Lipid Oxidation and Quality
ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019
LIPID OXIDATION AND QUALITY
LOQ 1a: Antioxidant Mechanism and Activity Chairs: Fereidoon Shahidi, Memorial University of Newfoundland, Canada; and Zhuliang Tan, DSM Nutritional Products, Canada
Antioxidant Activity and Mechanism of Action mechanism. Methods used: The distribution of of Natural Extracts: Their Impact on Color and antioxidant in the scallop adductor muscle and Lipid Stability in Meat Products S.P.J. Namal their action in chelating metal ions and Senanayake*, Camlin Fine Sciences, USA quenching of free radicals was examined in situ. Maintaining the appearance and red color Meanwhile, POV, TBARS, AV, and contents of are very important to retail shelf-life of fresh TAG, FFA, PC, PE, protein carbonyl, total meat products. If the meat is dark or discolors phenols, phospholipase, lipases and early, then consumers will not purchase the lipoxygenase (LOX) were determined. meat. Improved color stability results in fewer Furthermore, the effects of the natural pulls, discounts and discards due to phenolics on the shelf life of dried scallop discoloration. One opportunity to improve color adductor muscle were predicted by Arrhenius stability in fresh meats is to supplement meat model. Results Using an in vivo imaging system, products with naturally-derived antioxidants. it was found that AOB could diffuse into the The goal of this study is to investigate the effect adductor muscle upon marinating, efficiently of plant-based extracts such as those derived retarded lipid oxidation during the drying and from acerola cherry, rosemary and green tea on storage process. The in situ antioxidant color and oxidative stability of fresh ground mechanisms of AOB as well as TP included beef products. In addition, the effect of these quenching of free radicals as detected by natural extracts on oxidative stability of cooked electron spin resonance, chelating metal ions meat products during storage will also be determined by confocal laser scanning evaluated. Antioxidant mechanism of action microscopy and inhibiting LOX. Upon marinating that are associated with each natural extract with AOB and TP, the contents of will also be discussed. eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) in adductor muscle Antioxidant Mechanism of Natural Phenolics decreased by less than 8% instead of >28% on Scallop Adductor Muscle During Drying and (without antioxidants) during the drying Storage Dayong Zhou*1, Hongkai Xie2, process. The shelf lives of AOB- and TP-treated Fereidoon Shahidi3, and Beiwei Zhu4,1Dalian dried adductor muscle were more than 1.70- Polytechnic University, China; 2National fold than that of dried control adductor muscle. Engineering Research Center of Seafood, China; Conclusions Overall, the antioxidants efficiently 3Memorial University of Newfoundland, Canada; maintained the high nutritive value of adductor 4College of Food Science & Technology, Dalian muscle in terms of its lipid components during Polytechnic University, China drying and storage. Objective The present work investigates the effect of natural antioxidant, tea polyphenols Influence of Antioxidants on Oxidation (TP) and antioxidant of bamboo leaves (AOB), Pathways Zhehan Jiang*, Suzanne M. Budge, against lipid oxidation in scallop’s adductor and Wei Xia, Dalhousie University, Canada muscle during the drying process and storage While lipid oxidation pathways have and demonstrates their in situ antioxidant traditionally focused on hydroperoxides and
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their scission products, there is increasing both tocopherol treated samples (0.1% and interest is describing alternative pathways, 2%), while hydroxy fatty acids were present in proceeding through production of alcohols and greater concentrations in the samples having epoxides. However, there has been little the higher α-tocopherol concentration. Coupled attention devoted to the effects of antioxidants with rates of formation, these data will help on these pathways. In this study, we focus on elucidate the importance of alternative the qualitative and quantitative analysis of pathways in triacylglycerol oxidation. epoxy and hydroxy fatty acids produced during oxidation of a single triacylglycerol, trilinolein, Stability and Stabilization of Edible Oils: Role in the presence and absence of α-tocopherol, to of Endogenous Antioxidants and Phenolipid better understand the diversity of products Addition Fereidoon Shahidi*, Memorial produced and the rates of their formation. University of Newfoundland, Canada Previous research suggested that while α- Edible oils are prone to oxidation and this is tocopherol has a well-known antioxidant effect generally dictated by their fatty acid at low concentrations, it may also function as a composition and degree of unsaturation as well prooxidant at high concentrations. To address as their positional distribution in the this, α-tocopherol was added to trilinolein at triacylglycerol molecules, minor components two concentrations (0.1% and 2% by mass) and present, and storage conditions. This study compared to a control sample without added examined the role of minor components on the tocopherol. All the samples were heated at 30 stability of selected oils by stripping them from °C with aliquots removed for analysis every 3 the samples. While stripped oils were generally days in a 15-day experimental cycle. Samples less stable than their unstripped counterparts were transmethylated with sodium methoxide, under Schaal oven conditions, the reverse was separated into epoxy and hydroxy fractions true under fluorescent light. In addition, with solid-phase extraction, and derivatized to selected phenolipids were tested for their trimethylsilyl ethers to mask hydroxide groups. antioxidant efficacy. Both the structural Gas chromatography-mass spectroscopy (GC- characteristics of the phenols as well as the MS) was used to identify the epoxy and hydroxy nature of the acyl group determined their components in each fraction, while GC with efficacy. Finally, the phenol moieties of flame ionization detection was used for phenolipids was released, at least partially, quantitative analysis. Preliminary data clearly upon simulated digestion and hence exerting showed that epoxy fatty acids did not form in their potential health effects.
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LOQ 1b / PRO 1b: Effect of Processing on Lipid Oxidation in Oils and Fats and Lipid-containing Foods Chairs: S.P.J. Namal Senanayake, Camlin Fine Sciences, USA; and Sean Liu, USDA, ARS, USA
Effects of Modified Phosphatidylcholine on to a decrease in formation of primary and Physical and Oxidative Stability of Omega-3 secondary oxidation products. Modified PCs in Delivery 70% Oil-in-Water Emulsions Betül combination with CAS and soybean PC thus Yesiltas*1, Ann-Dorit Moltke Sørensen2, Pedro J. improved the physical and oxidative stability of Garcia-Moreno2, Sampson Anankanbil3, Zheng 70% fish oil-in-water emulsions compared to Guo4, and Charlotte Jacobsen2,1National Food emulsions produced with only CAS as an Institute, Technical University of Denmark, emulsifier. Denmark; 2Technical University of Denmark, Denmark; 3Dept. of Engineering, Aarhus Effect of Maillard Reaction Conditions on University, Denmark; 4Aarhus University, Physicochemical Properties and Oxidative Denmark Stability of Microencapsulated Chia Oil Vanesa The objective of this study was to Y. Ixtaina1, Bernd W.K Diehl2, Claudia N. investigate the effects of modified Copado1, and Mabel Tomás*1,1CIDCA (CONICET- phosphatidylcholine (PC) with different alkyl UNLP), Argentina; 2Spectral Service AG, chain lengths (C14 and C16) and covalently Germany attached caffeic acid on the oxidative and Chia oil presents a very high content of physical stability of high fat 70% fish oil-in- PUFAs, which are very susceptible to lipid water emulsions. It is hypothesized that 1) oxidation. Some techniques, such as modified PC improves the physical stability of microencapsulation, have been developed to emulsions when used in combination with protect this type of oils. Many studies showed sodium caseinate (CAS) and soybean PC, by its that Maillard reaction products (MRPs) have high surface activity as a surfactant, and that 2) anti-oxidative properties and can be used as modified PC enhances oxidative stability due to wall material for microencapsulation. The the attachment of caffeic acid to the glycerol objective of this study was to characterize the backbone of PC, which brings the antioxidant in physicochemical properties of the vicinity of oil-water interface. Physical microencapsulated chia seed oil MRPs, as wall stability of the emulsions were analyzed using material, obtained by different heat treatments. droplet size, viscosity, zeta potential, interfacial Chia O/W emulsions were composed by NaCas, tension, and protein content in the aqueous lactose, and chia oil (10, 15 % wt/wt). The phase. Peroxide value, changes in tocopherol aqueous phase was heated at different content and secondary volatile oxidation temperatures (60 and 100°C) for 30 min to products were determined to evaluate oxidative promote the MRPs formation. Then, the stability. Results showed that the physical microcapsules were obtained by spray-drying stability of the emulsions was improved with the emulsions. All the systems showed high increasing concentrations of added modified microencapsulation efficiency ( 99%).̴ The PCs. Modified PC C14 showed higher physical moisture content and water activity (aw25ºC) of stability compared to modified PC C16 by microcapsules ranged between 0.020-2.998 % providing smaller oil droplets and higher (d.b.) and 0.243-0.470, respectively. In terms of viscosity as well as higher zeta potential. On the oxidative stability, the accelerated oxidative other hand, oxidative stability was higher for test (Rancimat) and the peroxide values (PV) the emulsions produced with modified PC C16; revealed a very significant influence of the heat increased concentration of modified PC C16 led treatment, with the highest induction time (ti)
