Lipid oxidation and related protein modifications in oil-in-water emulsions

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1 Lipid oxidation and related protein modifications in oil-in-water emulsions C. Berton-Carabin, M.-H. Ropers, D. Guibert, V. Solé, C. Genot May 6 th, th AOCS AnnualMeeting San Antonio, Texas

2 Context of the study Lipid oxidation: Major cause of degradation of food products containing unsaturated fatty acids Degradation of sensory quality Degradation of nutritional quality Degradation of health-value In complex food products, oxidation targets other components than UFA e.g., protein oxidation Degradation of nutritional quality Schaich 28. in. Lipid Oxidation Pathways. AOCS Press. Degradation of functional properties Degradation of sensory quality

3 Context of the study O/W emulsions: suitable model systems to investigate the oxidative phenomena Oil Interface Adsorbed protein layer Aqueous phase Control of various parameters (i.e. oilphase, oil volume fraction, emulsifiers, droplet size, ph,.) Unadsorbed proteins Waraho et al 211 Trends Food Sci Technol 22:3-13.

4 Context of the study: oxidation in O/W emulsions Protective effect of effect of excess proteins in the aqueous phase Lipid ox (mmol O 2 /kg oil) Betalactoglobulin Time (h) Lipid ox (mmol O 2 /kg oil) Beta-casein Time (h) % adsorbed BLG [aqueous phase BLG] (g/l) % adsorbed BCN [aqueous phase BCN] (g/l) Regular BLGstabilized emulsion 7% 1.5 Regular BCNstabilized emulsion 91%.45 BLG-stabilized emulsion + excess BLG 39% 6.1 BCN-stabilized emulsion + excess BCN 64% 3.6 Berton et al., 211 J. Colloid Interface Sci. Berton et al., 211 J. Agric. Food Chem.

5 Context of the study: oxidation in O/W emulsions Mechanisms possibly involved in the protective effects of protein emulsifiers - Non-covalent binding(metalions, hydroperoxides, ) - Scavengingof free radicals; reducing properties(sh, ) - Covalent binding(reaction products Higherinterface thicknessand cohesiveness? Locating antioxidantsat interface Repelling/attracting metal ions depending on ph? Oxidative reactions and interactions of adsorbed and unadsorbed proteins before and during oxidation? Interface stabilised by only proteins do not protect the lipid phase against oxidation Protein-stabilized O/W interfaces are more heterogeneous than surfactant stabilized interfaces Berton et al., 212 J. Colloid Interface Sci. Berton et al., 212 Food Chem

6 Context of the study In multiphase systems, which of both reactions (lipid vs protein oxidation) first starts? R, M n+ Hyp 1: Lipid oxidation starts, then lipid radicals / lipid oxidation products (e.g., aldehydes) attack interfacial proteins Gardner, 1979 J. Agric. Food Chem. Karel et al., 1975 J. Agric. Food Chem. Dalsgaard et al., 21 Dairy Sci. Technol. Hyp 2: Interfacial proteins get oxidized, then the reaction propagates to the inner lipids Ostdal et al., 22 Free Radic. Biol. Med. Salminen et al., 21 J. Am. Oil Chem. Soc.

7 Aim of the study Getting new insights on the chemical co-modifications (oxidation) of lipids and proteins in O/W emulsion systems Regarding TIME (the sequence of the reactions)... Regarding LOCATION (where at a mesoscopic scale reactions occur)

8 Experimental approach: 1. emulsion design Dairy proteins β-lactoglobulin (BLG) Bovine serum albumin (BSA) Formulate protein-stabilized O/W emulsions Rapeseed oil ~ tocopherols 3% w/w Controlled concentration of unadsorbed proteins Minimum concentration in the aqueous phase to get stable emulsions β-casein (BCN) d 32 ~ µm Buffer, ph 6.7 Incubation in various oxidation conditions FeSO 4 /EDTA 1/1 2 µm FeCl 3 /NaAsc 1/1 5 µm MetMb1 µm AAPH 1 mm 25 C 33 C, no initiator

9 Experimental approach: 2. kinetics Preparation of emulsions t = Incubation t = 48 / 72 h Oxygen consumption (GC) O 2 Volatile compounds Volatile compounds (SPME GC) Measurement of oxidation parameters Evaluation of overall protein modifications Front-surface fluorescence Conjugated dienes

10 Results 1. Phasing of lipid oxidation and protein modifications Ex : BCN-stabilized emulsion FeSO 4 /EDTA 1/1 2 µm 25 C Tryptophan fluorescence Oxygen consumption Fluorescence intensity (I/I ) t 1/2 (Trp) Time (h) t 1/2 (O2) Lipid ox (mmol O 2 /kg oil) Half-times of reactions Berton et al., 211 J. Agric. Food Chem. Berton et al., 212 Food Chem.

