Engeletin CAS NO.572-31-6

Min.Order: 10 Milligram
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Engeletin
572-31-6
standard supplier in China

Quick Details

ProName: Engeletin
CasNo: 572-31-6
Molecular Formula: C21H22O10
Appearance: detailed see specifications
Application: analysis,activity test,Botanical Refer...
DeliveryTime: 1-3?working?days?after?confirming?the?...
PackAge: According to the clients requirement.
Port: China main port
ProductionCapacity: 1 Metric Ton/Day
Purity: ≥98%
Storage: Store at 2~8°C
Transportation: by air or by ocean shipping
LimitNum: 10 Milligram
Plant of Origin: Chinese herbal medicine
Testing Method: NMR/MS/HPLC
Product Ecification: 1mg-1kg
Heavy Metal: <10ppm
Voluntary Standards: company standard
Storage: Store in dry, dark and ventilated plac...
PackAge: Brown vial HDPE plastic bottle

Superiority

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers.
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.

Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
E.Traditional Chinese Medicine compounds library

1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
3.Provide various screening libraries and more inhibitor products;
4.Provide separation and structural determination of natural products;
5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries

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.

Details

Chemical Properties of Engeletin

Cas No.	572-31-6
PubChem ID	6453452	Appearance	White powder
Formula	C₂₁H₂₂O₁₀	M.Wt	434.4
Type of Compound	Flavonoids	Storage	Desiccate at -20°C
Synonyms	Dihydrokaempferol 3-rhamnoside; Engelitin
Solubility	DMSO : ≥ 83.3 mg/mL (191.76 mM) *"≥" means soluble, but saturation unknown.
Chemical Name	(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
SMILES	CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O
Standard InChIKey	VQUPQWGKORWZII-WDPYGAQVSA-N
Standard InChI	InChI=1S/C21H22O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-25,27-28H,1H3/t8-,15-,17+,18+,19+,20-,21-/m0/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 Engeletin

The leaves of Engelhardtia roxburghiana Wall.

