Synthetic polyphenol antioxidants inhibit the formation of active carboxyl compounds in cooking oil

Lu Yongxuan, Lu Lishuang, Dong Wenjiang, Institute of Spice and Beverages, School of Food and Pharmaceutical Engineering, Nanjing Normal University, and Dong Wenjiang of the Institute of Spice and Beverages of the Chinese Academy of Tropical Agricultural Sciences, among others, published an online article on
Journal of Agricultural and Food Chemistry
called "The Formation of Reactive Carbonyl Species in Oil Edible" By Synthetic Polyphenol Antioxidants, the research system describes the peroxide values (POV), Rancimat induction time (RIT), and ACR/GO/MGO formation processes in different vegetable oils (corn oil, soybean oil, palm oil) with changes in heating time and temperature. This article was
by Journal of Agricultural and Food Chemistry
online January 17, 2021. Professor Lu Lishuang and Dong Wenjiang, associate researchers, are co-authors of this paper.
highlight:
Introduction
oils and fats play an important role in food quality, determining the quality, flavor and nutrition of food. However, high-temperature treatment can lead to lipid peroxidation, degradation, and the formation of active carbide-based compounds (RCS), such as acrylic (ACR), acetaldehyde (GO) and methyl acetaldehyde (MGO), it is worth noting that the toxicity of lipid peroxide is mainly due to the life of secondary products such as MGO, GO and ACR, RCS can induce cell damage and protein glycosylation, resulting in the production of late glycosylation products (advanced AGEs) to induce a variety of diseases. Studies at home and abroad have shown that a variety of natural or synthetic polyphenol antioxidants help to delay the oxidation of oils and fats, but whether they can effectively inhibit the formation of RCS during the heating process of edible oils and fats has received little attention.
Lu Lishuang and Dong Wenjiang were published on January 17, 2021 in the international Top1 regional journal
Journal of Agricultural
Food Chemistry co-published a research paper entitled":
Inhibitory Activity on The Formation of Reactive Carbonyl Species in Edible Oil by Synthetic Polyphenol Antioxidants." The system describes the peroxidation values (POV), Rancimat induction time (RIT) and ACR/GO/MGO formation processes in different vegetable oils (corn oil, soybean oil, palm oil) with changes in heating time and temperature. The capture ability of synthetic antioxidants (PG, TBHQ, BHT and BHA) on ACR/GO/MGO during grease heating and roast beef burgers was studied, and the inhibition mechanisms formed by PG/GO/MGO were analyzed by LC-MS/MS and TBHQ. The first purification obtained the PG-ACR-MGO addition and studied the inhibition mechanism of PG's simultaneous reaction with a variety of RCSs. New knowledge is provided for a further understanding of the ability of synthetic polyphenol antioxidants to simultaneously remove RCS.
Results and Discussion
1.
The dynamics of
POV, RIT and ACR/GO/MGO levels during grease heating
and the effect of heating temperature on them
an accelerated oxidation test using Rancimat, as shown in Figure 1-A-C, the ACR/GO/MGO content of corn oil, soybean oil, palm oil increases over time and then reaches equilibrium; The POV peaks with the extension of the heating time and then gradually decreases. After the peak of POV, the ACR/GO/MGO level rose sharply. It is worth noting that a certain amount of ACR, GO and MGO was produced in the initial stages before POV peaked, even before the oil oxidated acid was defeated. Corn, soybean and palm oil contain 30 times, 60 times and 140 times NGOs, respectively, and GO is 10 times higher than MGO. Although corn oil has better oxidation stability than soybean oil, it still produces high LEVELs of GO during heating, which may be related to unsaturated fatty acids found in corn and soybean oil. With the increase of heating time and temperature, the content of ACR/GO/MGO in corn oil increased dramatically, as shown in Figure 1-D-H. Large amounts of hydrogen peroxide (the main initial product) are easily decomposed at high temperatures, resulting in a sharp increase in ACR/GO.
1 Dynamics of POV, RIT and ACR/GO/MGO levels during heating of cooking oil at 170 degrees C (A. Soybean oil;B. corn oil; C. palm oil); temperature effects on the formation of POV, RIT and ACR/GO/MGO during corn oil heating (D. 130 degrees C; E. 150 degrees C; F. 170 degrees C; G.190 degrees C; H. 210 degrees C)
2.
Effects of PG, TBHQ, BHA and BHT on ACR/GO/MGO formation in corn oil
PG and TBHQ reduce the formation of ACRs/GO/MGOs in corn oil at doses (Figures 2- A and -C) and time (Figures 2- D and -F) at 170 degrees C, while the common antioxidant butyl hydroxyanisole, BHA) and butyl hydroxytoluene (BHT) showed low inhibitory activity, indicating that once RCS is produced during heating, BHA and BHT are difficult to remove. After heating 30 min, PG's ability to remove ACR is significantly better than TBHQ, only about 10% lower than urin, considering that the capture ACR ability of coutin can be maintained for a long time, it is recommended that in the process of grease processing, certin and PG use together.
2 Effects of synthetic antioxidants on ACR/GO/MGO formation in corn oil.
: Different capital letters indicate significant differences between different antioxidants (
P
<0.05), different lowercase letters indicate significant differences under different concentrations (A-C)/time (D-F) (
P
<0.05)
3.
