LWT - Food Science and Technology 184 (2023) 115004

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LWT
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Synthesis of triacetylferulic resveratrol ester and its assessment on the

oxidative stability of fish oil during accelerated oxidative storage
Zhiyong Xue a, Chenxi Zhang a, Juan Liu a, Qing Li a, Yuanyuan Yao b, Yalin Yang b, Chao Ran b,
Zhen Zhang b, *, Zhigang Zhou b, c, **
a
Hubei Key Laboratory of Biomass Fibers and Eco-dyeing & Finishing, College of Chemistry and Chemical Engineering, Wuhan Textile University, Wuhan, China
b
China-Norway Joint Lab on Fish Gut Microbiota, Institute of Feed Research, Chinese Academy of Agricultural Sciences, Beijing, 100081, China
c
Key Laboratory for Animal Nutrition and Feed Science of Hubei Province, Wuhan Polytechnic University, Wuhan, 430000, China

A R T I C L E I N F O A B S T R A C T

Keywords: A new antioxidant triacetylferulic resveratrol ester (TRE) was synthesized and characterized in the current
Synthesis research. The scavenging activity of TRE against 2,2-diphenyl-1-picrylhydrazyl (DPPH•) and 2,2-azino-bis (3-
Fish oil ethylbenzothiazoline-6-sulfonic acid) (ABTS•+) free radicals was carried out by comparison with tert-
Ferulic acid
butylhydroxyquinone (TBHQ), ferulic acid and resveratrol. The inclusion of TRE as an oil stabilizer in fish oil
Oxidative stability
was also investigated by assessing lipid oxidation parameters such as peroxide value (POV), TBARS value and p-
Resveratrol
anisidine value (pAV) under accelerated storage conditions (12 days, 80 ◦ C). The changes in fatty acid
composition were monitored by infrared spectroscopy and gas chromatography–mass spectrometry. The results
showed that the oxidation stability of fish oil supplemented with TRE was better than that of fish oil containing
TBHQ, ferulic acid and resveratrol during the whole storage period. Further, the formation of oxidation products
in fish oil followed a first-order kinetic model, and adding TRE effectively lowered down the reaction rate
constants. Therefore, TRE can be used as a strong antioxidant for tackling oxidative processes.

1. Introduction
Fish oil is the oil extracted from marine pelagic fish species such as
swordfish, cod, mackerel and salmon (Lv, Wang, Zhang, Lv, & Yu,
2020). Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)
belong to long-chain n-3 polyunsaturated fatty acids (PUFAs) that are
greatly abundant in fish oil. These PUFAs have a range of beneficial
effects in humans. They can not only promote retina and brain devel­
opment in infants, but also reduce symptoms in people with cardio­
vascular disease and depression (Albert et al., 2015). Besides, fish oil is a
very important source of lipids, especially in Marine animal farming,
and plays an important part in achieving optimal growth and health in
aquatic animals (Yu et al., 2022). However, fish oil is extremely prone to
oxidation and rancidity because of the presence of these PUFAs. The
oxidation of long chain PUFAs involves a series of complex chemical
reactions, including the cleavage of unsaturated bonds and the forma­
tion of various toxic oxidation products (Hwang, Fhaner,
Winkler-Moser, & Liu, 2018; Liang et al., 2018). The oxidation products,
such as peroxides, alcohols, aldehydes, and carboxylic acids, can cause
rancid odors and unpleasant flavours, color changes, and low nutritional
value (Agregan et al., 2017). Hence, the oxidation is related to the
nutritional value and security of fish oil, and how to prevent the
oxidation is always a problem that people try to solve. One of the most
effective and convenient ways to keep oil products rich in PUFAs from
oxidation is adding substances such as antioxidants that block the un­
desirable effects of oxygen. Antioxidants can delay or inhibit lipid
oxidation by trapping and neutralizing free radicals, quenching singlet
oxygen, removing oxygen, chelating metal ions, etc (Agregan et al.,
2017; Huang et al., 2017). A variety of effective synthetic antioxidants
have been widely used such as tert-butylhydroxyquinone (TBHQ),
butylated hydroxytoluene (BHT), propyl gallate (PG), and butylated
hydroxyanisole (BHA), and they can effectively protect PUFAs from
oxidative deterioration.
