alpha-Mangostin

Names

[ Name ]:
alpha-Mangostin

[Synonym ]:
1,3,6-Trihydroxy-7-methoxy-2,8-di(3-methyl-2-butenyl)xanthone
Mangostin
1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
alpha-mangostin
EINECS 448-420-7
a-Mangostin
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one
9H-Xanthen-9-one, 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-buten-1-yl)-
1,3,6-Trihydroxy-7-méthoxy-2,8-bis(3-méthyl-2-butèn-1-yl)-9H-xanthén-9-one
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methyl-2-buten-1-yl)-9H-xanthen-9-one
9H-Xanthen-9-one, 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
MFCD00135200

Biological Activity

[Description]:

Alpha-mangostin is a dietary xanthone with broad biological activities, such as antioxidant, anti-allergic, antiviral, antibacterial, anti-inflammatory and anticancer effects. It is an inhibitor of mutant IDH1 (IDH1-R132H) with a Ki of 2.85 μM.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Others

[Target]

IC50: 2.85 μM (IDH1-R132H)[1]

[In Vitro]

Alpha-mangostin exhibits a selective inhibitory effect on IDH1-R132H, but not on IDH1. Alpha-mangostin competitively inhibits the binding of alpha-mangostin (α-KG) to IDH1-R132H. The structure–relationship study reveals that alpha-mangostin exhibits the strongest core inhibitor structure. Alpha-mangostin selectively promotes demethylation of 5-methylcytosine (5mC) and histone H3 trimethylated lysine residues in IDH1 (+/R132H) MCF10A cells[1]. Cell proliferation significantly decreases in a dose-dependent manner in the cells treated with alpha-mangostin. Alpha-mangostin also increases the levels of Bax (pro-apoptotic), cleaved caspase-3, cleaved caspase-9 and cleaved-poly(ADP-ribose) polymerase (PARP)[2]. Alpha-mangostin significantly inhibits light-induced degeneration of photoreceptors and 200 μM H2O2-induced apoptosis of RPE cells. 200 μM H2O2-induced generation of reactive oxygen species (ROS) and light-induced generation of malondialdehyde (MDA) are suppressed by alpha-mangostin[3].

[In Vivo]

Alpha-mangostin reduces risk of liver fibrosis through the decrease in p53 expression as compared to the TAA_DMSO treatment. The serum levels of the liver enzymes AST and ALT after treatment with α-mangostin decrease as compared to DMSO alone[4].

[Cell Assay]

IDH1+/+ and IDH1 MCF10A cells are grown in DMEM/F-12 media, supplemented with 5% horse serum, 20 ng/mL EGF, 0.5 μg/mL hydrocortisone, 10 μg/mL insulin. IDH1+/+ and IDH1 MCF10A cells are seeded in 6 well plates. After an exposure to 5 μM alpha-mangostin. cells are collected after indicated times and the viable cell number is calculated, using hemacytometer counting[1].

[Animal admin]

Rats: Male Wistar rats are divided into 3 groups and treated with intraperitoneal injections of TAA (200 mg/kg). One subgroup is left untreated whereas the other two are treated either with 100 mg/kg alpha-mangostin or vehicle alone (80% DMSO, 20% water), which are administered intraperitoneally 3 times per weekfor a total of4 weeks. The incidence offibrotic nodules on the liver and the serum levels of the liver enzymes aspartate transaminase (AST) and alanine transaminase (ALT) are measured[4].

[References]

[1]. Kim HJ, et al. Discovery of α-mangostin as a novel competitive inhibitor against mutant isocitrate dehydrogenase-1. Bioorg Med Chem Lett. 2015 Dec 1;25(23):5625-31.

[2]. Lee HN, et al. Antitumor and apoptosis-inducing effects of α-mangostin extracted from the pericarp of the mangosteen fruit (Garcinia mangostana L.) in YD-15 tongue mucoepidermoid carcinoma cells. Int J Mol Med. 2016 Apr;37(4):939-48.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
640.1±55.0 °C at 760 mmHg

[ Melting Point ]:
182ºC

[ Molecular Formula ]:
C₂₄H₂₆O₆

[ Molecular Weight ]:
410.460

[ Flash Point ]:
220.3±25.0 °C

[ Exact Mass ]:
410.172943

[ PSA ]:
100.13000

[ LogP ]:
5.45

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.624

[ Storage condition ]:
2-8°C

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Hazard Codes ]:
T

[ Risk Phrases ]:
25

[ Safety Phrases ]:
45

[ RIDADR ]:
UN 2811 6.1 / PGIII

[ RTECS ]:
ZD6122420

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Alpha-mangostin induces changes in glutathione levels associated with glutathione peroxidase activity in rat brain synaptosomes.

Nutr. Neurosci. 15(5) , 13-9, (2012)

In a previous report, we have characterized the antiperoxidative properties of alpha-mangostin in different toxic models tested in nerve tissue preparations.Here, the modulatory effects of this xantho...

A miniaturized flow-through cell to evaluate skin permeation of endoxifen.

Int. J. Pharm. 441(1-2) , 433-40, (2013)

Endoxifen, an anti-estrogenic agent, has been recently implicated in the use of breast cancer. Its physicochemical properties make it a good candidate for transdermal delivery. However, as an investig...

Neuroprotective effect of α-mangostin and curcumin against iodoacetate-induced cell death.

Nutr. Neurosci. 15(5) , 34-41, (2012)

Curcumin is a phenolic yellow curry pigment with anti-inflammatory and antioxidant activities and α-mangostin is a xanthone isolated from mangosteen fruit with antioxidant properties. Iodoacetate (IAA...