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| forchlorfenuron |
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| CHEBI:81861 |
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| A member of the class of phenylureas that is urea substituted by a phenyl group and a 2-chloropyridin-4-yl group at positions 1 and 3 respectively. It is a plant growth regulator widely used in agriculture for improving fruit quality and fruit size. |
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This entity has been manually annotated by the ChEBI Team.
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| ChemicalBook:CB3343940, eMolecules:535946, ZINC000000402792 |
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more structures >>
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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js Jmol JavaScript applet jmolApplet0_object__481567221982786__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__481567221982786__) call loadScript javascripts\jsmol\core\corestate.z.js viewerOptions: { "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:81861","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__481567221982786__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"481567221982786","bgcolor":"#000" } (C) 2012 Jmol Development Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $ java.vendor: j2s java.version: 0.0 os.name: j2s Access: ALL memory: 0.0/0.0 processors available: 1 useCommandThread: false appletId:jmolApplet0_object (signed) starting HoverWatcher_1 getValue emulate = null defaults = "Jmol" getValue boxbgcolor = null getValue bgcolor = #000 backgroundColor = "#000" getValue ANIMFRAMECallback = null getValue APPLETREADYCallback = Jmol._readyCallback APPLETREADYCallback = "Jmol._readyCallback" getValue ATOMMOVEDCallback = null getValue CLICKCallback = null getValue ECHOCallback = null getValue ERRORCallback = null getValue EVALCallback = null getValue HOVERCallback = null getValue LOADSTRUCTCallback = null getValue MEASURECallback = null getValue MESSAGECallback = null getValue MINIMIZATIONCallback = null getValue PICKCallback = null getValue RESIZECallback = null getValue SCRIPTCallback = null getValue SYNCCallback = null getValue STRUCTUREMODIFIEDCallback = null getValue doTranslate = null language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__481567221982786__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol 245 - Ideal conformer Mrv1927 10122114093D starting HoverWatcher_5 Time for openFile(245 - Ideal conformer Mrv1927 10122114093D 27 28 0 0 0 0 999 V2000 5.2850 0.8830 -0.5250 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.8560 0.2500 0.4510 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9280 -0.8190 -0.1240 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3450 0.7320 0.8280 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5110 0.0500 0.4790 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5330 -1.3420 0.4100 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7050 -1.9790 0.0600 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7970 -1.2870 -0.2070 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8170 0.0320 -0.1540 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6830 0.7440 0.1830 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9760 0.9540 0.7070 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2120 0.5000 0.2360 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4860 -0.8620 0.2010 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7070 -1.3070 -0.2650 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6570 -0.4000 -0.6970 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3870 0.9560 -0.6640 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1700 1.4080 -0.1940 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3980 1.5520 1.3420 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6430 -1.9140 0.6290 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7300 -3.0570 0.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7040 1.8240 0.2160 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9250 1.7770 1.2190 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7440 -1.5710 0.5380 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9200 -2.3660 -0.2920 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6110 -0.7510 -1.0620 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1310 1.6620 -1.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9620 2.4680 -0.1640 H 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 14 13 2 0 0 0 0 14 15 1 0 0 0 0 9 10 2 0 0 0 0 9 8 1 0 0 0 0 13 12 1 0 0 0 0 15 16 2 0 0 0 0 3 2 2 0 0 0 0 10 5 1 0 0 0 0 8 7 2 0 0 0 0 2 11 1 0 0 0 0 2 4 1 0 0 0 0 12 11 1 0 0 0 0 12 17 2 0 0 0 0 5 4 1 0 0 0 0 5 6 2 0 0 0 0 7 6 1 0 0 0 0 16 17 1 0 0 0 0 4 18 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 M END): 17 ms reading 27 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 27 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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| Forchlorfenuron is a plant growth regulator. It has been approved for use on kiwifruit and grapes in the United States, and it has been associated with news of watermelons exploding in China. |
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Read full article at Wikipedia
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| InChI=1S/C12H10ClN3O/c13-11-8-10(6-7-14-11)16-12(17)15-9-4-2-1-3-5-9/h1-8H,(H2,14,15,16,17) |
| GPXLRLUVLMHHIK-UHFFFAOYSA-N |
| ClC1=NC=CC(NC(=O)NC2=CC=CC=C2)=C1 |
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plant growth regulator
A chemical, natural or artificial, that can affect the rate of growth of a plant.
