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Methylswertianin

CAS# 22172-17-4

Methylswertianin

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Quality Control of Methylswertianin

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Chemical structure

Methylswertianin

3D structure

Chemical Properties of Methylswertianin

Cas No. 22172-17-4 SDF Download SDF
PubChem ID 5281653 Appearance White crystalline powder
Formula C15H12O6 M.Wt 288.26
Type of Compound Xanthones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1,8-dihydroxy-2,6-dimethoxyxanthen-9-one
SMILES COC1=C(C2=C(C=C1)OC3=CC(=CC(=C3C2=O)O)OC)O
Standard InChIKey PUECEVJMPDNNHT-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H12O6/c1-19-7-5-8(16)12-11(6-7)21-9-3-4-10(20-2)14(17)13(9)15(12)18/h3-6,16-17H,1-2H3
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 Methylswertianin

The herbs of Swertia bimaculata

Biological Activity of Methylswertianin

In vitro

The xanthones gentiacaulein and gentiakochianin are responsible for the vasodilator action of the roots of Gentiana kochiana.[Pubmed: 14531031]

Planta Med. 2003 Aug;69(8):770-2.

Gentiana kochiana Perr. et Song. (Gentianaceae), a plant used in the traditional medicine of Tuscany (Italy) as antihypertensive remedy, exerts a vasodilator action on in vitro aortic rings that is probably linked to the blocking of the ryanodine-sensitive Ca++ channels.
METHODS AND RESULTS:
In the present study, three known xanthones were isolated from the crude methanolic extract of the roots: gentiacaulein, gentiakochianin, and Swertiaperennin. The first two showed a vasorelaxing activity in rat aortic preparations, pre-contracted by 3 microM norepinephrine (pIC50 = 5.00 +/- 0.032 for gentiacaulein, pIC50 = 4.95 +/- 0.068 for gentiakochianin), 20 mM KCl (pIC50 = 4.90 +/- 0.15 for gentiacaulein; 4.59 +/- 0.069 for gentiakochianin), or 5 mM caffeine; on the contrary, in the same conditions, Swertiaperennin did not show any vasodilator effect.
CONCLUSIONS:
In conclusion, gentiacaulein and gentiakochianin seem to be the compounds responsible for the vasorelaxing properties of the crude extract of Gentiana kochiana roots.

Protocol of Methylswertianin

Structure Identification
Records of Natural Products, 2016, 10(3):287-293.

Antiplasmodial Activity and Cytotoxicity of Isolated Compound from the Stem Bark of Anthocleistaliebrechtsiana[Reference: WebLink]


METHODS AND RESULTS:
One new cerebroside derivative, namely liebrechtsianoside A (1), along with five known compounds: tetracosanoic acid (2), Swertiaperennin (3), decussatin (4), swertianin (5) and β-sitosterol glucoside (6) were isolated from the the stem bark of Anthocleista liebrechtsiana. Their structures were elucidated by interpretation of NMR and MS data, and by comparison of these data with those reported in literature.
CONCLUSIONS:
Compound 1 showed the highest antiplasmodial activity against Dd2 chloroquine-resistant strain of Plasmodium falciparum.

Methylswertianin Dilution Calculator

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Preparing Stock Solutions of Methylswertianin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4691 mL 17.3455 mL 34.6909 mL 69.3818 mL 86.7273 mL
5 mM 0.6938 mL 3.4691 mL 6.9382 mL 13.8764 mL 17.3455 mL
10 mM 0.3469 mL 1.7345 mL 3.4691 mL 6.9382 mL 8.6727 mL
50 mM 0.0694 mL 0.3469 mL 0.6938 mL 1.3876 mL 1.7345 mL
100 mM 0.0347 mL 0.1735 mL 0.3469 mL 0.6938 mL 0.8673 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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References on Methylswertianin

Xanthones from Swertia punctata.[Pubmed:12377236]

Phytochemistry. 2002 Oct;61(4):415-20.

Isolation of 1-O-primeverosyl-3,8-dihydroxy-5-methoxyxanthone and 1-O-gentiobiosyl-3,7-dimethoxy-8-hydroxyxanthone, along with five known xanthones, isobellidifolin, methylbellidifolin, isoswertianin, Methylswertianin and norswertianin-1-O-beta-D-glucoside, from the roots of Swertia punctata is reported. In the aerial parts four xanthones, bellidifolin, methylbellidifolin, swertianolin and mangiferin, and flavone-C-glucoside, isoorientin were identified. The chemotaxonomic and pharmacological significance of these results is discussed.