Ferulic acid, a phytochemical classified as a hydroxycinnamic acid,

* Corresponding author.
** Corresponding author. China-Norway Joint Lab on Fish Gut Microbiota, Institute of Feed Research, Chinese Academy of Agricultural Sciences, Beijing, 100081,
China.
E-mail addresses: zhangzhen@caas.cn (Z. Zhang), zhouzhigang03@caas.cn (Z. Zhou).

https://doi.org/10.1016/j.lwt.2023.115004
Received 28 February 2023; Received in revised form 19 June 2023; Accepted 22 June 2023
Available online 23 June 2023
0023-6438/© 2023 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-
nc-nd/4.0/).
Z. Xue et al.
was first isolated from the seeds and leaves of plants (Dulong, Kouassi,
Labat, Le Cerf, & Picton, 2018). Ferulic acid possesses antioxidant, an­
tiplatelet aggregation, antibacterial, anti-thrombosis, and anti-cancer
activities, and is widely used as an antioxidant for fats in food in­
dustries (Amic, Markovic, Dimitric Markovic, Milenkovic, & Stepanic,
2020). As a multipotent antioxidant, ferulic acid is highly effective at
scavenging free radicals because of its conjugated structure.
Electron-donating groups such as 3-methoxy and the 4-hydroxyl group
on the benzene ring of ferulic acid contribute to the antioxidant effect
(Singh et al., 2021). However, the poor lipophilicity of ferulic acid is the
main limiting factor for its wide application (Nicks et al., 2012).
Recently, improving the lipophilicity by modifying the functional
groups of ferulic acid has aroused great interest of researchers (Wu et al.,
2020). Furthermore, it has been observed that modified ferulic acid
derivatives such as ferulic paeonol ester (Yu et al., 2021), triterpene
alcohol monoesters (Pellerito et al., 2020) and alkyl ferulate have higher
antioxidant activity than the acid itself (Chigorimbo-Murefu, Riva, &
Burton, 2009).
Resveratrol (3,4ˊ,5-trihydroxy-trans-stilbene), a polyphenol com­
pound also known as astragaltriol, is present in a variety of plant species
such as peanuts, pistachio, different types of berries and grapes (Chen
et al., 2021; Xia, Daiber, Förstermann, & Li, 2017). It has a very
powerful antioxidant effect, as well as a wide range of physiological
activities (anti-atherosclerosis, anti-cancer, anti-inflammatory, anti­
bacterial, etc), which are largely based on its antioxidant activity (Oh &
Shahidi, 2018). Nevertheless, when resveratrol is used in lipophilic
systems, its application could be compromised due to its hydrophilicity
caused by the three hydroxyl groups, and also limited by its low
chemical stability (Hosseini Berenji et al., 2021). However, the problems
could be overcome by various modifications of the native structure,
including both changes in the stilbene skeleton and transformations in
functional groups (Semenov, Balakireva, Tarasova, Semenova, & Zul­
fugarov, 2020). In fact, it was reported that the structural modifications
using chlorogenic acid, epigallocatechin gallic acid and rosmarinic acid
as templates can maximize their antioxidant activities (Oh & Shahidi,
2018).
Inspired by the above information, triacetylferulic resveratrol ester
(TRE, Fig. 1) was synthesized and its chemical characteristics were also
investigated in the current study. The anti-oxidative activities of TBHQ,
ferulic acid, resveratrol and TRE were evaluated by DPPH and ABTS
assay. Further, the oxidative stability of fish oil before and after addition
of these compounds during accelerated storage up to 12 days at 80 ◦ C
under dark were also investigated. The oxidation of fish oil under
accelerated condition was monitored by determining peroxide values
(POV), thiobarbituric acid reactive substance (TBARS) contents and
para-anisidine values (pAV). The changes in fatty acid composition in
fish oil was studied using modern gas chromatography–mass spec­
trometry (GC–MS), and the generation of oxidation compounds at
Fig. 1. Synthetic route of TRE.
2
LWT 184 (2023) 115004
different oxidation stages were monitored by infrared spectroscopy (IR).
2. Materials and methods
2.1. Materials
Fish oil was purchased from Zhejiang Xinglong Ma Industry Co., Ltd.
