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gamma-Mangostin

CAS# 31271-07-5

gamma-Mangostin

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Quality Control of gamma-Mangostin

Number of papers citing our products

Chemical structure

gamma-Mangostin

3D structure

Chemical Properties of gamma-Mangostin

Cas No. 31271-07-5 SDF Download SDF
PubChem ID 5464078 Appearance White-yellowish powder
Formula C23H24O6 M.Wt 396.4
Type of Compound Xanthones Storage Desiccate at -20°C
Synonyms Demethylmangostin; Normangostin
Solubility DMSO : 250 mg/mL (630.63 mM; Need ultrasonic)
Chemical Name 1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
SMILES CC(=CCC1=C(C=C2C(=C1O)C(=O)C3=C(C(=C(C=C3O2)O)O)CC=C(C)C)O)C
Standard InChIKey VEZXFTKZUMARDU-UHFFFAOYSA-N
Standard InChI InChI=1S/C23H24O6/c1-11(2)5-7-13-15(24)9-18-20(22(13)27)23(28)19-14(8-6-12(3)4)21(26)16(25)10-17(19)29-18/h5-6,9-10,24-27H,7-8H2,1-4H3
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 gamma-Mangostin

The fruits of Garcinia mangostana

Biological Activity of gamma-Mangostin

Descriptiongamma-Mangostin is a dual agonist that activates both PPARδ and PPARα, is also a novel competitive antagonist for the 5-HT2A receptors in vascular smooth muscles and platelets.gamma-Mangostin has free radical scavenging activity, and antiproliferative and apoptotic activity in HepG2 cells, and exhibits antihypertensive, anti-inflammatory, analgesic effects. gamma-Mangostin could as a preventive agent of the metabolic syndrome, and could serve as a micronutrient for colon cancer prevention.
TargetsPPAR | COX | PGE | Calcium Channel | 5-HT Receptor | NF-kB | IkB | Potassium Channel | IKK
In vitro

Antileptospiral activity of xanthones from Garcinia mangostana and synergy of gamma-mangostin with penicillin G.[Pubmed: 23866810]

BMC Complement Altern Med. 2013 Jul 19;13:182.

Leptospirosis, one of the most widespread zoonotic infectious diseases worldwide, is caused by spirochetes bacteria of the genus Leptospira. The present study examined inhibitory activity of purified xanthones and crude extracts from Garcinia mangostana against both non-pathogenic and pathogenic leptospira. Synergy between gamma-Mangostinand penicillin G against leptospires was also determined.
METHODS AND RESULTS:
Minimal inhibitory concentrations (MIC) of crude extracts and purified xanthones from G. mangostana and penicillin G for a non-pathogenic (L. biflexa serovar Patoc) and pathogenic (L. interrogans serovar Bataviae, Autumnalis, Javanica and Saigon) leptospires were determined by using broth microdilution method and alamar blue. The synergy was evaluated by calculating the fractional inhibitory concentration (FIC) index. The results of broth microdilution test demonstrated that the crude extract and purified xanthones from mangosteen possessed antileptospiral activities. The crude extracts were active against all five serovars of test leptospira with MICs ranging from 200 to ≥ 800 μg/ml. Among the crude extracts and purified xanthones, garcinone C was the most active compound against both of pathogenic (MIC =100 μg/ml) and non-pathogenic leptospira (MIC = 200 μg/ml). However, these MIC values were higher than those of traditional antibiotics. Combinations of gamma-Mangostin with penicillin G generated synergistic effect against L. interrogans serovars Bataviae, Autumnalis and Javanica (FIC = 0.52, 0.50, and 0.04, respectively) and no interaction against L. biflexa serovar Patoc (FIC =0.75). However, antagonistic activity (FIC = 4.03) was observed in L. interrogans serovar Saigon.
CONCLUSIONS:
Crude extracts and purified xanthones from fruit pericarp of G. mangostana with significant antibacterial activity may be used to control leptospirosis. The combination of xanthone with antibiotic enhances the antileptospiral efficacy.

