Bellidifolin

CAS# 2798-25-6

Bellidifolin

2D Structure

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Bellidifolin

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Chemical Properties of Bellidifolin

Cas No. 2798-25-6 SDF Download SDF
PubChem ID 5281623 Appearance Powder
Formula C14H10O6 M.Wt 274.22
Type of Compound Xanthones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1,5,8-trihydroxy-3-methoxyxanthen-9-one
SMILES COC1=CC(=C2C(=C1)OC3=C(C=CC(=C3C2=O)O)O)O
Standard InChIKey JDIORNFCMMYMLF-UHFFFAOYSA-N
Standard InChI InChI=1S/C14H10O6/c1-19-6-4-9(17)11-10(5-6)20-14-8(16)3-2-7(15)12(14)13(11)18/h2-5,15-17H,1H3
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 Bellidifolin

The plants of Gentiana species.

Biological Activity of Bellidifolin

Description1. Bellidifolin has anti-oxidation, anti-inflammatory and antitumor actions. 2. Bellidifolin may contribute to the protective effects associated with nerve injury initiated by hypoxia by mechanisms related to inhibition of cell apoptosis independent of the ERK pathway. 3. Bellidifolin exhibits hepatoprotective activities in vitro and in vivo. 4. Bellidifolin shows an antifungal effect (MIC values of 50 microg/mL). 5. Bellidifolin could be useful for treating type-2 diabetes, likely via the improvement of insulin resistance (IR). 6. Bellidifolin shows interesting inhibitory activity of monoamine oxidases (MAO) A.
TargetsERK | p38MAPK | Caspase | ROS | PI3K | LDL | MAO

Bellidifolin Dilution Calculator

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Preparing Stock Solutions of Bellidifolin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.6467 mL 18.2335 mL 36.4671 mL 72.9341 mL 91.1677 mL
5 mM 0.7293 mL 3.6467 mL 7.2934 mL 14.5868 mL 18.2335 mL
10 mM 0.3647 mL 1.8234 mL 3.6467 mL 7.2934 mL 9.1168 mL
50 mM 0.0729 mL 0.3647 mL 0.7293 mL 1.4587 mL 1.8234 mL
100 mM 0.0365 mL 0.1823 mL 0.3647 mL 0.7293 mL 0.9117 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 Bellidifolin

Anti-diabetic effect of methylswertianin and bellidifolin from Swertia punicea Hemsl. and its potential mechanism.[Pubmed:19962285]

Phytomedicine. 2010 Jun;17(7):533-9.

In this study, we continued to investigate the hypoglycemic activity of Swertia punicea Helmsl., the hypoglycemic and hypolipidemic effects of methylswertianin and Bellidifolin from the active ethyl acetate (EtOAc) fraction, and the potential mechanism(s) underlying the improvement of insulin resistance. Streptozotocin (STZ)-induced type 2 diabetic male BABL/c mice treated with methylswertianin and Bellidifolin at different doses (orally, 200 and 100mg/kg body wt./day) for 4 weeks were analyzed in comparison to untreated mice. The results proved that methylswertianin and Bellidifolin significantly reduced fasting blood glucose (FBG). The administration of both compounds also improved the oral glucose tolerance and lowered fasting serum insulin (FINS). Moreover, post-administration evaluation revealed lower serum total cholesterol (TC), low density lipoprotein cholesterol (LDL) and triglyceride (TG) levels and increased relative high density lipoprotein cholesterol (HDL) concentrations (HDL/TC). Methylswertianin and Bellidifolin appeared to improve insulin resistance by enhancing insulin signaling. The expression levels of insulin-receptor alpha subunit (InsR-alpha), insulin-receptor substrate-1 (IRS-1), and phosphatidylinositol 3-kinase (PI3K) were also increased after administration. Meanwhile, methylswertianin and Bellidifolin increased hepatic glycogen content, decreased glucokinase (GK) activities and increased glucose-6-phosphatase (G6Pase) activities. In conclusion, these result indicated that methylswertianin and Bellidifolin could be useful for treating type-2 diabetes, likely via the improvement of insulin resistance (IR).

Xanthones from Gentianella amarella ssp. acuta with acetylcholinesterase and monoamine oxidase inhibitory activities.[Pubmed:18336006]

J Nat Prod. 2008 May;71(5):895-7.

Two new xanthone glycosides, corymbiferin 3-O-beta-D-glucopyranoside (1) and swertiabisxanthone-I 8'-O-beta- d-glucopyranoside (2), were isolated from Gentianella amarella ssp. acuta, along with eight known xanthones: triptexanthoside C, veratriloside, corymbiferin 1-O-glucoside, swertianolin, norswertianolin, swertiabisxanthone-I, bellidin, and Bellidifolin, four of them identified for the first time in G. amarella ssp. acuta. The isolation was conducted mainly by centrifugal partition chromatography, and the structures of the isolated compounds were established on the basis of spectrometric data including 2D NMR and mass spectrometry. Xanthones were weakly active against acetylcholinesterase (AChE), except triptexanthoside C, which inhibited AChE with an IC(50) of 13.8 +/- 1.6 microM. Some compounds were active against monoamine oxidases (MAO): bellidin and Bellidifolin showed interesting inhibitory activity of MAO A, while swertianolin, the 8-O-glucopyranoside form of Bellidifolin, gave 93.6% inhibition of MAO B activity at 10(-5) M.

Protective effects of bellidifolin in hypoxia-induced in pheochromocytoma cells (PC12) and underlying mechanisms.[Pubmed:28895799]

J Toxicol Environ Health A. 2017;80(22):1187-1192.

