Food Chemistry 358 (2021) 129854

Contents lists available at ScienceDirect

Food Chemistry
journal homepage: www.elsevier.com/locate/foodchem

Short communication

Determination of 1-methylcyclopropene residues in vegetables and fruits

based on iodine derivatives
Maofeng Dong 1, Guangyue Wen 1, Junshun Li , Tan Wang , Jiaqing Huang , Yubo Li ,
Hongxia Tang , Qiang Sun , Weimin Wang *
Pesticide Safety Evaluation Research Center, Institute for Agro-food Standards and Testing Technology, Shanghai Academy of Agricultural Sciences, Shanghai 2011106,
China

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

Keywords: An innovative method was established for the determination of 1-methylcyclopropene (1-MCP) in vegetables and
1-methylcyclopropene fruits. Due to its small molecular weight and low boiling point, it was difficult to obtain quantitative analysis for
GC–MS/MS 1-MCP, especially at the residual level. In this work, based on its iodine derivatives, 1-MCP was derived to 1,2-
Vegetables
diiodo-1-methylcyclopropane, which was much easier for trace and accurate chromatographic analysis. During
Fruits
the method validation, the method validation results were satisfactory in terms of linearity (4 ~ 400 µg/L, and
Chemical compounds studied in this article:
R2 ≥ 0.959), matrix effect (− 89% ~ − 13%), accuracy (80 ~ 100%), sensitivity (limits of quantification, 5 μg/kg)
1-Methylcyclopropene (PubChem CID:
151080)
and precision (relative standard deviations ≤ 19%), which was in accordance with the Chinese guidelines for the
1,2-diiodo-1-methylcyclopropane (PubChem testing of pesticide residues in crops. Finally, the proposed analytical method was used to monitor the 1-MCP
CID: 11573113) residue levels in commercially available samples, and all the values were below 5 µg/kg, which satisfied the
EU or Japan MRLs of 1-MCP.

1. Introduction 25 ◦ C vapor pressure and 54 g/mol molecular weight), it was difficult

Currently, 1-methylcyclopropene (1-MCP, C4H6) is a landmark
development in postharvest technology for vegetables and fruits (Liu,
Gao, Chen, Fang, & Wu, 2019; Xie, Feng, Chen, & Zhang, 2020). As a
competitive inhibitor of ethylene perception, 1-MCP works by strongly
binding to ethylene receptor sites, thus preventing binding and the
subsequent signaling that triggers ripening and senescence(Baswal,
Dhaliwal, Singh, Mahajan, & Gill, 2020; Liu et al., 2019; Zhang et al.,
2020). A previous paper also suggested that 1-MCP could influence key
proteins closely associated with the synthesis and response of lignin,
cellulose, ethylene, and abscisic acid (Lin et al., 2018; Xie, Feng, Chen, &
Zhang, 2020). Focusing on the mechanism of 1-MCP and its preservation
effect, many studies had been published addressing issues such as
postharvest lignification, the disassembly of cell wall polysaccharides,
sorption dynamics, the chlorophyll degradation pathway, and the
preservation of various foods (Baswal et al., 2020; Du et al., 2020;
Flaherty et al., 2018; Lim et al., 2016; Lin et al., 2018; Liu et al., 2019; Lv
et al., 2020; Xie et al., 2020).
Due to its special physical and chemical properties (570 mm Hg at
to achieve effective and accurate quantitative analysis of 1-MCP
compared with other pesticides (https://pubchem.ncbi.nlm.nih.
gov/compound/151080#section=LogP). In the previous literatures,
GC-FID equipped with the head space technology tool was the only
detection method (Dong, Rao, Zhu, & Huber, 2019; Lee, Huber,
Watkins, & Hurr, 2012). However, because of its low sensitivity, GC-
FID was usually used for the determination of constant compounds.
According to its molecular formula, GC–MS was a good selection,
which was much more sensitive than GC-FID. But, due to the low
boiling point, the chromatographic retention was another challenge
for GC separation with solvent and matrix. And, the molecular weight
(54 g/mol) of 1-MCP was so small that it was interfering with impu­
rities on GC–MS. Meanwhile, the strict maximum residue limit (MRL)
put forward higher requirements for analytical methods. At present,
Japan has established 0.01 mg/kg as its MRL on apple, pear, and
Japanese persimmon (http://db.ffcr.or.jp/front/pesticide_detail?
id=75375). The European Union (EU) set stricter MRLs on various
foods, and the MRL values ranged from 0.01 mg/kg to 0.05 mg/kg,
referring to 378 foods (https://ec.europa.eu/food/plant/pestic