Antitumour and free radical scavenging effects of γ-mangostin isolated from Garcinia mangostana pericarps against hepatocellular carcinoma cell.[Pubmed: 23927480]

J Pharm Pharmacol. 2013 Sep;65(9):1419-28.

Liver cancer is one of the highest rate diseases in southeastern Asia. Recently, many of functional foods and alternative medicines are very popularly utilized to prevent chronic diseases and cancer in Taiwan. In this study, we wanted to select and develop some of novel effectual agents or phytochemicals of gamma-Mangostin for clinical management or prevent hepatocellular carcinoma cell (HCC).
METHODS AND RESULTS:
Lipid peroxidation (LPO) is an autocatalytic mechanism which induced tissue injure and carcinogenesis. In this study, the inhibitory activity of gamma-Mangostin on oxidative damage induced rat mitochondria LPO, the free radical scavenging of gamma-Mangostin and the apoptotic effects of gamma-Mangostin on HepG2 cells were investigated. gamma-Mangostin processed activity to inhibit LPO and scavenge 2,2-diphenyl-1-picrylhydrazyl. gamma-Mangostin showed antiproliferative activity and induced nuclear condensation and apoptotic bodies appearance under Giemsa staining by microscopic observation. In addition, gamma-Mangostin showed increases of hypodiploid cells via propidium iodide, 2'7'-dichlorofluorescein diacetate, and 3,3'-dihexyloxacarbocyanine iodide staining by flow cytometry analysis in HepG2 cells.
CONCLUSIONS:
gamma-Mangostin has demonstrated free radical scavenging activity, and antiproliferative and apoptotic activity in HepG2 cells. The proof suggests that gamma-Mangostin is a lead compound candidate for clinical management or prevent HCC.

Mechanisms of vasorelaxation to gamma-mangostin in the rat aorta.[Pubmed: 23513467]

J Med Assoc Thai. 2012 Dec;95 Suppl 12:S63-8.

To investigate the effects of gamma-Mangostin on vascular tone and its mechanisms in the isolated rat aorta.
METHODS AND RESULTS:
Aortic rings from male Wistar rats were precontracted with methoxamine. Changes in tension were measured using an isometric force transducer and recorded on the MacLab recording system. Vasorelaxant effects of gamma-Mangostin were studied in the presence of 300 microM N(G)-nitro L-arginine methyl ester (L-NAME), 10 microM 1H-[1,2,4] oxadiazolo-[4,3-a] quinoxalin-1-one (ODQ), 10 microM indomethacin, 60 mM KCl, 5 mM tetraethylammonium (TEA), 10 microM glibenclamide, 1 mM4-aminopyridine (4-AP) or 30 microM barium chloride (BaCl2). Moreover the effects of gamma-Mangostin on contraction to CaCl2 were evaluated. gamma-Mangostin (1-100 microM) induced a concentration-dependent vasorelaxation in rat aortic rings precontracted with methoxamine. This effect was significantly reduced after removal of the endothelium and after pretreatment of the rings with L-NAME, ODQ, high KCl solution, or TEA. However, vasorelaxant responses to gamma-Mangostin were not altered by indomethacin, 4-AP, BaCl2 or glibenclamide. Moreover, contractions to CaCl2 (10 mM-30 mM) were reduced by pre-treatment with gamma-Mangostin (10 and 100 microM).
CONCLUSIONS:
gamma-Mangostin causes vasorelaxation which is mediated via the NO-cGMP pathway. Moreover activation of K+ channels and inhibition of extracellular Ca2+ influx from the extracellular space are largely involved in the relaxant effects of gamma-Mangostin. These data suggest that gamma-Mangostin may acts as an antihypertensive agent.

In vivo

New medicinal properties of mangostins: analgesic activity and pharmacological characterization of active ingredients from the fruit hull of Garcinia mangostana L.[Pubmed: 20064550 ]

Pharmacol Biochem Behav. 2010 Apr;95(2):166-72.

