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3-Isomangostin

CAS# 19275-46-8

3-Isomangostin

2D Structure

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3D structure

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3-Isomangostin

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Chemical Properties of 3-Isomangostin

Cas No. 19275-46-8 SDF Download SDF
PubChem ID 13873655 Appearance Yellow powder
Formula C24H26O6 M.Wt 410.46
Type of Compound Xanthones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5,9-dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)-3,4-dihydropyrano[3,2-b]xanthen-6-one
SMILES CC(=CCC1=C2C(=CC(=C1OC)O)OC3=CC4=C(CCC(O4)(C)C)C(=C3C2=O)O)C
Standard InChIKey KJCDBAVVDILRMP-UHFFFAOYSA-N
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 3-Isomangostin

The fruits of Garcinia mangostana

Biological Activity of 3-Isomangostin

Description3-Isomangostin is a potent human aldose reductase inhibitor with an IC50 of 3.48 uM; it is also an acetylcholinesterase selective inhibitor. 3-Isomangostin has free radical scavenging activity; it shows antiplasmodial activity with IC50 values in the range of 4.71-11.40 uM.
TargetsATPase | Potassium Channel | Antifection
In vitro

In vitro antiplasmodial activity of benzophenones and xanthones from edible fruits of Garcinia species.[Pubmed: 24963617]

Planta Med. 2014 Jun;80(8-9):676-81.

Species of Garcinia have been used to combat malaria in traditional African and Asian medicines, including Ayurveda. In the current study, we have identified antiplasmodial benzophenone and xanthone compounds from edible Garcinia species by testing for in vitro inhibitory activity against Plasmodium falciparum. Whole fruits of Garcinia xanthochymus, G. mangostana, G. spicata, and G. livingstonei were extracted and tested for antiplasmodial activity.
METHODS AND RESULTS:
Garcinia xanthochymus was subjected to bioactivity-guided fractionation to identify active partitions. Purified benzophenones (1-9) and xanthones (10-18) were then screened in the plasmodial lactate dehydrogenase assay and tested for cytotoxicity against mammalian (Vero) cells. The benzophenones guttiferone E (4), isoxanthochymol (5), and guttiferone H (6), isolated from G. xanthochymus, and the xanthones α-mangostin (15), β-mangostin (16), and 3-Isomangostin (17), known from G. mangostana, showed antiplasmodial activity with IC50 values in the range of 4.71-11.40 µM. Artemisinin and chloroquine were used as positive controls and exhibited IC50 values in the range of 0.01-0.24 µM.
CONCLUSIONS:
The identification of antiplasmodial benzophenone and xanthone compounds from G. xanthochymus and G. mangostana provides evidence for the antiplasmodial activity of Garcinia species and warrants further investigation of these fruits as dietary sources of chemopreventive compounds.

Health and Wellness Product from Mangosteen (Garcinia mangostana L.) Rind: Bioactive Potentials[Reference: WebLink]

International Journal of Biotechnology for Wellness Industries, 2015, 3(4):111-20.

70% AE contained phenolics 60.08± 0.213 mg/g and xanthones 22.56± 0.317 mg/g. HPLC analysis revealed a spectrum of phenolic acids such as gallic, chlorogenic, caffeic, epicatechin, catechin and ferulic acids at various levels.
METHODS AND RESULTS:
Potent Free Radical Scavenging (FRS) activity, cytoprotectivity, DNA protectivity, H + K + ATPase inhibitory (PPAI) activities were observed in 70% AE. Gallic/tannic acid appear to contribute to antioxidant activity; while ferulic acid was responsible for PPAI activity in 70%AE. Among xanthones, although-mangostin was the dominating component, gartanin, 8 deoxygartanin and 3-Isomangostin contributed to FRS activity. The products were prepared from 70%AE which are sensorially acceptable.
CONCLUSIONS:
Data thus for the first time delineate the specific health beneficial role of both phenolic and xanthone constituents in MSR particularly with higher abundance of phenolics than xanthones.

Protocol of 3-Isomangostin

Kinase Assay

Inhibitory effects of α-mangostin on mammalian DNA polymerase, topoisomerase, and human cancer cell proliferation.[Pubmed: 23811100]

The inhibitory activity of aldose reductase in vitro by constituents of Garcinia mangostana Linn.[Pubmed: 25636870]

Prenylated xanthones from mangosteen as promising cholinesterase inhibitors and their molecular docking studies.[Pubmed: 25172794]

Phytomedicine. 2014 Sep 25;21(11):1303-9.