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and the lowest PV for microcapsules obtained in mixed emulsion droplets, but not when the from emulsions with 15% content oil and oils were in isolated droplets. These results aqueous phase submitted to heath treatment of indicated that dilution with more stable lipids 100°C, 30 min. presents an effective strategy to delay lipid oxidation in food emulsions systems. Impact of Ratios of Polyunsaturated and Saturated Fatty Acids on Oxidation Kinetics in Effective Prevention of Oxidative Deterioration Oil/Water Emulsions Raffaella Inchingolo1, D. of Fish Oil by the Combination of Amine- Julian J. McClements2, Eric A. Decker2, and compounds and General Antioxidants Mariko Mitchell D. Culler*2,1University of Uemura1, Masashi Hosokawa1, Kazuo Massachusetts, USA; 2University of Miyashita*1, Ai Iwashima-Suzuki2, and Hiroaki Massachusetts Amherst, USA Kubouchi2,1Hokkaido University, Japan; Recently, demand for clean-label food 2Megmilk Snow Brand Co. Ltd., Japan products has necessitated new strategies for EPA and DHA, abundant in fish oil, are preventing lipid oxidation as consumers known to have significant biochemical and become skeptical of synthetic antioxidants. One physiological effects primarily linked to potential strategy is to dilute more easily improvement of human health, especially oxidized, unsaturated fatty acids with more cardiovascular and brain health. However, the oxidatively stable oils, thereby decreasing incorporation of fish oil into foods and oxidation by increasing the time needed for beverages is often challenging as fish oil is very fatty acid free radicals to diffuse to and oxidize easily oxidized and can cause undesirable other fatty acids. This strategy has proved flavors. In the present study, we demonstrate effective in bulk oils but not oil-in-water the successful prevention of volatile formation emulsions. The effect of diluting fish oil with in fish oil oxidation by amine-compounds. increasing concentrations of medium chain Several kinds of amine-compounds such as triglycerides (MCT) on oxidative stability of oil- butylamine, stearylamine, and spermine could in-water emulsions was investigated using show antioxidant activity and this activity thiobarbituric acid reactive substances assay increased with increasing the number of amine (TBARS), lipid hydroperoxides, and head-space groups. In addition, their antioxidant activity aldehydes. Dilutions up to 1:20 of fish oil in MCT synergistically increased in the presence of were found to extend the lag phase of lipid general antioxidants such tocopherols, oxidation markers from 1 to 5 days in oil-in- hydroxytyrosol, and carnosic acid. For example, water emulsions stabilized by Tween 80. To the volatile formation was completely inhibited verify that the dilution was effective, two by the combination of spermine and α- emulsions were prepared, one with fish oil and tocopherol up to 5000 hr after incubation of the other with MCT, and the 2 emulsions were purified fish oil triacylglycerol at 50°C. On the blended to have the same fish oil:MCT ratios. other hand, amine-compounds having hydroxyl The same protective effect was not observed group(s) had no antioxidant activity without any when the oils were in separate droplets, general antioxidants, while they showed a indicating dilution is responsible for the strong antioxidant activity in the presence of protective effect. Emulsions containing high tocopherols. The most likely mechanism for the oleic sunflower oil were also examined as a antioxidant activity of amine-compounds is the more commonly used oil in food production. formation of antioxidants by the amino- The protective effect was again demonstrated carbonyl reaction between the amine group
– 4 – ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019 and the carbonyl group of aldehydes, which are measurement. However, it is not possible to use formed in a very early stage of the fish oil peroxide value alone to judge the actual quality oxidation. of rendered protein meals because hydroperoxides decompose readily during Determination of Lipid Oxidation Parameters storage. To avoid misinterpretation of peroxide in Solid Non-oil Matrices and the Impacts on values, it is crucial to understand the oxidation the Pet Food Industry B.J. Bench*, Tyson Foods, history of the meal samples, which can be USA determined using other indicators such as p- Most pet food products consist of rendered anisidine values, hexanal and/or 2,4-decadienal animal protein meals and fats as one of the contents, as well as TOTOX (“total oxidation”) major building blocks in pet food diets. As pet values. p-Anisidine values, headspace volatile food ingredients start to degrade via the lipid aldehydes, specifically, the hexanal and/or 2,4- oxidation phenomenon it undergoes changes decadienals, and TOTOX values are not affecting odor, flavor, nutritional quality and commonly utilized to assess lipid oxidation in palatability. Several parameters can be these products. Ultimately, correlating these measured as means of determining oxidative analytical parameters to companion animal stability and shelf-life of rendered protein meals palatability will provide guidance on what pet and finished pet food products. In pet food ingredient and food manufacturers can utilize products containing oils and fats, peroxide to determine lipid oxidation. value is a popular oxidative stability
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LOQ 2a: Oxidation and Antioxidants in High Protein Foods Chairs: Michelle Peitz, Archer Daniels Midland Co., USA; and David Johnson, Kalsec Inc., USA; and Minwei Xu, North Dakota State University, USA
Increasing Oxidative, Microbial and Color Muscle Model System: Effect of pH and Stability of Fresh Meats: Mechanism and Tocopherol Ling Liu, Jie Yin, and Mark P. Application Min Hu*, DuPont Nutrition & Richards*,University of Wisconsin-Madison, USA Health, USA Effects of Maillard reaction products (MRPs) Meat products are easily oxidized and as inhibitors of hemoglobin-mediated lipid spoiled. It is critical, therefore, to prevent oxidation were evaluated in washed cod muscle spoilage bacteria growth and maintain the (WCM) and washed turkey breast muscle quality attributes of fresh meats such as flavor, (WTM) during storage at 2°C storage. MRPs color and texture. Clearly, natural antioxidants were prepared by reacting equimolar glucose like ascorbic acid, green tea extract and with lysine at 110°C for 2 h. The cooled solution rosemary extract can greatly inhibit lipid was used immediately or stored at 4°C oxidation and maintain red color of fresh compared to -20°C prior to use. MRPs were ground meats. Some antimicrobials can not only added at 75-900 μmol/kg washed muscle (as a inhibit microbial growth but maintain the red dilution of the glucose and lysine concentration color of fresh meats. Further, adding the blend in the heated mixture). Bovine hemoglobin (Hb) of natural antioxidants and antimicrobials could was added to promote lipid oxidation at 44 be more efficacious in increasing oxidative, μmol heme/kg washed muscle. pH values microbial and color stability of fresh meats. examined were 5.6 and 6.6. Lipid peroxides and However, the mechanisms of these antioxidants thiobarbituric acid reactive substances (TBARS) and antimicrobials to increase the oxidative, were used as markers of primary and secondary microbial and color stability have not been lipid oxidation products, respectively. Alpha completely elucidated. In-depth research on the tocopherol was measured by high pressure mechanism would help develop new liquid chromatography with fluorescence antioxidant and antimicrobial products, thus detection. MRPs strongly inhibited Hb-mediated extending the shelf life of fresh meats. In this lipid oxidation in WCM (p presentation, we will discuss possible mechanisms: (1) how natural antioxidants such Pea Protein Isolate/Gum Arabic Glycation as polyphenols and ascorbic acid effectively Improves the Oxidative Stability of Oil-in- maintain the cheery red color and prevent lipid Water Emulsions Bingcan Chen*, North Dakota and pigment oxidation; (2) how some of State University, USA antimicrobials keep red color of fresh meats, The current work presented the feasibility and (3) how the blend of antioxidant and of modifying pea protein via glycation to antimicrobial extend red color, inhibit lipid produce a dual effect food ingredients. Pea oxidation and spoilage bacterial growth in fresh protein isolate (PPI) was glycated with gum meats, effectively, and how antioxidant and Arabic (GA) under variable incubation time. The antimicrobial work together to fight hydrogen properties and functionalities of modified PPI peroxide and reduce heme pigment was characterized by SDS-PAGE, FT-IR, and SEM. metmyoglobin and MbFe(IV)=0 to The physical properties and the oxidative oxymyoglobin, as well as prevent lipid oxidation stability of corn oil-in-water emulsions in fresh meats. stabilized by modified PPI was examined. We Maillard Reaction Products as Antioxidants in a found the emulsions prepared by modified PPI
– 6 – ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019 had smaller particle size, higher surface charge, the modified PPI formed a barrier that prevents and stronger steric hindrance to prevent the the transition metal from interacting with droplets against environmental stresses. The hydroperoxides, thus enhancing the oxidative emulsion oxidation kinetic study indicated that stability of emulsion.
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LOQ 2b Special Session to Honor Dr. Michael Eskin’s 50 Years of Research in Fats and Oils Chairs: Michelle Peitz, Archer Daniels Midland Co., USA; and David Johnson, Kalsec Inc., USA; and Minwei Xu, North Dakota State University, USA
Mustard and Canola-Derived Canolol: The Ramblings and Raps of an Aging Lipid Challenges and 0pportunities. Usha Thiyam- Chemist. N.A. Michael Eskin, University of Hollander, Food and Human Nutritional Manitoba, Canada Sciences, University of Manitoba, Canada I have been privileged to spend the last 50 Canolol extracted from mustard and canola years of my professional career at the has been the focus of our research for the last University of Manitoba in Winnipeg, Canada. It ten years. Multiple substrates namely seed, wasn’t too long after my arrival that I found crude oil, distillates, protein, and the by- myself part of an incredible team that product press cake were investigated for established canola oil as a viable commercial canolol and related products. While it has been product. Later work dealt with a variety of shown to have potent antioxidant properties, it interesting problems that presented themselves is limited for commercial use unless it can be including sedimentation. At the same time I produced in adequate amounts. Scale-up developed a simple colorimetric method for production is limited due to potential measuring rancidity based on hydroperoxides structural-alteration and degradation. These which required 500 mg of oil and some 40 years structure-production challenges and proposed later used the Iatroscan to develop a method pathways drawn from the literature and our for measuring rancidity requiring only multiple projects will be addressed in this micrograms of oil. Parallel work on a mucilage paper. An improved method for the production from yellow mustard recently showed it had of canola will require heat, enzymes and strong emulsifying properties as well as pressurized treatment and will be presented as antioxidant activity. Current work on canola well. It is evident that canolol has considerable with Dr. Usha Thyam-Hollander is focussed on potential as an antioxidant. Our work over the canolol, the subject of the next presentation. past ten years was conducted in collaboration The lipid raps are a fairly recent development with Dr. N.A.M Eskin. with the first one presented at the AOCS Conference in California in 2012 with several other released since then including the latest one on fat-soluble vitamins.
