Gartanin

CAS# 33390-42-0

Gartanin

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Quality Control of Gartanin

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Chemical structure

Gartanin

3D structure

Chemical Properties of Gartanin

Cas No. 33390-42-0 SDF Download SDF
PubChem ID 5281633 Appearance Yellow powder
Formula C23H24O6 M.Wt 396.4
Type of Compound Xanthones Storage Desiccate at -20°C
Solubility Soluble in chloroform
Chemical Name 1,3,5,8-tetrahydroxy-2,4-bis(3-methylbut-2-enyl)xanthen-9-one
SMILES CC(=CCC1=C(C2=C(C(=C1O)CC=C(C)C)OC3=C(C=CC(=C3C2=O)O)O)O)C
Standard InChIKey OJXQLGQIDIPMTE-UHFFFAOYSA-N
Standard InChI InChI=1S/C23H24O6/c1-11(2)5-7-13-19(26)14(8-6-12(3)4)22-18(20(13)27)21(28)17-15(24)9-10-16(25)23(17)29-22/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 Gartanin

The stem bark of Garcinia mangostana

Biological Activity of Gartanin

Description1. Gartanin possesses potent antioxidant, anti-inflammatory, antifungal and antineoplastic properties. 2. Gartanin induces protective autophagy mainly by JNK-Bcl-2 pathway. 3. Gartanin is an androgen receptor degradation enhancer. 4. Gartanin is a potential neuroprotective agent against glutamate-induced oxidative injury partially through increasing Nrf-2-independed HO-1 and AMPK/SIRT1/PGC-1αsignaling pathways. 5. Gartanin has anti-proliferation effect in T98G cells, which is most likely via cell cycle arrest modulated by autophagy, which is regulated by PI3K/Akt/mTOR signalling pathway, while its anti-migration effect is most likely via suppression of MMP-2/-9 activity which is involved in MAPK signalling pathway.
TargetsBcl-2/Bax | Caspase | JNK | p53 | mTOR | Nrf2 | ROS | HO-1 | AMPK | Sirtuin | PI3K | Akt | MMP(e.g.TIMP) | MAPK

Gartanin Dilution Calculator

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Preparing Stock Solutions of Gartanin

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 Gartanin

Gartanin Protects Neurons against Glutamate-Induced Cell Death in HT22 Cells: Independence of Nrf-2 but Involvement of HO-1 and AMPK.[Pubmed:27161377]

Neurochem Res. 2016 Sep;41(9):2267-77.

Oxidative stress mediates the pathogenesis of neurodegenerative disorders. Gartanin, a natural xanthone of mangosteen, possesses multipharmacological activities. Herein, the neuroprotection capacity of Gartanin against glutamate-induced damage in HT22 cells and its possible mechanism(s) were investigated for the first time. Glutamate resulted in cell death in a dose-dependent manner and supplementation of 1-10 microM Gartanin prevented the detrimental effects of glutamate on cell survival. Additional investigations on the underlying mechanisms suggested that Gartanin could effectively reduce glutamate-induced intracellular ROS generation and mitochondrial depolarization. We further found that Gartanin induced HO-1 expression independent of nuclear factor erythroid-derived 2-like 2 (Nrf2). Subsequent studies revealed that the inhibitory effects of Gartanin on glutamate-induced apoptosis were partially blocked by small interfering RNA-mediated knockdown of HO-1. Finally, the protein expression of phosphorylation of AMP-activated protein kinase (AMPK) and its downstream signal molecules, Sirtuin activator (SIRT1) and peroxisome proliferator-activated receptor-gamma coactivator-1alpha (PGC-1alpha), increased after Gartanin treatment. Taken together, these findings suggest Gartanin is a potential neuroprotective agent against glutamate-induced oxidative injury partially through increasing Nrf-2-independed HO-1 and AMPK/SIRT1/PGC-1alpha signaling pathways.

Gartanin, an isoprenylated xanthone from the mangosteen fruit (Garcinia mangostana), is an androgen receptor degradation enhancer.[Pubmed:27019217]

Mol Nutr Food Res. 2016 Jun;60(6):1458-69.

SCOPE: Androgen receptor (AR) has been a target of prostate cancer for nearly seven decades. In the last several years there has been an interest in identifying compounds that promote degradation of the androgen receptor. In the present study, Gartanin, an isoprentylated xanthone in the mangosteen fruit, was evaluated for enhancing AR degradation, and inducing the unfolded protein response pathway. METHODS AND RESULTS: The interaction of Gartanin with the ligand-binding domain was characterized using a fluorescence polarization cell-free assay and cell-based FRET assay. Western blot analysis identified modulation of ER stress markers (BiP, PERK, IRE1, and CHOP) along with androgen receptor degradation. A computation simulation was performed to identify possible orientations of Gartanin with the ligand-binding domain. Utilizing a cell-free and cell-based FRET assays Gartanin was found to interact with the ligand-binding domain through a solely antagonist interaction. Interestingly, inhibition of CHOP, a critical component of the ER stress pathway, was observed to stabilize AR. CONCLUSIONS: Gartanin is an isoprenylated xanthone that promotes AR degradation with evidence suggesting this process is critically regulated by the unfolded protein response pathway.

Gartanin induces cell cycle arrest and autophagy and suppresses migration involving PI3K/Akt/mTOR and MAPK signalling pathway in human glioma cells.[Pubmed:27491646]

J Cell Mol Med. 2017 Jan;21(1):46-57.

