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Lipid oxidation in emulsified foods: An overview of recent progress Charlotte Jacobsen Research group for Bioactives – analysis and application Division of Food Technology [email protected]
November 2015 Latin American Oil Congress World Congress on Oils and Fats
2 DTU Food, Technical University of Denmark
Outline • Introduction • Factors affecting oxidation in complex emulsified foods • Effect of oil quality • Effect of ingredients • Optimization of production process • Introduction to antioxidants in emulsified foods • Effect of antioxidant addition including lipophilisation • Conclusions • Acknowledgements
November 2015 Latin American Oil Congress World Congress on Oils and Fats
3 DTU Food, Technical University of Denmark
Lipid oxidation
Unpleasant flavors, Nutrient loss, Texture, Color, Functionality
Lipid oxidation is one of the most important chemical degradation processes
Oxidized lipids Rancidity
Food emulsions: Mayonnaise, salads & dressing, yoghurt, milk
Fish
Bulk oil
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Oxidation and analysis of oxidation
Volatile oxidation products Rancid off-flavour
Hydroperoxides: peroxide value (PV) or conjugated dienes
Volatiles: Anisidine value, TBARS, GC/MS (HS, DHS, SPME)
Sensory evaluation
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Factors that can affect lipid oxidation in emulsified foods:
Oil Water
1. Ingredients (Amount, type and quality)
3. The surface charge
2. pH
5. Oil droplet size / surface area
4. Viscosity
6. Processing conditions
7. Antioxidants
AO
AO
AO
+ +
+ +
Fe 3+
Fe 2+
Emulsifier at the interface (Structure/thickness)
Emulsifier in the aqueous phase (Antioxidative properties)
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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The role of emulsifiers
Berton-Carabin, C., Ropers, M.-H., Genot, C. (2014). Comprehensive Reviews in Food Science and Food Safety, 13, 945-977
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Effect of oil quality
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Milk with a fish oil and rapeseed oil mixture
0
1
2
3
Milk FRO 0.1 FRO 0.5 FRO 1.0 FRO 2.0 Day 1 Day 4
Day 8
Fishy taste
[0-9]
Let et al., 2005. Int. Dairy J. 15:173-182
Fish oil enriched milk
Oil quality affects the food quality
→ seems that PV needs to be
≤ 0.1 meq/kg fish oil
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Effect of food composition
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Effect of fish oil concentration and emulsifier type in fish oil enriched mayonnaise (20 oC)
0 25 50 75 100 1250
50
100
150
200
250
300
350
M_STD
M_4%FO
M_10%FOM_14%FO
MP_STD
MP_14%FO
Storage time [days]
1-pe
nten
-3-o
ne [n
g / g
]
Rancid (Flavour)
0 40.0
2.5
5.0
7.5
10.0
12.5M_STDM_4%FOM_10%FOM_14%FOMP_STDMP_14%FO
Storage time [Months]
• Oxidation increased with
increasing fish oil conc.
