Oxidation 101 What is oxidation and how to measure it?
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1 xidation 1 What is oxidation and how to measure it? Presented by Thu Dinh, Ph.D. Department of Animal and Dairy Sciences Mississippi State University
2 verview xidation: major concern of deterioration in quality of foods Generation of reactive oxygen-rich precursors Chain-propagating free radicals by reactive oxygen species (RS) Double bonds of PUFA attacked, peroxide linkages formed Protein side-chains altered and cross-linked Contributing factors: metal catalysts, collapse of in vivo biological antioxidant system, postharvest processing (mixing, heating), environmental exposure. Degradation products: derivatives of fatty acids (peroxides, aldehydes, ketones) and protein (protein aldehydes, crosslinks) Changes in sensory attributes and functional properties of fat and protein July 3, Pet Food Alliance Meeting Kansas City, KS Slide #2
3 verview Necessity of xidation Assessment We can only manage what we can measure Measure current oxidative status Predict future oxidative status Develop preventative measures Establish oxidation threshold: effects on sensory, technological, and nutritional quality July 3, Pet Food Alliance Meeting Kansas City, KS Slide #3
4 verview Challenges of xidation Assessment Purpose of the assessment Appropriate markers Matrix effects Methodology Chain reactions and lifespan of oxidative species: moving targets Protein oxidation July 3, Pet Food Alliance Meeting Kansas City, KS Slide #4
5 Lipid Composition Fatty acid composition of chicken, pork, and beef fat tissues USDA Nutrient Database for Standard Reference Composition Chicken Pork Beef #05047: Chicken, broilers or fryers, separable fat, raw #006: Pork, fresh, separable fat, raw Total fat 68% 66% 71% #1301: Beef, retail cuts, separable fat, raw SFA 20.3%; 16:0 and 18:0 23.0%; 16:0 and 18:0 2.5%; 16:0 and 18:0 MUFA 30.3%; 16:1 and 18:1 28.0%; 16:1 and 18:1 30.%; 16:1 and 18:1 PUFA 14.2%; 18:2 and 18:3 13.2%; 18:2 and 18:3 2.6%; 18:2 and 18:3 Moisture 28.% 24.8% 20.2% Protein 3.7%.3% 8.2% July 3, Pet Food Alliance Meeting Kansas City, KS Slide #5
6 Lipid Composition Predominant MUFA in animal fat Palmitoleic acid leic acid H H ACD/ChemSketch Freeware July 3, Pet Food Alliance Meeting Kansas City, KS Slide #6
7 Lipid Composition Predominant PUFA in animal fat Linoleic acid Linolenic acid H H ACD/ChemSketch Freeware July 3, Pet Food Alliance Meeting Kansas City, KS Slide #7
8 Lipid xidation Initiation Initiated by an free-radical attack (e.g. RS such as H) R H + H R + H H (H 2 ) C adjacent to C=C, alkyl radicals rearrangement of C=C conjugated dienes in PUFA July 3, Pet Food Alliance Meeting Kansas City, KS Slide #8
9 Lipid xidation Propagation Radical coupling R + 2 R very reactive peroxide radicals Atom transfer R + R H R H + R hydroperoxides Fragmentation R R + 2 Re-arrangement (conjugated diens) Cyclization H 2 C July 3, Pet Food Alliance Meeting Kansas City, KS Slide #
10 Lipid xidation Standard Reduction Potential of RS H has the greatest potential to be reduced to water, which is why it is such a potent oxidizer or initiator of free radicals July 3, Pet Food Alliance Meeting Kansas City, KS Slide #
11 Lipid xidation Reactivity of RS to abstract allylic H H July 3, Pet Food Alliance Meeting Kansas City, KS Slide #
12 Lipid xidation Initiation and propagation R H + H R + H H (H 2 ) R + 2 R R + R H R H + R leic acid H H H H H 8 H H H 8 H 8 H ACD/ChemSketch Freeware July 3, Pet Food Alliance Meeting Kansas City, KS Slide #12
13 Lipid xidation Initiation and propagation R H + H R + H H (H 2 ) R + 2 R R + R H R H + R Linoleic acid 13 H H 13 H H 12 H ACD/ChemSketch Freeware July 3, Pet Food Alliance Meeting Kansas City, KS Slide #13