(Zhejiang, China). Ferulic acid and resveratrol were purchased from
Shanghai Maclin Biochemical Technology Co., Ltd. (Shanghai, China).
Both DPPH and ABTS were got from Shanghai Yuanye Bio-Technology
Co., Ltd. (Shanghai, China). All other chemical reagents used in the
experiments were commercially available, either in analytical or optical
grade. Silica gel columns (Merck, Kieselgel 60, 70–230 mesh) with ethyl
acetate/petroleum ether as an eluent were used to purify the synthesized
new compounds. Nuclear magnetic resonance (NMR) spectra of the new
compounds with CDCl3 as solvent were acquired on a Bruker spec­
trometer (DPX 300, USA). IR (KBr) spectra of the new compounds and
fish oil samples were recorded on a BIORAD Tensor 27 spectrometer
with 0.5 cm− 1 resolution (Brucker Optics, Germany).
2.2. Synthesis of TRE
o-Acetylferulic acid was synthesized according to the previous re­
ports (Yu et al., 2017). TRE synthesis was carried out as follows:
o-Acetylferulic acid (4.7 g, 0.02 mol), resveratrol (1.141 g, 0.005 mol),
EDC⋅HCl (7.11 g, 0.036 mol), DMAP (4-dimethylaminopyridine) (0.30
g, 0.0025 mol) and dichloromethane (100 mL) were added in a
round-bottomed flask. The yellow reaction liquid was continuously
stirred at room temperature for 4 h, and then a lot of ice-water was
added when the reaction was completed. The resulting mixture was
extracted with ether (3 × 500 mL), and the organic phases were mixed
together and washed with water (2 × 200 mL) before drying with
anhydrous MgSO4 for 24 h. Recovery of ether after decompression, the
resulting residue was first purified by silica gel column chromatography
(ethylacetate/petroleum ether) and then recrystallized to produce TRE
as a white powder (3.76 g, yield 87%, content >98%).1H NMR (400
MHz, CDCl3) δ 7.79–7.74 (m, 3H, CH), 7.46 (d, J = 8.0 Hz, 2H, CH), 7.14
(d, J = 24.0 Hz, 2H, Ar–H), 7.11–7.07 (m, 8H, Ar–H), 7.03–7.00 (m, 5H,
Ar–H), 6.98–6.93 (m, 1H, Ar–H), 6.50 (d, J = 16.0 Hz, 3H, CH), 3.80 (d,
J = 4.0 Hz, 9H, OCH3), 2.26 (s, 9H, COCH3); 13C NMR (100 MHz, CDCl3)
δ 168.77, 165.17, 164.85, 151.53, 151.48, 150.54, 146.02, 141.90,
139.65, 133.09, 133.02, 127.27, 121.53, 117.17, 114.54, 111.51,
111.47, 55.98, 20.67; IR (cm− 1) 1726 (O– – C–O), 1633 (C–– C), 1463
(Ph), 1508 (Ph), 1593 (Ph), 2937 (C–C).
2.3. Radical scavenging activity
TBHQ, resveratrol, TRE and ferulic acid were separately dissolved in
ethanol/N, N-dimethylformamide (DMF) and diluted to 25, 50, 75, 100
and 125 μM. The DPPH radical scavenging abilities of the obtained so­
lutions with different concentrations were determined according to the
method described in the previous literature (Liu et al., 2018). Briefly,
different concentrations of samples (2 mL) were added to 2 mL of DPPH•
ethanol solution (0.5 mmol/L). After shaking the resulting colorless
mixture well, they were left in a dark place for 30 min at room tem­
perature (20 ◦ C) and turned yellow. The absorbance of the resulting
yellow liquids was then measured and recorded at 517 nm by
spectrophotometer.
The ABTS assay was conducted by using the method described pre­
viously (Liu et al., 2018; Zheng, Zhao, Xiao, Zhao, & Su, 2016). Briefly,
the two solutions (7 mmol/L ABTS solution and 2.45 mmol/L potassium
persulfate solution) were mixed in a 1:1 vol ratio to form ABTS•+ radical
cations. The mixture was placed in a dark place at ambient temperature
for 12–16 h to yield a dark colored ABTS working liquid. Since ABTS
radical has maximum absorption at 734 nm, it was then diluted with
anhydrous ethanol to a target absorbance (734 nm, 0.7 ± 0.02). Then,
Z. Xue et al.
600 μL of different concentrations of sample solutions were allowed to
react with 5 mL of ABTS•+ working liquid for 10 min at 37 ◦ C in the
dark. Afterwards, the absorbance of the resulting mixtures with lighter
color at 734 nm was measured.
