alpha-Mangostin

alpha-Mangostin
Product Name alpha-Mangostin
CAS No.: 6147-11-1
Catalog No.: CFN97050
Molecular Formula: C24H26O6
Molecular Weight: 410.5 g/mol
Purity: >=98%
Type of Compound: Xanthones
Physical Desc.: Yellow powder
Targets: Estrogen receptor | NO | PKC | Calcium Channel | ATPase | Potassium Channel | STAT | Caspase | ROS | MMP(e.g.TIMP) | FAK | ERK | NF-kB | PPAR | GLUT | Bcl-2/Bax | JNK | Histamine Receptor | Progestogen receptor
Source: The fruits of Garcinia mangostana.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Price: $40/20mg
Alpha-Mangostin has neuroprotective, anti-cancer, antifungal, neuroprotective, renoprotective, antioxidant and anti-inflammatory activities. Alpha-Mangostin exhibits peripheral and central antinociception through modulation of opioid and vanilloid receptors, the glutamatergic system, and the larginine/NO/cGMP/PKC/K(+)-ATP pathways; it suppresses phorbol 12-myristate 13-acetate-induced MMP-2/MMP-9 expressions via alphavbeta3 integrin/FAK/ERK and NF-kappaB signaling pathway in human lung adenocarcinoma A549 cells. Alpha-Mangostin is also a novel competitive histamine H1 receptor antagonist in smooth muscle cells.
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Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

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The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Biochem Biophys Res Commun. 2014 Oct 10;453(1):75-80.
    Inhibition of CHOP accentuates the apoptotic effect of α-mangostin from the mangosteen fruit (Garcinia mangostana) in 22Rv1 prostate cancer cells.[Pubmed: 25261723]
    The mangosteen (Garcinia mangostana) fruit has been a popular food in Southeast Asia for centuries and is increasing in popularity in Western countries.
    METHODS AND RESULTS:
    We identified alpha-Mangostin as a primary phytochemical modulating ER stress proteins in prostate cancer cells and propose that alpha-Mangostin is responsible for exerting a biological effect in prostate cancer cells. Two human prostate cancer cell lines, 22Rv1 and LNCaP, and prostate epithelial cells procured from two patients undergoing radical prostatectomy were treated with alpha-Mangostin and evaluated by RT-PCR, Western blot, fluorescent microscopy and siRNA transfection to evaluate ER stress. Next, we evaluated alpha-Mangostin for microsomal stability, pharmacokinetic parameters, and anti-cancer activity in nude mice. alpha-Mangostin significantly upregulated ER stress markers in prostate cancer cells. Interestingly, alpha-Mangostin did not promote ER stress in prostate epithelial cells (PrECs) from prostate cancer patients. CHOP knockdown enhanced alpha-Mangostin-induced apoptosis in prostate cancer cells. alpha-Mangostin significantly suppressed tumor growth in a xenograft tumor model without obvious toxicity.
    CONCLUSIONS:
    Our study suggests that alpha-Mangostin is not the only active constituent from the mangosteen fruit requiring further work to understand the complex chemical composition of the mangosteen.
    Evid Based Complement Alternat Med. 2015;2015:740238.
    α-Mangostin Improves Glucose Uptake and Inhibits Adipocytes Differentiation in 3T3-L1 Cells via PPARγ, GLUT4, and Leptin Expressions.[Pubmed: 25873982]
    Obesity has been often associated with the occurrence of cardiovascular diseases, type 2 diabetes, and cancer. The development of obesity is also accompanied by significant differentiation of preadipocytes into adipocytes.
    METHODS AND RESULTS:
    In this study, we investigated the activity of alpha-Mangostin, a major xanthone component isolated from the stem bark of G. malaccensis, on glucose uptake and adipocyte differentiation of 3T3-L1 cells focusing on PPARγ, GLUT4, and leptin expressions. alpha-Mangostin was found to inhibit cytoplasmic lipid accumulation and adipogenic differentiation. Cells treated with 50 μM of alpha-Mangostin reduced intracellular fat accumulation dose-dependently up to 44.4% relative to MDI-treated cells. Analyses of 2-deoxy-D-[(3)H] glucose uptake activity showed that alpha-Mangostin significantly improved the glucose uptake (P < 0.05) with highest activity found at 25 μM. In addition, alpha-Mangostin increased the amount of free fatty acids (FFA) released. The highest glycerol release level was observed at 50 μM of alpha-Mangostin. qRT-PCR analysis showed reduced lipid accumulation via inhibition of PPARγ gene expression. Induction of glucose uptake and free fatty acid release by alpha-Mangostin were accompanied by increasing mRNA expression of GLUT4 and leptin.
    CONCLUSIONS:
    These evidences propose that alpha-Mangostin might be possible candidate for the effective management of obesity in future.
