for kinetic modeling. STEROIDS, 116, 52-59 [10.1016/j.steroids.2016.10.004].
C. Barnaba; M. T. Rodríguez-Estrada; G. Lercker; H. S. García; I. G. Medina-Meza
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/576066
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