2.4. Determination of oxidative stability
2.4.1. Sample preparation
TBHQ (0.0499 g), ferulic acid (0.0583 g), resveratrol (0.0685 g) and
TRE (0.2649 g) were separately mixed with 5 mL of DMF (N, N-dime­
thylformamide). The resulting solutions and 5 mL of DMF without any
antioxidant addition (for control) were separately added to the fresh fish
oil (300 g). After ultrasonic mixing at room temperature for 30 min, 10
mL of each mixture was placed in polypropylene centrifuge tubes and
then stored in an oven at 80 ◦ C for 12 days in dark, with sampling taken
every 2 days. The control and test samples were prepared in triplicate.
2.4.2. POV, TBARS and pAV
POV assay of all samples was measured according to GB/T
5538–2005/ISO 3960:2001 with a slight modification (Zhang et al.,
2010). The TBARS detection method is the same as the previous methods
with slight modifications (Agregan et al., 2017; Wang et al., 2011). pAV
was determined to follow the formation of secondary oxidation products
according to the previous reports (Liu, Ramirez, Yang, & Ciftci, 2020;
Umeda & Jorge, 2021).
2.4.3. IR spectroscopy
IR spectra of the fish oil samples were acquired in the absorbance
range of 500–4000 cm− 1 with 0.5 cm− 1 spectral resolution on a Tensor
27 spectrometer system (Brucker Optics, Germany). The fish oil samples
were firstly diluted with dichloromethane to a suitable concentration. A
drop of the diluted fish oil was placed onto the surface of the potassium
bromide tablet for each measurement. The spectra were normalized to
facilitate comparison.
2.4.4. Fatty acid composition
Fatty acids in fish oil were derived into fatty acid methyl esters
(FAMEs) and their composition was determined by gas chromatography-
mass spectrometry (GC-MS) according to the previous reports (Lepage &
Roy, 1986). A Thermo Trace1300 gas chromatograph-ISQ7000 mass
spectrometer (GC-MS, New York, USA) equipped with a fused silica DB-5
column (length 60 mm × inner diameter 0.25 mm × film thickness 0.25
μm) was employed for the separation and quantification of the FAMEs.
Helium with a flow rate of 1.5 mL min− 1 was unsurprisingly employed
as a carrier gas. The heating procedure of the column was as follows:
140 ◦ C for 5 min, heated up to 180 ◦ C at 10 ◦ C min− 1, followed by
heating up to 210 ◦ C at 2 ◦ C min− 1, and finally ramped up to 260 ◦ C at
10 ◦ C min− 1 and held for 10 min. The detector temperature, injected
volume of sample and split ratio was 260 ◦ C, 1 μL and 30:1, respectively.
The mass spectrum was acquired at 70 eV in the electron impact (EI)
mode at m/z 33–550. Chromeleon7.0 was used for mass spectrometry
and chromatographic analysis. The NIST 17 database and Excel 2016
software were used to sort, summarize and edit the output data. The
concentrations of all FAMEs were calculated based on the retention
time, known concentration and detected peak area of the internal
standard.
2.5. Statistical analysis
All the analytical tests (except IR analysis) were carried out in trip­
licate and data were reported as a mean value with its standard devia­
tion (mean ± SD). An ANOVA test was employed to compare the mean
values of each parameter, and significant differences between the means
were tested using Tukey’s multiple comparison test (P < 0.05). All sta­
tistical analyses through the full text were performed by SPSS version 26
software (Chicago, IL, USA).