    J Pharmacol Sci. 2004 May;95(1):33-40.
    Alpha-mangostin induces Ca2+-ATPase-dependent apoptosis via mitochondrial pathway in PC12 cells.[Pubmed: 15153648]
    We investigated the cell death effects of eight xanthones on PC12 rat pheochromocytoma cells.
    METHODS AND RESULTS:
    Among these compounds, alpha-Mangostin, from the fruit hull of Garcinia mangostana L., had the most potent effect with the EC(50) value of 4 microM. alpha-Mangostin-treated PC12 cells demonstrated typical apoptotic DNA fragmentation and caspase-3 cleavage (equivalent to activation). The flow cytometric analysis indicated that this compound induced apoptosis in time-and concentration-dependent manners. alpha-Mangostin showed the features of the mitochondrial apoptotic pathway such as mitochondrial membrane depolarization and cytochrome c release. Furthermore, alpha-Mangostin inhibited the sarco(endo)plasmic reticulum Ca(2+)-ATPase markedly. There was a correlation between the Ca(2+)-ATPase inhibitory effects and the apoptotic effects of the xanthone derivatives. On the other hand, c-Jun NH(2)-terminal kinase (JNK/SAPK), one of the signaling molecules of endoplasmic reticulum (ER) stress, was activated with alpha-Mangostin treatment.
    CONCLUSIONS:
    These results suggest that alpha-Mangostin inhibits Ca(2+)-ATPase to cause apoptosis through the mitochondrial pathway.
    Bioorg Med Chem. 2004 Nov 15;12(22):5799-806.
    Preferential target is mitochondria in alpha-mangostin-induced apoptosis in human leukemia HL60 cells.[Pubmed: 15498656]
    Our previous study has shown that alpha-Mangostin, a xanthone from the pericarps of mangosteen, induces caspase-3-dependent apoptosis in HL60 cells. In the current study, we investigated the mechanism of apoptosis induced by alpha-Mangostin in HL60 cells.
    METHODS AND RESULTS:
    alpha-Mangostin-treated HL60 cells demonstrated caspase-9 and -3 activation but not -8, which leads us to assume that alpha-Mangostin may mediate the mitochondrial pathway in the apoptosis. Parameters of mitochondrial dysfunction including swelling, loss of membrane potential (deltapsim), decrease in intracellular ATP, ROS accumulation, and cytochrome c/AIF release, were observed within 1 or 2 h after the treatment. On the other hand, alpha-Mangostin-treatment did not affect expression of bcl-2 family proteins and activation of MAP kinases. These findings indicate that alpha-Mangostin preferentially targets mitochondria in the early phase, resulting in indication of apoptosis in HL60 cells. Furthermore, we examined the structure-activity relationship between xanthone derivatives including alpha-Mangostin and the potency of deltapsim-loss in HL60 cells. Interestingly, replacement of hydroxyl group by methoxy group remarkably decreased its potency. It was also shown that the cytotoxicity substantially correlated with deltapsim decrease.
    CONCLUSIONS:
    These results indicate that alpha-Mangostin and its analogs would be candidates for preventive and therapeutic application for cancer treatment.
    Cell Biochem Biophys. 2010 Sep;58(1):31-44.
    Alpha-mangostin suppresses phorbol 12-myristate 13-acetate-induced MMP-2/MMP-9 expressions via alphavbeta3 integrin/FAK/ERK and NF-kappaB signaling pathway in human lung adenocarcinoma A549 cells.[Pubmed: 20652762]
    The purpose of this study is to investigate the anti-metastatic effect of alpha-Mangostin on phorbol 12-myristate 13-acetate (PMA)-induced matrix metalloproteinase-2 (MMP-2) and matrix metalloproteinase-9 (MMP-9) expressions in A549 human lung adenocarcinoma cells.
    METHODS AND RESULTS:
    Firstly, alpha-Mangostin could inhibit PMA-induced abilities of the adhesion, invasion, and migration. Data also showed alpha-Mangostin could inhibit the activation of alphavbeta3 integrin, focal adhesion kinase (FAK), and extracellular signal-regulated kinase1/2 (ERK1/2) involved in the downregulation the enzyme activities, protein and messenger RNA levels of MMP-2 and MMP-9 induced by PMA. Next, alpha-Mangostin also strongly inhibited PMA-induced degradation of inhibitor of kappaBalpha (IkappaBalpha) and the nuclear levels of nuclear factor kappa B (NF-kappaB). Also, a dose-dependent inhibition on the binding abilities of NF-kappaB by alpha-Mangostin treatment was further observed. Furthermore, reduction of FAK or ERK1/2 phosphorylation by FAK small interfering RNA (FAK siRNA) potentiated the effect of alpha-Mangostin. Finally, the transient transfection of ERK siRNA significantly down-regulated the expressions of MMP-2 and MMP-9 concomitantly with a marked inhibition on cell invasion and migration.