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View more via ChEBI Ontology
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1-(2-chloropyridin-4-yl)-3-phenylurea
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1-(2-chloro-4-pyridyl)-3-phenylurea
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Alan Wood's Pesticides
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CPPU
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ChemIDplus
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N-(2-chloro-4-pyridinyl)-N'-phenylurea
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Alan Wood's Pesticides
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N-(2-chloro-4-pyridyl)-N'-phenylurea
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ChemIDplus
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N-(2-chloropyridin-4-yl)-N'-phenylurea
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Alan Wood's Pesticides
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N-phenyl-N'-(2-chloro-4-pyridyl)urea
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ChEBI
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4PU-30
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PPDB
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CN-11-3183
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ChEBI
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Fulmet
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ChEBI
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KT-30
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ChemIDplus
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PreStage
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PPDB
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Prestige
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PPDB
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Sitofex
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ChEBI
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SKW 20010
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PPDB
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Trigger
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PPDB
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245
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PDBeChem
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358
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PPDB
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84301
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ChemSpider
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C18604
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KEGG COMPOUND
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forchlorfenuron
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Alan Wood's Pesticides
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Forchlorfenuron
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Wikipedia
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HMDB0252436
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HMDB
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| View more database links |
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68157-60-8
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CAS Registry Number
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ChemIDplus
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Wang Q, Su H, Yue N, Li M, Li C, Wang J, Jin F (2021)
Dissipation and risk assessment of forchlorfenuron and its major metabolites in oriental melon under greenhouse cultivation.
Ecotoxicology and environmental safety 225, 112700 [PubMed:34500385]
[show Abstract]
Forchlorfenuron is a widely used plant growth regulator. The uptake of forchlorfenuron and its major metabolites poses a potential risk for human health. However, little is known about the dissipation of forchlorfenuron and its major metabolites in agricultural food. In this study, the metabolite 4-hydroxyphenyl-forchlorfenuron was first identified in oriental melon, which exhibited the highest level of residues of 4.42-5.12 μg/kg on the 4-7th days after application. Forchlorfenuron was found to be dissipated rapidly in melon at the recommended application rates, with half-lives ranging from 1.20 to 1.33 days. The rate of dissipation of 4-hydroxyphenyl-forchlorfenuron was greater than that of metabolism from forchlorfenuron in the oriental melon. However, the other metabolite, 3-hydroxyphenyl-forchlorfenuron, was not detected in oriental melon. The risk assessment showed that the acute and chronic dietary exposure risks of forchlorfenuron in oriental melon were 0.0011-0.0037% and 0.06-0.12%, respectively, suggesting little health risk to Chinese consumers. | Gong G, Kam H, Tse YC, Giesy JP, Seto SW, Lee SM (2021)
Forchlorfenuron (CPPU) causes disorganization of the cytoskeleton and dysfunction of human umbilical vein endothelial cells, and abnormal vascular development in zebrafish embryos.
Environmental pollution (Barking, Essex : 1987) 271, 115791 [PubMed:33401215]
[show Abstract]
Forchlorfenuron (CPPU) has been used worldwide, to boost size and improve quality of various agricultural products. CPPU and its metabolites are persistent and have been detected frequently in fruits, water, sediments, and organisms in aquatic systems. Although the public became aware of CPPU through the exploding watermelon scandal of 2011 in Zhenjiang, China, little was known of its potential effects on the environment and wildlife. In this study, adverse effects of CPPU on developmental angiogenesis and vasculature, which is vulnerable to insults of persistent toxicants, were studied in vivo in zebrafish embryos (Danio rerio). Exposure to 10 mg CPPU/L impaired survival and hatching, while development was hindered by exposure to 2.5 mg CPPU/L. Developing vascular structure, including common cardinal veins (CCVs), intersegmental vessels (ISVs) and sub-intestinal vessels (SIVs), were significantly restrained by exposure to CPPU, in a dose-dependent manner. Also, CPPU caused disorganization of the cytoskeleton. In human umbilical vein endothelial cells (HUVECs), CPPU inhibited proliferation, migration and formation of tubular-like structures in vitro. Results of Western blot analyses revealed that exposure to CPPU increased phosphorylation of FLT-1, but inhibited phosphorylation of FAK and its downstream MAPK pathway in HUVECs. In summary, CPPU elicited developmental toxicity to the developing endothelial system of zebrafish and HUVECs. This was do, at least in part due to inhibition of the FAK/MAPK signaling pathway rather than direct interaction with the VEGF receptor (VEGFR). | Zhu D, Ping L, Qian R, Chen C, Hong Y, Tong Z, Yang X (2021)
Dissipation behavior, residue dynamics, and dietary risk assessment of forchlorfenuron in postharvest kiwifruits during simulated cold chain logistics and store shelf life.