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LWT 184 (2023) 115004
3. Results and discussion
3.1. Radical scavenging activity detection
As Fig. 2 (a) reported, the DPPH radical scavenging activity of
resveratrol, ferulic acid and TRE was measured at different concentra­
tions as compared to TBHQ. Noticeably, the activity curves of TBHQ,
ferulic acid and resveratrol for scavenging DPPH radicals were very
similar in shape. However, the highest DPPH quenching activity of
TBHQ reached a value of 95.53 ± 0.39%, whereas those of ferulic acid
and resveratrol were only 58.86 ± 0.84% and 25.80 ± 1.20%. TBHQ
owned the highest anti-DPPH• activity, followed by ferulic acid,
resveratrol and TRE. Fig. 2 (b) summarized the quenching activity of
TBHQ, ferulic acid, resveratrol and TRE against the ABTS free radical
cations. A concentration-dependent scavenging activity against ABTS
radical cations was observed in all of the samples except TRE, and the
scavenging activities decreased as follows: resveratrol > TBHQ > ferulic
acid > TRE.
In general, (poly) phenolic compounds are thought to scavenge free
radicals primarily through three known mechanisms: (i) HAT (H atom
transfer), (ii) SET-PT (single electron transfer-proton transfer), and (iii)
SPLET (sequential proton loss electron transfer) (Biela, Rimarcik, Sen­
ajova, Kleinova, & Klein, 2020; Thuy, Van Trang, & Son, 2020). There
are two hydroxyl groups on the benzene ring of TBHQ, but only one
hydroxyl group on the benzene ring of ferulic acid. The introduction of
p-hydroxyl on the benzene ring of TBHQ enhances the H atom transfer,
electron transfer, or deprotonation ability of –OH, thereby improving its
ability to scavenger free radicals (Xue et al., 2020). Thus, due to the two
hydroxyl groups and p-hydroxyl, TBHQ showed significantly higher
scavenging capacity for DPPH and ABTS free radicals than ferulic acid
did (P < 0.05). TRE had almost no free radical scavenging activity on
DPPH and ABTS free radicals because of the protected phenolic hy­
droxyl. Because no exposed phenolic hydroxyl groups in TRE, the H
atom transfer, single electron transfer-proton transfer, or sequential
proton loss electron transfer processes did not work, and TRE cannot
quench free radicals.
Resveratrol has the least resistance to DPPH free radicals among the
three antioxidants (resveratrol, TBHQ and ferulic acid), however, its
anti-ABTS activity was the highest. The differences in the activities of
resveratrol against free radicals can be attributed to the formation of
intermolecular hydrogen bonds (Chen et al., 2020; Farhoosh, Johnny,
Asnaashari, Molaahmadibahraseman, & Sharif, 2016). The intra­
molecular hydrogen bonds of the (poly) phenolic compounds were
referred as improving causes of the antioxidant activity, whereas the
intermolecular hydrogen bonds were considered as a possible cause of
reduced antioxidant capacity (Farhoosh et al., 2016). In the present
study, DPPH assay performed in an ethanol system, whereas ABTS assay
reacted in a water system. Resveratrol might more easily form inter­
molecular hydrogen bonds with ethanol, which prevented hydrogen
abstraction to a certain extent, thereby reducing the antioxidant effi­
ciency (Farhoosh et al., 2016). Hence, resveratrol presented a much
lower anti-DPPH activity than TBHQ. Further, it is widely believed that
the antioxidant activity of resveratrol is mainly achieved through the
HAT mechanism, while the SPLET and ET-PT mechanisms have smaller
contribution to its free radical scavenging activity (Mikulski, Szeląg,
Molski, & Górniak, 2010). In HAT mechanism, bond dissociation
enthalpy (BDE) of resveratrol in water is lower than that in ethanol
(Mikulski et al., 2010; Phan Thi, Ninh The, & Mancini, 2020). BDE value
is the main indicator to evaluate the antiradical activity of (poly)
phenolic compounds, thus the inhibitory effect of resveratrol on ABTS
radical is much greater than that on DPPH radical. In addition, the
antioxidant capacities of (poly) phenolic compounds are generally
proportional to the number of phenolic hydroxyl groups (no more than
four hydroxyl groups on the benzene ring) (Chen et al., 2020). Resver­
atrol has three active phenolic hydroxyl groups, so its scavenging ac­
tivity on ABTS radicals is significantly higher than TBHQ.
Z. Xue et al.
Fig. 2. Scavenging effects on DPPH (a) and ABTS (b) radical of TBHQ, ferulic acid, resveratrol and TRE.