Nonprenylated Xanthones from Gentiana lutea, Frasera caroliniensis, and Centaurium erythraea as Novel Inhibitors of Vascular Smooth Muscle Cell Proliferation.[Pubmed:26580586]

Molecules. 2015 Nov 13;20(11):20381-90.

Aberrant proliferation of vascular smooth muscle cells (VSMC) plays a major role in restenosis, the pathological renarrowing of the blood vessel lumen after surgical treatment of stenosis. Since available anti-proliferative pharmaceuticals produce unfavorable side effects, there is high demand for the identification of novel VSMC proliferation inhibitors. A natural product screening approach using a resazurin conversion assay enabled the identification of gentisin (1) from Gentiana lutea as a novel inhibitor of VSMC proliferation with an IC50 value of 7.84 microM. Aiming to identify further anti-proliferative compounds, 13 additional nonprenylated xanthones, isolated from different plant species, were also tested. While some compounds showed no or moderate activity at 30 microM, 1-hydroxy-2,3,4,5-tetramethoxyxanthone (4), swerchirin (6), and Methylswertianin (7) showed IC50 values between 10.2 and 12.5 microM. The anti-proliferative effect of 1, 4, 6, and 7 was confirmed by the quantification of DNA synthesis (BrdU incorporation) in VSMC. Cell death quantification (determined by LDH release in the culture medium) revealed that the compounds are not cytotoxic in the investigated concentration range. In conclusion, nonprenylated xanthones are identified as novel, non-toxic VSMC proliferation inhibitors, which might contribute to the development of new therapeutic applications to combat restenosis.

Anti-inflammatory activity of compounds isolated from Swertia mussotii.[Pubmed:29117731]

Nat Prod Res. 2017 Nov 9:1-4.

Six compounds were isolated from an ethanol extract of Swertia mussotii and identified as 2-phenylethyl-beta-D-glucoside (1), amaroswerin (2), 1,3,7,8-tetrahydroxyxanthone (3), swertiamarine (4), 1,3,8-trihydroxy-5-methoxyxanthone (5) and Methylswertianin (6). Compounds 1, 2 and 6 were isolated from S. mussotii for the first time. The anti-inflammatory activities of the compounds were evaluated by determining their effect on the production of NO by LPS-stimulated RAW264.7 cells. Amaroswerin was the most potent inhibitor of NO release, with an IC50 value of 5.42 mug/mL. Treatment with amaroswerin inhibited expression of iNOS at both protein and mRNA levels. Amaroswerin also dose-dependently suppressed production of TNF-alpha, IL-6 and IL-1beta and reduced expression of mRNA for these LPS-stimulated pro-inflammatory mediators. Amaroswerin thus inhibits the expression of iNOS, TNF-alpha, IL-6 and IL-1beta by downregulating transcription in LPS-induced RAW264.7 macrophage cells, indicating that amaroswerin may be a valuable therapeutic agent for the treatment of inflammatory diseases.

[Chemical constituents from petroleum ether fraction of Swertia chirayita and their activities in vitro].[Pubmed:29235293]

Zhongguo Zhong Yao Za Zhi. 2017 Oct;42(19):3764-3769.

The present work is to study the chemical constituents from petroleum ether fraction of Tibetan medicine Swertia chirayita by column chromatography and recrystallization. The structures were identified by physical and chemical properties and spectral data as swerchirin (1), decussatin (2), 1,8-dihydroxy-3,5,7-trimethoxyxanthone (3), 1-hydroxy-3,5,7,8-tetramethoxyxanthone (4), bellidifolin (5), 1-hydroxy-3, 7-dimethoxyxanthone (6), Methylswertianin (7), 1-hydroxy-3,5-dimethoxyxanthone (8), erythrodiol (9), oleanolic acid (10), gnetiolactone (11), scopoletin (12), sinapaldehyde (13), syringaldehyde (14), and beta-sitosterol (15). Compounds 3, 4, 9, 11-14 were isolated from S. chirayita for the first time. Compounds 9 and 12 were firstly isolated from the genus Swertia. The cytotoxic activities of compounds 1, 2, 5, 7 and 8 against human pancreatic cancer cell lines SW1990 and BxPC-3,and the protective effects of these compounds against hydrogen peroxide (H2O2)-induced oxidative stress in human endothelium-derived EA.hy926 were investigated in vitro. The results showed no obvious effect at the high concentration of 50 mumol*L(-)(1).

Description

Methylswertianin is an active constituent in Swertia punicea Hemsl, with anti-diabetic effect. Methylswertianin could be useful for treating type-2 diabetes, likely via the improvement of insulin resistance (IR).

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