Bellidifolin, a xanthone compound derived from plants of Gentiana species, is known to exert a variety of pharmacological activities including anti-oxidation, anti-inflammatory and antitumor actions as well as a protective effect on cerebral ischemic nerve injury. The aim of this study was to examine the protective effects of Bellidifolin on nerve injury produced by hypoxia and possible underlying mechanisms using pheochromocytoma cells (PC12). Data showed that the viability of PC12 cells subjected to hypoxia resulted in a significant decrease; however; pretreatment with certain concentrations of Bellidifolin (20 or 40 mumol/L) prior to hypoxia significantly increased the survival rate. The results of immunohistochemical staining analysis revealed that there were no marked alterations in the expression of pERK protein between all Bellidifolin groups while the expression of p-p38MAPK protein was significantly enhanced by hypoxia. Pretreatment with different concentrations of Bellidifolin followed by hypoxia significantly decreased the expression of p-p38MAPK protein. The results of western blot analysis showed that hypoxia induced the expression of the MAPK signaling pathway downstream of the key apoptosis factor caspase-3. Compared to hypoxia, the expression of caspase-3 in the presence of belliidifolin was significantly lower. Data suggest that Bellidifolin may contribute to the protective effects associated with nerve injury initiated by hypoxia by mechanisms related to inhibition of cell apoptosis independent of the ERK pathway, but may involve blockade of p38MAPK signaling pathway activation and downstream caspase-3 expression.

Two xanthones from Swertia punicea with hepatoprotective activities in vitro and in vivo.[Pubmed:24690777]

J Ethnopharmacol. 2014 May 14;153(3):854-63.

ETHNOPHARMACOLOGICAL RELEVANCE: Swertia punicea Hemsl. (Gentianaceae) is more commonly known as "Ganyan-cao" and used mainly as a traditional Chinese folk medicine for the treatment of acute bilious hepatitis, cholecystitis, fever, intoxification and jaundice. MATERIALS AND METHODS: The active hepatoprotective constituents of Swertia punicea were purified using various column chromatography techniques. The structures of two isolated compounds were determined on the basis of spectroscopic data interpretation such as NMR analysis. The hepatoprotective activities of isolated compounds were evaluated by using hepatotoxicity in vitro and dimethylnitrosamine-induced rat hepatic fibrosis in vivo, respectively. RESULTS: Two xanthones, 1, 7-dihydroxy-3, 4, 8-trimethoxyxanthone (1) and Bellidifolin (2) were isolated from the stems of Swertia punicea. The compounds 1 and 2 exhibited notable hepatoprotective activities against carbon tetrachloride (CCl4) -induced HepG2 cell damage, and effectively alleviated the levels of aspartate transaminase (AST), lactate dehydrogenase (LDH), superoxide dismutase (SOD) and malonic dialdehyde (MDA) induced by CCl(4) in a concentration-dependent manner. Co-treatment with compound 2 significantly increased the cell viability compared with N-acetyl-p-aminophenol (APAP) treatment. Compound 2 also alleviated APAP-induced hepatotoxicity by increasing glutathione (GSH) content and decreasing hydroxyl free radical (.OH) levels and reactive oxygen specises (ROS) production. In addition, the protective effect of compound 1 significantly alleviated DMN-induced liver inflammation and fibrosis. Oral administration of compound 1 recovered the reduction of albumin (ALB) and reversed the elevation of serum alanine transaminase (ALT), AST and total bilirubin (TBIL) in dimethylnitrosamine (DMN)-induced fibrotic rats. Severe oxidative stress induced in fibrotic rats was evidenced by a 1.5-fold elevation in MDA and a fall in the SOD activity, and treatment with compound 1 protected against these adverse effects. Recovery of rat liver tissue against DMN-induced hepatocellular necrosis, inflammatory changes and hepatic fibrosis by compound 1 is also confirmed by H&E and Masson stained histopathological evaluation of liver tissue. CONCLUSION: Two xanthones from Swertia punicea exhibited hepatoprotective activities in vitro (compounds 1 and 2) and in vivo (compound 1), respectively.

Antimicrobial and antioxidant activities of Gentianella multicaulis collected on the Andean Slopes of San Juan Province, Argentina.[Pubmed:22486039]

Z Naturforsch C. 2012 Jan-Feb;67(1-2):29-38.

The infusion of the aerial parts of Gentianella multicaulis (Gillies ex Griseb.) Fabris (Gentianaceae), locally known as 'nencia', is used in San Juan Province, Argentina, as stomachic and as a bitter tonic against digestive and liver problems. The bioassay-guided isolation of G. multicaulis extracts and structural elucidation of the main compounds responsible for the antifungal and free radical scavenging activities were performed. The extracts had strong free radical scavenging effects in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay (45-93% at 10 microg/mL) and ferric-reducing antioxidant power (FRAP) assay at 200 microg/mL. DemethylBellidifolin (4) had high antioxidant activity in the DPPH and FRAP assay. The dermatophytes Microsporum gypseum, Trichophyton mentagrophytes, and T. rubrum were moderately inhibited by the different extracts (MIC values of 125-250 microg/mL). DemethylBellidifolin (4), Bellidifolin (5), and isoBellidifolin (6) showed an antifungal effect (MIC values of 50 microg/mL), while swerchirin (3) was less active with a MIC value of 100 microg/mL. In addition, oleanolic acid (1) and ursolic acid (2) were also isolated. These findings demonstrate that Gentianella multicaulis collected in the mountains of the Province of San Juan, Argentina, is an important source of compounds with antifungal and antioxidant activities.

Description

Bellidifolin is a xanthone isolated from the stems of Swertia punicea, with hepatoprotective, hypoglycemic, anti-oxidation, anti-inflammatory and antitumor activities. Bellidifolin also acts as a viral protein R (Vpr) inhibitor.

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