3.2. Stability evaluation of the test compounds on fish oil during
accelerated storage
Generally, POV is an indicator of the amount of primary oxidation
products while TBARS and pAV indicate the amount of secondary
oxidation products (Zhang, Zhang, Xie, & Che, 2019). The POV, TBARS
and pAV results of the fish oil samples with and without antioxidants
during the accelerated storage were depicted in Fig. 3. As can be seen in
the pictures, the POV, TBARS and pAV values of all the samples were
positively related to the heat treatment time (P < 0.05). Especially, these
values were seen to increase in acceleration after the fourth day. During
the accelerated storage at 80 ◦ C, the POV, TBARS and pAV values of the
samples reduced in the following order: control > ferulic acid > TBHQ
> resveratrol > TRE, which demonstrated that these four antioxidants
had significant inhibitory effect on rancidity of fish oil by reducing the
formation of primary and secondary oxidation products. Additionally,
TRE had the strongest antioxidant capacity, followed by resveratrol,
TBHQ and ferulic acid. The strongest antioxidant activity of TRE can be
attributed to the fact that one molecule of TRE contains three molecules
of acetylferulic acid and one molecule of resveratrol. Another possible
Fig. 3. The influence of TBHQ, ferulic acid, resveratrol and TRE on POV (a), TBARS (b) and pAV (c) of fish oil samples during the accelerated storage at 80 ◦ C for
12 days.
4
LWT 184 (2023) 115004
reason is that the two ester groups in TRE promote an increase in its
lipophilicity and stability, leading to its antioxidant activity going up.
Our result acquired is in agreement with those of the previous studies,
that is, phenolic compounds with modified functional groups had
stronger antioxidant effect (Higgins, Filip, Afsar, & Hayes, 2020; Wang,
Hwang, & Lim, 2015; Yu et al., 2017; Yu et al., 2021). As mentioned
earlier, the antioxidant activity of phenolic compounds was proportional
to the number of phenolic hydroxyl groups (less than four). The number
of phenolic hydroxyl groups decreased in the order of three, two, and
one for resveratrol, TBHQ and ferulic acid, respectively. Therefore,
resveratrol, TBHQ and ferulic acid showed progressively reduced anti­
oxidant capacity in this study. The antioxidant effects of the four anti­
oxidants have been confirmed by the POV, TBARS and pAV assay, and
TRE can be used as a more effective antioxidant to inhibit the oxidation
of fish oil during the accelerated storage.
The kinetics study of fish oil oxidation is very important for under­
standing the degradation mechanism of the samples. Reactions rates of
lipid oxidations are usually described by zero-order or first-order reac­
tion (Rodrigues et al., 2017; Solaesa, Sanz, Melgosa, & Beltrán, 2018;
Yeşilsu & Özyurt, 2019). Kinetic lines of zero-order or first-order
Z. Xue et al. LWT 184 (2023) 115004

reaction were drawn by plotting the changes or the logarithm of the
changes of POV, TBARS or pAV versus time. Reaction rate constants (k)
were determined from the slope of the kinetic lines. Table 1 lists k values
together with the quality of the fitting (R2). The addition of ferulic acid,
TBHQ, resveratrol and TRE effectively reduced the reaction rate con­
stants, that is, these antioxidants significantly lowered down the
generating speed of primary and secondary oxidation products in fish
oil. And TRE can surprisingly minimize the k values, which proved that
TRE had the best inhibitory effect on the generation of oxidation prod­
ucts. Furthermore, the better fitting for the natural logarithm of the
concentration of POV, TBARS or pAV was obtained for a first-order re­
action. Therefore, the formation of oxidation products in fish oil fol­
lowed a first-order kinetic model in this study. This result agrees with
the previous studies of fish oil oxidation kinetic models (Dahl & Malcata,
1999; Sullivan, Budge, & St-Onge, 2011).
