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2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

CAS# 82373-94-2

2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

Catalog No. BCN1340----Order now to get a substantial discount!

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Quality Control of 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

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Chemical structure

2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

3D structure

Chemical Properties of 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

Cas No. 82373-94-2 SDF Download SDF
PubChem ID 5321884 Appearance White powder
Formula C20H22O9 M.Wt 406.39
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms 2,3,4',5-Tetrahydroxystilbene 2-O-D-glucoside;55327-45-2
Solubility DMSO : ≥ 35 mg/mL (86.13 mM)
H2O : 10 mg/mL (24.61 mM; Need ultrasonic)
*"≥" means soluble, but saturation unknown.
Chemical Name (2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES C1=CC(=CC=C1C=CC2=CC(=CC(=C2OC3C(C(C(C(O3)CO)O)O)O)O)O)O
Standard InChIKey JAYVHSBYKLLDJC-DSNJPTTOSA-N
Standard InChI InChI=1S/C20H22O9/c21-9-15-16(25)17(26)18(27)20(28-15)29-19-11(7-13(23)8-14(19)24)4-1-10-2-5-12(22)6-3-10/h1-8,15-18,20-27H,9H2/b4-1+/t15-,16-,17+,18-,20+/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

The roots of Polygonum multiflorum

Biological Activity of 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

Description2,3,5,4'-Tetrahydroxyldiphenylethylene-2-O-glucoside(TSG) has potential to the prevention and treatment of Alzheimer's diseases, it not only prevents over-expression of α-synuclein at an early stage, but also reverses the increased expression of α-synuclein and inhibits the aggregation at the late stage of Tg mice. TSG suppresses PDGF-BB-induced PASMCs proliferation is associated with an inhibition of AKT / GSK3β signaling pathways. TGS, emodin and physcion also have the lipid regulation activity to an overall synergy.
TargetsAkt | GSK-3 | P450 (e.g. CYP17) | HMG-CoA Reductase | LDL
In vitro

Hepatoxicity of major constituents and extractions of Radix Polygoni Multiflori and Radix Polygoni Multiflori Praeparata.[Pubmed: 21840387]

J Ethnopharmacol. 2011 Oct 11;137(3):1291-9.

Radix Polygoni Multiflori (RPM) and Radix Polygoni Multiflori Praeparata (RPMP) were traditionally widely used as Chinese herbal medicine. However, liver adverse reactions caused by RPM or RPMP were frequently reported all around the world recent years. The aim of this study was to study the cytotoxicities of RPM, RPMP and their major constituents on human liver cell L-02 simultaneously.
METHODS AND RESULTS:
Multi-assays, including MTT assay, neutral red uptake (NRU) assay, LDH leakage percentage and liver enzyme secretion (AST, ALT and ALP) were used. Cytotoxicities of major chemical constituents of RPM, 2, 3, 5, 4'-tetrahydroxy-stilbene-2-O-β-D-glucoside (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside,TSG), physcion and emodin, were tested. The cytotoxicities of water, 50% ethanol and 95% ethanol extractions of RPM and RPMP were tested. HPLC-DAD analysis was carried to reveal the content change of TSG, physcion and emodin after the processing procedure. The TD(50) of TSG, physcion and emodin in MTT assay were >10,000 μM, 2853.61 μM and 520.37 μM. In the NRU assay, the TD(50) of TSG, physcion and emodin were much smaller (1401.53 μM, 1140.00 μM, and 3.80 μM). Emodin induced much severe liver enzyme secretion than TSG and physcion. Cell proliferation and LDH leakage rate showed no difference between RPM and RPMP extractions, but ALP, AST and ALT secretions in RPMP extractions were significant lower than that of PMR groups. Water extractions of RPM and RPMP were less toxic than any other solvent in most of the assays. Positive correlation was found between the TSG/emodin ratio and MTT survival rate. The emodin/physcion ratio also showed positive correlation with the LDH leakage percentage. CONCLUSIONS: In conclusion, Radix Polygonum multiflorum and Radix Polygonum multiflorum Praeparata were not liver injure inducing in our in vitro assays. However, the processing produce of RPM could reduce its effect on both cell proliferation and enzyme secretion of liver cell. Judging from cell proliferation, integrity of cell membrane and enzyme secretion, three major chemical constituents of RPM: TSG, physcion and emodin showed no, moderate and severe cytotoxicity against human liver cell line L-02 respectively. Chemical constituents-cytotoxicity relationship investigation revealed that TSG and physcion probably had attenuating effect to emodin. The attenuating mechanisms were still under investigation.