Impact of PG and TBHQ on ACR/GO/MGO formation in corn oil roast beef burgers
and
LC-MS
/
MS
Analysis
PG eliminates ACR, MGO and GO in dose-dependent ways; 0.2 g/kg PG cleared 58.0% ACR, 46.9% GO and 58.9% MGO in corn oil roast beef patties, and PG was caught twice as efficiently as TBHQ (Figures 3-A and-C). The beef burger was analyzed by LC-MS/MS and found the products of PG-GO, PG-MGO, PG-ACR, as well as substances with the same mass-to-load ratio as PG-ACR-MGO, TBHQ-MGO, TBHQ-ACR molecular ion peaks.
effects of Figures 3 PG (A) and TBHQ (C) on ACR/GO/MGO in beef burgers with corn oil added. Add PG (B) and TBHQ (D) to the beef patty and bake in the oven with a total ion chromatography.
: Different capital letters indicate significant differences between different concentration samples (
P
<0.05), different lowercase letters indicate significant differences between different RCSs (
P
<0.05)
4.
Purification and Structural Identification of PG-ACR-MGO
Based on information collected by LC-MS/MS in roast beef burgers, we assume that PG can capture an ACR molecule and an MGO molecule to form PG-ACR-MGO. To further verify its structure, we purified the reaction mixture and analyzed it with HHRMS, MS/MS, NMR (
1
H,
13
C, DEPT, HSQC, HMBC) data (Table 1), PG-ACR-MGO structure 4.
1 PG and PG-ACR-MGO
1
H (400 MHz) and
13
C (150 MHz)
Figure 4 PG-ACR-MGO structure and key HMBC correlation.
5.
PG
simultaneously capture A
CR
,
GO
,
MGO
mechanism
Team previous studies have shown that PG-MGO, PG-GO, PG, PG is formed when PG reacts with ACR, GO, MGO, respectively -ACR, PG-2ACR, and we also found these additions in heavy oil cakes and roast beef burgers, but it is not clear which RCS is more sensitive and more likely to react with PG; how PG clears them when reacting in the same way as ACR, GO, and MGO, whether there is a priority, or if it occurs randomly. Therefore, we studied the products of PG and ACR, GO and MGO at different temperatures and times. The results showed that PG was captured in order under 80 degrees C and concentration ratio of 1:1:1: 1 in order: ACR, MGO, GO; The additions of PG-ACR-MGO, PG-MGO-GO and PG-2ACR can be observed after reaction 4 h (Figure 5-B). PG reacts with ACR, GO, MGO (1:1:1:1) at room temperature and does not form a product even if the time is extended to 4 h. PG as an inhibitor of RCS is suitable for medium- and high-temperature food processing, but not for at room temperature storage.
Figure 5 PG and ACR/GO/MGO simultaneously react to HPLC-DAD (A) and Total Ion Chromatography (B)
Communication Author
Lu Lishuang, female, born in February 1969, Ph.D., postdoctoral professor, professor, graduate tutor of NCA-T usa. A leader in food engineering at Nanjing Normal University's School of Food and Pharmaceutical Engineering. More than 80 core journal papers were published by first or correspondent authors, and SCI included 30 (20 in Q1). Authorize 3 national invention patents. Chaired the National Natural Science Foundation of Jiangsu Province, Jiangsu Province Natural Science Foundation, Jiangsu Provincial Education Department Fund, the Ministry of Science and Technology 863 project sub-topics, Zhejiang Natural Science Foundation, Hainan Province innovation team, Cebu City, modern agricultural key research and development and other topics.
2008 school "blue project" outstanding young backbone teachers.
awarded the title of outstanding graduate tutor in 2016. In 2016, he was selected as the 13th batch of Jiangsu Province's "Six Talent Peaks".
Reviews in Food Science and Nutrition, Journal of Agricultural and Food Chemistry (winner of the Outstanding Reviewer Award in 2018), Food chemistry, Food and Function, Food and Chemical Toxicology International.
Dong Wenjiang, male, born in November 1985, Ningxia Shizushan, Ph.D., Associate Researcher, Master's Tutor, Central China Agricultural University, Ningxia University and other universities. The main research directions are food flavor chemistry, high-value development and utilization of food resources, food authenticity traceability identification and so on. Selected as the third level candidate of "515 Talent Project" in Hainan Province, the first batch of young people from The South China Sea in Hainan Province, the top talents of Hainan Province, the "100 Thousand Talent Project" of Tropical Agriculture in China- "The Thousand People Program", the head of the innovation research team of Hainan Natural Science Foundation, National Natural Science Foundation of China communication review experts, Hainan Province Science and Technology Department project library experts, the Chinese Academy of Thermal Sciences coffee industry innovation team backbone experts, international coffee quality taster, gold cup extraction intermediate barista, China Tropical Crop Society coffee professional committee member, Yunnan Boutique Coffee Association executive director. The first finisher won the second prize of Hainan Province Science and Technology Progress Award (2019), presided over 3 projects of NSF (face, youth, emergency management project), Hainan Natural Science Foundation Innovation Research Team, Hainan Natural Science Foundation, central public welfare research institute basic scientific research business expenses and other projects 6 projects; Journal of Agricultural and Food Chemistry, Industrial Crops and Products and other journals published more than 40 papers, including more than 20 SCI papers, first or correspondent SCI papers included 15 (total impact factor 55.339), ESI high cited papers 1; Trends in Analysis Chemistry, Food Chemistry, Food Re