Garcinone C

CAS# 76996-27-5

Garcinone C

2D Structure

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Garcinone C

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Chemical Properties of Garcinone C

Cas No. 76996-27-5 SDF Download SDF
PubChem ID 44159808 Appearance Yellow powder
Formula C23H26O7 M.Wt 414.5
Type of Compound Xanthones Storage Desiccate at -20°C
Solubility Soluble in acetone, chloroform, diethyl ether, ethyl acetate and methanol; practically insoluble in water
Chemical Name 1,3,6,7-tetrahydroxy-8-(3-hydroxy-3-methylbutyl)-2-(3-methylbut-2-enyl)xanthen-9-one
SMILES CC(=CCC1=C(C=C2C(=C1O)C(=O)C3=C(C(=C(C=C3O2)O)O)CCC(C)(C)O)O)C
Standard InChIKey HLOCLVMUASBDDP-UHFFFAOYSA-N
Standard InChI InChI=1S/C23H26O7/c1-11(2)5-6-12-14(24)9-17-19(21(12)27)22(28)18-13(7-8-23(3,4)29)20(26)15(25)10-16(18)30-17/h5,9-10,24-27,29H,6-8H2,1-4H3
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 Garcinone C

The fruits of Garcinia mangostana

Biological Activity of Garcinone C

Description1. Garcinone C is the most potent inhibitor of AChE. 2. Garcinone C is the most active compound against both of pathogenic (MIC =100 μg/ml) and non-pathogenic leptospira (MIC = 200 μg/ml). 3. Garcinone C exhibits either significant or moderate cytotoxicity against MCF-7, A549, Hep-G2 and CNEhuman cancer cell lines in vitro.
TargetsAChR | Antifection

Garcinone C Dilution Calculator

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Garcinone C Molarity Calculator

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Preparing Stock Solutions of Garcinone C

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4125 mL 12.0627 mL 24.1255 mL 48.2509 mL 60.3136 mL
5 mM 0.4825 mL 2.4125 mL 4.8251 mL 9.6502 mL 12.0627 mL
10 mM 0.2413 mL 1.2063 mL 2.4125 mL 4.8251 mL 6.0314 mL
50 mM 0.0483 mL 0.2413 mL 0.4825 mL 0.965 mL 1.2063 mL
100 mM 0.0241 mL 0.1206 mL 0.2413 mL 0.4825 mL 0.6031 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 Garcinone C

A new xanthone from the pericarp of Garcinia mangostana.[Pubmed:24555285]

Nat Prod Commun. 2013 Dec;8(12):1733-4.

A new prenylxanthone, garcimangostanol (1), was isolated from the EtOAc-soluble partition of the ethanol extract of the pericarp of Garcinia mangostana L., along with three known compounds, namely 8-deoxygartanin (2), 1-isomangostin (3), and Garcinone C (4). The structure of compound 1 was elucidated on the basis of its 1D, 2D NMR and MS data. Compounds 1-4 exhibited either significant o r moderate cytotoxicity against MCF-7, A549, Hep-G2 and CNEhuman cancer cell lines in vitro with IC50 values from 4.0 +/- 0.3 to 23.6+/- 1.5 microM by MTT colorimetric assay.

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.

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.

Description

Garcinone C, a xanthone derivative, is a natural compound extracted from Garcinia oblongifolia Champ that is used as an anti-inflammatory, analgesia, astringency and granulation-promoting medicine, and has potential cytotoxic effects on certain cancers. Garcinone C stimulates the expression levels of ATR and 4E-BP1, while efficiently inhibiting the expression levels of cyclin B1, cyclin D1, cyclin E2, cdc2, Stat3 and CDK7. Garcinone C significantly inhibits cell viability of the human Nasopharyngeal carcinoma (NPC) cell lines CNE1, CNE2, HK1 and HONE1 in a time‑ and dose‑dependent manner.

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