In vivo

Tetrahydroxystilbene glucoside antagonizes age-related α-synuclein overexpression in the hippocampus of APP transgenic mouse model of Alzheimer's disease.[Pubmed: 23160059]

Restor Neurol Neurosci. 2013;31(1):41-52.

To investigate the mRNA and protein alterations of α-synuclein in the brain of Alzheimer's disease-like mouse model at the different ages, and to evaluate the effects of 2,3,5,4'-tetrahydroxy stilbene-2-O-β-D-glucoside ( 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside,TSG) on α-synuclein expression.
METHODS AND RESULTS:
TSG (120 or 240 μmol kg(-1)d(-1)) was intragastrically administered to APPV717I transgenic (Tg) mice at 4- or 10-month-old for 6 months. mRNA expression of α-synuclein increased in hippocampus in 4 month to 16 month old Tg mice compared with age-matched control. α-synuclein protein expression in hippocampus also increased in 4 month to 16 month old Tg mice significantly. Significant down-regulation of α-synuclein mRNA and protein expression in hippocampus was found after treatment of TSG for 6 months in both 10- and 16-month-old Tg mice. Production of dimer and tetramer of α-synuclein protein in Tg mice was inhibited after treatment with TSG.
CONCLUSIONS:
The expression and aggregation of α-synuclein was age-dependently increased in Tg mice. TSG not only prevents over-expression of α-synuclein at an early stage, but also reverses the increased expression of α-synuclein and inhibits the aggregation at the late stage of Tg mice. TSG may have potential to the prevention and treatment of Alzheimer's diseases.

Protocol of 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

Kinase Assay

In vitro effects of active components of Polygonum Multiflorum Radix on enzymes involved in the lipid metabolism.[Pubmed: 24680992]

J Ethnopharmacol. 2014 May 14;153(3):763-70.

Raw and processed Polygoni Multiflori Radix (PMR and PMRP) are used in the prevention and treatment of non-alcoholic fatty liver disease (NAFLD), hyperlipidemia or related diseases. In our previous research, 2, 3, 5, 4'-tetrahydroxy-stilbene-2-O-β-D-glucoside (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside,TSG) displayed the most important role in the total cholesterol (TC) lowering effect among all the chemical constituents of Polygonum multiflorum. Emodin and physcion displayed more favorable triglyceride (TG) reducing effects than TSG. However, there are few researches focus on the approach and mechanism of how do Polygonum multiflorum exhibit good lipid regulation activity. The targeted sites of active substances of Polygonum multiflorum are still not clearly elucidated. This research pays close attention to how major chemical components of Polygonum multiflorum affect the TC and TG contents in liver cells.
METHODS AND RESULTS:
In this research, a sensitive, accurate and rapid in vitro model, steatosis hepatic L02 cell, was used to explore target sites of active chemical substances of Polygonum multiflorum for 48h. Steatosis hepatic L02 cell was exposed to emodin, physcion and TSG, respectively. The contents of four key enzymes in the pathway of synthesis and decomposition of TC and TG were investigated after exposure. Meanwhile, the contents of lipid transfer protein were also tested. The diacylgycerol acyltransferase 1 (DGAT1) controlled the biosynthesis of TG from free fatty acids while 3-hydroxy-3-methyl-glutaryl-CoA reductase (HMG-CoA reductase) limited the biosynthesis of TC. Hepatic triglyceride lipase (HTGL) and cholesterol 7α-hydroxylase (CYP7A) played the key role in the lipolysis procedure of TG and TC. The synthesis of TC and TG in steatosis L02 cells were apparently increased in the model group compared to the control group. Intracellular contents of HMG-CoA reductase and DGAT1 increased 32.33% and 56.52%, while contents of CYP7A and HTGL decreased 21.61% and 47.37%. Emodin, physcion and TSG all showed down-regulation effects on HMG-CoA reductase, while up-regulation effects on CYP7A. The most remarkable effect on HMG-CoA reductase was found on emodin. Emodin could reduce the DGAT1 content from 438.44 ± 4.51 pg/mL in model group to 192.55 ± 9.85 pg/mL (100 μm). The content of HTGL in 300 μm physcion group was 3.15 ± 0.15 U/mL, which was more significantly effective than the control, lovastatin and fenofibrate group.
CONCLUSIONS:
TSG could raise the content of CYP7A and then promote the lipolysis of cholesterol. Moreover, TSG also showed the best LDL-reducing effect. Emodin could inhibit HMG-CoA reductase and DGAT1, which were key enzymes in the synthesis of TC and TG. Physcion increased the content of HTGL, and then could boost the lipolysis of triglyceride. At the same time, physcion showed the best VLDL-reducing effect. In view of the above conclusions, we contributed the lipid regulation activity to an overall synergy of TSG, emodin and physcion.