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ANA 2c / LOQ 2c: Chemical and Sensory Methods to Predict Food Stability Chairs: J. David Pinkston, Archer Daniels Midland Co., USA; and Lan Ban, Kemin Food Technologies, USA
The Effect of Rosemary Extract and Co., Ltd; 3Wilmar Biotechnology R&D Center Phospholipase A2 on the Color Stability and (Shanghai) Co., Ltd., China Lipid Oxidation of Fresh Pork Sausage James Frying is a very popular food preparation Whalin*, Ling Liu, and Mark P. Richards, method in both food and catering industry. University of Wisconsin-Madison, USA Deep fried food is always popular by their The objective of this study was to special flavor, delicious taste and crispy texture determine if a combination of rosemary extract in the surface of fried food. Frying oil is one of (RE) and phospholipase A2 (PLA2) could the most important factor affecting the fried stabilize color and limit lipid oxidation in pre- food quality and sensory. During deep frying, rigor pork sausage as well or better than different reactions happened including synthetic (Syn) antioxidants. We hypothesized autoxidation, polymerization and degradation. the combination of PLA2 and RE would stabilize Both the volatile compounds and non-volatile color and lipid better than either PLA2 or RE compounds formed during frying. These individually and as well as synthetic compounds affect both the sensory of fried antioxidants. Sausage was manufactured from food and the quality of the frying oil. In this sows within one hour post-exsanguination. presentation, the detailed composition in the Sausages were stored in the dark at -20°C (up to polar compounds will be analyzed, including 245 days) prior to light display for nine days of both volatile compounds and the non-volatile refrigerated storage. Color stability was polar compounds include free fatty acids, measured based on redness. Peroxide values diglycerdies, oxidized triglycerides mono, (PVs) were measured spectrophotometrically dimers and polymers. The difference of the and headspace hexanal were measured via gas composition in degraded compounds with chromatography (GC) as markers of lipid different frying oils will be compared. By oxidation. Sausage with RE and RE+PLA2 compared the degraded products in the exhibited better color stability than the different oils, the effect of fatty acids profile will synthetic antioxidants. However, the synthetic also be discussed. The effect of the total polar antioxidants had less lipid oxidation as compounds composition of the frying oil on the measured by headspace hexanal. RE and PLA2 sensory and quality of the different frying oil had lower PV than RE alone at one time point of will be discussed. cold storage. In conclusion, RE and PLA2 decreased lipid oxidation (compared to RE) and Improvement of Flavour and Stability of High- enhanced color stability (compared to Syn) and oleic Sunflower Oil by Onion Frying Chang offer an alternative to synthetic antioxidants in Chang*, and Xingguo Wang,Jiangnan University, pork sausage. China High-oleic sunflower oil has been received The Effect of Volatile and Non-volatile more attentions by its prolonged stability and Degraded Products on the Performance of positive impacts on low-density lipoprotein Frying Oil Junmei Liang*1, Fuhuan Niu2, and cholesterol, but flavour qualities of its fried Yuan Rong Jiang3, 1Wilmar (Shanghai) foods and itself were not satisfactory. The Biotechnology Research & Development center objective of this study was to improve sensory Co., Ltd, China; 2Wilmar (Shanghai) characteristics of high-oleic sunflower oil with Biotechnology Research & Development center an advantageous oxidative stability by onion
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frying. Aroma compounds formed in high-oleic reflect the antioxidants performance. In this sunflower oil during the processes of heating study, selected antioxidants were evaluated in and onion frying were investigated, as bulk oil and a low moisture food by OSI and compared with palm oil and soybean oil. Onion Oxipres respectively. Those accelerated tests frying developed four times more volatiles in were compared to ambient storage condition the high-oleic sunflower oil than the simple which monitored oxidative byproducts and heating process. Other than aldehydes, sensory change. The study reveals interesting hydrocarbons, alcohols, and ketones resulting observations. First, accelerated tests cannot from lipid oxidation, onion frying also brought reflect the actual antioxidants performance in furans, furanones, furfurals, and phenols into foods. The combination of rosemary extract and the frying oils via Maillard reaction of amino ascorbic acid performed the best in improving acids with reducing sugars and aldehydes. In shelf-life in biscuits, but Oxipres showed comparison with palm oil and soybean oil, high- tocopherols the best. The discrepancy possibly oleic sunflower oil exhibited the highest flavour came from different antioxidants chemical intensity after continuous frying of 16 h at 160 stability. Second, physical stability is crucial for °C, especially on some representative volatiles ascorbic acid in extending bulk oils shelf-life [e.g., 2-n-octylfuran, dihydro-5-pentyl-2(3H)- which cannot be captured by OSI. Third, only furanone, and furfural]. Moreover, total polar ambient oxidative byproducts well-correlated to compounds and fatty acids profiles of the ambient sensory evaluation. Abusive storage heated and onion fried oils were comparatively conditions resulted in poor correlation between studied. A great loss of flavonoids in onions the two. In summary, sensory acceptance took place during frying to effectively prevent scores well-correlated to chemical markers in oxidative deterioration of the oils by inhibiting biscuit at ambient condition, and the physical the formation of polar compounds and trans stability of an insoluble antioxidant closely fatty acids under deep frying. In conclusion, correlated to its shelf-life extension capabilities. sensory quality of high-oleic sunflower oil was Limited correlation was seen between highly significantly optimized by onion frying with an abusive acceleration tests (Oxipres and OSI) and unignorable bonus on oxidative stability under actual antioxidant performance in extending frying conditions. oxidative shelf-life in food systems.
Correlation of Oxidative Shelf-life to Test Evaluation of Oxipres™ Apparatus to Study Conditions and Physical Stability of Oxidative Stability and Antioxidant Activity Antioxidants Chia-Yu F. Shen*, Kristen Robbins, Cindy Tian*,Kalsec, Inc., USA and Lan Ban,Kemin Food Technologies, USA When studying the stability of oils and oil Oxidative stability of foods and beverages is containing foods, accelerated tests are regularly related to their intrinsic physical and chemical used, where the rate of oxidation is enhanced properties. Effective and clean-labeled either by using higher temperature or by antioxidants are strongly demanded by market- addition of prooxidants. Oxipres™ apparatus, driven customers to improve the unsatisfactory which shares similar principle as the ASTM oxidative stability. Antioxidants have been fast Oxygen Bomb method, provides a fast way to screened by accelerated tests, including examine stability of diverse applications oxidative stability index (OSI), Oxipres and compared to other methods such as elevated temperature storage stability. Accelerated Shelf Life Testing (ASLT) and However, those accelerated tests may not truly Oxidative Stability Index (OSI). As a preliminary
– 10 – ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019 work to develop an Oxipres™ system to screen sample size were studied. Temperature showed natural antioxidants, different matrices were the biggest impact on induction time, whereas studied to determine the optimum condition for O2 pressure and sample size affected various each. Bulk oil, salty cracker, cookie, and matrices differently. All above factors also dressing were selected to represent different showed influence on the oxidation rate and food types in terms of different oil, protein, total oxygen consumption. Initial work on the sugar and water content. Testing conditions development of model systems for screening including temperature, oxygen pressure, and antioxidant activities will also be discussed.