• Previous data: Egg yolk and low pH
main factors responsible for lipid oxidation
• Milk protein resulted in increased oxidation
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Effect of the Ingredients: Mayonnaise-based Shrimp Salad
Sørensen, Nielsen & Jacobsen, 2010, Eur. J. Lipid Sci. Technol. 112, 476-487
0 10 20 30 40 50 600
50
100
150
200
250
S_STDS_STD_FO
S_FO_S
S_FO_A
Storage time [days]
2-pe
nten
al [n
g / g
sam
ple]
2 10 24 36 50 570
25
50
75 S_STDS_STD_FOS_FO_S
Storage time [days]
Inte
nsity
(T-R
anci
d)
Shrimp & asparagus Shrimp, asparagus & FO
Asparagus & FO
Shrimp & FO Shrimp & FO
Shrimp & asparagus Shrimp, asparagus & FO
• Salads without asparagus were more oxidised
• Salads without shrimps were the least oxidised
• The panel could not discriminate between standard salad with or
without fish oil
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Comparing Milk and Drinking yoghurt: Effect of Ingredients in Yoghurt
• Fish oil enriched milk oxidised much faster than fish oil enriched
yoghurt
• Ingredients added to yoghurt did not affect oxidation
Intensity of fishy off-flavour (0-9):
Nielsen, Klein & Jacobsen, 2009, Eur. J. Lipid Sci. Technol. 111, 337-345
Week 0 Week 1 Week 3
Milk 5.4 ± 1.5 6.0 ± 2.4 7.4 ± 1.0
Yoghurt (CA+P+FS)
0.0 ± 0.1 0.5 ± 1.0 0.4 ± 0.7
Yoghurt (CA+P)
0.4 ± 0.5 0.9 ± 1.4 1.0 ± 1.3
Yoghurt (CA)
0.4 ± 0.5 0.7 ± 1.0 1.3 ± 0.9
Yoghurt 0.5 ± 0.4 0.8 ± 1.0 1.6 ± 1.2
CA: Citric acid; P: Pectin; FS: Fruit preparation and sugar
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Comparing Milk and Yoghurt: Antioxidant Assays on Peptide Fractions in Yoghurt
Crude protein
>30 10-30 3-10 <3 Radical scavenging (DPPH)
+++ +++ +++ ++ ++
Metal chelation + + + +++ +++
Reducing power + + + ++ +++
Peptide fractions (KDa)
Farvin, Nielsen, Baron & Jacobsen, 2010 Food Chem. 123, 1081-1089.
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Comparing Milk and Yoghurt: Oxidative Stability of Milk with Peptide Fractions from Yoghurt
0 2 4 6 8 10 12 140
1
2
3
4
5
6
7
M+RO
M+FO
M+FO+CPP
M+FO+3-10KDa
M+FO+<3KDa
Storage time (Days)
1-pe
nten
e-3-
ol (n
g/g
emul
sion
)
Low molecular weight peptides reduce oxidation
Farvin, Nielsen, Baron & Jacobsen, 2010 Food Chem. 123, 1081-1089.
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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LC-MS/MS characterisation of peptides
>30 kDa
10-30 kDa
3-10 kDa
<3 kDa
Absorbance at 210 nm
Fractions > 3 kDa
were dominated
by peptides from
caseins. Phosphory-
lated peptides were
not found.
Fraction < 3 kDa
dominated by free
amino acids
Farvin, Nielsen, Baron & Jacobsen, 2010, Food Chem. 123, 1090-1097.
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Optimising processing conditions
- Temperature and pressure
- Type of equipment
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Effect of Emulsification Conditions: Milk Affected by Temperature and Pressure
• Homogenization with a low temperature and a low pressure leads to more oxidation than a high temperature and a high pressure!
0 3 8
1 4 7 11 0
5
10
15
Temp. 72C/Pressure 5 MPa
Temp. 50C/Pressure 22.5 MPa
Temp. 72C/Pressure 22.5 MPa
Temp. 50C/Pressure 5MPa
2-hexenal
[ng/g milk]
Days of storage at 2°C
Let, Jacobsen, Sørensen & Meyer (2007), J. Agric. Food Chem. 55:1773-1780
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Homogenisation Conditions Affect Protein Composition at the Interface
Sørensen, Baron, Brüggemann, Pedersen & Jacobsen (2007) J. Agric. Food Chem. 55:1781-1789
Pressure [MPa]
Temperature [°C]
β -lactoglobulin α -casein α -casein
Reference, no treatment 4.92 5.18 4.19
5 50 8.01 5.94 5.14
72 10.17 4.28 4.09
15 50 9.36 5.21 5.08
72 14.56 4.55 4.59
22.5 50 9.45 4.56 4.23
72 13.72 3.68 3.74
s1 s2
+ - -
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Homogenisation conditions affect surface behaviour of proteins
Casein: green Lactoferrin: red Lipids: blue
Fish oil enriched milk
50 °C, 50 bar Fish oil enriched milk
72 °C, 225 bar
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Effect of emulsification equipments Microfluidizer vs.