Structure Identification
Gene. 2014 Aug 15;547(1):126-35.

Transcriptome profiling and digital gene expression analysis of Fallopia multiflora to discover putative genes involved in the biosynthesis of 2,3,5,4'-tetrahydroxy stilbene-2-O-β-D-glucoside.[Pubmed: 24967942]

The compound 2,3,5,4'-tetrahydroxy stilbene-2-O-ß-d-glucoside (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside,THSG) synthesized by Fallopia multiflora (F. multiflora) exhibits pharmacological potency. However, the mechanistic details of its biosynthesis pathway are still vague.
METHODS AND RESULTS:
To clear this ambiguity, we performed de novo transcriptome assembly and digital gene expression (DGE) profiling analyses of F. multiflora using the Illumina RNA-seq system. RNA-seq generated approximately 70 million high-quality reads that were assembled into 65,653 unigenes (mean length=750 bp), including 26,670 clusters and 38,983 singletons. A total of 48,173 (73.4%) unigenes were annotated using public protein databases with a cut-off e-value above 10(-5). Furthermore, we investigated the transcriptome difference of four different F. multiflora tissues using DGE profiling. Variations in gene expression were identified based on comparisons of transcriptomes from various parts of a high-level THSG- and a low-level THSG-producing F. multiflora plant. Clusters with similar differential expression patterns and enriched metabolic pathways with regard to the differentially expressed genes putatively involved in THSG biosynthesis were revealed for the first time.
CONCLUSIONS:
Our data provides the most comprehensive sequence resource regarding F. multiflora so far. Taken together, the results of this study considerably extend the knowledge on THSG production.

2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside Dilution Calculator

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Preparing Stock Solutions of 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4607 mL 12.3035 mL 24.6069 mL 49.2138 mL 61.5173 mL
5 mM 0.4921 mL 2.4607 mL 4.9214 mL 9.8428 mL 12.3035 mL
10 mM 0.2461 mL 1.2303 mL 2.4607 mL 4.9214 mL 6.1517 mL
50 mM 0.0492 mL 0.2461 mL 0.4921 mL 0.9843 mL 1.2303 mL
100 mM 0.0246 mL 0.123 mL 0.2461 mL 0.4921 mL 0.6152 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

2,3,4',5-tetrahydroxystilbene 2-O-D-glucoside isolats from the roots of Polygonum species, inhibits the formation of 5-HETE, HHT and thromboxane B2, although less strongly. [1]

References:
[1]. Kimura Y et al. Effects of stilbenes on arachidonate metabolism in leukocytes. Biochim Biophys Acta. 1985 Apr 25;834(2):275-8.

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References on 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

In vitro effects of active components of Polygonum Multiflorum Radix on enzymes involved in the lipid metabolism.[Pubmed:24680992]

J Ethnopharmacol. 2014 May 14;153(3):763-70.