Environmental science and pollution research international 28, 20002-20011 [PubMed:33410058]
[show Abstract]
Forchlorfenuron (CPPU) is often applied during the cultivation of kiwifruit to produce larger fruit. To address degradation patterns of CPPU during simulated cold chain logistics and simulated shelf life of the fruit after harvest, appropriate storage methods and safe consumption behavior can be investigated. In this study, an ultra-high-performance liquid chromatography-tandem mass spectrometry method was adopted to detect CPPU residues under different conditions. CPPU in kiwifruit stored at 6 °C had a half-life of 40.8-77.0 days. However, when kiwifruit was stored at 0 °C under simulated cold chain storage conditions, the half-life of CPPU was 63.0-115.5 days, implying that lower storage temperatures can reduce the degradation rate of CPPU. The residues of CPPU in kiwifruit pulp declined with time, and the reduction followed the first-order kinetics equation. More CPPU residues were present in the pulp of postharvest kiwifruit treated with exogenous ethylene than in the pulp of untreated kiwifruit. Thus, using exogenous ethylene for artificial ripening after harvest is not recommended. We determined that the appropriate cold chain storage temperature is 6 °C. It is recommended that the public select kiwifruit stored for at least 2 weeks. The estimated chronic and acute dietary risk quotients of CPPU are ≤ 0.79% and ≤ 0.11%, respectively. Therefore, it is highly unlikely that consumers will be poisoned by CPPU due to kiwifruit consumption. Our results provide scientific evidence regarding the adoption of appropriate kiwifruit storage methods and consumption behavior to enhance consumption safety. | Ren Y, Xiang P, Xie Q, Yang H, Liu S (2021)
Rapid analysis of forchlorfenuron in fruits using molecular complex-based dispersive liquid-liquid microextraction.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 38, 637-645 [PubMed:33721551]
[show Abstract]
The main sample preparation method for analysis of pesticide residues in fruits is QuEChERS. In this study, a novel sample preparation method using molecular complex-based dispersive liquid-liquid microextraction is introduced with detection of forchlorfenuron by high-performance liquid chromatography coupled with diode array and mass spectrometric detection. Sample treatment involves initial extraction of a 5 g sample with 3 mL acetonitrile, and then the selective concentration of the analyte is performed using 150 µL tributyl phosphate by forming intermolecular hydrogen bonds with the analyte. The extraction mechanism was proved using ATR-FTIR. Under the optimised conditions, recovery rates varied between 88% and 107% for various sample matrices spiked at three levels in the range 0.01-0.1 mg kg-1. Intra-day and inter-day repeatabilities were in the ranges of 2.2-8.0% and 1.6-9.5%, respectively. Detection limit and quantitation limit were 0.33 µg kg-1 and 1.09 µg kg-1 for diode-array detection; 0.01 µg kg-1 and 0.04 µg kg-1 for tandem mass spectrometry detection. This method was successfully applied for the analysis of 149 various fruits. The analyte was found in 4 of the 149 samples and the contents were not over the specific maximum residue limit established by domestic and international regulations. | Zhao N, Ze S, Liu N, Hu L, Ji M, Li Q, Yang B (2021)
Exogenous phytohormone application and transcriptome analysis of Mikania micrantha provides insights for a potential control strategy.
Genomics 113, 964-975 [PubMed:33610796]
[show Abstract]
Effective and complete control of the invasive weed Mikania micrantha is required to avoid increasing damages. We exogenously applied indole 3-acetic acid (IAA), gibberellin (GA), and N-(2-Chloro-4-pyridyl)-N'-phenylurea (CPPU), and their combinations i.e. IAA + CPPU (IC), GA + CPPU (GC), and GA + IAA + CPPU (GIC), at 5, 10, 25, 50, and 75 ppm against distilled water as a control (CK), to examine their effects on the weed. The increasing concentrations of these hormones when applied alone or in combination were fatal to M. micrantha and led towards the death of inflorescences and/or florets. CPPU and GIC were found as the most effective phytohormones. Transcriptome analysis revealed differential regulation of genes in auxin, cytokinin, gibberellin and abscisic acid signaling pathways, suggesting their role in the prohibition of axillary bud differentiation. Collectively, CPPU and GIC at a high concentration (75 ppm) could be used as a control measure to protect forests and other lands from the invasion of M. micrantha. | Tyagi K, Maoz I, Kochanek B, Sela N, Lerno L, Ebeler SE, Lichter A (2021)
Cytokinin but not gibberellin application had major impact on the phenylpropanoid pathway in grape.
Horticulture research 8, 51 [PubMed:33642590]
[show Abstract]
Cytokinin and gibberellic acid (GA) are growth regulators used to increase berry size in seedless grapes and it is of interest to understand their effects on the phenylpropanoid pathway and on ripening processes. GA3 and synthetic cytokinin forchlorfenuron (N-(2-chloro-4-pyridyl)-N'-phenylurea, CPPU) and their combination were applied to 6 mm diameter fruitlets of 'Sable Seedless', and berries were sampled 51 and 70 days (d) following application. All treatments increased berry size and delayed sugar accumulation and acid degradation with a stronger effect of CPPU. CPPU, but not GA, reduced berry color and the levels of anthocyanins. While CPPU reduced the levels of anthocyanins by more than 50%, the combined treatment of GA+CPPU reduced the levels by about 25% at 51 d. CPPU treatment had minor effects on flavonols content but increased the levels of monomeric flavan-3-ols by more than two-fold. Phloroglucinol analysis using HPLC showed that proanthocyanidin content was significantly increased by CPPU, whereas mean degree of polymerization was reduced from 26 to 19. Volatile analysis by GC-MS showed changes in composition with CPPU or GA treatment with potential impact on flavor. RNA-seq analysis showed that GA had a minor overall effect on the transcriptome whereas CPPU had pronounced effects on gene expression at both 51 and 70 d. Comparing the control and CPPU at similar Brix of ca. 19.7°, a reduced expression of stilbene synthases (STSs) including their regulators MYB14 and MYB15, and other phenylpropanoid-related genes was observed in CPPU-treated grapes. Overall, our study shows that CPPU had a major influence on the phenylpropanoid pathway and affected multiple ripening-related processes. | Shan T, Zhang X, Guo C, Guo S, Zhao X, Yuan Y, Yue T (2021)
Identity, Synthesis, and Cytotoxicity of Forchlorfenuron Metabolites in Kiwifruit.