In central nervous system, glioma is the most common primary brain tumour. The diffuse migration and rapid proliferation are main obstacles for successful treatment. Gartanin, a natural xanthone of mangosteen, suppressed proliferation, migration and colony formation in a time- and concentration-dependent manner in T98G glioma cells but not in mouse normal neuronal HT22 cells. Gartanin, at low micromole, led to cell cycle arrest in G1 phase accompanied by inhibited expression level of G1 cell cycle regulatory proteins cyclin D1, while increased expression level of cyclin-dependent kinase inhibitor p27Kip1. In addition, the secretion and activity of matrix metalloproteinases 2/9 (MMP-2/-9) were significantly suppressed in T98G cells treated with Gartanin, and it might result from modulating mitogen-activated protein kinases (MAPK) signalling pathway in T98G glioma cells. Moreover, Gartanin significantly induced autophagy in T98G cells and increased GFP-LC3 punctate fluorescence accompanied by the increased expression level of Beclin 1 and LC3-II, while suppressed expression level of p62. Gartanin treatment resulted in obvious inhibition of PI3K/Akt/mTOR signalling pathway, which is important in modulating autophagy. Notably, Gartanin-mediated anti-viability was significantly abrogated by autophagy inhibitors including 3-methyladenine (3-MA) and chloroquine (CQ). These results indicate that anti-proliferation effect of Gartanin in T98G cells is most likely via cell cycle arrest modulated by autophagy, which is regulated by PI3K/Akt/mTOR signalling pathway, while anti-migration effect is most likely via suppression of MMP-2/-9 activity which is involved in MAPK signalling pathway.

Gartanin induces autophagy through JNK activation which extenuates caspase-dependent apoptosis.[Pubmed:25955534]

Oncol Rep. 2015 Jul;34(1):139-46.

Hepatocellular carcinoma (HCC) is the third leading cause of cancer-related death worldwide. Development of novel agents to eradicate liver cancer cells is required for treatment of HCC. Gartanin, a xanthone-type compound isolated from mangosteen, is known to possess potent antioxidant, anti-inflammatory, antifungal and antineoplastic properties. In the present study, we investigated the cytotoxic effect of Gartanin on HCC and explored the cell death mechanism. We showed that Gartanin induced both the extrinsic and intrinsic apoptotic pathways, which were interconnected by caspase-8, -9 and -3 activation. We also provided convincing evidence that Gartanin induced autophagy in various cancer cells, as demonstrated by acridine orange staining of intracellular acidic vesicles, the degradation of p62, the conversion of LC3-I to LC3-II and GFP-LC3 punctate fluorescence. Additionally, Gartanin induced the formation of typical autophagosomes and autolysosomes and enhanced the degradation rate of intracellular granule(s), including mitochondria. Notably, Gartanin-mediated apoptotic cell death was further potentiated by pretreatment with autophagy inhibitors (3-methyladenine and bafilomycin A1) or small interfering RNAs against the autophagic genes (Atg5). These findings suggested that Gartanin-mediated autophagic response protected against eventual cell death induced by Gartanin. Moreover, Gartanin treatment led to phosphorylation/activation of JNK and JNK-dependent phosphorylation of Bcl-2. Importantly, JNK inhibitor (SP600125) inhibited autophagy yet promoted Gartanin-induced apoptosis, indicating a key requirement of the JNK-Bcl-2 pathway in the activation of autophagy by Gartanin. Taken together, our data suggested that the JNK-Bcl-2 pathway was the critical regulator of Gartanin-induced protective autophagy and a potential drug target for chemotherapeutic combination.

The effect of gartanin, a naturally occurring xanthone in mangosteen juice, on the mTOR pathway, autophagy, apoptosis, and the growth of human urinary bladder cancer cell lines.[Pubmed:23682785]

Nutr Cancer. 2013;65 Suppl 1:68-77.

Garcinia mangostana, often referred to as mangosteen, is a fruit grown in Southeast Asia and has been used for centuries as a local beverage and natural medicine. Its bioactive compounds, xanthones (i.e., Gartanin, alpha-mangostin, etc), have reported effects on ailments ranging from skin infections and inflammation to urinary tract infections. We demonstrate that mangosteen xanthones (i.e., Gartanin and alpha-mangostin) at pharmacologically achievable concentrations inhibit the growth of cancer cell lines from different stages of human urinary bladder cancer. The growth inhibitory effects of Gartanin in mouse embryonic fibroblasts are at least in part dependent on the existence of p53 or TSC1. Indeed, further studies have shown that Gartanin treatment of bladder cancer cell lines T24 and RT4 resulted in a marked suppression of p70S6 and 4E-BP1 expression and induction of autophagy, suggesting the inhibition of the mTOR pathway. In addition, Gartanin downregulated the expression of Bcl-2 and activated the p53 pathway leading to apoptosis induction. Together, these results suggested that Gartanin is a multiple targeting agent that is suitable for further study into its chemopreventive properties for human urinary bladder cancer.

Description

Gartanin is a natural xanthone of mangosteen, with antioxidant, anti-inflammatory, antifungal, neuroprotective and antineoplastic properties. Gartanin induces cell cycle arrest and autophagy and suppresses migration in human glioma cells.

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