    CONCLUSIONS:
    Presented results indicated alpha-Mangostin is a novel, effect, anti-metastatic agent that functions by downregulating MMP-2 and MMP-9 gene expressions.
    Eur J Pharmacol. 1996 Oct 31;314(3):351-6.
    Pharmacological properties of alpha-mangostin, a novel histamine H1 receptor antagonist.[Pubmed: 8957258]

    METHODS AND RESULTS:
    In the isolated rabbit thoracic aorta and guinea-pig trachea, alpha-Mangostin inhibited histamine-induced contractions in a concentration-dependent manner in the presence or absence of cimetidine, a histamine H2 receptor antagonist. But KCl-, phenylephrine- or carbachol-induced contractions were not affected by alpha-Mangostin. The concentration-contractile response curve for histamine was shifted to the right in a parallel manner by alpha-Mangostin. In the presence of chlorpheniramine, a histamine H1 receptor antagonist, alpha-Mangostin did not affect the relaxation of the rabbit aorta induced by histamine. In the guinea-pig trachea, alpha-Mangostin had no effect on the relaxation induced by dimaprit, a histamine H2 receptor agonist. alpha-Mangostin caused a concentration-dependent inhibition of the binding of [3H]mepyramine, a specific histamine H1 receptor antagonist to rat aortic smooth muscle cells. Kinetic analysis of [3H]mepyramine binding indicated the competitive inhibition by alpha-Mangostin.
    CONCLUSIONS:
    These results suggest that alpha-Mangostin is a novel competitive histamine H1 receptor antagonist in smooth muscle cells.
    Exp Toxicol Pathol. 2009 Sep;61(5):491-501.
    ROS scavenging capacity and neuroprotective effect of alpha-mangostin against 3-nitropropionic acid in cerebellar granule neurons.[Pubmed: 19108999 ]
    alpha-Mangostin is a xanthone with antioxidant properties isolated from mangosteen fruit. The reactive oxygen species (ROS) scavenging capacity and the potential protective effect of alpha-Mangostin against the mitochondrial toxin 3-nitropropionic acid (3-NP) in primary cultures of cerebellar granule neurons (CGNs) were studied in the present work. It was found that alpha-Mangostin was able to scavenge in a concentration-dependent way singlet oxygen, superoxide anion and peroxynitrite anion. In contrast, alpha-Mangostin was unable to scavenge hydroxyl radicals and hydrogen peroxide. Furthermore, alpha-Mangostin was able to ameliorate in a concentration-dependent way the neuronal death induced by 3-NP. This protective effect was associated with an amelioration of 3-NP-induced reactive oxygen species formation.
    CONCLUSIONS:
    It is concluded that alpha-Mangostin is able to scavenge directly several ROS and has a neuroprotective effect against 3-NP in primary cultures of CGNs, which is associated with its ability to ameliorate 3-NP-induced ROS production.
    Biol Res Nurs. 2015 Jan;17(1):68-77.
    Mechanisms of α-mangostin-induced antinociception in a rodent model.[Pubmed: 25504952 ]
    Elucidate the antinociceptive mechanisms of alpha-Mangostin isolated from Garcinia malaccensis Linn.
    METHODS AND RESULTS:
    Male mice/rats (n = 6/group) were used in this between-group study. To determine α-mangostin's antinociceptive profile, animals were given alpha-Mangostin orally (3, 30, or 100 mg/kg) 60 min before the start of the abdominal constriction or formalin tests. To explore alpha-Mangostin's mechanisms of action, we performed (i) the hot plate test with naloxone (5 mg/kg) pretreatment to verify involvement of opioid receptors; (ii) the abdominal constriction test with 20 mg/kg l-arginine, N(G)-nitro-l-arginine methyl esters (l-NAME), methylene blue (MB), l-arginine plus l-NAME, or l-arginine plus MB or 10 mg/kg glibenclamide pretreatment to verify involvement of the l-arginine/nitric oxide (NO)/cyclic guanosine monophosphate (cGMP) and K -ATP pathways; and (iii) the paw-licking test using capsaicin (1.6 μg capsaicin/paw), glutamate (10 μmol glutamate/paw), or phorbol 12-myristate 13-acetate (PMA; 0.05 µg/paw) to verify involvement of vanilloid receptors, the glutamatergic system, and protein kinase C (PKC). RESULTS: alpha-Mangostin significantly inhibited nociception (p < .05) in all models. Only naloxone, l-arginine, methylene blue, PMA, and glibenclamide affected alpha-Mangostin antinociception significantly (p < .05).
    CONCLUSIONS:
    alpha-Mangostin exhibits peripheral and central antinociception through modulation of opioid and vanilloid receptors, the glutamatergic system, and the l-arginine/NO/cGMP/PKC/K( )-ATP pathways.
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