Journal of agricultural and food chemistry 69, 9529-9535 [PubMed:34382788]
[show Abstract]
Forchlorfenuron (CPPU) is a plant growth regulator widely used in kiwifruit production. Although research on the toxicological and environmental effects of CPPU is well-established, the nature and toxicological properties of its metabolites are much less well-known. Using high resolution mass spectrometry and nuclear magnetic resonance, the CPPU previously unidentified metabolites in Xuxiang and Jinyan kiwifruit were identified as N-(2-chloro-4-pyridinyl)-N'-(2-hydroxy-4-methoxyphenyl)-urea (metabolite 1) and N-phenyl-N'-4-pyridinylurea (metabolite 2, CAS: 1932-35-0). Their structures were confirmed by synthesis (metabolite 1) and by comparison with a commercial standard (metabolite 2). Quantitative studies demonstrate that CPPU and its metabolites are mainly retained in the kiwifruit peel, while the content is dependent on the nature of the peel surface, with the smoother peel of Jinyan kiwifruit retaining smaller amounts of the compound. Cell viability experiments in Caco2 and Lo2 cells show that the metabolites may have a lower cytotoxicity compared to the parent compound CPPU. | Ping L, Xu B, Zhou Q, Hong Y, Sun Q, Wang J, Zhu D (2021)
Comparative Pharmacokinetic Study of Forchlorfenuron in Adult and Juvenile Rats.
Molecules (Basel, Switzerland) 26, 4276 [PubMed:34299551]
[show Abstract]
Forchlorfenuron (CPPU) is a plant growth regulator extensively used in agriculture. However, studies on CPPU pharmacokinetics are lacking. We established and validated a rapid, sensitive, and accurate liquid chromatography-mass spectrometry method for CPPU detection in rat plasma. CPPU pharmacokinetics was evaluated in adult and juvenile rats orally treated with 10, 30, and 90 mg/kg of the compound. The area under the plasma drug concentration-time curve from 0 to 24 h (AUC), at the final time point sampled (AUC0-t), and the maximum drug concentration of CPPU increased in a dose-dependent manner. The pharmacokinetic parameters AUC0-t and absolute bioavailability were higher in the juvenile rats than in adult rats. The mean residence time and AUC0-t of juvenile rats in the gavage groups, except for the 10 mg/kg dose, were significantly higher in comparison to those observed for adult rats (p < 0.001). The plasma clearance of CPPU in juvenile rats was slightly lower than that in the adult rats. Taken together, juvenile rats were more sensitive to CPPU than adult rats, which indicates potential safety risks of CPPU in minors. | Cong L, Wu T, Liu H, Wang H, Zhang H, Zhao G, Wen Y, Shi Q, Xu L, Wang Z (2020)
CPPU may induce gibberellin-independent parthenocarpy associated with PbRR9 in 'Dangshansu' pear.
Horticulture research 7, 68 [PubMed:32377358]
[show Abstract]
Parthenocarpy is a valuable trait in self-incompatible plants, such as pear. N-(2-chloro-4-pyridyl)-N'-phenylurea (CPPU), a synthetic cytokinin analog, can induce parthenocarpy in pear (Pyrus spp.), but the mechanism of induction is unclear. To investigate the role of gibberellin in CPPU-induced parthenocarpy in pear, CPPU supplemented with paclobutrazol (PAC) was sprayed onto 'Dangshansu' pear. We found that the fruit set rate of pear treated with CPPU supplemented with PAC was identical to that in a CPPU-alone treatment group. In regard to cell development, CPPU mainly promoted hypanthium cell division and expansion, and PAC application had no influence on CPPU-induced cell development. RNA sequencing revealed that gibberellin 20 oxidase and gibberellin 3 oxidase genes were not differentially expressed following CPPU treatment. According to the analysis of fruit phytohormone content, the CPPU treatments did not induce gibberellin biosynthesis. These results suggest that CPPU-induced parthenocarpy may be gibberellin independent in 'Dangshansu' pear. After CPPU treatment, the indole acetic acid (IAA) content in fruit was significantly increased, and the abscisic acid (ABA) content was significantly decreased. Similarly, RNA sequencing revealed that many genes involved in the auxin and ABA pathways were significantly differentially expressed in the CPPU treatment groups; among them, indole-3-pyruvate monooxygenase (YUCCA) was significantly upregulated and 9-cis-epoxycarotenoid dioxygenase (NCED) was significantly downregulated. IAA and ABA may thus play important roles in CPPU-induced parthenocarpy. PbTwo-component response regulator9 (PbRR9), PbYUCCA4, and PbNCED6 were then selected to further elucidate the mechanism of CPPU-induced parthenocarpy. A yeast one-hybrid assay indicated that PbRR9 can combine with the PbYUCCA4 and PbNCED6 promoters. Dual luciferase assays revealed that PbRR9 can promote and repress the activities of the PbYUCCA4 and PbNCED6 promoters, respectively. After the transient expression of PbRR9 in fruits, PbYUCCA4 expression was significantly upregulated, and PbNCED6 expression was significantly downregulated. This study uncovered a CPPU-induced parthenocarpy mechanism that is different from that in tomato. CPPU may upregulate PbYUCCA4 and downregulate PbNCED6 by upregulating PbRR9, thereby increasing IAA content and decreasing ABA content to ultimately induce parthenocarpy in 'Dangshansu' pear. However, because only a single time point was used and because 'botanical' and 'accessory' fruits have different structures, this conclusion is still preliminary. | Li P, Lu Y, Cao J, Li M, Yang C, Yan H (2020)
Imidazolium ionic-liquid-modified phenolic resin for solid-phase extraction of thidiazuron and forchlorfenuron from cucumbers.
