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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

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

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

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

wgk_germany

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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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
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)
Jeremy J Johnson et al.
Carcinogenesis, 33(2), 413-419 (2011-12-14)
There is a need to characterize promising dietary agents for chemoprevention and therapy of prostate cancer (PCa). We examined the anticancer effect of α-mangostin, derived from the mangosteen fruit, in human PCa cells and its role in targeting cell cycle-related
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
Fabiola Gutierrez-Orozco et al.
Journal of agricultural and food chemistry, 61(16), 3891-3900 (2013-04-13)
Information about the anti-inflammatory activity and metabolism of α-mangostin (α-MG), the most abundant xanthone in mangosteen fruit, in human cells is limited. On the basis of available literature, we hypothesized that α-MG will inhibit the secretion of pro-inflammatory mediators by
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