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ANA 3c / LOQ 3a: Advanced Analytical Techniques for Lipid Oxidation Chairs: Matthew Fhaner, University of Michigan-Flint, USA; and Rick Della Porta, Pepsico/Frito-Lay, USA
New Method for the Investigation of Oxidation Objectives: during thermal process of oil, a Stability of Fats, Oils and Complex Food wide variety of chemical reactions occur, which Products Carolin Edinger*, Anton Paar ProveTec lead to the formation of kinds of compounds GmbH, Germany with high molecular and polarity, for instance The quality of fats and oils strongly depends oxidize triglycerides (ox-TG), oxidized on their oxidation stability. In this contribution a triglycerides dimer (TGD), oxidized triglycerides new method for evaluating the oxidation oligo (TGO), diacylglycerol and some free fatty stability of fats and oils by determining the acids. The analysis of polar compounds induction period is introduced. Under generated during thermal process of oils and its accelerated conditions (elevated temperature biochemical function evaluation are necessary. and pure oxygen pressure) a sample of 5 mL/4 g Methods: we used HPLC, LS-MS to separate and is examined in a sealed stainless steel test analyze the polar compounds, established chamber. Typical conditions of the method are saturated – unsaturated fatty acids systems to temperatures between 80 °C – 140 °C and an investigate the connections between the final initial oxygen pressure of 700 kPa. These products and the fatty acids composition. conditions initiate a rapid oxidation process, Studied their biochemical functions in vitro and which is monitored by recording the pressure in vivo. Results: 1. The polar compounds in the until a predefined pressure drop. It was found frying oil can induce gene mutation and that the elapsed time until the pressure drop is chromosome variation. At the same time, the directly related to the oxidation stability of the intake of polar compounds interferes with the sample. Correlation and precision studies metabolism of lipid, causing liver function demonstrate the method’s effectiveness. Due damage and affecting the health of the body. 2. to the defined oxygen volume in the closed test The results of cell experiments showed that the chamber, the oxygen consumption can be toxicity of oxidized triglycerides in polar calculated. Furthermore, we observed compounds was greater than others. 3. New Arrhenius behaviour with regard to the applied types of fatty acids, such as epoxy fatty acids temperature, enabling the user to determine and hydroxyl fatty acids, are produced during the activation energy of a specific oxidation the frying process. By the ESR method, the process. Beneficially, the oxidation stability of thermal oxidation mechanism of the frying oil is complex food products can be investigated explored to explain the complex reaction since even solid samples can be measured process in the frying system. Conclusions: this without prior sample preparation. The study help us to have a better understanding of significantly reduced measurement time and a polar compounds generated during thermal high repeatability of the method represent its process of oils. major advantages, allowing for quick and direct measurement of the oxidation stability for Electrochemistry as an Analytical Tool for research, process and test bench control. Monitoring Antioxidant and Omega-3 Fatty Acid Levels during Degradation Matthew Analysis of Polar Compounds Generated during Fhaner*, University of Michigan-Flint, USA Thermal Process of Oils and its Biochemical Electrochemical methods have been utilized Function Evaluation Chen Cao*, Yongjiang Xu, for investigating antioxidant systems due to fast and Yuanfa Liu, Jiangnan University, China analysis times, low cost, direct quantitative
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capabilities, and useful limits of detection and Science, University of Massachusetts, Amherst, linear range. Specifically, voltammetric methods USA; 2University of Massachusetts Amherst, such as square-wave voltammetry (SWV), USA provide a direct correlation between analytical The body of literature on the impact of signal and analyte concentration making it emulsion particle size on oxidation rates is possible to monitor antioxidant levels during unclear. This could be because emulsions are degradation of lipid products. Our group has typically polydisperse and the oxidation rate of worked to correlate voltammetric oxidation individual droplets is impossible to discern. currents of antioxidants with changes in lipid Flow cytometry is a technique for studying profile of omega-3 fatty acids as monitored via individual cells and their subpopulations using gas chromatography with flame ionization fluorescence technologies. It is possible that detection (GC-FID). Over a three week individual emulsion droplets could also be degradation study, sesamol, rosemary extract, characterized by flow cytometry as a novel and butylated hydroxytoluene were approach for studying lipid oxidation. Typical supplemented into stripped commercial fish oil emulsion droplets are too small to be visualized and exposed to elevated temperatures. by flow cytometer so emulsions were prepared Antioxidant levels were assessed via SWV to have droplets > 2 μm; weighting agent and oxidative peak currents while two specific fatty xanthane gum were added to minimize acids, eicosapentaenoic acid (EPA) and creaming during storage. A radical-sensitive docosahexaenoic acid (DHA), were monitored lipid-soluble fluorescence probe (BODIPY using GC-FID. It was determined that SWV does 665/676) was added to the lipid used to not act as a predictive tool for how well an prepare the emulsion so that the susceptibility antioxidant species will protect a specific fatty of individual emulsion droplets could be acid. SWV was successful in providing insights determined. The results showed that in a as to the rate of antioxidant depletion over the polydisperse emulsion system, small droplets course of the study, albeit no significant were oxidized faster than large droplets. Using difference was observed between the mixtures of emulsions with and without antioxidants used. An unexpected finding was prooxidants, it was possible to see the transfer that SWV was able to monitor oxidation peaks of prooxidants between droplets, a process that for EPA and DHA and this data mirrored that of is influenced by surfactant and salt the well-established GC-FID FAME method that concentrations. For example, surfactants was run in parallel to SWV studies. The results micelles can transport prooxidants to suggest SWV may fit a niche need for real-time neighboring non-oxidized droplets when analysis of antioxidant levels and potentially surfactant concentration was higher than fatty acid quality in commercial and industrial critical micelle concentration (CMC). Transfer of applications. prooxidants was promoted by adding salt which could be attributed to the effect of salt on CMC. Application of Flow Cytometry as Novel This study showed the good potential for Technology in the Study of Lipid Oxidation in applying flow cytometry on oxidation of Oil-in-Water Emulsions Peilong Li*1, D. Julian J. individual emulsion droplets. McClements2, and Eric A. Decker2,1Dept. of Food
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LOQ 3b: Specialty Oils: Phytochemicals, Extraction and Oxidative Stability Chairs: Hong-Sik Hwang, USDA, ARS, NCAUR, USA; Ignacio Vieitez, UdelaR, Uruguay; and Alex Kripps, Caldic USA, USA
Supercritical Fluid Extraction of Black Sesame allows obtaining an increase in the yield and Seeds and Study of the Functional Properties content of total phenols, for each extraction Obtained in Comparison with the Extraction by condition. Additionally, an increase in the IP is Soxhlet Method Ignacio Vieitez*1, Florencia also observed. Jorge1, Elena Dutto1, Lucia Velazco1, and Cecilia Abirached2,1UdelaR, Uruguay; 2PEDECIBA Development of pulse protein-polyphenol Química, Dept. de Ciencia y tecnología de los conjugates for improved oxidative stability of Alimentos, Universidad de la República, flaxseed oil-in-water emulsions Saakshi Uruguay Parolia1, Rick Green2, Michael Nickerson3, and Sesame is an important oilseed due to its Supratim Ghosh*3,1University of Sasatchewan, high lipid content. This seed contains 40-50% of Canada; 2POS Bio-Sciences, Canada; 3University lipids (mainly polyunsaturated lipids). In the of Saskatchewan, Canada present study, the extraction with supercritical The objectives of the present work were to fluids using CO2 as a solvent was evaluated in develop lentil proteins isolate (LPI) and plant order to obtain functional additives in black polyphenol conjugates, determine their sesame seeds, and compared to Soxhlet structural and functional characteristics and use method, which is one of the conventional them to prepare flaxseed oil-in-water emulsions procedures used for lipid extraction. for improved oxidative stability. Polyphenols Supercritical extractions were performed in a are potent antioxidants, and when complexed laboratory scale system. Extractions were to proteins at the oil droplet interface, could performed with the following operating contribute to enhanced stability of flaxseed oil conditions: 40ºC, 300 or 400 bar, average CO2 emulsion compared to when the proteins and flow of 0.5 sL/min and alternatively, some the polyphenols were used separately. The extractions were done in the presence of 10% interaction between the polyphenols wt (related to CO2) of ethanol as co-solvent. To (quercetin, ellagic acid) and LPI was achieved by evaluate the antioxidant power of the different a grafting method where the degree of extracts obtained, they were added to purified conjugation was higher for quercetin compared sunflower oil (p-SFO) stripped off from natural to ellagic acid. FTIR results showed a change in antioxidants, at different concentrations (1 and the secondary structure of the conjugated 5%). Induction period (IP) of the oxidation protein. A reduction in surface hydrophobicity process was determined by an accelerated and intrinsic fluorescence for the conjugates oxidation method at 100ºC (Rancimat compared to the control indicated potential equipment). Also, the content of total phenols polyphenol binding to the aromatic amino acids (Folin-Ciocalteu method) and total tocopherols of the proteins. Antioxidant capacities, (HPLC) were determined, as well as fatty acids estimated using the DPPH scavenging and FRAP composition (GC). When the p-SFO was added assays, were found to be higher for the with 5% with the extracts obtained at 40°C/ conjugates compared to the pure polyphenols. 400bar or 40°C/400bar/co-solvent (10%), its RIP The flaxseed oil emulsions prepared with the (IP relative to that of the starting p-SFO= 1.5 h) conjugates had similar long-term stability was 2.0 or 3.0, respectively. The use of ethanol compared to the emulsion prepared with LPI. as co-solvent in the supercritical extraction The peroxide and p-anisidine values of flaxseed
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oil were significantly lower in the emulsions supplements shifted hepatic fatty acid stabilized with the conjugates compared to LPI composition toward a decrease in n-6/n-3 PUFA alone and when the pure polyphenols were ratio. BRSO may also lead to inhibit lipogenesis added directly to the emulsion aqueous phase. and promote lipolysis via up-regulation of The presence of polyphenols at the oil-water PPARα and down-regulation of SREBP-1c. These interface by conjugating them with LPI was results suggest that BRSO have beneficial better at preventing lipid oxidation in emulsions bioactivities and applicability to food industry. compared to when they were present in the bulk phase. Effects of Deacidification Methods on High FFA Containing Oils Obtained from Sea Buckthorn Physicochemical Characteristics and Berry Longkai Shi*, Ruijie Liu, Ming Chang, Bioactivities of Black Raspberry Seed Oil Keum Qingzhe Jin, and Xingguo Wang,Jiangnan Taek Hwang*1, Hee Jae Lee2, Taehwan Lim2, and University, China Hana Jung2,1Seoul National Univeristy, Korea; High free fatty acid (FFA) containing sea 2Seoul National Univeristy, South Korea buckthron oil (SBO) was deacidified using five Black raspberry (Rubus occidentalis) seed oil different methods and the impacts of (BRSO) can be a potent functional ingredient deacidification on acid value, phytochemical due to its unique fatty acid composition and and free radical scavenging capacity of the SBO rich tocopherol content compared to other were evaluated. Although deacidification of oil vegetable oils. Black raspberry seeds accounted using solvent extraction and alkali refining for about 50% in the dried berry and contained exhibited excellent deacidification efficiencies more than 17% crude oil. BRSO was high in (89.21% and 98.95%, respectively), low oil polyunsaturated fatty acids (PUFA) including yields as well as high neutral lipid and minor about 57% linoleic and 29% α-linolenic acids. component losses were observed. In contrast, Total tocopherols in the BRSO extracted by amidated, molecular distilled and esterified SBO hexane were 175 mg per 100 g oil, in which γ- showed not only satisfied acid value, but also tocopherol was the most, followed by α- low loss of the neutral lipid. Especially, the tocopherol and δ-tocopherol. It was enzymatic deacidification methods (amidation investigated how dietary BRSO intake affected and esterification) showed nearly 100% of oil inflammation and lipid profile through animal yield using ethanolamine and glycerol as the studies. When male C57BL/6 mice (5 weeks old) acyl acceptors, respectively. Further, the were fed high-fat diet having 50% calories from enzymic deacidified oils and molecular distilled lard and 10% from BRSO for 12 weeks, mRNA oil exhibited higher retention rates of the expressions of NF-κB-associated pro- micronutrients and antioxidant capacities inflammatory markers were down-regulated compared to the crude SBO. This is the first and anti-inflammatory markers were up- time that multiple deacidification methods have regulated. Similar results were observed when been used to neutralize the FFA of the high acid C57BL/KsJ-db/db mice (6 weeks old) were fed SBO, and the obtained results hold the potential AIN-93G diet with BRSO substituted for soybean to be applied industrially in the future. oil for 10 weeks. In both cases of high-fat diet- induced obese and db/db mice, BRSO