3.3. Infrared spectra of fish oil with TRE
Fig. 4 demonstrates the IR spectra of fish oil containing TRE heated at
80 ◦ C for different times, which comprises the range between 4000 and
400 cm− 1. Since the concentration of TRE was not high enough to be
detectable in the IR spectrum, the treated samples had the same bands as
fish oil without TRE (Kurtulbaş, Bilgin, & Şahin, 2018). Most of the
spectral information was observed from 1800 to 600 cm− 1 and 3150 to
2800 cm− 1 regions. Fig. 4 (a) shows a representative IR spectrum of the
unheated initial sample with visible peaks at 3013, 2928, 2854, 1743,
1680, 1462, 1377, 1265, 1148, 1099 and 741 cm− 1. These feature peaks
were designated according to previous IR studies of oils (Kurtulbaş et al.,
2018; Suri, Singh, Kaur, Yadav, & Singh, 2020; Wang et al., 2011; Wu
et al., 2013). A slight increase in peak intensities were observed at 2928,
2854, 1743, 1462, 1377, 1148 and 1099 cm− 1, whereas the peak in­
tensities decreased at 3013, 1680, 1265 and 741 cm− 1. And the changes
in the peak intensity became more significant with the extension of
heating time. The two relatively sharp peaks at 2928 and 2854 cm− 1 in
the picture were caused by asymmetric and symmetric stretching vi­
brations of the CH2 groups. The peak observed at 1743 cm− 1 was
ascribed to C– – O stretching in esters. The medium bands located at 1462
and 1377 cm− 1 donates the C–H bending of alkanes. The absorption
peaks at 1148 and 1099 cm− 1 were from the C–O of the ester groups.
Additionally, the peaks at 3013 and 1680 cm− 1 were assigned to the
stretching vibration of cis C– – C. The feature absorption peaks at 1265
and 741 cm− 1 involved the rocking and bending out vibration of –(CH2)
n– and –HC– CH– (cis). A slight increase in peak strength at 2928, 2854,
– opment of more effective antioxidants. However, the safety of TRE has
1462 and 1377 cm− 1 with an increase in heating time might be due to
the disappearance of cis-olefinic C–H double bonds in unsaturated fatty
acids (Suri et al., 2020). The variations of peak intensity at 1743, 1148
and 1099 cm− 1 corresponded to the formation of secondary oxidation
products and hydrolysis of carbonyl ester functional groups into ke­
tones. The reduction of peak intensity at 3013, 1680, 1265 and 741
cm− 1 was due to the disappearance of cis C– – C and the breaking of the
long chains of unsaturated fatty acids. The infrared spectroscopy anal­
ysis revealed that with the extension of heating time, unsaturated fatty
acids in fish oil were gradually decomposed, but oxidation products
were gradually formed.
3.4. GC–MS analysis
The effect of TRE on fatty acid composition of fish oil in the accel­
erated storage test is shown in Table 2. According to the above results,
among the four antioxidants, TRE had the most excellent antioxidant
activity, and the fish oil samples stored at 80 ◦ C on days 0 and 12 showed
the greatest difference in POV, TBARS, pAV and IR spectra. Thus, a total
of 34 fatty acids were identified by GC–MS analysis in the initial fish oil,
as well as the control and the fish oil with TRE stored at 80 ◦ C for 12
days. As shown in Table 2, the contents of polyunsaturated fatty acids
(C22:6, C22:5, C22:4, C22:2, C20:5, C20:4, C20:3, C20:2, C18:3 and
C18:2, PUFA), monounsaturated fatty acids (C24:1, C22:1, C20:1,
C19:1, C18:1, C17:1, C16:1 and C14:1, MUFA) and saturated fatty acids
(C23:0, C22:0, C21:0, C20:0, C18:0, C17:0, C16:0, C15:0, C14:0, C13:0,
and C12:0, SFA) in Control (12) were significant lower than those in
Control (0). Interestingly, the inclusion of TRE effectively suppressed the
decrease of PUFA, MUFA as well as SFA content in TRE (12). Similar
trends were also found in the contents of ΣPUFA, ΣMUFA and ΣSFA in
Control (0), Control (12) and TRE (12). At high temperatures, the
cleavage of C– – C in long-chain fatty acids leads to the release of low-
boiling fatty acids and the formation of primary and secondary oxida­
tion products, lowering the PUFA, MUFA, and SFA content per unit
volume of fish oil (Miyashita, Uemura, & Hosokawa, 2018). The result is
similar to the previous studies on the oxidation of fish oil under high
temperature treatment (Wang et al., 2011; Yu et al., 2021). The finding
herein confirms once again that TRE exhibited favourable antioxidant
effects and is preferable for effectively avoiding the oxidation of fish oil.