14 Lipid xidation Initiation and propagation R H + H R + H H (H 2 ) R + 2 R R + R H R H + R Linolenic acid H H H H H H H 12 H H ACD/ChemSketch Freeware July 3, Pet Food Alliance Meeting Kansas City, KS Slide #14
15 Lipid xidation Hydroperoxide degradation and termination Degradation R H R + H hydroperoxide degradation H very reactive Chain reaction to form secondary products and more free radicals R-C + RH RH + R alcohols R RCH + R aldehydes (e.g., malondialdehyde, MDA) R RCR + R ketones Termination of free radicals R + R R R R + R RR R + R RR + 2 termination to non-radicals July 3, Pet Food Alliance Meeting Kansas City, KS Slide #15
16 Lipid xidation Hydroperoxide degradation overview R1 CH R2 + H isomerized peroxides R1 R1 C- cleavage aldehydes CH HC R2. aldehyde esters R2 C-C cleavage R1 R 3. R 3 H propogation alcohols CH H + H R2 termination R 4. R 3 H ketones R1 C R2 + R 4 H ACD/ChemSketch Freeware July 3, Pet Food Alliance Meeting Kansas City, KS Slide #16
17 Lipid xidation Degradation products leic acid: 8-, -, -, and -H Frankel, E Lipid oxidation. Prog. Lipid Res. 1:1 22. July 3, Pet Food Alliance Meeting Kansas City, KS Slide #17
18 Lipid xidation Degradation products Linoleic acid: - and 13-H Frankel, E Lipid oxidation. Prog. Lipid Res. 1:1 22. July 3, Pet Food Alliance Meeting Kansas City, KS Slide #18
19 Lipid xidation Degradation products Linolenic acid: - and 13-H Frankel, E Lipid oxidation. Prog. Lipid Res. 1:1 22. July 3, Pet Food Alliance Meeting Kansas City, KS Slide #1
20 Lipid xidation Degradation products 4-hydroxy-2,3-trans-nonenal (4-HNE) H H H H CH H H H H July 3, Pet Food Alliance Meeting Kansas City, KS Slide #20 H H ACD/ChemSketch Freeware
21 Lipid xidation Degradation products Malondialdehyde (MDA): there are various precursors Linolenic acid H CH H July 3, Pet Food Alliance Meeting Kansas City, KS Slide #21 H H H ACD/ChemSketch Freeware
22 Lipid xidation Degradation products Malondialdehyde (MDA): there are various precursors Tsikas, 2012 July 3, Pet Food Alliance Meeting Kansas City, KS Slide #22
23 Lipid xidation Non-radical process without an initiator Photooxidation Myoglobin (+light) sensitized Mb* Mb* + 2 Mb + 2 * (singlet/excited oxygen) 2 * + R H R H July 3, Pet Food Alliance Meeting Kansas City, KS Slide #23
24 Lipid xidation Non-radical process without an initiator Enzymatic oxidation lipoxygenases 2 + R H R H July 3, Pet Food Alliance Meeting Kansas City, KS Slide #24
25 Lipid xidation ther decomposition or re-arrangement of hydroperoxides Hydroxyepoxide Epoxide monoenes Epoxide hydroxy dienes ther dialdehydes Ketodienes Di-/tri-hydroxy esters Polymerized peroxides Various volatile carbonyl compounds July 3, Pet Food Alliance Meeting Kansas City, KS Slide #25
26 Lipid xidation Lipid oxidation products - Summary Short half-life species o o Reactive oxygen species ther free radicals Primary products o Conjugated dienes o Hydroperoxides o Endo-/cyclic peroxides o Hydroxyepoxide o xidative polymers (peroxides) Secondary products: o Hydrocarbons o Aldehydes o Ketones o Alcohols o Short-chain carboxylic acid o Esters July 3, Pet Food Alliance Meeting Kansas City, KS Slide #26
27 Lipid xidation Assessment Peroxide value (PV) PV: amount of peroxide oxygen present in sample, indicating oxidative stability Unit: milliequivalents (meq) of oxygen per kg of sample Initial stages of oxidation: formation rate > decomposition rate Later stages of oxidation: formation rate < decomposition rate Heat (cooking, rendering, etc.) accelerates hydroperoxide decomposition July 3, Pet Food Alliance Meeting Kansas City, KS Slide #27
