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M6824

Sigma-Aldrich

gamma-Mangostin

≥98% (HPLC)

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

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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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
K Furukawa et al.
Nihon yakurigaku zasshi. Folia pharmacologica Japonica, 110 Suppl 1, 153P-158P (1998-03-21)
A crude methanolic extract of the fruit hull of Garcinia mangostana L. inhibited the contraction of the isolated rabbit aorta induced by histamine and serotonin. The extract has been fractionated by silica gel chromatography, monitoring the pharmacological activity to give
N Chairungsrilerd et al.
Planta medica, 62(5), 471-472 (1996-10-01)
A crude methanolic extract of the fruit hull of Mangosteen, Garcinia mangostana L. inhibited the contractions of isolated thoracic rabbit aorta induced by histamine and serotonin. The extract of the fruit hull has been fractionated by silica gel chromatography, monitoring
Z X Lu et al.
Chemico-biological interactions, 114(1-2), 121-140 (1998-09-23)
A series of prenylated xanthones are variously potent inhibitors of the catalytic subunit (cAK) of rat liver cyclic AMP-dependent protein kinase (PKA), rat brain Ca2+ and phospholipid-dependent protein kinase C (PKC), chicken gizzard myosin light chain kinase (MLCK), wheat embryo
N Chairungsrilerd et al.
Naunyn-Schmiedeberg's archives of pharmacology, 357(1), 25-31 (1998-02-12)
Gamma-mangostin, purified from the fruit hull of the medicinal plant Garcinia mangostana caused a parallel rightwards shift of the concentration/response curve for the contraction elicited by 5-hydroxytryptamine (5-HT) in the rabbit aorta (pA2 = 8.2) without affecting the contractile responses
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