The fruit hull of Garcinia mangostana L. contains oxygenated and prenylated phenol derivatives, such as xanthones or xanthen-9H-ones, and is used by people in Southeast Asia as a traditional medicine for the treatment of abdominal pain, dysentery, wound infections, suppuration, and chronic ulcer. We isolated the active ingredients from the crude ethanol extract of G.mangostana L. (CEM) and investigated their analgesic effects and underlying mechanisms.
METHODS AND RESULTS:
CEM at intragastric (i.g.) doses of 0.5, 1, and 3 g/kg clearly exhibited antinociceptive effects in the hot-plate and acetic acid-induced writhing tests in mice. Two isolated compounds, alpha-mangostin and gamma-Mangostin, exhibited analgesic effects at doses of 25 and 50 mg/kg (i.g.) in the hot-plate and formalin tests, respectively. CEM at doses of 0.5, 1, and 3 g/kg significantly inhibited xylene-induced release of inflammatory mediators. CEM, alpha-mangostin, and gamma-Mangostin each dose-dependently demonstrated the ability to scavenge reactive oxygen species.
CONCLUSIONS:
In conclusion, our results demonstrate that CEM and mangostins possess potent peripheral and central antinociceptive effects in mice and suggest that xanthones may be developed as novel analgesics and anti-inflammatory drugs.

Protocol of gamma-Mangostin

Kinase Assay

γ-Mangostin from Garcinia mangostana pericarps as a dual agonist that activates Both PPARα and PPARδ.[Pubmed: 24317060]

Biosci Biotechnol Biochem. 2013;77(12):2430-5.

We tested the peroxisome proliferator-activated receptor (PPAR)δ agonistic activity of a Garcinia mangostana pericarp extract to develop a treatment for the metabolic syndrome, and demonstrated gamma-Mangostin to be an active compound on the basis of a luciferase reporter gene assay.
METHODS AND RESULTS:
gamma-Mangostin induced the expression of the uncoupling protein-3 (UCP-3) gene which is related to energy expenditure and fat metabolism in L6 cells. We showed that gamma-Mangostin is a dual agonist that activates both PPARδ and PPARα. gamma-Mangostin also induced the expression of acyl-CoA synthase and carnitine palmitoyl-transferase 1A genes in HepG2 cells.
CONCLUSIONS:
These results suggest the potential of gamma-Mangostin as a preventive agent of the metabolic syndrome.

Cell Research

gamma-Mangostin inhibits inhibitor-kappaB kinase activity and decreases lipopolysaccharide-induced cyclooxygenase-2 gene expression in C6 rat glioma cells.[Pubmed: 15322259 ]

Gamma-mangostin, a micronutrient of mangosteen fruit, induces apoptosis in human colon cancer cells.[Pubmed: 22759914]

Molecules. 2012 Jul 3;17(7):8010-21.

Recently colorectal cancer rates have increased rapidly in Taiwan. The treatment of colorectal cancer includes surgery, radiation therapy and chemotherapy. Mangosteen (Garcinia mangostana) is a famous Asian tropical fruit. gamma-Mangostin is a xanthone derivative isolated from the fruit hull. In previous studies, we found evidence of anti-inflammatory and anti-brain tumor activities in gamma-Mangostin. In this study, we performed further studies to assess the apoptotic effects of gamma-Mangostin on colorectal adenocarcinoma cells HT29.
METHODS AND RESULTS:
gamma-Mangostin showed concentration and time-dependent cytotoxic effects on HT29 cells. Microscopic observation under Giemsa staining showed that gamma-Mangostin induced cellular swelling and the appearance of apoptotic bodies, characteristic of apoptosis in HT29 cells. In addition, flow cytometry analysis showed an increase of hypodiploid cells in gamma-Mangostin-treated HT29 cells, while enhancement of intracellular peroxide production was detected in the same gamma-Mangostin-treated cells by DCHDA assay and DiOC6(3) staining.
CONCLUSIONS:
In view of the above results, gamma-Mangostin has demonstrated anticancer activity and induces apoptosis in HT29 colorectal adenocarcinoma cells. The evidence suggests that gamma-Mangostin could serve as a micronutrient for colon cancer prevention and is a potential lead compound for the development of anti-colon cancer agents.

