chiral cyflumetofen; enantioselective degradation; distribution
Abstract :
[en] Ultra-performance convergence chromatography is an environmentally-friendly analytical
method that uses dramatically reduced amounts of organic solvents. In addition, a robust and highly sensitive chiral separation method was developed for the novel chiral acaricide cyflumetofen by using
ultra-performance convergence chromatography coupled with tandem mass spectrometry, which shows that stereoisomer recoveries determined for various apple parts ranged from 78.3% to 119.9%, with the relative standard deviations being lower than 14.0%. The half-lives of (-)-cyflumetofen and (+)-cyflumetofen obtained under 5-fold applied dosage equal to 22.13 and 22.23 days, respectively. For 1.5-fold applied dosage, the respective values were determined as 22.42 and 23.64 days, i.e., the
degradation of (-)-cyflumetofen was insignificantly favored over that of its enantiomer. Importantly, cyflumetofen was unevenly distributed in apples, with its relative contents in apple peel, peduncle, and pomace equal to 50%, 22%, and 16%, respectively. The proposed method can be used to efficiently separate and quantify chiral pesticide with advantages of a shorter analysis time, greater sensitivity, and better environmental compatibility. Additionally, the consumption of apples with residue of cyflumetofen did not pose a health risk to the population if the cyflumetofen applied under satisfactory agricultural practices after the long-term dietary risk assessment.
Disciplines :
Food science
Author, co-author :
GUO, Jing ✱; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences/Key Laboratory of Agro-products Quality and Safety Control in Storage and Transport Process/Laboratory of Agro-products Quality Safety Risk Assessment, Ministry of Agriculture
LIU, Yongguo; Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University (BTBU),
WANG, Fengzhong; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences/Key Laboratory of Agro-products Quality and Safety Control in Storage and Transport Process/Laboratory of Agro-products Quality Safety Risk Assessment, Ministry of Agriculture,
KONG, Zhiqiang; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences/Key Laboratory of Agro-products Quality and Safety Control in Storage and Transport Process/Laboratory of Agro-products Quality Safety Risk Assessment, Ministry of Agriculture,
Sun, Yufeng; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences/Key Laboratory of Agro-products Quality and Safety Control in Storage and Transport Process/Laboratory of Agro-products Quality Safety Risk Assessment, Ministry of Agriculture,
LU, JIA; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences/Key Laboratory of Agro-products Quality and Safety Control in Storage and Transport Process/Laboratory of Agro-products Quality Safety Risk Assessment, Ministry of Agriculture,
JIN, Nuo; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences/Key Laboratory of Agro-products Quality and Safety Control in Storage and Transport Process/Laboratory of Agro-products Quality Safety Risk Assessment, Ministry of Agriculture,
HUANG, Yatao; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences/Key Laboratory of Agro-products Quality and Safety Control in Storage and Transport Process/Laboratory of Agro-products Quality Safety Risk Assessment, Ministry of Agriculture,
LIU, Jiameng; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences/Key Laboratory of Agro-products Quality and Safety Control in Storage and Transport Process/Laboratory of Agro-products Quality Safety Risk Assessment, Ministry of Agriculture,
Francis, Frédéric ; Université de Liège - ULiège > Agronomie, Bio-ingénierie et Chimie (AgroBioChem) > Gestion durable des bio-agresseurs
FAN, Bei; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences/Key Laboratory of Agro-products Quality and Safety Control in Storage and Transport Process/Laboratory of Agro-products Quality Safety Risk Assessment, Ministry of Agriculture,
✱ These authors have contributed equally to this work.