* Corresponding author.
E-mail address: 173915883@qq.com (W. Wang).
1
These authors contributed equally to this work.

https://doi.org/10.1016/j.foodchem.2021.129854
Received 11 February 2021; Received in revised form 14 April 2021; Accepted 14 April 2021
Available online 20 April 2021
0308-8146/© 2021 Elsevier Ltd. All rights reserved.
M. Dong et al.
ides/eu-pesticidesdatabase/mrls/?event=details&pest_res_ids
=4&product_ids=&v=1&e=search.pr). It was unreasonable and
inconsistent that despite the existence of limits, no suitable residue
analysis method could be selected.
In this work, a brand-new, simple, and reliable analytical method
was proposed for the determination of 1-MCP in vegetables and
fruits. First, referencing the patent “Stable ethylene inhibiting com­
pounds and method for their preparation” (EP1388529A2), 1-MCP
was transformed to 1,2-diiodo-1-methylcyclopropane (C4H6I2)
when 1-MCP was mixed with iodine. During the reaction, the double
bond of 1-MCP was broken, and two iodides were added. After the
derivative reaction, 1-MCP became 1,2-diiodo-1-methylcyclopro­
pane. The molecular weight of 1,2-diiodo-1-methylcyclopropane is
307.9 g/mol, and the boiling point is 214.8 ± 23.0 ◦ C at 760 mmHg,
which reflects greater stability and superiority for chromatographic
analysis (http://www.chemspider.com/Chemical-Structure.974
7883.html). Then, the instrumental analysis condition of 1,2-
diiodo-1-methylcyclopropane was developed. In terms of linearity,
accuracy, precision, matrix effect and sensitivity, the proposed
analytical method was validated in accordance with the guidelines of
the pesticide analytical method of China (NY/T 788-2018, 2018) and
SANTE criteria (Commission, 2019). Finally, as an application, the
proposed method was utilized to monitor the 1-MCP residue in
commercially available samples.
2. Experimental
2.1. Materials
Standard solutions of 1-MCP (3.5%) were obtained from Shanghai
Yuanye Biological Technology Co., LTD (Shanghai, China). HPLC-
grade chemicals, including methanol, n-hexane and ammonium ace­
tate, were purchased from ANPEL Laboratory Technologies, Inc.
(Shanghai, China). Sodium hydroxide and iodine, which were both
analytically pure, were purchased from ANPEL Laboratory Technolo­
gies, Inc. (Shanghai, China).
Standard solutions of 1-MCP (1000 mg/L) were obtained by dis­
solving the accurately weighed solid in methanol and by storing it at
− 20 ◦ C in darkness.
The derivatization reagents were prepared following the steps below:
in an ice water bath, 17.7 g of iodine, 100 mL of methanol and 2.7 g of
ammonium acetate were successively added to a 250 mL reagent bottle
and left for 20 min.
The standard solution of 1,2-diiodo-1-methylcyclopropane was pre­
pared by derivatization, following this step: in an ice water bath, the
standard solution of 1-MCP was added to 5 mL of derivatization reagent
and treated as described in Section 2.2. Then, standard solutions of 1,2-
diiodo-1-methylcyclopropane in n-hexane were obtained and diluted
with n-hexane or matrix.
The samples in the study were all purchased from the agricultural
market, and were storage at − 20 ◦ C after homogenization.
2.2. Sample preparation
Homogeneous samples (5.0 g) were accurately weighed into 15 mL
PTFE centrifuge tubes. According to the patent “Stable ethylene inhib­
iting compounds and method for their preparation” (EP1388529A2), the
reaction was carried out. After adding 5 mL of derivatization reagent,
the mixtures were held for 10 min in an ice water bath, vortexed
vigorously for 20 min, and ultrasonicated for 10 min. Then, 2.5 mL of n-
hexane was added and vortexed for 2 min, and sodium hydroxide so­
lution (1 mol/L) was added until the color disappeared to eliminate
excess iodine. The tube was vortexed again for 30 s and centrifuged at
1000 × g for 5 min. Finally, 1 mL of supernatant was passed through a
0.22-µm nylon filter and analyzed by GC–MS/MS.
2
Food Chemistry 358 (2021) 129854
2.3. GC–MS/MS conditions
The target compound (1,2-diiodo-1-methylcyclopropane) was
determined by GC–MS/MS (GCMS-TQ 8040; Shimadzu Corp., Tokyo,
Japan), which was equipped with an electron bombardment ion source