ETHNOPHARMACOLOGY RELEVANCE: Raw and processed Polygoni Multiflori Radix (PMR and PMRP) are used in the prevention and treatment of non-alcoholic fatty liver disease (NAFLD), hyperlipidemia or related diseases. In our previous research, 2, 3, 5, 4'-tetrahydroxy-stilbene-2-O-beta-D-glucoside (TSG) displayed the most important role in the total cholesterol (TC) lowering effect among all the chemical constituents of Polygonum multiflorum. Emodin and physcion displayed more favorable triglyceride (TG) reducing effects than TSG. However, there are few researches focus on the approach and mechanism of how do Polygonum multiflorum exhibit good lipid regulation activity. The targeted sites of active substances of Polygonum multiflorum are still not clearly elucidated. This research pays close attention to how major chemical components of Polygonum multiflorum affect the TC and TG contents in liver cells. MATERIALS AND METHODS: In this research, a sensitive, accurate and rapid in vitro model, steatosis hepatic L02 cell, was used to explore target sites of active chemical substances of Polygonum multiflorum for 48h. Steatosis hepatic L02 cell was exposed to emodin, physcion and TSG, respectively. The contents of four key enzymes in the pathway of synthesis and decomposition of TC and TG were investigated after exposure. Meanwhile, the contents of lipid transfer protein were also tested. The diacylgycerol acyltransferase 1 (DGAT1) controlled the biosynthesis of TG from free fatty acids while 3-hydroxy-3-methyl-glutaryl-CoA reductase (HMG-CoA reductase) limited the biosynthesis of TC. Hepatic triglyceride lipase (HTGL) and cholesterol 7alpha-hydroxylase (CYP7A) played the key role in the lipolysis procedure of TG and TC. RESULTS: The synthesis of TC and TG in steatosis L02 cells were apparently increased in the model group compared to the control group. Intracellular contents of HMG-CoA reductase and DGAT1 increased 32.33% and 56.52%, while contents of CYP7A and HTGL decreased 21.61% and 47.37%. Emodin, physcion and TSG all showed down-regulation effects on HMG-CoA reductase, while up-regulation effects on CYP7A. The most remarkable effect on HMG-CoA reductase was found on emodin. Emodin could reduce the DGAT1 content from 438.44 +/- 4.51 pg/mL in model group to 192.55 +/- 9.85 pg/mL (100 mum). The content of HTGL in 300 mum physcion group was 3.15 +/- 0.15 U/mL, which was more significantly effective than the control, lovastatin and fenofibrate group. CONCLUSIONS: TSG could raise the content of CYP7A and then promote the lipolysis of cholesterol. Moreover, TSG also showed the best LDL-reducing effect. Emodin could inhibit HMG-CoA reductase and DGAT1, which were key enzymes in the synthesis of TC and TG. Physcion increased the content of HTGL, and then could boost the lipolysis of triglyceride. At the same time, physcion showed the best VLDL-reducing effect. In view of the above conclusions, we contributed the lipid regulation activity to an overall synergy of TSG, emodin and physcion.

Hepatoxicity of major constituents and extractions of Radix Polygoni Multiflori and Radix Polygoni Multiflori Praeparata.[Pubmed:21840387]

J Ethnopharmacol. 2011 Oct 11;137(3):1291-9.

ETHNOPHARMACOLOGICAL RELEVANCE: Radix Polygoni Multiflori (RPM) and Radix Polygoni Multiflori Praeparata (RPMP) were traditionally widely used as Chinese herbal medicine. However, liver adverse reactions caused by RPM or RPMP were frequently reported all around the world recent years. The aim of this study was to study the cytotoxicities of RPM, RPMP and their major constituents on human liver cell L-02 simultaneously. MATERIALS AND METHODS: Multi-assays, including MTT assay, neutral red uptake (NRU) assay, LDH leakage percentage and liver enzyme secretion (AST, ALT and ALP) were used. Cytotoxicities of major chemical constituents of RPM, 2, 3, 5, 4'-tetrahydroxy-stilbene-2-O-beta-D-glucoside (TSG), physcion and emodin, were tested. The cytotoxicities of water, 50% ethanol and 95% ethanol extractions of RPM and RPMP were tested. HPLC-DAD analysis was carried to reveal the content change of TSG, physcion and emodin after the processing procedure. RESULTS: The TD(50) of TSG, physcion and emodin in MTT assay were >10,000 muM, 2853.61 muM and 520.37 muM. In the NRU assay, the TD(50) of TSG, physcion and emodin were much smaller (1401.53 muM, 1140.00 muM, and 3.80 muM). Emodin induced much severe liver enzyme secretion than TSG and physcion. Cell proliferation and LDH leakage rate showed no difference between RPM and RPMP extractions, but ALP, AST and ALT secretions in RPMP extractions were significant lower than that of PMR groups. Water extractions of RPM and RPMP were less toxic than any other solvent in most of the assays. Positive correlation was found between the TSG/emodin ratio and MTT survival rate. The emodin/physcion ratio also showed positive correlation with the LDH leakage percentage. CONCLUSIONS: In conclusion, Radix Polygonum multiflorum and Radix Polygonum multiflorum Praeparata were not liver injure inducing in our in vitro assays. However, the processing produce of RPM could reduce its effect on both cell proliferation and enzyme secretion of liver cell. Judging from cell proliferation, integrity of cell membrane and enzyme secretion, three major chemical constituents of RPM: TSG, physcion and emodin showed no, moderate and severe cytotoxicity against human liver cell line L-02 respectively. Chemical constituents-cytotoxicity relationship investigation revealed that TSG and physcion probably had attenuating effect to emodin. The attenuating mechanisms were still under investigation.