4. Conclusions
In summary, the new compound TRE has been synthesized and
routinely characterized, and its antioxidant activity was also evaluated
by radical scavenging activity detection and fish oil oxidation experi­
ment. TRE had stronger inhibitory effect on fish oil oxidation than
resveratrol, TBHQ and ferulic acid does. The inhibitory effect on
oxidation followed the order TRE > resveratrol > TBHQ > ferulic acid.
Therefore, this title compound is of significance for the future devel­
not yet been addressed, so there is still a lot of work to be done before the
product is finally marketed.
CRediT authorship contribution statement
Zhiyong Xue: Methodology, Investigation, Writing – review &
editing. Chenxi Zhang: Investigation. Juan Liu: Formal analysis. Qing

Table 1
Kinetic rate constant (k) and R2 of fish oil samples
n (order of reaction) Samples POV TBARS pAV
a 2 a 2
k R k R ka R2

zero-order Control 4.7 ± 0.4 0.963 84.3 ± 7.8 0.953 2.9 ± 0.6 0.818
TBHQ 3.5 ± 0.4 0.921 59.2 ± 7.0 0.922 2.4 ± 0.3 0.887
Ferulic acid 4.3 ± 0.4 0.949 64.0 ± 6.6 0.946 2.3 ± 0.2 0.965
Resveratrol 2.9 ± 0.4 0.884 58.0 ± 5.2 0.954 2.3 ± 0.4 0.872
TRE 2.8 ± 0.3 0.930 39.5 ± 7.1 0.833 1.2 ± 0.2 0.869
First-order Control 0.105 ± 0.003 0.996 0.160 ± 0.014 0.954 0.110 ± 0.008 0.973
TBHQ 0.087 ± 0.006 0.978 0.130 ± 0.014 0.942 0.083 ± 0.006 0.965
Ferulic acid 0.103 ± 0.006 0.978 0.140 ± 0.010 0.971 0.082 ± 0.005 0.980
Resveratrol 0.087 ± 0.012 0.893 0.120 ± 0.010 0.966 0.081 ± 0.008 0.944
TRE 0.079 ± 0.006 0.972 0.100 ± 0.014 0.901 0.053 ± 0.006 0.933
a 1
Units of k for POV (meq⋅kg− h− 1); for TBARS ((mg MAD⋅kg− 1
h− 1) and for pAV (h− 1).

5
Z. Xue et al. LWT 184 (2023) 115004

Fig. 4. (a) The IR spectrum of fish oil with TRE on day 0; (b) IR spectra of fish oil with TRE at 80 ◦ C for different heating times.

Declaration of competing interest

Table 2
Total fatty acid composition of the fish oil samples.
None.
Fatty acid (mg Fish oil samples (storage days)
mL− 1)
Control (0) Control (12) TRE (12) Data availability
c a bc
C12:0 1.296 ± 0.115 0.875 ± 0.081 1.102 ± 0.088
C13:0 0.926 ± 0.039c 0.626 ± 0.016a 0.730 ± 0.042b Data will be made available on request.
C14:0 2.070 ± 1.254c 1.401 ± 1.185a 1.865 ± 1.319bc
C14:1 0.662 ± 0.045c 0.431 ± 0.026a 0.536 ± 0.022b Acknowledgements
C15:0 10.769 ± 1.043c 7.508 ± 0.584a 9.378 ± 0.402ab
C16:0 137.965 ± 81.775 ± 4.921a 113.090 ± 9.505b
11.996c This work was supported by grants from National Natural Science
C16:1 18.177 ± 1.024c 10.399 ± 0.576a 14.301 ± 1.072b Foundation of China (NSFC 32061133004, 31925038, 21602163 and
C17:0 8.884 ± 0.369b 7.560 ± 0.223a 8.913 ± 0.502b U21A20267). and Hubei Key Laboratory of Biomass Fibers & Eco-
C17:1 1.902 ± 0.113c 1.578 ± 0.084a 1.803 ± 0.111bc
Dyeing & Finishing（Wuhan Textile University），No. STRZ201907.
C18:0 1.657 ± 0.161c 0.847 ± 0.042a 1.225 ± 0.126b
C18:1 236.417 ± 137.897 ± 206.309 ±
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