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LOQ 4a: Development of Novel Antioxidants Chairs: John Sander, Kemin Agrifood, USA; Min Hu, DuPont Nutrition & Health, USA; and Yu Zhao, Penn State University, USA
Enzyme Assisted Extraction of Antioxidant interesting results will be presented in the Ingredients from Seaweeds Sabeena Farvin conference. Koduvayur Habeebullah*1, Zainab Al-Sattari2, Sakhina Al-Haddad2, Saja Fakhraldeen 2, Opposite Antioxidative Activity Variation of Surendraraj Alagarsamy2, and Faiza Al-Yamani2, Soluble Free and Soluble Bound Phenolic 1Environmental and Life Science Research Compounds during Yellow Pea Germination Center, Kuwait Institute for Scientific Research, Minwei Xu*, and Bingcan Chen, North Dakota Kuwait; 2Kuwait Institute for Scientific Research, State University, USA Kuwait Germination is an effective process to Enzymatic pre-treatment has been improve the antioxidative activity of phenolic considered as a novel and an effective way to compounds in pulse seeds. This research aims release bound compounds from seaweeds. In to study the dynamic change of antioxidative the present study, antioxidant activities of activity of soluble phenolic compounds during enzymatic extracts from eleven species of yellow pea germination and unveil the seaweeds collected from Kuwait coast were mechanism based on phenolic composition and evaluated using four in-vitro assays. The molar mass. After germination, soluble free and seaweeds were enzymatically hydrolyzed to soluble bound phenolic compounds were prepare water-soluble extracts with five extracted and their antioxidative activities were carbohydrate degrading enzymes (Viscozyme, evaluated in both in vitro and in stripped Celluclast, AMG, Termamyl and Ultraflo) and soybean oil (SSO)-in-water emulsion system. three proteases (Neutrase, Flavourzyme and Liquid chromatography coupled with Alcalase). In general, cabohydrases were good electrospray ionization quadrupole time-of- in extracting radical scavenging compounds and flight mass spectrometry (LC-ESI-QTOF-MS) and proteases were useful in extracting compounds size-exclusion chromatography with multiangle- with iron chelating activity. Antioxidant rich light-scattering and refractive-index detection seaweed extracts could be obtained when S. (SEC-MALS-RI) were employed to analyze the boveanum, M. pericladose, C. cornuta, phenolic composition and molar mass, Cladophora sp are hydrolysed with viscozyme, respectively. Antioxidative activity of soluble alcalase, neutrase and ultrafo. Whereas free phenolic compounds increased in both antihypertensive rich seaweed extract could be oxygen radical absorbance capacity (ORAC) and prepared from M. pericladose and Cladophora SSO-in-water emulsion system, while that of sp by digesting with alcalase and neutrase soluble bound phenolic compounds decreased respectively. The fractionation of these extracts with germination. Coupled with the revealed that the phenolic rich fractions were chemometric analysis, phloridzin (4), quercetin resposible for the antiradical and reducing (9), hesperetin (14), glyzaglabrin (15), and power, where as the protein and polysaccharide pinocembrin (16) were speculated as the pivotal rich fractions were resposible for iron chelating phenolic compounds responsible for the activity. The anti-hypertensive properties are hydrogen donating capacity. In addition, mainly due to protein rich fractions. Thus we decreased molecular weight accompanied with can make tailor made seaweed extracts with the decrease of antioxidative activity in SSO-in- specific properties by using enzymes. The water emulsion system that testified steric
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hindrance theory: moieties of soluble bound Covalent bonding of polyphenols to phenolic compounds have protective and dual hemoglobins represents a novel mechanism by antioxidative effect. which plant-based antioxidants can affect oxidative processes in muscle foods. Structural determination of polyphenols bound to hemoglobins: Mechanisms of anti- Impact of Intrinsic Chemical Properties and oxidative and pro-oxidative effects Jie Yin, External Emulsion State on Antioxidant Mark P. Richards*, Wenjing Zhang, and Craig Performance in Food Emulsions Yvonne Bingman,University of Wisconsin-Madison, USA Gildemaster*, Joan Randall, and Lan Ban,Kemin The objectives were to determine i) the Food Technologies, USA crystal structure of hemoglobins that form Chelating agents such as EDTA sequester covalent adducts with polyphenols, and ii) metal ions, whereas many phenolic compounds relate structural aspects of adducts to oxidative serve as free radical scavengers. EDTA is cost properties of hemoglobin. Caffeic acid and effective, however, there is a negative image epigallocatechin gallate (EGCG) were reacted due to its synthetic origin, non-biodegradable with bovine, porcine, trout and turkey nature, and being a possible environmental hemoglobin (Hb). Electrospray-ionization mass hazard. In this study both intrinsic and external spectroscopy was used to determine factors were evaluated, which might influence adduction(s) of polyphenols to alpha and beta the performance of an antioxidant molecule. In chains of Hb. Protein crystallography was used the first study, the chemical and to determine the three-dimensional structure electrochemical properties of EDTA and plant of protein-polyphenol adducts. Changes in lipid extracts were evaluated for their different oxidation capacity were assessed by measuring modes of action. Chelating assay and cyclic Hb auto-oxidation, heme dissociation, ferryl Hb voltammetry were used to examine EDTA and formation, and Hb-mediated lipid oxidation in natural plant extracts in vitro. Electron washed muscle. Caffeic acid and EGCG bound at paramagnetic resonance (EPR) was used in Cys130 of the H-helix in turkey Hb alpha chains. ranch dressing matrix to assess free radical Caffeic acid bound at Cys93 of the F-helix in accumulations over time. The second study was bovine and porcine Hb beta chains. Adduction designed to identify if different physical increased Hb auto-oxidation whereas heme properties of food emulsions, such as emulsion dissocation and ferryl Hb formation were stability and droplet size distributions, are decreased. The Hb-EGCG adduct more correlated with the efficacy from the same effectively inhibited lipid oxidation compared to treatment. The performance of the ingredients the Hb-CA adduct. Structural evidence was evaluated in real time in ranch dressings suggested enhanced access of solvent to the that had the same composition but different distal heme pocket of Hb-CA to explain emulsion states. From both studies, common increased Hb auto-oxidation and decreased plant extracts (rosemary, green tea and access of solvent to the proximal pocket to spearmint extracts) were used to compare to explain decreased heme dissociation. Electron EDTA. Results have confirmed earlier transfer from bound polyphenol to O2 liganded hypotheses that EDTA was able to both chelate to the heme-iron can contribute to the and alter redox potential of Fe(II)/Fe(III) pair, increased auto-oxidation of Hb-CA while while natural plant extracts didn’t have electron transfer to the heme iron may explain significant chelating capabilities in acidic foods, the decreased ferryl Hb formation in Hb-CA. and performance was largely driven by their
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free radical scavenging capabilities. In addition, quinone) back to their reduced forms (i.e., the physical state of the emulsion affected the carnosic acid), which may further extend the antioxidant performance to some degree oxidative stability of oil systems. The efficacy of regardless of their mode of action. another polar antioxidant, green tea extract, was also investigated using an oil delivery Mechanistic Investigation and Efficacy of Polar system. Oil-dispersible green tea was tested Antioxidants to Stabilize Bulk Oil David R. alone and in combination with rosemary Johnson*, Laura Lafond, Xin Tian, and Nora extract, to stabilize bulk oil, frying oil, and bulk Yang, Kalsec Inc., USA oil that was then used in a baked good Consumer perceptions over synthetic food application. Analysis by oxidative stability index antioxidants have led the food industry to seek (OSI), peroxide value (PV), total polar alternative natural solutions to prevent lipid compounds (TPC), and headspace aldehydes oxidation in bulk oil systems. Natural (hexanal) showed a protective effect of oil antioxidant strategies, such as rosemary dispersible green tea that in some cases extract, provide some protective effect to matched that of TBHQ. Overall, results suggest stabilize oil. However, rosemary extract alone that incorporating polar antioxidants into bulk falls short of reaching the efficacy of synthetic oil can provide enhanced oxidative protection antioxidants, such as TBHQ. To achieve and may be related to free radical scavenging or antioxidant stability that rivals that of TBHQ in antioxidant regeneration. bulk oil, polar antioxidants (such as ascorbic acid or green tea extract) can be used. [Canceled] Physicochemical properties of black Combining these polar extracts with rosemary bean protein hydrolysates and their extract can produce even greater antioxidant antioxidant activities in oil phase Zhaojun protection. In this study, the mechanistic Zheng*1, Yuanfa Liu2, Yongjiang Xu1, Chen Cao1, actions of how ascorbic acid and rosemary and Jinwei Li1,1Jiangnan University, China; interact to stabilize oil was investigated. Results 2School of Food Science and Technology, State suggest that ascorbic acid can reduce oxidized Key Laboratory of Food Science and Technology, rosemary components (e.g., carnosic acid Jiangnan University, China
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LOQ 4b: Frying Oils: Industry Perspective and Novel Solutions Chairs: Shawn Pan, Bunge North America, USA; Cindy Tian, Kalsec, Inc., USA; and Chandra Ankolekar, Kemin Industries Inc., USA