Mol Pharmacol. 2004 Sep;66(3):667-74.

We investigated the effect of gamma-Mangostin purified from the fruit hull of the medicinal plant Garcinia mangostana on spontaneous prostaglandin E(2) (PGE(2)) genase release and inducible cyclooxy-2 (COX-2) gene expression in C6 rat glioma cells.
METHODS AND RESULTS:
An 18-h treatment with gamma-Mangostin potently inhibited spontaneous PGE(2) release in a concentration-dependent manner with the IC(50) value of approximately 2 microM, without affecting the cell viability even at 30 microM. By immunoblotting and reverse-transcription polymerase chain reaction, we showed that gamma-Mangostin concentration-dependently inhibited lipopolysaccharide (LPS)-induced expression of COX-2 protein and its mRNA, but not those of constitutive COX-1 cyclooxygenase. Because LPS is known to stimulate inhibitor kappaB (IkappaB) kinase (IKK)-mediated phosphorylation of IkappaB followed by its degradation, which in turn induces nuclear factor (NF)-kappaB nuclear translocation leading to transcriptional activation of COX-2 gene, the effect of gamma-Mangostin on the IKK/IkappaB cascade controlling the NF-kappaB activation was examined. An in vitro IKK assay using IKK protein immunoprecipitated from C6 cell extract showed that this compound inhibited IKK activity in a concentration-dependent manner, with the IC(50) value of approximately 10 microM. Consistently gamma-Mangostin was also observed to decrease the LPS-induced IkappaB degradation and phosphorylation in a concentration-dependent manner, as assayed by immunoblotting. Furthermore, luciferase reporter assays showed that gamma-Mangostin reduced the LPS-inducible activation of NF-kappaB-and human COX-2 gene promoter region-dependent transcription. gamma-Mangostin also inhibited rat carrageenan-induced paw edema.
CONCLUSIONS:
These results suggest that gamma-Mangostin directly inhibits IKK activity and thereby prevents COX-2 gene transcription, an NF-kappaB target gene, probably to decrease the inflammatory agent-stimulated PGE(2) production in vivo, and is a new useful lead compound for anti-inflammatory drug development.

Animal Research

Gamma-mangostin, a novel type of 5-hydroxytryptamine 2A receptor antagonist.[Pubmed: 9459569]

Naunyn Schmiedebergs Arch Pharmacol. 1998 Jan;357(1):25-31.

gamma-Mangostin, purified from the fruit hull of the medicinal plant Garcinia mangostana caused a parallel rightwards shift of the concentration/response curve for the contraction elicited by 5-hydroxytryptamine (5-HT) in the rabbit aorta (pA2 = 8.2) without affecting the contractile responses to KCl, phenylephrine (alpha1) or histamine (H1).
METHODS AND RESULTS:
The perfusion pressure response of rat coronary artery to 5-HT (5-HT2A) was reduced concentration dependently by gamma-Mangostin (IC50 = 0.32 microM). 5-HT amplified, ADP-induced aggregation of rabbit platelets (5-HT2A) was inhibited by gamma-Mangostin (IC50 = 0.29 microM), whereas that induced by thrombin was not affected, nor did gamma-Mangostin affect 5-HT-induced contraction of the guinea-pig ileum (5-HT3)in the presence of 5-HT1, 5-HT2 and 5-HT4 receptor antagonists. Furthermore, 5-HT-induced contraction of the rat fundus (5-HT2B) and 5-HT-induced relaxation of the rabbit aorta in the presence of ketanserin (5-HT1) and carbachol-induced contraction of the guinea-pig ileum (muscarinic M3) were not affected by gamma-Mangostin (5 microM). gamma-Mangostin inhibited [3H]spiperone binding to cultured rat aortic myocytes (IC50 = 3.5 nM). The Kd for [3H]spiperone binding was increased by gamma-Mangostin (3 nM) from 11.7 to 27.4 nM without affecting Bmax.
CONCLUSIONS:
These results suggest that gamma-Mangostin is a novel competitive antagonist, free from a nitrogen atom, for the 5-HT2A receptors in vascular smooth muscles and platelets.