11 Results 1. Phasing of lipid oxidation and protein modifications Ex : BCN-stabilized emulsion FeSO 4 /EDTA 1/1 2 µm 25 C L Trp Fluorescence intensity (I/I ) Time (h) L O2 Lipid ox (mmol O 2 /kg oil) Lag-times of reactions Berton et al., 212 J. Agric. Food Chem. Genot et al., 213 Lipid Ox.: Challenges Food Syst.

12 Results 1. Phasing of lipid oxidation and protein modifications Half-times of reactions FeSO 4 /EDTA 1/1 2 µm 25 C Tryptophan fluorescence t 1/2 (Trp) (h) BLG BSA BCN t 1/2(Trp) =.67 t 1/2 (O2) 7.7 FeCl 3 /NaAsc 1/15 µm 25 C 33 C, no initiator MetMb1 µm 25 C AAPH 1 mm 25 C Oxygen consumption t 1/2 (O2) (h) Protein modifications and lipid oxidation are time-linked phenomena Berton et al., 212 J. Agric. Food Chem. Genot et al., 213 Lipid Ox.: Challenges Food Syst.

13 Results 1. Phasing of lipid oxidation and protein modifications Lag-times of reactions Tryptophan fluorescence L Trp (h) 5 BLG BSA 4 BCN 3 2 L Trp < L O 2 FeSO 4 /EDTA 1/1 2 µm 25 C FeCl 3 /NaAsc 1/15 µm 25 C 33 C, no initiator MetMb1 µm 25 C AAPH 1 mm 25 C Oxygen consumption L O2 (h) Protein modifications precede lipid oxidation in protein-stabilized emulsions Berton et al., 212 J. Agric. Food Chem. Genot et al., 213 Lipid Ox.: Challenges Food Syst.

14 Experimental approach: 3. location Evaluation of protein oxidation Preparation of emulsions t = Incubation t = 48 / 72 h Creamed phase (adsorbed proteins) Front-surface fluorescence Protein solubility & aggregation Aqueous phase (unadsorbed proteins) Protein-bound carbonyls Whole emulsion

15 Results 2. Location of protein modifications Comparison of Trp fluorescence quenching in adsorbed vs unadsorbed proteins: BLG-stabilized emulsion FeSO 4 /EDTA 1/1 2 µm 25 C Whole emulsion Creamed phase Aqueous phase Intensity (AU) t = t = 24 h 1 t = 48 h λ (nm) Intensity (AU) t = t = 24 h t = 48 h λ (nm) Intensity (AU) 3 25 t = 2 15 t = 24 h 1 5 t = 48 h λ (nm) Adsorbed proteins undergo extensive modification Berton et al., 212 J. Agric. Food Chem. Genot et al., 213 Lipid Ox.: Challenges Food Syst.

16 Results 3. Adsorbed proteins undergo extensive oxidation BLG-stabilized emulsion FeSO 4 /EDTA 1/1 2 µm 25 C % soluble proteins Protein solubility in GuCl 6 M: Carbonyls (µmol/g soluble proteins) Time (h) Protein-bound carbonyls in the soluble proteins: Emulsion Aqueous phase Creamed phase SDS-PAGE: Non-reducing conditions t t 24 t 48 Non-soluble proteins? Reducing conditions S-S reduction Berton et al., 212 J. Agric. Food Chem. Genot et al., 213 Lipid Ox.: Challenges Food Syst.

17 Conclusion Towards a comprehensive scheme? Slow down / delay lipid oxidation Unadsorbed proteins No decrease in solubility No aggregation Moderate but early decrease of fluorescence Low carbonyl formation O 2 LOO 1 Free radicals, metal ions R HO Fe 2+ Fe Adsorbed proteins 4 O 2 L 5 LH L Unsaturated lipids (LH) LOOH Aldehydes 6 High decrease in protein solubility Aggregation (partly S-S induced) Complete extinction of protein fluorescence, High carbonyl formation Time INITIATION PROPAGATION TERMINATION Genot et al., 213 Lipid Ox.: Challenges Food Syst.

18 Further work to do list - Analyse and characterize the modifications of the unsoluble proteins - Understand the mechanisms underlaying Trp fluorescence decrease - Characterize the modifications of the proteins(nature & extent; preferred locations of modifiedaminoacids; adsorbed vs unadsorbed protein) - More rapid kineticapproach: characterizethe first stepsof unadsorbedand adsorbed protein modifications in relation to the initial steps of lipid oxidation - Integratedchemical/mathematicalmodelstakingaccountthe location of the reactants, their dynamics and complex/ imbricated reaction schemes - Effects on protein digestibility; health effects? Keeping realistic food models or real foods

19 Thank you for your attention Acknowledgements: ph-d funding of CB

20 Lipid oxidation and related protein modifications in oil-in-water emulsions C. Berton-Carabin, M.-H. Ropers, D. Guibert, V. Solé, C. Genot May 6 th, th AOCS AnnualMeeting San Antonio, Texas

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