Practical Application of Amino Acids as Natural snack foods frying oil application. Objective / Antioxidants for Frying Hong-Sik Hwang*1, Jill Hypothesis There are different types of Moser1, Kenneth M. Doll1, Mayuresh Gadgil2, vegetable oil and animal fat used in frying oil and Sean Liu3,1USDA, ARS, NCAUR, USA; application. The finished products range from 2Bradley University, USA; 3USDA, ARS, USA different types of snacks foods (for example Our previous study showed that amino chips, nuts etc..). One of the major problems acids were excellent natural antioxidants for facing in snacks foods industries is oil frying oils. We conducted further studies on degradation due to an increase in the free fatty their activities, especially, for their practical acids and other undesired components. This application. Antioxidant activities of amino article provides an overview of the advantage of acids was compared to synthetic antioxidant, adsorbent treatment in snack foods frying oil tert-butylhydroquinone (TBHQ), and leading application and reduction in free fatty acids. commercial natural antioxidants including Method Used The oil quality parameters like tocopherols and rosemary extract in soybean oil free fatty acids and peroxide are measured at 180 ºC. Sensory impact and labeling will also using the Foodlab analysis system. Results be discussed. Factors affecting their activities Vegetable oil and edible oil samples were such as lipophilicity, basicity, effect of side collected from a different industrial application. chains and other functional groups, and Before the adsorbent treatment, free fatty acid chelation of metals will be discussed. We found and peroxide of oil samples were measured. that, in general, higher lipophilicity, higher The oil sample was heated in Lab scale pilot basicity, and longer alkyl chain increased the R&D set up. The adsorbent used in these trials antioxidant activity of an amino acid although was up to 2% of the weight of cooking oil. After there were some exceptions. The chelation of 10 minutes of reaction & mixing time, started metals by an amino acid and antioxidant activity filtration. Then measured free fatty acids and of secondary products produced by reactions peroxide. The free fatty acids reduced 60-75% between an amino acid and oxidation products, and peroxide reduced 5-15% for the selected oil which were known to be important factors for samples Conclusion Adsorbent treatment in its activity, did not play critical roles at frying snacks foods frying oil application is economical temperatures. Peptides and protein and extends the life of cooking oil. hydrolysates have drawn interest as potential natural antioxidants for frying. We compared Capturing the Value of Fry Life Extension their antioxidant activities with amino acids. Through High Oleic Oils Susan Knowlton*, Although protein hydrolysates and dipeptides DuPont Company, Pioneer, USA also showed strong antioxidant activity in High oleic oils, compared to their soybean oil at 180 ºC, their activities were not conventional counterparts, offer food service as strong as some single amino acids. establishments many benefits not the least of which is the extension of fry life. High oleic oils The Advantage of Adsorbent Treatment in are resistant to oxidation and therefore do not Snack Foods Frying Oil Application Joby break down as quickly as oils that have higher Ulahanan*,Crystal Filtration Co., USA amounts of polyunsaturated fatty acids. When The advantage of Adsorbent treatment in oils oxidize, polymeric materials resulting from
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oxidation accumulate in the oil and ultimately product distribution and delivery system in a coat the surfaces on which they come in company, it may take anywhere from days to contact. Sensory changes also result ultimately weeks, or even months before the product leading to unpalatable food prepared in the appears on the store shelf. Companies which degraded oil. Restaurants have a difficult time have store-door delivery capability and district knowing when to change out their fry oils due or distribution warehouses of their own can to the lack of a universal standard in the US. control the time it takes from the day of Many choose to change out their oils based on production to the day the store receives them. color or a weekly management schedule. In The companies that use distributors for their contrast, many European countries impose products, generally suffer from the delay in the limits based on a measurement of ‘total polars’ delivery of the product and sometimes, the through legislation. Tests for ‘total polars’ exist product may have only a fraction of the but the equipment, complexity, or cost is often remaining time specified on the product code beyond the means of a typical restaurant date by the time the product is purchased and establishment. This session will discuss work to consumed. In addition, the distribution system date on developing a simple, inexpensive test to cannot guarantee the high-temperature measure total polars in fry oils. exposure the product might be exposed to during storage and transit. Oxidized and rancid High Oleic Soybean for Frying Tammy Bratton*, flavor in the product can develop due to Bunge Loders Croklaan, USA degradation of the oil used in frying or baking. High oleic soybean oil has been in testing The oil degradation can also come from the market for over decades. This research is ingredients that contain natural lipids in them. studying its pros and cons for frying and The consumer may complain about the bad providing basics for further improvement of product flavor. One statistic about the customer high oleic soybean. complaint is that 1 out of 100 consumers, who have experienced bad flavor in the product and Achieving Desired Shelf Life for Fried and found it unacceptable flavor, would contact the Baked Products Monoj K. Gupta*,MG Edible Oil product manufacturer. Remaining 99 Consulting International, Inc., USA consumers may just switch to another brand of Achieving desired shelf life in fried and the same product. This paper addresses the baked products is one of the major goals of the basic factors that can affect product shelf life food industry. Modern day products are and offer some remedies that could be applied distributed through the warehouse and then by the manufacturers of the product to improve appear on the shelves of the super markets or the shelf life of the same. convenience stores. Depending on the mode of
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LOQ-P: Lipid Oxidation and Quality Poster Session Chair: Scott Bis, Kemin Industries Inc., USA
1. Determination of Triacylglycerol Oxidation this study, reliable TGOOH analysis were Mechanisms using Liquid Chromatography- achieved by MS/MS (MS/MS/MS) analysis and tandem Mass Spectrometry. Shunji Kato*1, authentic references, in the level of molecular Naoki Shimizu2, Yurika Otoki1, Junya Ito2, species/geometrical isomers. And it was Masayoshi Sakaino3, Takashi Sano4, Takahiro demonstrated that photo- and auto-oxidation Eitsuka2, Teruo Miyazawa5, and Kiyotaka products were characteristically detected in Nakagawa1, 1Tohoku University, Japan; 2Food photo-oxidized oil and thermal-oxidized oil, and Biodynamic Chemistry Laboratory, respectively. These method is valuable in the Graduate School of Agricultural Science, Tohoku understanding of oil and food oxidation University, Japan; 3Innovation Development mechanisms, and may be applied to the Section, J-OIL MILLS, INC., Japan; 4J-Oil Mills, development of useful methods for food Inc.., Japan; 5Food and Biotechnology production. 1) S. Kato et al., npj Science of Innovation Project, New Industry Creation Food, 2 (2018). Hatchery Center (NICHe), Tohoku University, Japan 2. Effect of Furan Fatty Acids and 3-methyl- Objective Triacylglycerol (TG), the main 2,4-nonanedione on Light-Induced Off-Odor in component of edible oil, is oxidized by thermal- Soybean Oil. Takashi Sano*1, Ryo Okabe1, or photo-oxidation to form TG hydroperoxide Maiko Iwahashi1, Jun Imagi1, Toshiro Sato1, (TGOOH). Since excessive amounts of TGOOH Eiichiro Fukusaki2, and Takeshi Bamba3, 1J-Oil and its subsequent oxidation products cause Mills, INC., Japan; 2Osaka University, Japan; not only the deterioration of oil quality but also 3Kyushu University, Japan various toxicities, controlling the oxidation of Objective: Soybean oil is one of the most edible oils is essential. Thereby understanding widely consumed vegetable oils. However, oxidation mechanisms that cause the formation under photooxidative conditions, this oil of TGOOH is necessary. Since isomeric develops a beany and green off-odor through a information of lipid hydroperoxide provides mechanism that has not yet been elucidated. In insights about oil oxidation mechanisms (e.g. this study, the effect of furan fatty acids and 3- auto- and photo-oxidation), we analysed methyl-2,4-nonanedione (3-MND) on odor TGOOH isomers in various oil such as canola oil, reversion in soybean oil was investigated. rice bran oil and fish oil. Methods We first Methods: Synthesized furan fatty acid (F3 acid, determined the most suitable TGOOH 96% purity), 3-MND (>99.0% purity) and 3- molecular species for the evaluation of each oil hydroxy-3-methyl-2,4-nonanedione (3-hydroxy- oxidation mechanisms using Q1 mass scan, 3-MND, 95.9% purity) were used in this study. product ion scan or neutral loss scan. As These chemicals were added into canola oil, and necessary, authentic references of the target photo oxidized under a fluorescent lump. The TGOOH isomers were prepared from oils were assessed by sensory evaluation and diacylglycerol and fatty acid hydroperoxide analyzed using GC/MS following our previous isomers. Discrimination of TGOOH isomers were protocol. In most experiments, pure soybean oil carried out by collision induced dissociation of was used as a positive control. Results: The sodiated TGOOH ion ([M+Na] +). Oxidized oil intensity of the off-odor was found to increase were diluted with hexane, and analysed by LC- with increasing amounts of F3 acid, and the MS/MS (MS/MS/MS). Results and Discussion In concentration of 3-MND was also found to
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increase. While the addition of 3-MND to canola 500 ppm RE (174%). PV and p-anisidine values oil produced a slight off-odor, the intensity of were significantly lower in the LRE oil than in the off-odor was much greater following light control but comparable to RE. However, exposure. We found that the off-odor was sensory analysis conducted on the French fries increased with increasing amounts of 3- by 10 panelists showed significant differences in hydroxy-3-MND. Further, the concentration 3- the score with LRE receiving higher liking scores hydroxy-3-MND in soybean oil was found to and higher preference than the RE French fries. increase during storage, paralleled that of 3- LRE contains potent antioxidants useful in frying MND. Conclusions: Our findings suggest that oils to improve their oxidative stability under the observed off-odor was likely attributable to repeated frying without any effect on the oil as the furan fatty acids present in the oil through well as sensory quality of French fries. the generation of 3-MND. In addition, 3- hydroxy-3-MND, which is derived from 3-MND, 4. Influence of Margarine and Oil was identified for the first time in light-exposed Composition on Phytosterols, Fatty Acid Profile soybean oil and shown to be one of the and Quality Parameters at High Heating compounds responsible for odor reversion. Temperatures. Jallah Smith1, Peace C. Asuzu2, Anh T.L Nguyen3, Benjamain M. Bougouneau4, 3. The Antioxidant Effect of Licorice Root Samuel A. Besong5, and Alberta N A Aryee*3, Extract in Retarding Lipid Oxidation in High 1Delaware State University, USA; 2College of Oleic Canola Frying Oil and Comparison to Agriculture & Related Sciences, Delaware State Rosemary Extract. Brandon Williams*1, Jane University, USA; 3Delaware State University, Whittinghill2, and Rachael Miller1, 1ICL USA; 4Dept. of Human Ecology, Delaware State Phosphate Solutions, USA; 2ICL Food Specialties, University; 5Dept. of Human Ecology, College of USA Agricultural Sciences, Delaware State University, The objective of the study was to USA investigate the effectiveness of licorice root Repeated heating of oils and margarines at extract (LRE) on the oxidative stability of high elevated temperatures produces decomposed oleic canola oil upon repeated frying and compounds which can affect; sensory, comparison to rosemary extract (RE). French nutritional and health properties. This study fries were fried in canola oil once every week investigated the effect of heating on oxidative for 3 weeks. A control oil, a 500 ppm LRE oil and stability and sterol content of njangsa seed oil a 500 ppm RE oil were used in the study. After (NSO), bush mango oil (BMO), soybean oil frying, oil samples were collected and analyzed (SBO), coconut oil (CCO), their derived after frying for oxidative stability using the margarines: BMO and NSO (BN), BMO and SBO Rancimat, free fatty acid, hexanal, peroxide (BS), CCO and NSO (CN), CCO and SBO (CS), and value and p-anisidine value. A hedonic scale was commercial margarines: blue bonnet and land used to determine the effect of the antioxidants O'Lakes. The tested margarines and oils were on the sensory quality of the French fries. The heated up to 20 and 120 min, respectively at results show that LRE is more effective in 130, 170 and 210oC. Changes in free fatty acid controlling oxidation during frying when (FFA), peroxide value (PV), anisidine value (ρ- compared to RE at the same usage level. The AV), fatty acid composition and sterols content; improvement on oxidative stability over the stigmasterol, sitosterol and campesterol were control oil was significantly higher using 500 determined titrimetrically, ppm of LRE (265%) in the frying oil than with spectrophotometrically and using GC-FID.