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Preparing Stock Solutions of gamma-Mangostin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.5227 mL 12.6135 mL 25.227 mL 50.4541 mL 63.0676 mL
5 mM 0.5045 mL 2.5227 mL 5.0454 mL 10.0908 mL 12.6135 mL
10 mM 0.2523 mL 1.2614 mL 2.5227 mL 5.0454 mL 6.3068 mL
50 mM 0.0505 mL 0.2523 mL 0.5045 mL 1.0091 mL 1.2614 mL
100 mM 0.0252 mL 0.1261 mL 0.2523 mL 0.5045 mL 0.6307 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 gamma-Mangostin

gamma-Mangostin inhibits inhibitor-kappaB kinase activity and decreases lipopolysaccharide-induced cyclooxygenase-2 gene expression in C6 rat glioma cells.[Pubmed:15322259]

Mol Pharmacol. 2004 Sep;66(3):667-74.

We investigated the effect of gamma-Mangostin purified from the fruit hull of the medicinal plant Garcinia mangostana on spontaneous prostaglandin E(2) (PGE(2)) genase release and inducible cyclooxy-2 (COX-2) gene expression in C6 rat glioma cells. An 18-h treatment with gamma-Mangostin potently inhibited spontaneous PGE(2) release in a concentration-dependent manner with the IC(50) value of approximately 2 microM, without affecting the cell viability even at 30 microM. By immunoblotting and reverse-transcription polymerase chain reaction, we showed that gamma-Mangostin concentration-dependently inhibited lipopolysaccharide (LPS)-induced expression of COX-2 protein and its mRNA, but not those of constitutive COX-1 cyclooxygenase. Because LPS is known to stimulate inhibitor kappaB (IkappaB) kinase (IKK)-mediated phosphorylation of IkappaB followed by its degradation, which in turn induces nuclear factor (NF)-kappaB nuclear translocation leading to transcriptional activation of COX-2 gene, the effect of gamma-Mangostin on the IKK/IkappaB cascade controlling the NF-kappaB activation was examined. An in vitro IKK assay using IKK protein immunoprecipitated from C6 cell extract showed that this compound inhibited IKK activity in a concentration-dependent manner, with the IC(50) value of approximately 10 microM. Consistently gamma-Mangostin was also observed to decrease the LPS-induced IkappaB degradation and phosphorylation in a concentration-dependent manner, as assayed by immunoblotting. Furthermore, luciferase reporter assays showed that gamma-Mangostin reduced the LPS-inducible activation of NF-kappaB-and human COX-2 gene promoter region-dependent transcription. gamma-Mangostin also inhibited rat carrageenan-induced paw edema. These results suggest that gamma-Mangostin directly inhibits IKK activity and thereby prevents COX-2 gene transcription, an NF-kappaB target gene, probably to decrease the inflammatory agent-stimulated PGE(2) production in vivo, and is a new useful lead compound for anti-inflammatory drug development.

Gamma-mangostin, a micronutrient of mangosteen fruit, induces apoptosis in human colon cancer cells.[Pubmed:22759914]

Molecules. 2012 Jul 3;17(7):8010-21.