Garcinia mangostana is a well-known tropical plant found mostly in South East Asia. The present study investigated acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of G. mangostana extract and its chemical constituents using Ellman's colorimetric method.
METHODS AND RESULTS:
Cholinesterase inhibitory-guided approach led to identification of six bioactive prenylated xanthones showing moderate to potent cholinesterases inhibition with IC50 values of lower than 20.5 μM. The most potent inhibitor of AChE was garcinone C while γ-mangostin was the most potent inhibitor of BChE with IC50 values of 1.24 and 1.78 μM, respectively. Among the xanthones, mangostanol, 3-Isomangostin, garcinone C and α-mangostin are AChE selective inhibitors, 8-deoxygartanin is a BChE selective inhibitor while γ-mangostin is a dual inhibitor. Preliminary structure-activity relationship suggests the importance of the C-8 prenyl and C-7 hydroxy groups for good AChE and BChE inhibitory activities. The enzyme kinetic studies indicate that both α-mangostin and garcinone C are mixed-mode inhibitors, while γ-mangostin is a non-competitive inhibitor of AChE. In contrast, both γ-mangostin and garcinone C are uncompetitive inhibitors, while α-mangostin is a mixed-mode inhibitor of BChE. Molecular docking studies revealed that α-mangostin, γ-mangostin and garcinone C interacts differently with the five important regions of AChE and BChE.
CONCLUSIONS:
The nature of protein-ligand interactions is mainly hydrophobic and hydrogen bonding. These bioactive prenylated xanthones are worthy for further investigations.

Phytomedicine. 2015 Jan 15;22(1):49-51.


METHODS AND RESULTS:
We investigated aldose reductase inhibition of Garcinia mangostana Linn. from Indonesia. Dichloromethane extract of the root bark of this tree was found to demonstrate an IC50 value of 11.98 µg/ml for human aldose reductase in vitro. From the dichloromethane fraction, prenylated xanthones were isolated as potent human aldose reductase inhibitors.
CONCLUSIONS:
We discovered 3-Isomangostin to be most potent against aldose reductase, with an IC50 of 3.48 µM.

Food Chem Toxicol. 2013 Sep;59:793-800.

We found that the ethanol extract of mangosteen (Garcinia mangostana L.) fruit rind had a strong inhibitory effect on mammalian DNA polymerase (pol) activity and isolated α-mangostin as a potent pol inhibitor from the extract.
METHODS AND RESULTS:
In this study, the inhibitory activities against mammalian pols by α-mangostin and its related five compounds, 3-Isomangostin, xanthone, 9,10-anthraquinone, 9-anthracenecarboxylic acid, and anthracene, were investigated. α-Mangostin was the most potent inhibitor of the mammalian pol species among the tested compounds, with IC₅₀ values of 14.8-25.6 μM. This compound also inhibited human DNA topoisomerases (topos) I and II activities with IC₅₀ values of 15.0 and 7.5 μM, respectively, but did not inhibit the activities of other DNA metabolic enzymes tested. α-Mangostin also did not directly bind to double-stranded DNA as determined by thermal transition analysis. α-Mangostin was found to suppress human colon HCT116 carcinoma cell proliferation with an LC₅₀ of 18.5 μM, inhibit the activity of cellular topos, halt cell cycle in the G2/M phase, and induce apoptosis.
CONCLUSIONS:
These results suggest that decreased proliferation by α-mangostin may be a result of the inhibition of cellular topos rather than pols, and α-mangostin might be an anticancer chemotherapeutic agent.

3-Isomangostin Dilution Calculator

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Preparing Stock Solutions of 3-Isomangostin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4363 mL 12.1815 mL 24.3629 mL 48.7258 mL 60.9073 mL
5 mM 0.4873 mL 2.4363 mL 4.8726 mL 9.7452 mL 12.1815 mL
10 mM 0.2436 mL 1.2181 mL 2.4363 mL 4.8726 mL 6.0907 mL
50 mM 0.0487 mL 0.2436 mL 0.4873 mL 0.9745 mL 1.2181 mL
100 mM 0.0244 mL 0.1218 mL 0.2436 mL 0.4873 mL 0.6091 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 3-Isomangostin

Prenylated xanthones from mangosteen as promising cholinesterase inhibitors and their molecular docking studies.[Pubmed:25172794]

Phytomedicine. 2014 Sep 25;21(11):1303-9.