Language :
English
Title :
Residue and Dietary Risk Assessment of Chiral Cyflumetofen in Apple
Alternative titles :
[en] 比利时
Publication date :
02 May 2018
Journal title :
Molecules
eISSN :
1420-3049
Publisher :
Multidisciplinary Digital Publishing Institute (MDPI), Switzerland
Wolfe, K.; Wu, X.; Liu, R.H. Antioxidant Activity of Apple Peels. J. Agric. Food Chem. 2003, 51, 609–614. [CrossRef] [PubMed]
Takahashi, N.; Nakagawa, H.; Sasama, Y.; Ikemi, N. Development of a new acaricide, cyflumetofen. J. Pestic. Sci. 2012, 37, 263–264. [CrossRef]
Hayashi, N.; Sasama, Y.; Takahashi, N.; Ikemi, N. Cyflumetofen, a novel acaricide—Its mode of action and selectivity. Pest Manag. Sci. 2013, 69, 1080–1084. [CrossRef] [PubMed]
Liu, W.; Gan, J.D.; Jury, W.A. Enantioselectivity in environmental safety of current chiral insecticides. Proc. Natl. Acad. Sci. USA 2005, 102, 701–706. [CrossRef] [PubMed]
Liu, Y.; Zhang, X.; Liu, C.; Yang, R.; Xu, Z.; Zhou, L.; Sun, Y.; Lei, H. Enantioselective and Synergetic Toxicity of Axial Chiral Herbicide Propisochlor to SP2/0 Myeloma Cells. J. Agric. Food Chem. 2015, 63, 7914–7920. [CrossRef] [PubMed]
Sun, D.; Pang, J.; Zhou, Z.; Jiao, B. Enantioselective environmental behavior and cytotoxicity of chiral acaricide cyflumetofen. Chemosphere 2016, 161, 167–173. [CrossRef] [PubMed]
Kong, Z.; Shan, W.; Dong, F.; Liu, X.; Xu, J.; Li, M.; Zheng, Y. Effect of home processing on the distribution and reduction of pesticide residues in apples. Food Addit. Contam. Part A 2012, 29, 1280–1287. [CrossRef] [PubMed]
Ling, Y.; Wang, H.; Yong, W.; Zhang, F.; Sun, L.; Yang, M.L.; Wu, Y.N.; Chu, X.G. The effects of washing and cooking on chlorpyrifos and its toxic metabolites in vegetables. Food Control 2011, 22, 54–58. [CrossRef]
Liu, N.; Dong, F.; Xu, J.; Liu, X.; Chen, Z.; Pan, X.; Chen, X.; Zheng, Y. Enantioselective separation and pharmacokinetic dissipation of cyflumetofen in field soil by ultra-performance convergence chromatography with tandem mass spectrometry. J. Sep. Sci. 2016, 39, 1363–1370. [CrossRef] [PubMed]
Gałuszka, A.; Migaszewski, Z.M.; Konieczka, P.; Namie´ snik, J. Analytical Eco-Scale for assessing the greenness of analytical procedures. Trends Anal. Chem. 2012, 37, 61–72. [CrossRef]
Płotka-Wasylka, J. A new tool for the evaluation of the analytical procedure: Green Analytical Procedure Index. Talanta 2018, 18, 204–209. [CrossRef] [PubMed]
Geng, Y.; Zhao, L.; Zhao, J.; Guo, B.; Ma, P.; Li, Y.; Zhang, T. Development of a supercritical fluid chromatography-tandem mass spectrometry method for the determination of lacidipine in beagle dog plasma and its application to a bioavailability study. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2014, 945–946, 121–126. [CrossRef] [PubMed]
Gong, X.; Qi, N.; Wang, X.; Lin, L.; Li, J. Ultra-performance convergence chromatography (UPC2) method for the analysis of biogenic amines in fermented foods. Food Chem. 2014, 162, 172–175. [CrossRef] [PubMed]
Du, T.T.; Stander, M.A.; Swart, A.C. A high-throughput UPC2-MS/MS method for the separation and quantification of C19 and C21 steroids and their C11-oxy steroid metabolites in the classical, alternative, backdoor and 11OHA4 steroid pathways. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2018, 1080, 71–81.