Journal of chromatography. A 1623, 461192 [PubMed:32505285]
[show Abstract]
An imidazolium ionic-liquid-modified phenolic resin (ILPR) was synthesized using 3-aminophenol as a functional monomer, glyoxylic acid as a green cross-linker, and polyethylene glycol 6000 as a porogen. The obtained ILPR showed better extraction of benzoylurea plant hormones thidiazuron and forchlorfenuron than the unmodified phenolic resin because the imidazolium IL provides more interaction modes with the analytes. ILPR, as a tailored adsorbent for solid-phase extraction, was coupled with high-performance liquid chromatography (ILPR‒SPE‒HPLC) for the simultaneous determination of thidiazuron and forchlorfenuron in cucumbers. Good linearity of the ILPR‒SPE‒HPLC method was obtained, ranging from 0.0100 to 5.00 μg g-1 with a correlation coefficient (r) ≥ 0.9999. The recoveries of spiked samples ranged from 91.4% to 100.7% with a relative standard deviation of ≤ 6.0%. | Li M, Guo X, Chen Y, Zhang K, Bai Q, Gao Z, Long F (2020)
The degradation of forchlorfenuron in the model kiwifruit juice by ultrasonic treatment
Journal of food processing and preservation. 44, Not Available [Agricola:IND606892712]
[show Abstract]
Forchlorfenuron (CPPU), as a plant growth regulator, is widely applied to promote fruits and vegetables yield. The degradation of CPPU in model kiwifruit juice by sonication was investigated in the present study. Results showed that bath sonication was effective in eliminating CPPU in model kiwifruit juice, and the ultrasonic power, time and temperature significantly influenced the degradation of phorate (p < .05). The maximum degradations were achieved 72.01% after the ultrasonic treatment at 600 W, 45°C for 40 min. The primary and secondary factor order of the key factors of ultrasonic treatment was temperature > treatment time > power through analysis of variance for response surface quadratic model. Furthermore, 3‐hydroxyphenyl‐forchlorfenuron and 4‐hydroxyphenyl‐forchlorfenuron were identified as the degradation products of CPPU by UPCL‐Q‐TOF‐MS. PRACTICAL APPLICATIONS: Kiwifruit had grown throughout the world owing to its good taste, flavor, and significant nutritional. Forchlorfenuron (1‐(2‐chloro‐4‐pyridyl)‐3‐phenylurea) is the most widely used plant growth regulators (PGR) for kiwifruit cultivation and protection. Ultrasonic treatment may effectively degrade PGR residues and mostly retain the sensory and nutritional quality of the product. Compared to other thermal treatments, forchlorfenuron subjected to ultrasonic treatment maybe show better removal efficiency. Thus, as an easy operation and low‐cost processing technology, ultrasonic technique may be commercially useful to develop forchlorfenuron residues in Kiwifruit juice and other PGR residues. CATALOGUE NUMBER OF CHEMICALS: Forchlorfenuron (purity > 99%) (PubChem CID: 93379); N‐propyl Ethylenediamine (PubChem CID: 15659); Citric Acid (PubChem CID: 311); Trisodium Citrate (PubChem CID: 6224); Saccharose (PubChem CID: 5988); Hydrochloric Acid (PubChem CID: 313); Acetonitrile (PubChem CID: 6342); Glacial Acetic Acid (PubChem CID: 176); Anhydrous Magnesium Sulfate (PubChem CID: 24083); Anhydrous Sodium Acetate (PubChem CID: 517045). | Qiu GL, Zhuang QG, Li YF, Li SY, Chen C, Li ZH, Zhao YY, Yang Y, Liu ZB (2020)
Correlation between fruit weight and nutritional metabolism during development in CPPU-treated Actinidia chinensis 'Hongyang'.