28 Lipid xidation Assessment Peroxide value (PV) Iodometry IUPAC Standard Method AAC fficial Methods of Analysis R-H + 2H + + 2KI I 2 + RH + H 2 + 2K + I 2 + 2Na 2 S 2 3 Na 2 S NaI LD: 0.5 meq/kg Strengths: fast, inexpensive, relatively easy unless lipid extraction is needed. Weakness: liberation of I 2 by air oxidation, absorption of I 2 by C=C bonds July 3, Pet Food Alliance Meeting Kansas City, KS Slide #28
29 Lipid xidation Assessment Peroxide value (PV) Ion oxidation: Based on ability of peroxides to oxidize ferrous ions (Fe 2+ ) to ferric ions (Fe 3+ ) Ammonium thiocyanate method Ammonium thiocyanate + ferric ions in acidic condition a colored complex measured at 500 nm LQ: 0.1 meq/kg; 1.5 to 2 times greater PV values than iodometry Weaknesses: naturally occurring ferric ions and hydrogen peroxide, too much solvent Strengths: direct reaction in both aqueous and organic solvent July 3, Pet Food Alliance Meeting Kansas City, KS Slide #2
30 Lipid xidation Assessment Peroxide value (PV) Ion oxidation Ferrous oxidation-xylenol (FX) orange method Fe II (orange)[+peroxide] Fe III [+xylenol orange] Fe III xylenol orange (purple) The blue-purple complex has a maximum absorbance between 550 and 600 nm Sensitivity: ~ iodometry (LQ = 0.5 meq/kg) Grintzalis, Zisimopoulos, Grune, Weber, & Georgiou (2013) Strength: simple, easy, fast, not affected by oxygen, kits available, adopted without lipid extraction Weakness: sample volume changes reactivity, unclear interactions with non-lipid components, varying molar absorptivity July 3, Pet Food Alliance Meeting Kansas City, KS Slide #30
31 Lipid xidation Assessment Peroxide value (PV) Chromatography Gas chromatography mass spectrometry detection (GC-MS) Reduced to more stable species Derivatized to more volatile compounds Determined by mass spectrometry High or Ultrahigh Pressure Liquid Chromatography (HPLC/UPLC) with UV/chemiluminescence/fluorescence detection Reduced to more stable or chromophoric structures R reacted to create chromophores Determined by mass spectrometry, UV, chemiluminescence, or fluorescence detector. July 3, Pet Food Alliance Meeting Kansas City, KS Slide #31
32 Lipid xidation Assessment Peroxide value (PV) Chromatography GC-MS example Hydroperoxides (R-H) reduced hydroxyesters (R-H) purified by silica gel Hydroxyesters trimethylsilyl ethers R--Si(CH 3 ) 3 GC-MS determination Wong & Hammond (177). Lipids, 12(6), July 3, Pet Food Alliance Meeting Kansas City, KS Slide #32
33 Lipid xidation Assessment Peroxide value (PV) Chromatography HPLC/UPLC examples Hydroperoxides + triphenylphosphine (TPP) triphenylphosphineoxide (TPP) TPP analyzed by HPLC-UV at 260 nm LD: 2.01 pmol hydroperoxides or 0.2 meq/kg in mg lipid Applicable for colored fats and oils or lipids extracted from dark meat or processed food containing a coloring agent. July 3, Pet Food Alliance Meeting Kansas City, KS Slide #33
34 Lipid xidation Assessment Conjugated dienes and trienes UV Spectroscopy for naturally occurring conjugated dienes and trienes Alternative for PV Conjugated dienes: two C=C separated by a single C-C Absorbance at 233 nm Conjugated trienes: 270 nm Strengths: fast, non-destructive, distinct property Weaknesses Peaked during early oxidation, decreased by hydroperoxide decomposition Fat extraction required verestimation: overlapped by absorbance of PUFA (baseline needed). Underestimation: oleic acid hydroperoxides only have one C=C Interferences by hydroperoxide decomposition products (carbonyl compounds) H Estévez, Morcuende, and Ventanas (200) H July 3, Pet Food Alliance Meeting Kansas City, KS Slide #34
35 Lipid xidation Assessment Conjugated dienes and trienes UV Spectroscopy: to measure peroxides Fatty acid hydroperoxides, oxodienes, and hydroxydienes are reduced by sodium borohydride Reduced products are dehydrated in acidic condition conjugated fatty acids with strongly chromophoric triene and tetraene structures Sum of absorbance changes at 268 and 301 nm measure the degree of oxidation PUFA type: abs 301 nm /abs 268 nm = 0 to 2.8; 0 = pure triene, 2.8 = pure tetraene xodienes: decrease of abs 275 nm during the reduction Fishwick & Swoboda (177) July 3, Pet Food Alliance Meeting Kansas City, KS Slide #35