two-stage Valve Homogenizer Delivery emulsions
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Effect of emulsification Equipment Fish oil-in-water emulsion
• Ingredients: – 10% fish oil – 1% emulsifier – 89% buffer
• Storage with iron for 14 days
Type of emulsifier
Transition metal ions
Processing conditions
+ +
+
+
Fe 3+
Fe 2+
Oil droplet size Microfluidizer
Two-stage valve homogenizer
69 MPa, 3 passes
80 MPa 50 MPa
4 passes 3 passes
CAS_M
WPI_M
CAS_H
WPI_H
Particle Size Distribution
0.01 0.1 1 10 100 1000 3000 Particle Size (µm)
0 1 2 3 4 5 6 7 8 9
10
Volu
me
(%)
1a Micro NaCas a - Average, 24. juni 2010 08:52:221b Micro NaCas a - Average, 24. juni 2010 08:58:403a Bord NaCas a - Average, 24. juni 2010 09:16:383b Bord NaCas a - Average, 24. juni 2010 09:22:46
CAS_M
Particle Size Distribution
0.01 0.1 1 10 100 1000 3000 Particle Size (µm)
0 1 2 3 4 5 6 7 8 9
Volu
me
(%)
2a Micro Valle a - Average, 24. juni 2010 09:04:312b Micro Valle a - Average, 24. juni 2010 09:10:184a Bord Valle a - Average, 24. juni 2010 09:29:054b Bord Valle a - Average, 24. juni 2010 09:35:26
CAS_H WPI_M
WPI_H
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Emulsification Equipment Results: PCA Biplot
• CAS vs WPI: Higher PV in CAS but less increase in volatiles than WPI – Metal chelation
• WPI_M vs WPI_H: Protein at the interface – Structure and thickness of interfacial layer
-0.15 -0.1 -0.05 0 0.05 0.1 0.15 0.2
-0.4
-0.3
-0.2
-0.1
0
0.1
0.2
0.3
t.t-2.4-Heptadienal_D 2-Hexenal_D14
2-Butenal_D4
t.t-2.4-Heptadienal_D
t.c-2.4-Heptadienal_D
t.t-2.4-Heptadienal_D
2-Butenal_D14
2-Hexenal_D10 t.t-2.4-Hexadienal_D4
4-Heptenal_D4
t.t-2.4-Hexadienal_D1
2-Hexenal_D4 Hexanal_D4 1-penten-3-one_D4 t.t-2.6-nonadienal_D4 Heptanal_D4 Pentanal_D4
2-Hexenal_D0
t.c-2.4-Heptadienal_D4
2-Hexenal_D7 Pentanal_D0
t.t-2.6-nonadienal_D10 2-Butenal_D10 t.c-2.4-Heptadienal_D10
t.t-2.4-Heptadienal_D7
Heptanal_D0
t.t-2.4-Hexadienal_D10
Propanal_D4 t.t-2.4-Hexadienal_D7
4-Heptenal_D0 t.t-2.6-nonadienal_D14
1-penten-3-one_D14
4-Heptenal_D10
Heptanal_D14
Pentanal_D14
Pentanal_D7
Propanal_D0
2-Butenal_D7
1-penten-3-one_D10
t.c-2.4-Heptadienal_D7
Hexanal_D0
t.t-2.4-Heptadienal_D0
Hexanal_D14
t.t-2.4-Hexadienal_D0
4-Heptenal_D14
1-penten-3-one_D7
2-Butenal_D0
t.t-2.6-nonadienal_D7
Pentanal_D10
4-Heptenal_D7 t.t-2.6-nonadienal_D0
Hexanal_D10 Heptanal_D10
Propanal_D14
1-penten-3-one_D0 Propanal_D7
Loadings PC#1 (58.670%)
PCA Loadings [Model 1]
Propanal_D10
t.c-2.4-Heptadienal_D0
Heptanal_D7 Hexanal_D7
PV_D7
PV_D14
PV_D10
PV_D4
PV_D0
Load
ings
PC
#2 (1
2.71
5%)
-8 -6 -4 -2 0 2 4 6 8 10
-4
-3
-2
-1
0
1
2
3
4
5
WPI_Ha
WPI_Hb
WPI_Mb
WPI_Ma
Scores PC#1 (58.670%)
PCA Scores [Model 1]
CAS_Ma
CAS_Ha CAS_Mb
CAS_Hb
Sco
res
PC
#2 (1
2.71
5%)
CAS_Ma
WPI_Mb
WPI_Hb
WPI_Ma
WPI_Ha
CAS_Ha CAS_Mb
CAS_Hb
Protein in aqueous phase:
WPI_M: 2.86 mg/mL
WPI_H: 4.96 mg/mL
Horn et al. (2012) Food Chemistry. 134, 803–810.