PeerJ 8, e9724 [PubMed:32864222]
[show Abstract]
Forchlorfenuron, N-(2-chloro-4-pyridyl)-N-phenylurea (CPPU), is often used to promote fruit growth and improve production. The role of CPPU in kiwifruit growth has been established. However, the correlation between fruit weight and nutritional metabolism during development after CPPU treatments remains largely undetermined. Here, we surveyed the variations in weight and nutrient components of the 'Hongyang' kiwifruit (Actinidia chinensis) when CPPU was sprayed on fruit 25 days after anthesis. The CPPU application did not significantly influence the dry matter, soluble solids, starch, vitamin C or protein concentrations. However, the fresh weight, length and maximum diameter were significantly increased compared with the control. Moreover, in fruit of the same developmental stage, the fructose, glucose and soluble sugar levels increased after the CPPU treatment, compared with the control. On the contrary, citric, quinic and titratable acid concentrations decreased. However, a correlation analysis between fresh weight and the nutritional contents revealed that CPPU did not affect the concentrations of the most abundant organic acids (quinic and citric) and sugars (glucose, fructose and sucrose), compared with control fruit of the same weight. Therefore, CPPU applications enhance 'Hongyang' kiwifruit weight/size. However, there were no significant differences in the nutritional qualities of treated and untreated fruit having the same weights. | Zhu D, Ping L, Shen X, Hong Y, Weng Q, He Q, Wang J, Wang J (2020)
Effects of prepubertal exposure to forchlorfenuron through prenatal and postnatal gavage administration in developing Sprague-Dawley rats.
Reproductive toxicology (Elmsford, N.Y.) 98, 157-164 [PubMed:32998050]
[show Abstract]
Forchlorfenuron (CPPU), a plant growth regulator, is widely used in agriculture. However, its long-term exposure effects on humans, especially neonates, remain unclear. Therefore, we investigated the developmental toxicity of prenatal and postnatal gavage administration of CPPU in rats. Pregnant Sprague-Dawley rats were administered 300 mg/kg/day CPPU by gavage from day 6 of gestation to the cessation of nursing. During weaning, rat offspring were administered 0, 30, 100, or 300 mg/kg/day CPPU for 4 weeks, followed by a 4-week CPPU-free recovery period. There were no significant differences in clinical symptoms, body weight, development indicators, serum biochemical parameters, sex hormone levels, sperm motility, relative organ weights, and histopathological changes among the 0-100 mg/kg/day CPPU groups. In the 300 mg/kg/day CPPU group, female rats exhibited decreased body weight, earlier time of vaginal opening (VO) and first estrus time (FE), elevated estradiol and blood urea nitrogen (BUN) levels, and upregulation of estrogen receptor 1 gene expression, whereas male rats only exhibited increases in serum BUN, creatinine, and glucose levels. Most changes were reversed after the recovery period. Furthermore, the endometrial epithelial height was significantly increased in female rats despite the absence of significant changes in uterine wall thickness and endometrial glands. Thus, CPPU may promote estradiol secretion, resulting in altered VO and FE and adverse effects in prepubertal female rats. These findings may be applied for risk assessment following CPPU exposure in humans. | Gong G, Kam H, Tse Y, Lee SM (2019)
Cardiotoxicity of forchlorfenuron (CPPU) in zebrafish (Danio rerio) and H9c2 cardiomyocytes.
Chemosphere 235, 153-162 [PubMed:31255755]
[show Abstract]
Forchlorfenuron (CPPU), as a plant growth regulator or herbicide/pesticide, is widely used in agriculture worldwide. It is adopted by most farmers due to its high efficacy for boosting size and improving the quality of fruit. However, CPPU was implicated in, and gained notoriety due to an incident of exploding watermelon that occurred in 2011. Subsequently, the wider community became aware of the potential risks it posed to living organisms and the ecosystem. In this study, we evaluated the effects of CPPU on the survival, cardiac morphology and function, as well as hematopoietic system, of zebrafish (Danio rerio). Notably, CPPU (2.5-12.5 μg/ml) induced cardiac morphology deformation, cardiac contractile dysfunction and erythrocyte reduction in zebrafish. Consistently, the mRNA expression levels of several cardiac and hematopoietic gene markers (myl7, gata4, mef2c, amhc, vmhc and gata1) were altered by CPPU treatment. In addition, CPPU caused cytotoxicity, cytoskeleton destruction and reduced corresponding proteins (Myl7, Gata4 and Mef2c) expression in H9c2 cardiomyocytes in vitro. Taken together, this study has identified the cardiotoxicity of CPPU in different experimental models and enhanced our understanding on the mechanism underlying the toxicity of CPPU to living organisms. | Yan B, Guo W (2019)
A novel identification method for CPPU-treated kiwifruits based on images.