Biological Activity of Engeletin

Description	Engeletin, a bioactive flavonoid, has multiple biological activities such as anti-diabetic and anti-inflammatory effects. Engeletin possesses potent inhibition of PGE2 release with IC50 values of 19.6 μg/ml; it inhibits a recombinant human aldose reductase (IC50 value=1.16 microM).
Targets	TLR \| NOS \| PGE2 \| IL Receptor \| COX \| TNF-α \| NO \| NF-kB \| p65 \| Aldose reductase
In vitro	Isolation and characterization of two flavonoids, engeletin and astilbin, from the leaves of Engelhardia roxburghiana and their potential anti-inflammatory properties.[Pubmed: 21476602] J Agric Food Chem. 2011 May 11;59(9):4562-9. Engeletin, a flavonoid compound, was isolated from the leaves of Engelhardia roxburghiana for the first time, along with astilbin, another flavonoid. METHODS AND RESULTS: The chemical structures of Engeletin and astilbin were confirmed by (1)H and (13)C nuclear magnetic resonance (NMR) and mass spectrometry (MS) spectra, and their anti-inflammatory activities were studied in lipopolysaccharide (LPS)-stimulated mouse J774A.1 macrophage cells. LPS induced the inflammatory state in macrophage cells and increased mRNA expressions of pro-inflammatory cytokines. Engeletin and astilbin exhibited remarkable inhibitory effects on interleukin (IL)-1β and IL-6 mRNA expression. Significant inhibition of LPS-mediated mRNA expressions were also seen in LPS binding toll-like receptor (TLR)-4, pro-inflammatory cytokine tumor necrosis factor (TNF)-α, IL-10, chemoattractant monocyte chemotactic protein (MCP)-1, and cyclooxygenase (COX)-2 genes. CONCLUSIONS: The reduced expression of these cytokines may alleviate immune response and reduce inflammatory activation, indicating that Engeletin and astilbin may serve as potential anti-inflammatory agents. An in vitro inhibitory effect on RAW 264.7 cells by anti-inflammatory compounds from Smilax corbularia Kunth.[Pubmed: 23393906] Asian Pac J Allergy Immunol. 2012 Dec;30(4):268-74. Smilax corbularia is a Thai medicinal plant locally known as 'Hua-Khao-Yen Neua', which is used for treating inflammatory conditions. To evaluate the anti-inflammatory effect of S. corbularia extracts and its isolated compounds by determination of inhibitory effects on lipopolysaccharide-stimulated PGE2 release, and TNF-alpha and NO production from RAW 264.7 cells. METHODS AND RESULTS: The inhibitory effect of aqueous and ethanolic extracts of this plant were determined on LPS-induced NO production, TNF-alpha and PGE2 release in RAW 264.7 cells, as an in vitro indication of possible anti-inflammatory activity. The compounds from active extract were isolated by bioassay-guided fractionation. Only the ethanolic extract of this plant inhibited TNF-alpha and NO production, with IC50 values of 61.97, and 83.90 microg/ml respectively. Three flavonols, Engeletin, astilbin and quercetin were isolated from the ethanolic extract. quercetin possessed the highest inhibitory effect on NO production with IC50 11.2 microg/ml (37.1 microM), whereas Engeletin and astilbin had no activity (IC50 >100 microg/ml). All three flavonols possessed potent inhibition of PGE2 release with IC50 values of 14.4, 19.6 and 19.9 microg/ml (33.2, 43.5 and 65.8 microM) respectively. Quercetin also exhibited the highest inhibitory effect on TNF-alpha production (IC50 = 1.25 microg/ml or 4.14 microM), but Engeletin and astilbin had no activity. CONCLUSIONS: This is the first report of isolated compounds from S. corbularia with potential anti-inflammatory effects, and the results support the use of this plant by Thai traditional doctors for treatment of inflammatory diseases.
In vivo	Engeletin Alleviates Lipopolysaccharide-Induced Endometritis in Mice by Inhibiting TLR4-mediated NF-κB Activation.[Pubmed: 27411287 ] J Agric Food Chem. 2016 Aug 10;64(31):6171-8. Engeletin (dihydrokaempferol 3-rhamnoside) is a flavanonol glycoside. It can be found in the skin of white grapes and white wine and is widely distributed in southeast Asia, and the leaves are used in a tea. Here, we explored the impact of Engeletin against the inflammatory reaction in a lipopolysaccharide (LPS)-induced endometritis mouse model. METHODS AND RESULTS: Engeletin treatment significantly attenuated uterus damage and decreased myeloperoxidase activity. ELISA and qPCR assays showed that Engeletin dose-dependently suppressed the expression of TNF-α, IL-1β, and IL-6. Molecular studies also demonstrated that the levels of iNOS, COX-2, and TLR4, along with their downstream molecules MyD88, IRAK1, TRAF6, and TAK1, were also suppressed by Engeletin. In addition, Engeletin treatment inhibited NF-κB signaling-pathway activation. Moreover, immunofluorescence analysis demonstrated that Engeletin suppressed NF-κB-p65 nuclear translocation. CONCLUSIONS: These data indicated the protective action of Engeletin against LPS-stimulated endometritis in mice via negative regulation of pro-inflammatory mediators via the TLR4-regulated NF-κB pathway.

Protocol of Engeletin

Structure Identification

J Fluoresc. 2012 Jan;22(1):511-9.

Binding of engeletin with bovine serum albumin: insights from spectroscopic investigations.[Pubmed: 21947612]

In this paper, several spectroscopic techniques were used to investigate the interaction of Engeletin (ELN) with bovine serum albumin (BSA).
METHODS AND RESULTS:
The analysis of UV-Vis absorption and fluorescence spectra revealed that ELN and BSA formed a static complex ELN-BSA, and ELN quenched the fluorescence of BSA effectively. According to the thermodynamic parameters ΔS(0) = 47.27 J·mol(-1)·K(-1) and ΔΗ(0) = -10.34 kJ·mol(-1), the hydrophobic and hydrogen bond interactions were suggested to be the major interaction forces between ELN and BSA.
CONCLUSIONS:
Raman spectroscopy indicated that the binding of ELN slightly changed the conformations and microenviroment of BSA and decreased the α-helix content of BSA.