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Higher increase in FFA content in oils and d.b., respectively. SEM micrographs showed margarines containing higher amount of that the microcapsules were spherical, without polyunsaturated fatty acids (PUFA) were cracks. Some of the particles presented concave observed than in highly saturated counterparts. and shriveled surfaces. The powder Generally, there was an increase in PV with dispersibility was measured by changes in the increasing temperature. Oils with higher obscuration as a function of time. Samples proportions of linoleic acid had a higher ρ-AV at analyzed at t=0d recorded a steeply increase in the end of heat treatment. Higher TOTOX the obscuration with the agitation time up to values were seen in oils with a higher ~1.5 min, after which it reached a constant proportion of PUFA. A decrease in sterol value. At t = 0, the microencapsulated chia oil content was observed in all tested oils and presented a ti=12.7h, being seven times greater margarines with increasing temperature, with a than that of the bulk oil. The addition of the greater reduction in stigmasterol content antioxidants increased the ti of the compared to β-sitosterol. This result suggest microencapsulated chia oil. Regarding the PV that the level of saturation and oxidative evolution, only the addition of ascorbyl stability may better predict oil behavior and palmitate maintained the PV under the limit properties during heating and provide valuable acceptable after 100 d of storage (25°C, information on the selection and utilization of darkness, HR 33%). Thus, microencapsulation by these oils and margarines in product spray drying of chia oil with ascorbyl palmitate development. addition could protect this oil against lipid oxidation during the processing and storage. 5. Oxidative Stability of Spray-dried Microencapsulated Chia Seed Oil with the 6. Antioxidative Polyphenols of Canola Meal: Addition of Antioxidants. Elizabeth Hoffmann1, Effect of High Pressure, Temperature and Claudia N. Copado2, Vanesa Y. Ixtaina*2, and Solvents. Usha Thiyam, Michael Eskin, and Mabel Tomás2, 1CIDCA, Argentina; 2CIDCA Ruchira Nandasiri* (Lipid Oxidation and Quality (CONICET-UNLP), Argentina Division Student Travel Grant Winner), Chia seed oil has a high content of University of Manitoba, Canada polyunsaturated fatty acids (PUFAs), giving it Canola meal, a by-product of the edible oil- nutritionally beneficial qualities, although pressing is a rich source of phenolic and determining its high susceptibility to oxidative antioxidant compounds. However, its deterioration. The microencapsulation and the application in the food and feed sector is still addition of natural antioxidants are alternatives limited in part due to greener, sustainable and to protect this oil during its processing and cost-effective extractability of phenolic storage. The objective of this work was to study compounds. Thus, use of high pressure and the physicochemical characteristics and the temperature, commonly associated with high oxidative stability of chia seed oil extractability of phenolic compounds is microencapsulated with different antioxidants investigated. Accelerated solvent extraction (rosemary extract, rosemary and chamomile (ASE) uses high pressure and temperature to extracts blend, ascorbyl palmitate) by spray- enhance extraction efficiency of antioxidant drying using inlet/outlet temperatures of phenolics. Moreover, ASE could be studied to 170/90°C, and sodium caseinate and lactose as obtain structure-activity based antioxidant wall material. The microencapsulation efficiency function against high pressure and temperature and the moisture content were >98% and <4% subjectively. This study evaluated the effect of
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temperature (140, 160 & 180 oC) and pressure acid, linoleic acid, or soy lecithin were mixed (1500 psi) on the extraction yield of phenolic with corn oil at concentrations of 0, 3, 6, and 9% compounds from canola meal relating to type of (w/w) to determine the effects of the solvent (ethanol and methanol) and amphiphilic compounds on the DA. The concentration of solvents (30%, 40%, 60% & moisture effects were evaluated using 5 70% v/v). The highest extraction of phenolic different saturated salt solution. Unoxidized compounds was obtained with 70% methanol fresh oils showed a wide range of DA, from 8% (20.72 ± 1.47 mg SAE / g DM) and 70% ethanol for canola oil to 33% for flaxseed oil. As the (24.71 ± 2.77 mg SAE / g DM) at 180 oC content of MAGs, lecithin, and moisture temperatures. A similar trend was observed for increased, DA of corn oils increased at different the antioxidant activity of the extracts (FRAP, rates, whereas addition of oleic and linoleic DPPH, ion chelation) as well as their total acids decreased DA of corn oil by 40%. DA flavonoid content. The structure related showed a strong correlation with the antioxidant activity of the extracts examined percentage of unsaturated fatty acids (R2= increased with the increase in the percentage of 0.883) in edible oils. Overall, DA of edible bulk the extracting solvent (p > 0.05). This study oils is strongly correlated with the content of established ASE as an efficient green method amphiphilic compounds, moisture content, and for extracting of phenolic compounds from degree of unsaturation of fatty acids. DA could canola meal, which could apply towards the be a reliable parameter to predict the oxidative production of natural bioactive compounds stability of edible oils. from agricultural by-products. 8. Antioxidant Effects on the Oxidative 7. Prediction of Oxidative Stability in Edible Stability in Bulk Oil Treated with Plasma Stress. Bulk Oils using Dielectric Constant Changes. HeeSun Na*1, SeungBeen Jo1, MiJa Kim2, and HeeSun Na*1, YunSik Woo2, SeungBeen Jo2, JaeHwan Lee3, 1Sungkyunkwan University, South MiJa Kim3, and JaeHwan Lee4, 1Sungkyunkwan Korea; 2Kangwon National University, South university, South Korea; 2Sungkyunkwan Korea; 3Dept. of Food Science and University, South Korea; 3Kangwon National Biotechnology, Sungkyunkwan University, University, South Korea; 4Dept. of Food Science Republic of Korea and Biotechnology, Sungkyunkwan University, Plasma is an ionized gas as the fourth state Republic of Korea of matter. Plasma treatment is a promising non- Dielectric constant (DA) in edible oils is thermal oxidative technique. Therefore, lipids affected by the degree of unsaturation in lipids with plasma stress may undergo oxidation. The and amphiphilic compounds. Presence of objectives of this study were to determine the amphiphilic compounds and moisture affects oxidative power of plasma treatment and to the oxidative stability in oils. The objectives of evaluate the antioxidant efficiency of selected this study was to determine the effects of compounds in plasma treated bulk oils. Stripped amphiphilic compounds on the changes in the corn oils (SCOs) treated with plasma jet were DA of edible oils. DA of seven edible oils with compared with 60 or 100 treatment by different degree of unsaturation were analyzing conjugated dienoic acid (CDA). determined by TESTO 270™ and expressed as Tocopherol homologs℃ in plasma℃ treated SCO percentage unit. Fatty acid composition of oils and medium-chain triacylglycerols (MCT) were was determined and oxidizability of oils was determined by using HPLC-fluorescence calculated. Monoacylglycerols (MAGs), oleic detector. To evaluate the antioxidant capacities
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in SCO, antioxidants including of TBHQ, alpha- proportion, with (BTWS) or without (BTWOS) tocopherol, sesamol, beta-carotene and EDTA sesamol. To determine the oxidative stability, were mixed with SCO at two concentrations of headspace oxygen content, conjugated dienoic 10 and 300 µmol. CDA, p-anisidine value, and acid (CDA) value, and p-anisidine value (p-AV) moisture content were determined. Degree of were measured by using GC/TCD and lipid oxidation by 10 min of plasma jet in SCO spectrophotometer. corresponded to 48 h of 60 and 2.5 h of After 3 days at 100°C treatment, the 100 . Stability of alpha-tocopherol in MCT headspace oxygen content of BTWS was treated with plasma jet was℃ lower by 6 fold significantly higher than beef tallow by 2 times than℃ those in SCO whereas 12 fold lower in case (p<0.05) whereas those of BTWOS was the of gamma-tocopherol. Under plasma jet, SCOs lowest. This pattern was also observed in CDA added with TBHQ, alpha-tocopherol, and value and p-AV. In addition, under the UV sesamol had significantly low values based on irradiation, BTWS showed the highest oxidative CDA (p sesamol> TBHQ> beta-carotene> EDTA stability which was almost 2 times better than in SCOs with plasma jet treatment. Moisture beef tallow and BTWOS based on headspace content in all samples decreased after plasma oxygen content and p-AV. Overall, sesamol treatment. Plasma treatment is one of strongest showed strong antioxidant capacity in the oxidation stressor and TBHQ, alpha-tocopherol, mixture of organogels and beef tallow. and sesamol could control the lipid oxidation in Therefore, sesamol could be a good antioxidant bulk oil by plasma treatment. in meat products containing organogels with high content of unsaturated fatty acids. 