(EI). A gas chromatographic column (HP-5, 30.0 m × 0.25 mm, 0.25 µm;
Agilent Technology (China) Co., LTD, Shanghai, China) was utilized to
separate the target compound. The injected volume was 1 μL, and the
flow rate of carrier gas (He, ≥99.999%) was 1.67 mL/min under con­
stant current mode. The temperatures of the injector, ion source and
connector of GC–MS were 180 ◦ C, 280 ◦ C, and 300 ◦ C, respectively. The
oven temperature was first held for 2 min at 60 ◦ C and then ramped at
10 ◦ C/min to 180 ◦ C, which was held for 1 min. Finally, the temperature
was ramped at 25 ◦ C/min to 280 ◦ C and held for 1 min. The MS/MS
conditions included the qualitative ion pair (181.10–140.9 m/z) and the
quantitative ion pair (181.10–54.10 m/z), attaining collision energies of
27 V and 15 V. Under the proposed conditions, the retention time of 1,2-
diiodo-1-methylcyclopropane was 7.15 min.
2.4. Method validation
For the proposed method, the validation was carried out, focused at
the linear, matrix effect, accuracy, precision, the limit of detection (LOD),
and limit of quantification (LOQ). First, in the range from 4 to 400 µg/L,
the linearity curve was depicted by five concentration levels and their
corresponding instrument response. Referring to published papers, the
matrix effect (ME) was obtained by determination of the solvent standard
curve and the matrix standard curve, using the following formula: ME =
(the slope of calibration curves in matrix − the slope of calibration curves
in solvent)/the slope of calibration curves in solvent × 100% (Dong et al.,
2016). By spiking at three levels with five replicates, the accuracy and
precision of the analytical method were investigated by the fortified re­
covery test in fruits (apple, grape, and mango) and vegetables (mushroom,
potato, and tomato). In the method validation, the standard solution of 1-
MCP was spiked into the homogeneous samples with different levels, and
it was transformed to 1,2-diiodo-1-methylcyclopropane by the derivative
reaction, and then the concentration of the derivative product 1,2-diiodo-
1-methylcyclopropane was determined using the GC–MS/MS. The ob­
tained concentration was converted to the concentration of 1-MCP for the
calculation of spiking recoveries. For the sensitivity of the analytical
method, the LOD was the concentration that provided three times the
signal-to-noise ratio, and for the LOQ, in according with the published
reports, the lowest spiked level was the LOQ of the analytical method
(Tang et al., 2021).
3. Results and discussion
3.1. Derivative confirmation
A time-of-flight mass spectrometer (TOF-MS), which is a common
tool to qualitatively analyze unknown compounds by detecting the
precise molecular weight as the high-resolution mass spectrum, was
used to identify 1,2-diiodo-1-methylcyclopropane. In this work, a
Water Premier GC-TOF MS under EI mode was used to detect 1,2-
diiodo-1-methylcyclopropane, and the separation was carried out on
a gas chromatographic DB-5 MS column (25.0 m × 250 µm, 0.25 µm).
The injected volume was 1 μL, and the flow rate of carrier gas (He,
≥99.999%) was 1.0 mL/min under constant current mode. The tem­
peratures of the injector, ion source and electron energy were 260 ◦ C,
220 ◦ C, and 70 eV, respectively. The oven temperature included: 60 ◦ C
as the initial temperature and hold 1 min; then up to 250 ◦ C with
15 ◦ C/min and hold 20 min; up to 295 ◦ C with 50 ◦ C/min and hold 15
min. The MS range was from 35 to 750 m/z. As shown in Fig. 1A, the
TOF-MS results showed that the precise molecular weight of the
derivation was 307.8558 m/z, which was similar to the theoretical
value of C4H6I2 (307.85589 m/z) (https://pubchem.ncbi.nlm.nih.
M. Dong et al.
Fig. 1. Chromatogram and mass spectrum of 1-MCP derivatives (1,2-diiodo-1-methylcyclopropane). (A): Mass spectrum of GC-TOF; (B): Chromatogram of GC–MS/
MS; (C): Mass spectrum of GC–MS/MS.
gov/compound/11573113#section=Computed-Properties). On the
other hand, as shown in Fig. 1A, when I- was lost, 181 m/z (C4H6I+)
was detected, and 127 m/z was I+. When the two I- were lost, 54 m/z
(C4H+2
6 ) was obtained. Therefore, the derivation was C4H6I2, proving