Recently colorectal cancer rates have increased rapidly in Taiwan. The treatment of colorectal cancer includes surgery, radiation therapy and chemotherapy. Mangosteen (Garcinia mangostana) is a famous Asian tropical fruit. gamma-Mangostin is a xanthone derivative isolated from the fruit hull. In previous studies, we found evidence of anti-inflammatory and anti-brain tumor activities in gamma-Mangostin. In this study, we performed further studies to assess the apoptotic effects of gamma-Mangostin on colorectal adenocarcinoma cells HT29. gamma-Mangostin showed concentration and time-dependent cytotoxic effects on HT29 cells. Microscopic observation under Giemsa staining showed that gamma-Mangostin induced cellular swelling and the appearance of apoptotic bodies, characteristic of apoptosis in HT29 cells. In addition, flow cytometry analysis showed an increase of hypodiploid cells in gamma-Mangostin-treated HT29 cells, while enhancement of intracellular peroxide production was detected in the same gamma-Mangostin-treated cells by DCHDA assay and DiOC6(3) staining. In view of the above results, gamma-Mangostin has demonstrated anticancer activity and induces apoptosis in HT29 colorectal adenocarcinoma cells. The evidence suggests that gamma-Mangostin could serve as a micronutrient for colon cancer prevention and is a potential lead compound for the development of anti-colon cancer agents.

Antitumour and free radical scavenging effects of gamma-mangostin isolated from Garcinia mangostana pericarps against hepatocellular carcinoma cell.[Pubmed:23927480]

J Pharm Pharmacol. 2013 Sep;65(9):1419-28.

OBJECTIVES: Liver cancer is one of the highest rate diseases in southeastern Asia. Recently, many of functional foods and alternative medicines are very popularly utilized to prevent chronic diseases and cancer in Taiwan. In this study, we wanted to select and develop some of novel effectual agents or phytochemicals of gamma-Mangostin for clinical management or prevent hepatocellular carcinoma cell (HCC). METHODS: Lipid peroxidation (LPO) is an autocatalytic mechanism which induced tissue injure and carcinogenesis. In this study, the inhibitory activity of gamma-Mangostin on oxidative damage induced rat mitochondria LPO, the free radical scavenging of gamma-Mangostin and the apoptotic effects of gamma-Mangostin on HepG2 cells were investigated. KEY FINDINGS: gamma-Mangostin processed activity to inhibit LPO and scavenge 2,2-diphenyl-1-picrylhydrazyl. gamma-Mangostin showed antiproliferative activity and induced nuclear condensation and apoptotic bodies appearance under Giemsa staining by microscopic observation. In addition, gamma-Mangostin showed increases of hypodiploid cells via propidium iodide, 2'7'-dichlorofluorescein diacetate, and 3,3'-dihexyloxacarbocyanine iodide staining by flow cytometry analysis in HepG2 cells. CONCLUSIONS: gamma-Mangostin has demonstrated free radical scavenging activity, and antiproliferative and apoptotic activity in HepG2 cells. The proof suggests that gamma-Mangostin is a lead compound candidate for clinical management or prevent HCC.

gamma-Mangostin from Garcinia mangostana pericarps as a dual agonist that activates Both PPARalpha and PPARdelta.[Pubmed:24317060]

Biosci Biotechnol Biochem. 2013;77(12):2430-5.

We tested the peroxisome proliferator-activated receptor (PPAR)delta agonistic activity of a Garcinia mangostana pericarp extract to develop a treatment for the metabolic syndrome, and demonstrated gamma-Mangostin to be an active compound on the basis of a luciferase reporter gene assay. gamma-Mangostin induced the expression of the uncoupling protein-3 (UCP-3) gene which is related to energy expenditure and fat metabolism in L6 cells. We showed that gamma-Mangostin is a dual agonist that activates both PPARdelta and PPARalpha. gamma-Mangostin also induced the expression of acyl-CoA synthase and carnitine palmitoyl-transferase 1A genes in HepG2 cells. These results suggest the potential of gamma-Mangostin as a preventive agent of the metabolic syndrome.