9. Effects of Sesamol on the Oxidative Stability of Canola Oil-based Organogels with 10. Influence of Oil Type on Epoxy Fatty Acid Beef Tallow. SeungBeen Jo*1, Heesun Na, Formation in Repeated Deep-frying of Seungmi Hong, MiJa Kim2, and JaeHwan Lee3, Potatoes. Ru Shen*1, Jingyi Meng2, Claire 1Sungkyunkwan University, South Korea; Schane2, Tilo Lamken2, William G. Helferich2, 2Kangwon National University, South Korea; and Nicki J. Engeseth2, 1University of Illinois, 3Dept. of Food Science and Biotechnology, USA; 2University of Illinois at Urbana- Sungkyunkwan University, Republic of Korea Champaign, USA Organogels are organic liquids entrapped by Repeat-utilization of frying oil results in organogelators through 3-dimensional frying oil deterioration and undesirable networks. The addition of antioxidants in compound formation. Epoxy fatty acids have organogels is required because of the high been used as an indicator in toxicological degree of unsaturation in organogel which evaluation of lipids. The objective of this accelerates lipid oxidation. Sesamol is one of research was to determine formation of the lignans present in sesame and used as an monoepoxy fatty acids (MEFA) in oils and foods antioxidant. The objective of this study was to during repeated deep-frying of potatoes. Frying evaluate the effects of sesamol in mixture of experiments were conducted with potato strips, beef tallow and canola oil-based organogel at 100 cycles at 180ºC in three oils: soybean oil 100°C and ultraviolet (UV) irradiation. (SO), refined palm olein (RPO) and stearin (RPS). Organogel was prepared using canola oil Oil and foods were analyzed from different and 10% (w/w) beeswax and 40 ppm (w/w) of cycles. Six MEFA were quantified using solid sesamol was added to the organogel. Beef phase extraction and GC characterization, tallow was mixed with organogel in 4:6 Repeated exposure to frying led to dramatic
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increases of oil MEFA: RPS>RPO>SO. After 100 emulsions with CGMH had significantly cycles, MEFA in RPS, RPO, SO were 5656.11, improved oxidative stability than the control 4138.11 and 1779.81 mg/kg, respectively. based on both TBARS and POV analysis. The 3- Compositional distribution of MEFA in TAFOs hour hydrolysate had slightly better antioxidant was directed by the original oil composition and performances in emulsion than the 1-hour altered significantly over time. Epoxy stearate hydrolysate. The emulsion with 5 mg/ml CGMH comprised the majority of MEFA for RPS and had the most effective inhibition on lipid RPO and epoxy oleate for SO. Over the course oxidation. The emulsion turbidity of 1-hour of repeated frying of food, the ratio of trans hydrolysate at 2.5 mg/ml had lower value than MEFA to total MEFA in RPS, RPO and SO other emulsions, and overall, the turbidity for 3- increased from 33.72, 0 and 0% to 66.38, hour hydrolysates had slightly higher value than 60.22% and 45.79 %, respectively. Oil quality that with 1-hour hydrolysate. Addition of CGHM impacted the food being fried directly: MEFA did not affect emulsion morphology and droplet accumulation in potatoes was greater when sizes. Zeta potential analysis showed that fried in RPS (496.21 mg/kg food) than RPO emulsions with 1-hour hydrolysate had more (312.12 mg/kg food) and SO (119.28 mg/kg negative charges with better emulsion stability food) at 100 cycles. Epoxy fatty acid formation than that with 3-hour hydrolysate at the same was highly dependent upon the type of frying pH. In conclusion, the CGMH was able to inhibit oil being utilized. Monounsaturated oil lipid oxidation and reduce the formation of accumulated MEFA to a greater extent than TBARS and POVs and could be a potential polyunsaturated oil. functional antioxidant for food emulsion applications. 11. Antioxidant Performances and Emulsifying Activity of Corn Gluten Meal Hydrolysate in 12. Proximate Composition, Fatty Acids Oil-in-Water Emulsions. Yanting Shen*1 (Lipid Profiles and Nutritionally Valuable Minerals of Oxidation and Quality Division Student Travel 10 Industrial Hemp Seeds Varieties. Minwei Grant Winner), Ruijia Hu2, and Yonghui Li1, Xu* and Bingcan Chen, North Dakota State 1Kansas State University, USA; 2Kansas State University, USA University, Grain Science and Industry, USA Due to its nutritional properties, industrial Corn gluten meal (CGM) is a protein-rich co- hemp(Cannabis sativa L.) has been reconsidered product generated during corn wet milling. In as a valuable specialty crop for both humans this study, corn gluten meal was hydrolyzed and domesticated animals in Canada and using enzyme (Neutrase) for 1 and 3 hours, European countries during the last decade. As a respectively, to obtain antioxidative protein result, industrial hemp seeds and hemp seeds hydrolysates (CGMH), which could be a food products have become available to the potential antioxidant to retard lipid oxidation in general public in these countries.In the current various food products. Our objective was to study, 10 varieties of industrial hemp grown in evaluate emulsion properties (e.g., emulsion North Dakota in 2017 were analyzed for their turbidity, stability, particle size, microstructure, proximate composition, nutritional minerals, zeta-potential, and partition) and oxidation and fatty acid profiles. The findings from this stability (e.g., POVs and TBARS) of oil-in-water study could help industry identify the industrial emulsions containing different types (1 and 3- hemp variety with greater quality for food hour hydrolysates) and amount (0, 1, 2.5 and 5 application. mg/ml) of CGMH. The results showed that the
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13. Aroma Characteristics of Fried Onion 14. Effect of Sinapic Esters Derivatives on the Prepared by Palm, High-oleic Sunflower, and Oxidative Stability of Omega-3 Fatty Acids Soybean Oils Frying. Chang Chang* and Enriched Emulsions Inar A. Castro1, Bruno Xingguo Wang, Jiangnan University, China Baréa2, Pierre Villeneuve3, Tayse Tayse Ferreira Onion frying has shown great interest to da Silveira*4, and Letícia Maeda household cooking because of intensive flavour Cajaíba4,1University of Sao Paulo, Brazil; 2CIRAD, and nutritional value provided by the onion; France; 3UMR IATE, CIRAD, France; 4University however, aroma characteristics of fried onion of São Paulo, Brazil are still unclear to hinder their prevalence in Oil-in-water (O/W) emulsions are important food industry. The objective of this research delivery systems of omega-3 fatty acids (n-3 was to examine changes of the flavour profiles FA), however, the high chemical instability of n- in fried onion in response to oil frying (e.g., 3 FA still challenges food producers. palm, high-oleic sunflower, and soybean oils at Lipophilization of phenolic compounds with 0-16 h continuous frying), and to determine key different chain lengths is a strategy used to aroma compounds of fried onion-like odour. increase their hydrophobicity and enhance their Flavour profiles (e.g., aldehydes, alkanes, antioxidative effectiveness in O/W emulsions. alkenes, alcohols, amines, furans, furfurals, However, other factors such as the electrical furanones, ketones, organic acids, and sulfur- charge of the emulsifier and emulsion pH play a containing compounds) were identified using role in the development of lipid oxidation. In headspace solid phase microextraction (HS- the present approach, we investigated SPME) combined with gas chromatography- interaction effects between chain length mass spectrometry (GC-MS) and -olfactometry increase of sinapic acid esters derivatives (C4, (GC-O). Overall, palm, high-oleic sunflower, and C8 and C12), different emulsion pH (3.0 and 7.0) soybean oils frying at 8 h quantitatively and and emulsifier charge (positively or negatively qualitatively generated more volatiles on the charged) using a factorial design 24. The O/W fried onion, especially aldehydes and sulfur- emulsions were enriched with echium seed oil containing compounds. Therefore, fried onions (Echium plantagineum), which contains 40% of treated by palm, high-oleic sunflower, and n-3 FA in its fatty acid composition. soybean oils (at 8 h) were carried forward to Malondyaldehyde (MDA) and volatiles (2,4- investigate key aroma compounds of fried heptadienal and 2,4-decadienal) were onion flavour. Findings indicated that the fried measured as responses. The results onion flavour mostly resulted from the demonstrated that an increase in the chain combination of 3-methyl butanal and 2-propen- length improved the oxidative stability of the 1-thiol in all fried onion. High-oleic sunflower oil emulsions (lower MDA and volatiles formation) and soybean oil fried onion were identified only when negatively charged emulsifiers were more oily by (E)-2-decenal and (E,E)-2,4- used at low pH (3.0), suggesting that decadienal whereas 4-ethyl-3-nonen-5-yne lipophilization could be more useful to protect contributed to the more intensive fried onion from oxidation emulsion-based foods flavour from palm oil. Of the fried onions presenting these characteristics, such as salad studied, 2-propen-1-thiol and 3-methyl butanal dressings. Therefore, our findings demonstrate were most promising key aroma compounds the importance of studying these factors in attributed to fried onion flavour, which was also conjunction in order to optimize emulsion affected by oil type. formulations for maximum oxidative protection of n-3 FA.
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