Tetrahydroxystilbene glucoside antagonizes age-related alpha-synuclein overexpression in the hippocampus of APP transgenic mouse model of Alzheimer's disease.[Pubmed:23160059]

Restor Neurol Neurosci. 2013;31(1):41-52.

PURPOSE: To investigate the mRNA and protein alterations of alpha-synuclein in the brain of Alzheimer's disease-like mouse model at the different ages, and to evaluate the effects of 2,3,5,4'-tetrahydroxy stilbene-2-O-beta-D-glucoside (TSG) on alpha-synuclein expression. METHODS: TSG (120 or 240 mumol kg(-1)d(-1)) was intragastrically administered to APPV717I transgenic (Tg) mice at 4- or 10-month-old for 6 months. RESULTS: mRNA expression of alpha-synuclein increased in hippocampus in 4 month to 16 month old Tg mice compared with age-matched control. alpha-synuclein protein expression in hippocampus also increased in 4 month to 16 month old Tg mice significantly. Significant down-regulation of alpha-synuclein mRNA and protein expression in hippocampus was found after treatment of TSG for 6 months in both 10- and 16-month-old Tg mice. Production of dimer and tetramer of alpha-synuclein protein in Tg mice was inhibited after treatment with TSG. CONCLUSIONS: The expression and aggregation of alpha-synuclein was age-dependently increased in Tg mice. TSG not only prevents over-expression of alpha-synuclein at an early stage, but also reverses the increased expression of alpha-synuclein and inhibits the aggregation at the late stage of Tg mice. TSG may have potential to the prevention and treatment of Alzheimer's diseases.

Transcriptome profiling and digital gene expression analysis of Fallopia multiflora to discover putative genes involved in the biosynthesis of 2,3,5,4'-tetrahydroxy stilbene-2-O-beta-D-glucoside.[Pubmed:24967942]

Gene. 2014 Aug 15;547(1):126-35.

The compound 2,3,5,4'-tetrahydroxy stilbene-2-O-ss-d-glucoside (THSG) synthesized by Fallopia multiflora (F. multiflora) exhibits pharmacological potency. However, the mechanistic details of its biosynthesis pathway are still vague. To clear this ambiguity, we performed de novo transcriptome assembly and digital gene expression (DGE) profiling analyses of F. multiflora using the Illumina RNA-seq system. RNA-seq generated approximately 70 million high-quality reads that were assembled into 65,653 unigenes (mean length=750 bp), including 26,670 clusters and 38,983 singletons. A total of 48,173 (73.4%) unigenes were annotated using public protein databases with a cut-off e-value above 10(-5). Furthermore, we investigated the transcriptome difference of four different F. multiflora tissues using DGE profiling. Variations in gene expression were identified based on comparisons of transcriptomes from various parts of a high-level THSG- and a low-level THSG-producing F. multiflora plant. Clusters with similar differential expression patterns and enriched metabolic pathways with regard to the differentially expressed genes putatively involved in THSG biosynthesis were revealed for the first time. Our data provides the most comprehensive sequence resource regarding F. multiflora so far. Taken together, the results of this study considerably extend the knowledge on THSG production.

Description

2,3,4',5-tetrahydroxystilbene 2-O-D-glucoside isolats from the roots of Polygonum species, inhibits the formation of 5-HETE, HHT and thromboxane B2, although less strongly.

Keywords:

2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside,82373-94-2,2,3,4',5-Tetrahydroxystilbene 2-O-D-glucoside;55327-45-2,Natural Products, buy 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside , 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside supplier , purchase 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside , 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside cost , 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside manufacturer , order 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside , high purity 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

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