that the derivative reaction achieves its intended purpose very well.
3.2. GC–MS/MS analyses
Then, the GC–MS/MS conditions of 1,2-diiodo-1-methylcyclopro­
pane were optimized and established. As shown in Fig. 1B, after in­
jection of the 1 mg/L standard solution, the retention time was 7.15
min under the proposed GC–MS/MS conditions, and first-order frag­
ment ions were obtained under scan mode, including 308 m/z (mo­
lecular ion), 181.10 m/z, 127 m/z and 54 m/z, which were coincident
with the GC-TOF-MS results. Moreover, 181 m/z was selected as the
parent ion due to its highest response and sufficient plasmid ratio.
Finally, under MRM mode, the MS/MS conditions were automatically
optimized and established. As shown in Fig. 1C, the secondary frag­
ment ion at 140.9 m/z was formed by the loss of [C3H6] from [C4H6I]+
(181.10 m/z), and the fragment ion at 54.10 m/z was formed by the
loss of [I] from [C4H6I]+ (181.10 m/z).
Therefore, the GC–MS/MS conditions were mature and certain,
including the qualitative ion pair (181.10–140.9 m/z), the quantitative
ion pair (181.10–54.10 m/z), and their electronic voltages.
3.3. Optimization of the extraction
As shown in the patent, the derivatization reagent included iodine,
ammonium acetate and methanol. Therefore, after derivatization, the
mixture contained iodine, ammonium acetate, methanol, water and
matrix, and 1,2-diiodo-1-methylcyclopropane was thought to be a fat-
soluble compound with log P 2.8 (http://www.chemspider.com/Ch
emical-Structure.9747883.html). Therefore, n-hexane was utilized to
extract the target, and the extraction efficiency was evaluated.
Spiking at 0.1 mg/L in 5 mL methanol, the recoveries of 1,2-diiodo-
1-methylcyclopropane with different volumes of n-hexane (1 mL, 2.5
mL, 5 mL, and 7.5 mL) were determined. The results showed that
regardless of the volume of n-hexane changed, all the recoveries were
3
Food Chemistry 358 (2021) 129854
acceptable, ranging from 93% to 111%, which showed that 1,2-diiodo-
1-methylcyclopropane was more dissolved in n-hexane than methanol.
However, when 1 mL n-hexane was selected, the relative standard
deviation (RSD) was 12.4%, which was much worse than that of the
others (1.72–6.77%), and it was difficult to remove 1 mL of solvent.
Therefore, 2.5 mL n-hexane was used to extract 1,2-diiodo-1-methyl­
cyclopropane from methanol.
During the derivative process, excess iodine was used and then
presented as atropurpureus. To eliminate the redundant iodine, as a
simple approach, sodium hydroxide solution (1 mol/L) was applied
and added until the color was transparent. Therefore, the extraction
and clean-up processes were specific and were estimated during
validation.
3.4. Method validation
After individually spiking at 4, 10, 40, 100, and 400 µg/L in the
matrixes or solvent, calibration curves were drawn and calculated. As
shown in Table 1, there was a good linear relationship between the
concentration of the target compound and the response of the in­
strument, and the coefficients (R2) of the calibration curves were
above 0.962. Then, for the MEs, there were a negative effect in the six
matrixes and the MEs were obvious, ranged from − 89% ~ − 13%.
Therefore, during the quantitative analysis, matrix-matched standard
solution was necessary. Carried out at three spiked levels and
repeated five times, the fortified recoveries and relative standard
deviations (RSDs) were fine in the recovery test, with values of
80–100% and 4–19%, respectively. The LOD was 0.8 µg/kg by esti­
mation under the signal noise ratio, and the LOQ was 5 µg/kg, which
was equal to the lowest spiked levels. Therefore, all the main pa­
rameters of this proposed method met the requirements of residue
analysis, and the LOD (5 µg/kg) was lower than the strictest limits
(10 µg/kg), which proved the good performance of this method.
Therefore, following the Chinese guidelines for the testing of pesti­
cide residues in crops (NY/T 788-2018, 2018) and SANTE criteria
(Commission, 2019), the validation results showed that the estab­
lishment method satisfied the determination of 1-MCP in vegetables
and fruits (Table 2).
M. Dong et al. Food Chemistry 358 (2021) 129854