Gamma-mangostin, a novel type of 5-hydroxytryptamine 2A receptor antagonist.[Pubmed:9459569]

Naunyn Schmiedebergs Arch Pharmacol. 1998 Jan;357(1):25-31.

gamma-Mangostin, purified from the fruit hull of the medicinal plant Garcinia mangostana caused a parallel rightwards shift of the concentration/response curve for the contraction elicited by 5-hydroxytryptamine (5-HT) in the rabbit aorta (pA2 = 8.2) without affecting the contractile responses to KCl, phenylephrine (alpha1) or histamine (H1). The perfusion pressure response of rat coronary artery to 5-HT (5-HT2A) was reduced concentration dependently by gamma-Mangostin (IC50 = 0.32 microM). 5-HT amplified, ADP-induced aggregation of rabbit platelets (5-HT2A) was inhibited by gamma-Mangostin (IC50 = 0.29 microM), whereas that induced by thrombin was not affected, nor did gamma-Mangostin affect 5-HT-induced contraction of the guinea-pig ileum (5-HT3)in the presence of 5-HT1, 5-HT2 and 5-HT4 receptor antagonists. Furthermore, 5-HT-induced contraction of the rat fundus (5-HT2B) and 5-HT-induced relaxation of the rabbit aorta in the presence of ketanserin (5-HT1) and carbachol-induced contraction of the guinea-pig ileum (muscarinic M3) were not affected by gamma-Mangostin (5 microM). gamma-Mangostin inhibited [3H]spiperone binding to cultured rat aortic myocytes (IC50 = 3.5 nM). The Kd for [3H]spiperone binding was increased by gamma-Mangostin (3 nM) from 11.7 to 27.4 nM without affecting Bmax. These results suggest that gamma-Mangostin is a novel competitive antagonist, free from a nitrogen atom, for the 5-HT2A receptors in vascular smooth muscles and platelets.

New medicinal properties of mangostins: analgesic activity and pharmacological characterization of active ingredients from the fruit hull of Garcinia mangostana L.[Pubmed:20064550]

Pharmacol Biochem Behav. 2010 Apr;95(2):166-72.

The fruit hull of Garcinia mangostana L. contains oxygenated and prenylated phenol derivatives, such as xanthones or xanthen-9H-ones, and is used by people in Southeast Asia as a traditional medicine for the treatment of abdominal pain, dysentery, wound infections, suppuration, and chronic ulcer. We isolated the active ingredients from the crude ethanol extract of G.mangostana L. (CEM) and investigated their analgesic effects and underlying mechanisms. CEM at intragastric (i.g.) doses of 0.5, 1, and 3 g/kg clearly exhibited antinociceptive effects in the hot-plate and acetic acid-induced writhing tests in mice. Two isolated compounds, alpha-mangostin and gamma-Mangostin, exhibited analgesic effects at doses of 25 and 50 mg/kg (i.g.) in the hot-plate and formalin tests, respectively. CEM at doses of 0.5, 1, and 3 g/kg significantly inhibited xylene-induced release of inflammatory mediators. CEM, alpha-mangostin, and gamma-Mangostin each dose-dependently demonstrated the ability to scavenge reactive oxygen species. In conclusion, our results demonstrate that CEM and mangostins possess potent peripheral and central antinociceptive effects in mice and suggest that xanthones may be developed as novel analgesics and anti-inflammatory drugs.

Mechanisms of vasorelaxation to gamma-mangostin in the rat aorta.[Pubmed:23513467]

J Med Assoc Thai. 2012 Dec;95 Suppl 12:S63-8.