Journal of the science of food and agriculture 99, 6234-6240 [PubMed:31250461]
[show Abstract]
BackgroundThe application of exogenous plant growth regulator, for example forchlorfenuron (CPPU), on kiwifruits has become an important factor that influences kiwifruit economic efficiency and the health development of the kiwifruit industry. Owing to the slight difference in calyx shape between the kiwifruits treated with CPPU (CPPU-treated kiwifruits) and the kiwifruits without CPPU treatment (CPPU-untreated kiwifruits), this study aims to provide a cheap, quick, convenient, and non-destructive method for identifying CPPU-treated kiwifruits based on the images of kiwifruits captured at visible lights.ResultsThe identification method includes three steps. Firstly, the kiwifruit was extracted from the background by using Otsu algorithm, hole filling operation and 'bwareaopen' function. Secondly, the calyx was extracted by using corrosion, image enhancement, hole filling and closing operations. Finally, the length/width ratio of the minimum enclosing rectangle of calyx region was calculated. The kiwifruit was regarded as a CPPU-treated kiwifruit if the length/width ratio of the rectangle was higher than 1.6. Otherwise, the kiwifruit was regarded as a CPPU-untreated one. The method had the total identification accuracy rate of 90.0% when the kiwifruit images were captured either by utilizing a smartphone at normal lighting condition or by using an image acquisition system.ConclusionThe programs run on computer and smartphone were developed, and they could realize kiwifruit identification in 0.6 s and 2 s, respectively. The study makes identifying CPPU-treated kiwifruits in online processing be realizable, and offers a convenient method for kiwifruit consumers. © 2019 Society of Chemical Industry. | Shi H, Liao J, Cui S, Luo Z, Ma X (2019)
Effects of Forchlorfenuron on the Morphology, Metabolite Accumulation, and Transcriptional Responses of Siraitia grosvenorii Fruit.
Molecules (Basel, Switzerland) 24, E4076 [PubMed:31718007]
[show Abstract]
Siraitia grosvenorii fruit, called luo-han-guo (LHG), have been used as a traditional Chinese medicine (TCM) and dietary supplements for many years. Mogrosides, the main bioactive ingredients in LHG, are commercially available worldwide as a non-sugar-based and noncaloric sweetener. However, the production cannot meet the increasing market demand because of the low content of mogrosides and the small size of LHG. Therefore, some advanced technologies have been applied for improving the quality of LHG. Forchlorfenuron (CPPU), a plant growth regulator, is widely applied to promote plant yield and the secondary metabolite synthesis. Here, the content of nine mogrosides and three intermediates in LHG that were treated with three different concentrations of CPPU were determined by LC-MS/MS and GC-MS, respectively. The total content of mogrosides in LHG treated with CPPU was not enhanced, and the proportion of some main bioactive ingredients, including mogroside V (MV), were decreased relative to that of the control treatment. Morphological and cytological observations showed CPPU could make an early lignification in fruit epidermal cells, and 5 or 25 mg L-1 CPPU could inhibit LHG growth. The expression levels of 24 key genes in the mogroside biosynthesis pathway were measured and revealed that genes downregulated in upstream, and different expressions of SgUGTs would affect the accumulations and proportions of mogrosides in LHG induced by CPPU. This was the first study that applied CPPU individually on LHG, and assessed effects of CPPU on the morphology, the accumulation of metabolites, and expression profiles of 24 structural genes. The CPPU effects on LHG were undesirable, including development inhibition and the decrease of main mogroside content. These will provide guidance for the rational application of CPPU. | Kopečný D, Končitíková R, Popelka H, Briozzo P, Vigouroux A, Kopečná M, Zalabák D, Šebela M, Skopalová J, Frébort I, Moréra S (2016)
Kinetic and structural investigation of the cytokinin oxidase/dehydrogenase active site.
The FEBS journal 283, 361-377 [PubMed:26519657]
[show Abstract]
Cytokinins are hormones that regulate plant development and their environmental responses. Their levels are mainly controlled by the cytokinin oxidase/dehydrogenase (CKO), which oxidatively cleaves cytokinins using redox-active electron acceptors. CKO belongs to the group of flavoproteins with an 8α-N1-histidyl FAD covalent linkage. Here, we investigated the role of seven active site residues, H105, D169, E288, V378, E381, P427 and L492, in substrate binding and catalysis of the CKO1 from maize (Zea mays, ZmCKO1) combining site-directed mutagenesis with kinetics and X-ray crystallography. We identify E381 as a key residue for enzyme specificity that restricts substrate binding as well as quinone electron acceptor binding. We show that D169 is important for catalysis and that H105 covalently linked to FAD maintains the enzyme's structural integrity, stability and high rates with electron acceptors. The L492A mutation significantly modulates the cleavage of aromatic cytokinins and zeatin isomers. The high resolution X-ray structures of ZmCKO1 and the E381S variant in complex with N6-(2-isopentenyl)adenosine reveal the binding mode of cytokinin ribosides. Those of ZmCKO2 and ZmCKO4a contain a mobile domain, which might contribute to binding of the N9 substituted cytokinins. | Zhang Z, Guo K, Bai Y, Dong J, Gao Z, Yuan Y, Wang Y, Liu L, Yue T (2015)
Identification, synthesis, and safety assessment of forchlorfenuron (1-(2-chloro-4-pyridyl)-3-phenylurea) and its metabolites in kiwifruits.
