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M3824

Sigma-Aldrich

α-Mangostin

≥98% (HPLC)

Synonym(s):

α-MG, alpha-Mangostin

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About This Item

Empirical Formula (Hill Notation):
C24H26O6
CAS Number:
6147-11-1
Molecular Weight:
410.46
EC Number:
448-420-7
MDL number:
MFCD00135200
UNSPSC Code:
12352212
PubChem Substance ID:
329817982
NACRES:
NA.25

Quality Level

200

Assay

≥98% (HPLC)

form

powder

solubility

methanol: 1 mg/mL, clear, very light yellow

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

COc1c(O)cc2Oc3cc(O)c(C\C=C(\C)C)c(O)c3C(=O)c2c1C\C=C(/C)C

InChI

1S/C24H26O6/c1-12(2)6-8-14-16(25)10-19-21(22(14)27)23(28)20-15(9-7-13(3)4)24(29-5)17(26)11-18(20)30-19/h6-7,10-11,25-27H,8-9H2,1-5H3

InChI key

GNRIZKKCNOBBMO-UHFFFAOYSA-N

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General description

α-Mangostin (α-MG) is the most abundant phytochemical derived from the pericarp of Garcinia mangostana L.. It is a tetraoxygenated diprenylated xanthone. The chemical structure of α-MG molecule is 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)- 9H-xanthen-9-one.

Application

α-Mangostin has been used:
  • to study its protective effect against oxidative stress mediated-retinal cell death
  • to study its role as an antigenotoxic agent in DNA protection against oxidative damage
  • to understand its anti-bacterial activity against Staphylococcus epidermidis RP62A

Biochem/physiol Actions

α-Mangostin displays various pharmacological properties both in in vitro and in vivo studies. These include antimicrobial, anticarcinogenic, antidiabetic, neuroprotective, hepatoprotective and anti-inflammatory properties.
Xanthone derivative isolated from mangosteen (Garcinia mangostana). Antioxidant and anti-inflammatory. α-mangostin has been shown to induce apoptosis via the mitochondrial pathway, reduce cell proliferation and inhibit tumorigenesis.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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DNA Protection against Oxidative Damage Using the Hydroalcoholic Extract of Garcinia mangostana and Alpha-Mangostin.
Carvalho-Silva R
Evidence-Based Complementary and Alternative Medicine : ECAM, 2016, 3430405-3430405 (2016)
Yuan Fang et al.
Scientific reports, 6, 21018-21018 (2016-02-19)
It is known that oxidative stress plays a pivotal role in age-related macular degeneration (AMD) pathogenesis. Alpha-mangostin is the main xanthone purified from mangosteen known as anti-oxidative properties. The aim of the study was to test the protective effect of
Abdalrahim F A Aisha et al.
Journal of pharmaceutical sciences, 101(2), 815-825 (2011-11-15)
α-Mangostin is an oxygenated heterocyclic xanthone with remarkable pharmacological properties, but poor aqueous solubility and low oral bioavailability hinder its therapeutic application. This study sought to improve the compound's solubility and study the mechanism underlying solubility enhancement. Solid dispersions of
Ali Ghasemzadeh et al.
Molecules (Basel, Switzerland), 23(8) (2018-07-26)
Since α-mangostin in mangosteen fruits was reported to be the main compound able to provide natural antioxidants, the microwave-assisted extraction process to obtain high-quality α-mangostin from mangosteen pericarp (Garcinia mangostana L.) was optimized using a central composite design and response
Xiaofang Quan et al.
PloS one, 7(3), e33376-e33376 (2012-03-20)
α-Mangostin, isolated from the hulls of Garcinia mangostana L., was found to have in vitro cytotoxicity against 3T3-L1 cells as well as inhibiting fatty acid synthase (FAS, EC 2.3.1.85). Our studies showed that the cytotoxicity of α-mangostin with IC(50) value
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