Garcinia mangostana is a well-known tropical plant found mostly in South East Asia. The present study investigated acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of G. mangostana extract and its chemical constituents using Ellman's colorimetric method. Cholinesterase inhibitory-guided approach led to identification of six bioactive prenylated xanthones showing moderate to potent cholinesterases inhibition with IC50 values of lower than 20.5 muM. The most potent inhibitor of AChE was garcinone C while gamma-mangostin was the most potent inhibitor of BChE with IC50 values of 1.24 and 1.78 muM, respectively. Among the xanthones, mangostanol, 3-Isomangostin, garcinone C and alpha-mangostin are AChE selective inhibitors, 8-deoxygartanin is a BChE selective inhibitor while gamma-mangostin is a dual inhibitor. Preliminary structure-activity relationship suggests the importance of the C-8 prenyl and C-7 hydroxy groups for good AChE and BChE inhibitory activities. The enzyme kinetic studies indicate that both alpha-mangostin and garcinone C are mixed-mode inhibitors, while gamma-mangostin is a non-competitive inhibitor of AChE. In contrast, both gamma-mangostin and garcinone C are uncompetitive inhibitors, while alpha-mangostin is a mixed-mode inhibitor of BChE. Molecular docking studies revealed that alpha-mangostin, gamma-mangostin and garcinone C interacts differently with the five important regions of AChE and BChE. The nature of protein-ligand interactions is mainly hydrophobic and hydrogen bonding. These bioactive prenylated xanthones are worthy for further investigations.

In vitro antiplasmodial activity of benzophenones and xanthones from edible fruits of Garcinia species.[Pubmed:24963617]

Planta Med. 2014 Jun;80(8-9):676-81.

Species of Garcinia have been used to combat malaria in traditional African and Asian medicines, including Ayurveda. In the current study, we have identified antiplasmodial benzophenone and xanthone compounds from edible Garcinia species by testing for in vitro inhibitory activity against Plasmodium falciparum. Whole fruits of Garcinia xanthochymus, G. mangostana, G. spicata, and G. livingstonei were extracted and tested for antiplasmodial activity. Garcinia xanthochymus was subjected to bioactivity-guided fractionation to identify active partitions. Purified benzophenones (1-9) and xanthones (10-18) were then screened in the plasmodial lactate dehydrogenase assay and tested for cytotoxicity against mammalian (Vero) cells. The benzophenones guttiferone E (4), isoxanthochymol (5), and guttiferone H (6), isolated from G. xanthochymus, and the xanthones alpha-mangostin (15), beta-mangostin (16), and 3-Isomangostin (17), known from G. mangostana, showed antiplasmodial activity with IC50 values in the range of 4.71-11.40 microM. Artemisinin and chloroquine were used as positive controls and exhibited IC50 values in the range of 0.01-0.24 microM. The identification of antiplasmodial benzophenone and xanthone compounds from G. xanthochymus and G. mangostana provides evidence for the antiplasmodial activity of Garcinia species and warrants further investigation of these fruits as dietary sources of chemopreventive compounds.

The inhibitory activity of aldose reductase in vitro by constituents of Garcinia mangostana Linn.[Pubmed:25636870]

Phytomedicine. 2015 Jan 15;22(1):49-51.

We investigated aldose reductase inhibition of Garcinia mangostana Linn. from Indonesia. Dichloromethane extract of the root bark of this tree was found to demonstrate an IC50 value of 11.98 microg/ml for human aldose reductase in vitro. From the dichloromethane fraction, prenylated xanthones were isolated as potent human aldose reductase inhibitors. We discovered 3-Isomangostin to be most potent against aldose reductase, with an IC50 of 3.48 microM.

Inhibitory effects of alpha-mangostin on mammalian DNA polymerase, topoisomerase, and human cancer cell proliferation.[Pubmed:23811100]

Food Chem Toxicol. 2013 Sep;59:793-800.

We found that the ethanol extract of mangosteen (Garcinia mangostana L.) fruit rind had a strong inhibitory effect on mammalian DNA polymerase (pol) activity and isolated alpha-mangostin as a potent pol inhibitor from the extract. In this study, the inhibitory activities against mammalian pols by alpha-mangostin and its related five compounds, 3-Isomangostin, xanthone, 9,10-anthraquinone, 9-anthracenecarboxylic acid, and anthracene, were investigated. alpha-Mangostin was the most potent inhibitor of the mammalian pol species among the tested compounds, with IC(5)(0) values of 14.8-25.6 muM. This compound also inhibited human DNA topoisomerases (topos) I and II activities with IC(5)(0) values of 15.0 and 7.5 muM, respectively, but did not inhibit the activities of other DNA metabolic enzymes tested. alpha-Mangostin also did not directly bind to double-stranded DNA as determined by thermal transition analysis. alpha-Mangostin was found to suppress human colon HCT116 carcinoma cell proliferation with an LC(5)(0) of 18.5 muM, inhibit the activity of cellular topos, halt cell cycle in the G2/M phase, and induce apoptosis. These results suggest that decreased proliferation by alpha-mangostin may be a result of the inhibition of cellular topos rather than pols, and alpha-mangostin might be an anticancer chemotherapeutic agent.

Description

3-Isomangostin, extracted from Garciniamangostana.L. shell, is a potent MutT homologue 1 (MTH1) inhibitor with an IC50 value of 52 nM. 3-Isomangostin would be an attractive chemical tool for the development of anticancer agents.

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