OBJECTIVE: To investigate the effects of gamma-Mangostin on vascular tone and its mechanisms in the isolated rat aorta. MATERIAL AND METHOD: Aortic rings from male Wistar rats were precontracted with methoxamine. Changes in tension were measured using an isometric force transducer and recorded on the MacLab recording system. Vasorelaxant effects of gamma-Mangostin were studied in the presence of 300 microM N(G)-nitro L-arginine methyl ester (L-NAME), 10 microM 1H-[1,2,4] oxadiazolo-[4,3-a] quinoxalin-1-one (ODQ), 10 microM indomethacin, 60 mM KCl, 5 mM tetraethylammonium (TEA), 10 microM glibenclamide, 1 mM4-aminopyridine (4-AP) or 30 microM barium chloride (BaCl2). Moreover the effects of gamma-Mangostin on contraction to CaCl2 were evaluated. RESULTS: gamma-Mangostin (1-100 microM) induced a concentration-dependent vasorelaxation in rat aortic rings precontracted with methoxamine. This effect was significantly reduced after removal of the endothelium and after pretreatment of the rings with L-NAME, ODQ, high KCl solution, or TEA. However, vasorelaxant responses to gamma-Mangostin were not altered by indomethacin, 4-AP, BaCl2 or glibenclamide. Moreover, contractions to CaCl2 (10 mM-30 mM) were reduced by pre-treatment with gamma-Mangostin (10 and 100 microM). CONCLUSION: gamma-Mangostin causes vasorelaxation which is mediated via the NO-cGMP pathway. Moreover activation of K+ channels and inhibition of extracellular Ca2+ influx from the extracellular space are largely involved in the relaxant effects of gamma-Mangostin. These data suggest that gamma-Mangostin may acts as an antihypertensive agent.

Antileptospiral activity of xanthones from Garcinia mangostana and synergy of gamma-mangostin with penicillin G.[Pubmed:23866810]

BMC Complement Altern Med. 2013 Jul 19;13:182.

BACKGROUND: Leptospirosis, one of the most widespread zoonotic infectious diseases worldwide, is caused by spirochetes bacteria of the genus Leptospira. The present study examined inhibitory activity of purified xanthones and crude extracts from Garcinia mangostana against both non-pathogenic and pathogenic leptospira. Synergy between gamma-Mangostin and penicillin G against leptospires was also determined. METHODS: Minimal inhibitory concentrations (MIC) of crude extracts and purified xanthones from G. mangostana and penicillin G for a non-pathogenic (L. biflexa serovar Patoc) and pathogenic (L. interrogans serovar Bataviae, Autumnalis, Javanica and Saigon) leptospires were determined by using broth microdilution method and alamar blue. The synergy was evaluated by calculating the fractional inhibitory concentration (FIC) index. RESULTS: The results of broth microdilution test demonstrated that the crude extract and purified xanthones from mangosteen possessed antileptospiral activities. The crude extracts were active against all five serovars of test leptospira with MICs ranging from 200 to >/= 800 mug/ml. Among the crude extracts and purified xanthones, garcinone C was the most active compound against both of pathogenic (MIC =100 mug/ml) and non-pathogenic leptospira (MIC = 200 mug/ml). However, these MIC values were higher than those of traditional antibiotics. Combinations of gamma-Mangostin with penicillin G generated synergistic effect against L. interrogans serovars Bataviae, Autumnalis and Javanica (FIC = 0.52, 0.50, and 0.04, respectively) and no interaction against L. biflexa serovar Patoc (FIC =0.75). However, antagonistic activity (FIC = 4.03) was observed in L. interrogans serovar Saigon. CONCLUSIONS: Crude extracts and purified xanthones from fruit pericarp of G. mangostana with significant antibacterial activity may be used to control leptospirosis. The combination of xanthone with antibiotic enhances the antileptospiral efficacy.

Description

Gamma-Mangostin is a novel competitive 5-hydroxytryptamine 2A (5-HT2A) receptors antagonist, purified from the fruit hull of the medicinal plant Garcinia mangostana. Gamma-Mangostin is a inhibitor of Transthyretin (TTR) fibrillization, it binds to the thyroxine (T4)-binding sites and stabilized the TTR tetramer. Gamma-Mangostin inhibits [3H] spiperone binding to cultured rat aortic myocytes (IC50=3.5 nM) and reduces The perfusion pressure response of rat coronary artery to 5-HT2A (IC50=0.32 µM) .

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