36 Lipid xidation Assessment Malondialdehyde determination Malondialdehyde: 1,3-propanedial Concentration of mg MDA/kg product Very commonly used indicator Assays: thiobarbituric acid reactive substances (TBARS) by VIS spectroscopy malondialdehyde by HPLC/VIS malondialdehyde by LC-MS or GC-MS H H July 3, Pet Food Alliance Meeting Kansas City, KS Slide #36
37 Lipid xidation Assessment Malondialdehyde determination Principles of methods MDA is extracted from samples MDA + TBA a red chromogen with max abs. at nm. Issues: o o o o o o MDA - the major TBA-reactive substance α- and β-unsaturated aldehydes (4-hydroxyalkenals) or saturated aldehydes (hexanal) Proteins and PUFA TBA impurities TBA/MDA ratio Antioxidants: propyl galate, EDTA, BHT July 3, Pet Food Alliance Meeting Kansas City, KS Slide #37
38 Lipid xidation Assessment Malondialdehyde determination: what are we measuring in TBARS? Pink pigment: λmax = 532 nm Unstable yellow interference: 455 nm Barbituric acid impurity: 1:1:1 TBA/MDA/barbituric acid (513 nm) 2:1 barbituric acid/mda (40 nm) Jardine et al., 2012 July 3, Pet Food Alliance Meeting Kansas City, KS Slide #38
39 Lipid xidation Assessment Malondialdehyde determination: alternative to TBA adduct 2,4-dinitrophenylhydrazine (DNPH) Pentafluorophenyl hydrazine Pentafluorobenzyl bromide Tsikas, 2012 July 3, Pet Food Alliance Meeting Kansas City, KS Slide #3
40 Lipid xidation Assessment Para-asinidine (p-asinidine): alternative for MDA The p-anisidine value: 0 times the optical density measured at 350 nm in a 1-cm cuvette of a solution containing 1.00 g of the oil in 0 ml of a mixture of solvent and reagent according to the method described. What it measures: aldehydes (principally 2 alkenals and 2,4 dienals), including non-volatile Reaction: aldehyde carbonyl bond on the p-anisidine amine group a Schiff base + NH 2 N N Strengths: very simple and rapid, correlated well with FX, PV, TBA, and volatile aldehydes Weaknesses: similar to other compounds (TBA, DNHP, etc.) that form adduct with aldehydes, values vary greatly among foods or lipids. July 3, Pet Food Alliance Meeting Kansas City, KS Slide #40
41 Lipid xidation Assessment Volatiles Lipid-derived volatiles Hexanal Propanal Nonanal 4-hydroxy-2 nonenal July 3, Pet Food Alliance Meeting Kansas City, KS Slide #41
42 Lipid xidation Assessment Volatiles Extraction and determination July 3, Pet Food Alliance Meeting Kansas City, KS Slide #42
43 Lipid xidation Assessment Volatiles Hexanal is the major aldehyde: most effective indicator??? The search for suitable markers July 3, Pet Food Alliance Meeting Kansas City, KS Slide #43
44 Lipid xidation Assessment Volatiles Hexanal is the major aldehyde: most effective indicator??? Predominant fatty acid in olive oil leic acid July 3, Pet Food Alliance Meeting Kansas City, KS Slide #44
45 xidation Assessment An complicate issue July 3, Pet Food Alliance Meeting Kansas City, KS Slide #45
46 Thoughts What is our goal? Are we using the right marker? Are we using the right method? What does the right marker looks like? Most abundant? Most stable? Most correlated? What does the right method looks like? Most precise (most repeatable and reproducible)? Most accurate (closest to trueness)? Most rugged July 3, Pet Food Alliance Meeting Kansas City, KS Slide #46
47 Thoughts Maybe developing the RIGHT method is not the answer Maybe it is to make the WRNG method do the right thing. July 3, Pet Food Alliance Meeting Kansas City, KS Slide #47
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