PV
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Effect of antioxidants
in omega-3 enriched foods
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Antioxidants
24
Antioxidants = Compounds that prevent or delay lipid oxidation
1) Primary antioxidants / Radical scavenging
2) Secondary antioxidants
Inactivate reactive radicals
Bind oxygen
Chelate metal ions
Quench singlet oxygen
Regenerate other antioxidants
November 2015 Latin American Oil Congress World Congress on Oils and Fats
25 DTU Food, Technical University of Denmark
Lipid oxidation
25
LH
X● XH
L●
O2
LOO●
LOOH
LH
Secondary oxidation products
and off flavors
I
Men+
Metal chelator
Radical
scavengers
Under certain conditions, antioxidants are also found to be prooxidants…
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Polar paradox hypothesis Interfacial phenomena in antioxidant activity
Air
Bulk oil Emulsion (o/w)
Air
Water
Oil
Oil Oil
● Hydrophilic
● Amphiphilic
● Lipophilic Antioxidants
● ● ● ●
●
●
●
●
●
●
●
●
●
●
●
●
● ●
● ●
● ●
● ●
● ● ●
●
●
● ●
● ●
Porter., 1993. Toxicol Ind Health, 9:93-122 and Frankel et al., 1994. J Agric Food Chem, 42:1054-1059
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Bulk oil – Physical structures
Chen et al., 2011. Crit Rev Food Sci Nutr, 51:901-916
Schematic illustration of some association colloids formed by minor constituents:
Physical structures:
↑ Lipid oxidation reactions
Alter effectiveness of AO
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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AO in fish oil enriched mayonnaise
0
40
80
120
160
200
0 1 2 3 4
2-Pe
nten
al [n
g/g
may
onna
ise]
Storage time [weeks]
No antioxidant
Nielsen et al., 2004. J. Agric. Food Chem. 52:7690-7699
EDTA
(6 & 24 ppm)
Lactoferrin
(700-2800 ppm)
& Phytic acid
(15-116 ppm)
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29 DTU Food, Technical University of Denmark
1. Very good protective effect of EDTA – best single antioxidant 2. Limited but still protective effect of tocopherols 3. Interestingly, no effect of adding both EDTA and tocopherol 4. Prooxidant effect of ascorbyl palmitate in high concentration
Results Antioxidants – Similar experiment in dressing
0
4
8
12
16
0 1 2 3 4 5 6 0
10
20
30
0 1 2 3 4 5 6
Weeks at room temperature Weeks at room temperature
NoAox
AscP- high
EDTA,
EDTA+γ-Toco
AscP- low
γ-Toco
Very good stability if all
3 antioxidants are added together
t,t-2,4-Heptadienal
[ng/g milk]
PV
[meq O2/kg oil]
AO in fish oil enriched dressing
Let et al., 2007. J. Agric. Food Chem. 55:2369-2375
November 2015 Latin American Oil Congress World Congress on Oils and Fats
30 DTU Food, Technical University of Denmark
AO in fish oil enriched milk
NoAox, EDTA EDTA+Toco
Toco Toco
0
2
6
10
14
0 2 4 6 8 10 12 0
6
12
18
0 2 4 6 8 10
AscP
AscP+EDTA