Journal of agricultural and food chemistry 63, 3059-3066 [PubMed:25757044]
[show Abstract]
Identification and evaluation of safety of forchlorfenuron ((1-(2-chloro-4-pyridyl)-3-phenylurea)), 1, metabolites after biotransformation in kiwifruit is the objective of this study. To elucidate properties of these metabolites, liquid chromatography hybrid ion trap time-of-flight mass spectrometry (LC-IT-TOF-MS) was applied, with MetID Solution and Formula Predictor Software in positive mode. Cytotoxicity of forchlorfenuron and its metabolites were tested through sulforhodamine B assays against normal Chinese hamster ovary cells (CHO). As deduced from characteristic fragment ions of forchlorfenuron, then confirmed by comparison with synthetic standards, as well as characterized by NMR and mass spectrometry techniques, results indicate the presence of 4-hydroxyphenyl-forchlorfenuron, 2, 3-hydroxyphenyl-forchlorfenuron, 3, and forchlorfenuron-4-O-β-D-glucoside, 5. Forchlorfenuron (IC50 = 12.12 ± 2.14 μM) and 4-hydroxyphenyl-forchlorfenuron (IC50 = 36.15 ± 1.59 μM), exhibits significant cytotoxicity against CHO, while 3-hydroxyphenyl-forchlorfenuron and forchlorfenuron-4-O-β-D-glucoside show no cytotoxicity. | Heasley LR, Garcia G, McMurray MA (2014)
Off-target effects of the septin drug forchlorfenuron on nonplant eukaryotes.
Eukaryotic cell 13, 1411-1420 [PubMed:25217460]
[show Abstract]
The septins are a family of GTP-binding proteins that form cytoskeletal filaments. Septins are highly conserved and evolutionarily ancient but are absent from land plants. The synthetic plant cytokinin forchlorfenuron (FCF) was shown previously to inhibit budding yeast cell division and induce ectopic septin structures (M. Iwase, S. Okada, T. Oguchi, and A. Toh-e, Genes Genet. Syst. 79:199-206, 2004, http://dx.doi.org/10.1266/ggs.79.199). Subsequent studies in a wide range of eukaryotes have concluded that FCF exclusively inhibits septin function, yet the mechanism of FCF action in nonplant cells remains poorly understood. Here, we report that the cellular effects of FCF are far more complex than previously described. The reported growth arrest of budding yeast cells treated with 1 mM FCF partly reflects sensitization caused by a bud4 mutation present in the W303 strain background. In wild-type (BUD4(+)) budding yeast, growth was inhibited at FCF concentrations that had no detectable effect on septin structure or function. Moreover, FCF severely inhibited the proliferation of fission yeast cells, in which septin function is nonessential. FCF induced fragmentation of budding yeast mitochondrial reticula and the loss of mitochondrial membrane potential. Mitochondria also fragmented in cultured mammalian cells treated with concentrations of FCF that previously were assumed to target septins only. Finally, FCF potently inhibited ciliation and motility and induced mitochondrial disorganization in Tetrahymena thermophila without apparent alterations in septin structure. None of these effects was consistent with the inhibition of septin function. Our findings point to nonseptin targets as major concerns when using FCF. | Kopecný D, Briozzo P, Popelková H, Sebela M, Koncitíková R, Spíchal L, Nisler J, Madzak C, Frébort I, Laloue M, Houba-Hérin N (2010)
Phenyl- and benzylurea cytokinins as competitive inhibitors of cytokinin oxidase/dehydrogenase: a structural study.
Biochimie 92, 1052-1062 [PubMed:20478354]
[show Abstract]
Cytokinin oxidase/dehydrogenase (CKO) is a flavoenzyme, which irreversibly degrades the plant hormones cytokinins and thereby participates in their homeostasis. Several synthetic cytokinins including urea derivatives are known CKO inhibitors but structural data explaining enzyme-inhibitor interactions are lacking. Thus, an inhibitory study with numerous urea derivatives was undertaken using the maize enzyme (ZmCKO1) and the crystal structure of ZmCKO1 in a complex with N-(2-chloro-pyridin-4-yl)-N'-phenylurea (CPPU) was solved. CPPU binds in a planar conformation and competes for the same binding site with natural substrates like N(6)-(2-isopentenyl)adenine (iP) and zeatin (Z). Nitrogens at the urea backbone are hydrogen bonded to the putative active site base Asp169. Subsequently, site-directed mutagenesis of L492 and E381 residues involved in the inhibitor binding was performed. The crystal structures of L492A mutant in a complex with CPPU and N-(2-chloro-pyridin-4-yl)-N'-benzylurea (CPBU) were solved and confirm the importance of a stacking interaction between the 2-chloro-4-pyridinyl ring of the inhibitor and the isoalloxazine ring of the FAD cofactor. Amino derivatives like N-(2-amino-pyridin-4-yl)-N'-phenylurea (APPU) inhibited ZmCKO1 more efficiently than CPPU, as opposed to the inhibition of E381A/S mutants, emphasizing the importance of this residue for inhibitor binding. As highly specific CKO inhibitors without undesired side effects are of major interest for physiological studies, all studied compounds were further analyzed for cytokinin activity in the Amaranthus bioassay and for binding to the Arabidopsis cytokinin receptors AHK3 and AHK4. By contrast to CPPU itself, APPU and several benzylureas bind only negligibly to the receptors and exhibit weak cytokinin activity. |
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