Chen, Z.; Dong, F.; Xu, J.; Liu, X.; Cheng, Y.; Liu, N.; Tao, Y.; Pan, X.; Zheng, Y. Stereoselective separation and pharmacokinetic dissipation of the chiral neonicotinoid sulfoxaflor in soil by ultraperformance convergence chromatography/tandem mass spectrometry. Anal. Bioanal. Chem. 2014, 406, 6677–6690. [CrossRef] [PubMed]
Kim, H.S.; Jin, M.C.; Kwon, B.I.; Lee, A.R.; Kim, H.K.; Lee, A.Y. Development and validation of an ultra-performance convergence chromatography method for the quality control of Angelica gigas Nakai. J. Sep. Sci. 2016, 39, 4035–4041. [CrossRef] [PubMed]
Marcic, D. Acaricides in modern management of plant-feeding mites. J. Pest Sci. 2012, 85, 395–408. [CrossRef]
Ullah, M.S.; Gotoh, T. Laboratory-based toxicity of some acaricides to Tetranychus macfarlanei and Tetranychus truncatus (Acari: Tetranychidae). Int. J. Acarol. 2013, 39, 244–251. [CrossRef]
Wang, Y.; Zhao, S.; Shi, L.; Xu, Z.; He, L. Resistance selection and biochemical mechanism of resistance against cyflumetofen in Tetranychus cinnabarinus (Boisduval). Pestic. Biochem. Physiol. 2014, 111, 24–30. [CrossRef] [PubMed]
Van, L.T.; Tirry, L.; Yamamoto, A.; Nauen, R.; Dermauw, W. The economic importance of acaricides in the control of phytophagous mites and an update on recent acaricide mode of action research. Pestic. Biochem. Physiol. 2015, 121, 12–21.
Zhao, H.Z.; Chen, Y.X.; Nan, L.I.; Xu, Y.; Sai-Nan, L.I.; Liu, W.H. Cytotoxicity of cyflumetofen on SH-SY5Y cells and possible mechanism. Chin. J. Pharmacol. Toxicol. 2017, 31, 318–324.
Xuan-Xiang, H.U.; Shao, M.H.; Hong, W.Y.; Yan-Jun, W.U.; Han-Yun, K.E.; Zhao, S.F.; Bureau, J.A. Residue dynamics and safely applying technology of cyflumetofen in strawberry. Acta Agric. Zhejiangensis 2014, 26, 1558–1563.
Liu, N.; Dong, F.; Chen, Z.; Xu, J.; Liu, X.; Duan, L.; Li, M.; Zheng, Y. Distribution behaviour of acaricide cyflumetofen in tomato during home canning. Food Addit. Contam. Part A 2016, 33, 824–830. [CrossRef] [PubMed]
Li, Y.; Dong, F.; Liu, X.; Xu, J.; Han, Y.; Zheng, Y. Chiral fungicide triadimefon and triadimenol: Stereoselective transformation in greenhouse crops and soil, and toxicity to Daphnia magna. J. Hazard. Mater. 2014, 265, 115–123. [CrossRef] [PubMed]
Li, M.; Liu, X.; Dong, F.; Xu, J.; Kong, Z.; Li, Y.; Zheng, Y. Simultaneous determination of cyflumetofen and its main metabolite residues in samples of plant and animal origin using multi-walled carbon nanotubes in dispersive solid-phase extraction and ultrahigh performance liquid chromatography- tandem mass spectrome. J. Chromatogr. A 2013, 1300, 95–103. [PubMed]
Yoshida, T.; Ikemi, N.; Takeuchi, Y.; Ebino, K.; Kojima, S.; Chiba, Y.; Nakashima, N.; Kawakatsu, H.; Saka, M.; Harada, T. A repeated dose 90-day oral toxicity study of cyflumetofen, a novel acaricide, in rats. J. Toxicol. Sci. 2012, 37, 91–104. [CrossRef] [PubMed]
Ye, M.; Nie, J.; Li, Z.; Cheng, Y.; Zheng, L.; Xu, G.; Yan, Z. Health risks of consuming apples with carbendazim, imidacloprid, and thiophanate-methyl in the Chinese population: Risk assessment based on a nonparametric probabilistic evaluation model. Hum. Ecol. Risk Assess. Int. J. 2016, 22, 1106–1121. [CrossRef]
Williams, A. Opportunities for chiral chemicals. Pestic. Sci. 1996, 46, 3–9. [CrossRef]
Prat, D.; Hayler, J.; Wells, A. A survey of solvent selection guides. Green Chem. 2014, 16, 4546–4551. [CrossRef]
Tobiszewski, M.; Tsakovski, S.; Simeonov, V.; Namie´ snik, J.; Penapereira, F. Correction: A solvent selection guide based on chemometrics and multicriteria decision analysis. Green Chem. 2015, 17, 4773–4785. [CrossRef]
European Commission. Guidance Document on Analytical Quality Control and Validation Procedures for Pesticide Residues Analysis in Food and Feed. SANTE/11813/2017. Available online: https://ec.europa.eu/food/sites/food/files/plant/docs/pesticides_mrl_guidelines_wrkdoc_2017-11813.pdf (accessed on 1 March 2018).