AscP+Toco
AscP+Toco+EDTA
RapeseedOil
t,t-2,4-Heptadienal
[ng/g milk]
PV
[meq O2/kg oil]
Days at 2°C Days at 2°C
1. Prooxidant effects of tocopherols when added to fish oil alone 2. No effect of EDTA 3. Ascorbyl palmitate highly protective against oxidation 4. Rapeseed oil highly protective against oxidation
Additional exp:
γ-tocopherol seems to work
-
α-tocopherol does not
Let et al., 2005. J. Agric. Food Chem. 53:5429-5437
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Antioxidant effects in fish oil enriched foods • Different antioxidants have very different effects in different
foods • Possibly due to different mechanisms of action and localizations
Tocopherol
Ascorbyl palmitate
Ascorbic acid
EDTA Propyl gallate/
Gallic acid
Lactoferrin Caffeic acid
Milk 1.5% fat
Weak anti Anti - Anti to no
- - -
Milk drink 5% fat
- Pro - Anti - Weak anti to pro
-
Drinking yoghurt 1.5% fat
- - - Anti - - -
Dressing 25% fat
Weak anti Pro - Anti - - -
Mayonnaise 80% fat
Weak anti to pro
Pro Pro Anti Pro Weak anti to pro
-
Energy bars 6.2% fat
Anti to weak pro
Pro - Pro
- - Pro
Pro: Prooxidative; Anti: Antioxidative
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Cut-off effect (Model emulsions, o/w)
Laguerre et al., 2009. J. Agric. Food Chem., 57:11335-11342
Phenolic compound + fatty alcohol = phenolipid
Conjugated Autoxidizable Triene (CAT) Assay Emulsion (o/w): Phosphate buffer (pH 7.2), Brij (17 µM), Tung oil (stripped, 115 µM)
AAPH (1 mM) as initiator
Laguerre et al., 2010. J. Agric. Food Chem., 58:2869-2876
Chlorogenic acid Rosmarinic acid
Optimal alkyl chain - Rosmarinates & Chlorogenates: C8 & C12
(Laguerre et al., 2008. Anal. Biochem., 380:282-290)
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Aqueous
phase
Cut-off effect (Model emulsions, o/w)
CCL
Ant
ioxi
dant
cap
acity
Alkyl chain length
0 n
Increased lipophilicity
Antioxidant (CCL) location
in an emulsion
CCL = Critical chain length
Decreased Oxidation
Modified from Laguerre et al., 2013. In: Lipid Oxidation: Challenges in Food systems, 261-295
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Caffeates as antioxidants
Conjugated Autoxidizable Triene (CAT) Assay
Emulsion (o/w): Phosphate buffer, Brij, Tung Oil. AAPH as initiator Sørensen et al. 2014. J. Agric. Food Chem. 62, 12553–12562
Efficacy of Caffeates
Caffeates with medium chain length
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Effect of lipophilisation of caffeic acid on oxidation in fish oil enriched milk
Treatments Concentration [μM] Control - Caffeic acid 100 Methyl caffeate 100 Butyl caffeate 100 Octyl caffeate 100 Dodecyl caffeate 100 Hexadecyl caffeate 100 Eicosyl caffeate 100
Storage: 5ºC,12 days (0, 3, 6, 9 and12)
Milk enriched with 0,5% of fish oil (total fat 1.5%)
Alemán et al. 2015 . Food Chemistry 167, 236-244.