Table 1
The linear range, linearity curves, linearly dependent coefficients and matrix effects of 1,2-diiodo-1-methylcyclopropane in vegetables and fruits.
Compound Sample Linear range (µg/L) Linear equation R2 Matrix effect (%)

1,2-diiodo-1-methylcyclopropane Solvent 4–400 y = 320920x − 1291.5 1 /

Apple y = 33719x + 1663.9 0.962 − 89
Grape y = 217936x + 1566.5 1 − 32
Mango y = 135331x + 958.77 1 − 58
Mushroom y = 279320x + 1143.3 1 − 13
Potato y = 153818x + 1198.1 1 − 52
Tomato y = 203824x + 455.87 1 − 36

Table 2
Recovery and precision (relative standard deviations, RSDs) of 1-MCP in vegetables and fruits (n = 5).
Matrix Fortified level (μg/kg) Recovery (%) RSD (%) Matrix Fortified level (μg/kg) Recovery (%) RSD (%)

Apple 5 93 7 Mushroom 5 91 16
50 80 15 50 100 12
500 90 6 500 91 12

Grape 5 87 8 Potato 5 87 15
50 100 8 50 90 13
500 99 6 500 92 10

Mango 5 87 19 Tomato 5 95 7
50 84 14 50 91 13
500 84 4 500 89 19

3.5. Method application the work reported in this paper.

To verify the applicability of the proposed method and investigate Acknowledgement

the residue of 1-MCP, 60 samples (10 apples, 10 grapes, 10 mangoes, 10
mushrooms, 10 potatoes and 10 tomatoes) were collected from the local
market, and 1-MCP was measured by the proposed method. The results
showed that all the residue levels of 1-MCP were below the LOQ (5 µg/
kg), as shown in Fig. S1. At that time, China had not yet formulated the
MRL for 1-MCP, but the residual levels of 1-MCP in the samples
consistently satisfied the EU MRLs.
4. Conclusions
The only reported study on determination of 1-MCP used GC-FID
for detection, which could not meet the requirements of residue
evaluation and the MRLs of the EU or Japan. Due to the small mo­
lecular weight and low boiling point of 1-MCP, it was difficult to
achieve effective quantitative analysis by conventional analytical
methods. Therefore, in our work, based on a simple and effective de­
rivative reaction, the 1-MCP was transformed to 1,2-diiodo-1-methyl­
cyclopropane for determination. The method was novel, simple,
effective and accurate and was firstly established for determination of
1-MCP in vegetables and fruits. Finally, to verify the applicability of
the method, this analytical method was applied to monitor the residue
levels of 1-MCP in 60 collated samples.
CRediT authorship contribution statement
Maofeng Dong: Data curation, Formal analysis, Investigation,
Project administration, Writing - original draft. Guangyue Wen: Data
curation, Methodology, Formal analysis. Junshun Li: Data curation,
Methodology. Tan Wang: Investigation, Validation. Jiaqing Huang:
Methodology. Yubo Li: Investigation, Validation. Hongxia Tang:
Methodology. Qiang Sun: Methodology. Weimin Wang: Conceptuali­
zation, Resources, Supervision.
Declaration of Competing Interest
The authors declare that they have no known competing financial
interests or personal relationships that could have appeared to influence
This work was supported by Shanghai Agriculture Commission
Project (2021, NO. 3-2).
Appendix A. Supplementary data
Supplementary data to this article can be found online at https://doi.
org/10.1016/j.foodchem.2021.129854.
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