Xu, R.; Mao, F.; Zhao, Y.; Wang, W.; Fan, L.; Gao, X.; Zhao, J.; Tian, H. UPLC Quantitative Analysis of Multi-Components by Single Marker and Quality Evaluation of Polygala tenuifolia Wild. Extracts. Molecules 2017, 22. [CrossRef] [PubMed]
Zhang, H.; Wang, X.; Qian, M.; Wang, X.; Xu, H.; Xu, M.; Wang, Q. Residue analysis and degradation studies of fenbuconazole and myclobutanil in strawberry by chiral high-performance liquid chromatography-tandem mass spectrometry. J. Agric. Food Chem. 2011, 59, 12012–12017. [CrossRef] [PubMed]
Chen, Z.; Dong, F.; Pan, X.; Xu, J.; Liu, X.; Wu, X.; Zheng, Y. Influence of Uptake Pathways on the Stereoselective Dissipation of Chiral Neonicotinoid Sulfoxaflor in Greenhouse Vegetables. J. Agric. Food Chem. 2016, 64, 2655–2660. [CrossRef] [PubMed]
Sun, M.; Liu, D.; Zhou, G.; Li, J.; Qiu, X.; Zhou, Z.; Wang, P. Enantioselective degradation and chiral stability of malathion in environmental samples. J. Agric. Food Chem. 2012, 60, 372–379. [CrossRef] [PubMed]
Han, Y.; Xu, J.; Dong, F.; Li, W.; Liu, X.; Li, Y.; Kong, Z.; Zhu, Y.; Liu, N.; Zheng, Y. The fate of spirotetramat and its metabolite spirotetramat-enol in apple samples during apple cider processing. Food Control 2013, 34, 283–290. [CrossRef]
European Food Safety Authority. Conclusion on the peer review of the pesticide risk assessment of the active substance cyflumetofen. EFSA J. 2006, 10. [CrossRef]
Nie, J.Y.; Li, Z.X.; Liu, C.D.; Fang, J.B.; Wang, C.; Guo, Y.Z.; Lei, S.R.; Li, H.F.; Xu, G.F.; Yan, Z. Risk Assessment of Pesticide Residues in Apples. Sci. Agric. Sin. 2014, 47, 3655–3667.
Lozowicka, B. Health risk for children and adults consuming apples with pesticide residue. Sci. Total Environ. 2015, 502, 184–198. [CrossRef] [PubMed]
He, D.; Ye, X.; Xiao, Y.; Zhao, N.; Long, J.; Zhang, P.; Fan, Y.; Ding, S.; Jin, X.; Tian, C. Dietary exposure to endocrine disrupting chemicals in metropolitan population from China: A risk assessment based on probabilistic approach. Chemosphere 2015, 139, 2–8. [CrossRef] [PubMed]
Szpyrka, E.; Walorczyk, S. Dissipation kinetics of fluquinconazole and pyrimethanil residues in apples intended for baby food production. Food Chem. 2013, 141, 3525–3530. [CrossRef] [PubMed]
Peterson, R.K. Comparing ecological risks of pesticides: The utility of a Risk Quotient ranking approach across refinements of exposure. Pest Manag. Sci. 2006, 62, 46–56. [CrossRef] [PubMed]