Preparing Stock Solutions of Engeletin

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.302 mL	11.5101 mL	23.0203 mL	46.0405 mL	57.5506 mL
5 mM	0.4604 mL	2.302 mL	4.6041 mL	9.2081 mL	11.5101 mL
10 mM	0.2302 mL	1.151 mL	2.302 mL	4.6041 mL	5.7551 mL
50 mM	0.046 mL	0.2302 mL	0.4604 mL	0.9208 mL	1.151 mL
100 mM	0.023 mL	0.1151 mL	0.2302 mL	0.4604 mL	0.5755 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.

References on Engeletin

Binding of engeletin with bovine serum albumin: insights from spectroscopic investigations.[Pubmed:21947612]

J Fluoresc. 2012 Jan;22(1):511-9.

In this paper, several spectroscopic techniques were used to investigate the interaction of Engeletin (ELN) with bovine serum albumin (BSA). The analysis of UV-Vis absorption and fluorescence spectra revealed that ELN and BSA formed a static complex ELN-BSA, and ELN quenched the fluorescence of BSA effectively. According to the thermodynamic parameters DeltaS(0) = 47.27 J.mol(-1).K(-1) and DeltaEta(0) = -10.34 kJ.mol(-1), the hydrophobic and hydrogen bond interactions were suggested to be the major interaction forces between ELN and BSA. Raman spectroscopy indicated that the binding of ELN slightly changed the conformations and microenviroment of BSA and decreased the alpha-helix content of BSA.

Isolation and characterization of two flavonoids, engeletin and astilbin, from the leaves of Engelhardia roxburghiana and their potential anti-inflammatory properties.[Pubmed:21476602]

J Agric Food Chem. 2011 May 11;59(9):4562-9.

Engeletin, a flavonoid compound, was isolated from the leaves of Engelhardia roxburghiana for the first time, along with astilbin, another flavonoid. The chemical structures of Engeletin and astilbin were confirmed by (1)H and (13)C nuclear magnetic resonance (NMR) and mass spectrometry (MS) spectra, and their anti-inflammatory activities were studied in lipopolysaccharide (LPS)-stimulated mouse J774A.1 macrophage cells. LPS induced the inflammatory state in macrophage cells and increased mRNA expressions of pro-inflammatory cytokines. Engeletin and astilbin exhibited remarkable inhibitory effects on interleukin (IL)-1beta and IL-6 mRNA expression. Significant inhibition of LPS-mediated mRNA expressions were also seen in LPS binding toll-like receptor (TLR)-4, pro-inflammatory cytokine tumor necrosis factor (TNF)-alpha, IL-10, chemoattractant monocyte chemotactic protein (MCP)-1, and cyclooxygenase (COX)-2 genes. The reduced expression of these cytokines may alleviate immune response and reduce inflammatory activation, indicating that Engeletin and astilbin may serve as potential anti-inflammatory agents.

Engeletin Alleviates Lipopolysaccharide-Induced Endometritis in Mice by Inhibiting TLR4-mediated NF-kappaB Activation.[Pubmed:27411287]

J Agric Food Chem. 2016 Aug 10;64(31):6171-8.

Engeletin (dihydrokaempferol 3-rhamnoside) is a flavanonol glycoside. It can be found in the skin of white grapes and white wine and is widely distributed in southeast Asia, and the leaves are used in a tea. Here, we explored the impact of Engeletin against the inflammatory reaction in a lipopolysaccharide (LPS)-induced endometritis mouse model. Engeletin treatment significantly attenuated uterus damage and decreased myeloperoxidase activity. ELISA and qPCR assays showed that Engeletin dose-dependently suppressed the expression of TNF-alpha, IL-1beta, and IL-6. Molecular studies also demonstrated that the levels of iNOS, COX-2, and TLR4, along with their downstream molecules MyD88, IRAK1, TRAF6, and TAK1, were also suppressed by Engeletin. In addition, Engeletin treatment inhibited NF-kappaB signaling-pathway activation. Moreover, immunofluorescence analysis demonstrated that Engeletin suppressed NF-kappaB-p65 nuclear translocation. These data indicated the protective action of Engeletin against LPS-stimulated endometritis in mice via negative regulation of pro-inflammatory mediators via the TLR4-regulated NF-kappaB pathway.

Description

Engeletin is a flavanonol glycoside isolated from hymenaea martiana, inhibits NF-κB signaling-pathway activation, and possesses anti-inflammatory, analgesic, diuresis, detumescence, and antibiosis effects.

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