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M6824

Sigma-Aldrich

gamma-Mangostin

≥98% (HPLC)

Synonym(s):

1,3,6,7-Tetrahydroxy-2,8-bis(3,3-dimethylallyl)xanthone, Demethylmangostin, Normangostin

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About This Item

Empirical Formula (Hill Notation):
C23H24O6
CAS Number:
31271-07-5
Molecular Weight:
396.43
MDL number:
MFCD00951752
UNSPSC Code:
12352200
NACRES:
NA.25

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

off-white to yellow

solubility

methanol: 1 mg/mL, colorless to yellow

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

OC1=CC(OC2=CC(O)=C(CC=C(C)C)C(O)=C2C3=O)=C3C(CC=C(C)C)=C1O

InChI

1S/C23H24O6/c1-11(2)5-7-13-15(24)9-18-20(22(13)27)23(28)19-14(8-6-12(3)4)21(26)16(25)10-17(19)29-18/h5-6,9-10,24-27H,7-8H2,1-4H3

InChI key

VEZXFTKZUMARDU-UHFFFAOYSA-N

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General description

The fruit hulls of mangosteen contain three major bioactive compounds namely, α-, β-, and γ-mangostin.

Application

γ-Mangostin has been used to study its inhibitory effect on Transthyretin (TTR) fibrillization, a homotetrameric protein involved in human hereditary amyloidosis.

Biochem/physiol Actions

The xanthone derivatives, namely α-, β-, and γ-mangostin have various biological activities including antiproliferative and anti-inflammatory activity, enhancement of natural killer (NK) cell activity, and antiviral effect against human immunodeficiency virus (HIV). γ-Mangostin is also reported to inhibit cyclooxygenase (COX-2) activity and NO production, which in turn reduces the level of prostaglandin E2. It is found to induce cell death in human colon cancer cells.
Xanthone derivative isolated from the mangosteen hull (Garcinia mangostana). Exhibits antioxidant and anticancer properties. Mangosteen xanthones inhibit inflammation in human adipocytes which is important in understanding obesity-associated inflammation and the development of insulin resistance.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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S X Chen et al.
Planta medica, 62(4), 381-382 (1996-08-01)
The ethanol extract of Garcinia mangostana L. (Guttiferae) showed potent inhibitory activity against HIV-1 protease. The activity-guided purification of the extract resulted in the isolation of two active, known compounds. The chemical structures of the isolated compounds were established by
Akkarach Bumrungpert et al.
The Journal of nutrition, 139(6), 1185-1191 (2009-05-01)
The xanthones, alpha- and gamma-mangostin (MG), are major bioactive compounds found in mangosteen and are reported to have antiinflammatory properties in several murine models. Given the association between obesity, chronic low-grade inflammation, and insulin resistance, we examined the effects of
Takeshi Yokoyama et al.
Scientific reports, 5, 13570-13570 (2015-08-28)
Transthyretin (TTR) is a homotetrameric protein involved in human hereditary amyloidoses. The discovery and development of small molecules that inhibit the amyloid fibril formation of TTR is one of the therapeutic strategies for these diseases. Herein, we discovered that γ-mangostin
Hui-Fang Chang et al.
Molecules (Basel, Switzerland), 17(7), 8010-8021 (2012-07-05)
Recently colorectal cancer rates have increased rapidly in Taiwan. The treatment of colorectal cancer includes surgery, radiation therapy and chemotherapy. Mangosteen (Garcinia mangostana) is a famous Asian tropical fruit. γ-Mangostin is a xanthone derivative isolated from the fruit hull. In
Keigo Nakatani et al.
Biochemical pharmacology, 63(1), 73-79 (2002-01-05)
The fruit hull of mangosteen, Garcinia mangostana L., has been used for many years as a medicine for treatment of skin infection, wounds, and diarrhea in Southeast Asia. In the present study, we examined the effect of gamma-mangostin, a tetraoxygenated
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