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Volatiles - Milk
Induction time
9 days CA C8
Not defined CA C1 CA C4
3 days Con CA C0
6 days CA C12
CA C16
CA C20
Con CA C0
CA C16
Day 12
CA C4 CA C1
CA C12
CA C8
CA C20
General trend of volatile development
Lowest concentration: CA C4 and CA C1
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Experimental design: Mayonnaise
Fish Oil Enriched Mayonnaise
• 80 % Fat (64% rapeseed oil, 16% Fish Oil, w/w), Egg yolk as emulsifier
• Antioxidants (solubilized in MeOH), Conc. 100 µM – Con, CA C0, CA C1, CA C4, CA C8 (+200), CA C12, CA C18
• Storage at 20oC for 4 weeks (Sampling days: 0, 3, 9, 12, 15, 21 and 28) Efficacy of the antioxidants
– Lipid hydroperoxides (Spectrophotometric)
– Secondary volatile oxidation products (GC-MS)
– Tocopherols (HPLC)
Alemán et al. 2015 . Food Chemistry 167, 236-244.
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Volatiles - Mayonnaise
9 days CA C0
CA C1
CA C8 200
12 days Con CA C4
CA C8
CA C12
CA C18
Induction time
Con CA C0
CA C18
CA C1
Day 28
CA C12 CA C8 200
CA C8
General trend of volatile development
Lowest concentration: CA C8 (200), CA C12, CA C4 and CA C8
CA C4
CA C12
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Discussion
Mayonnaise No effect CA C0, CA C1, CA C18 Less efficient antioxidants Most efficient antioxidants CA C4, CA C8, CA C12
Increased conc. increased effect
Milk
No effect Less efficient antioxidants
CA C0, CA C8 - C20 Most efficient antioxidants CA C1, CA C4
The “cut-off” effect is influenced by the food system
It is not possible to predict optimal chain length in food products based on CAT assay
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Inhibition effects of ferulates in fish oil enriched milk
□ PV
■ 1-penten-3-one,
○ 1-penten-3-ol,
● 2-pentenal,
♦ 2-hexanal,
▲ 2,4-heptadienal
+ 2,6-nonadienal
Sørensen, A.-D. M., Lyneborg, K.S., Villeneuve, P., Jacobsen, C. (2015) J. Functional Foods doi: 10.1016/j.jff.2014.04.008
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Natural antioxidants in mayonnaise salads (tuna)
0 10 20 30 40 50 600
255075
100125150175200225
Storage time [days]
2-pe
nten
al [n
g / g
] Reference
Thyme 1%
Rosemary 1%
Oregano 1%
Formation of volatiles:
Reference > Thyme > Rosemary > Oregano
Sørensen et al., 2010. Eur. J. Lipid Sci. Technol. 112:476-487
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Antioxidant effects of extracts from seaweed (Fucus vesiculosus) in mayonnaise
0
2
4
6
8
10
12
0 10 20 30
PV (m
eq O
2/kg
oil)
Days
Peroxide value
0
50
100
150
200
250
300
0 10 20 30
ng/
g m
ayon
nais
e
Day
1-Penten-3-ol
EtC1
EtC2
AcC1
AcC2
WOC1
WOC2
WYC1
WYC2
REF
Water
Acetone + Ethanol Honold et al. Submitted to Food Chemistry
November 2015 Latin American Oil Congress World Congress on Oils and Fats
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Evaluation of compounds contributing to activity in mayonnaise
Phenolic compounds
Oxidation products – later stage of storage
Astaxanthin
Fucoxanthin
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Conclusions • Ingredients can affect lipid oxidation
• Oil quality is more important in some systems than in others
• The emulsifiers used as ingredients and the composition of the
interface in emulsions affect lipid oxidation
• Emulsification processes must be optimised to minimise oxidation
• Type of emulsification equipment can affect oxidation
• The same antioxidant can have very different effects in different food systems
• Polar antioxidants can be modified to have an optimal chain length for each food system
• Natural antioxidants from seaweed have promising effects
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Acknowledgements
• Caroline Baron
• Nina Skall Nielsen
• Mette Bruni Let
• Anna F. Horn
• Ann-Dorit Moltke Sørensen
• Anne S. Meyer
• Anna Klein
• Sabeena Farvin
• Lis Berner
• Inge Holmberg
• Trang Vu
• Jane Jørgensen
• Mercedes Aleman
• Ditte B Hermund
• Philipp J Honold