| Identification | More | [Name]
Mangostin | [CAS]
6147-11-1 | [Synonyms]
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one
1,3,6-TRIHYDROXY-7-METHOXY-2,8-DI(3-METHYL-2-BUTENYL)XANTHONE
Mangosteen
mangostin
MANGOSTINE
Momordica Fruit P.E.
Fructus Monordicae extract
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3,3-dimethylallyl)xanthone
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methyl-2-buten-1-yl)-9H-xanthen-9-one
NSC 139154
NSC 27593
NSC 30552
α-Mangosten
a-Mangosten
a-Mangostin
1,3,6-Trihydroxy-2,8-diprenyl-7-methoxy-9H-xanthene-9-one
7-Methoxy-1,3,6-trihydroxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthene-9-one | [EINECS(EC#)]
683-120-1 | [Molecular Formula]
C24H26O6 | [MDL Number]
MFCD00135200 | [Molecular Weight]
410.46 | [MOL File]
6147-11-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow Crystalline Solid | [Melting point ]
180-182°C | [Boiling point ]
640.1±55.0 °C(Predicted) | [density ]
1.265±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
methanol: soluble1mg/mL, clear, very light yellow | [form ]
powder | [pka]
7.22±0.20(Predicted) | [color ]
faint yellow to yellow | [Usage]
It was isolated from Garcinia mangostana Linn (Guttiferae). It is an anti-inflammatory agent | [λmax]
346nm(MeOH)(lit.) | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. | [InChI]
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 | [InChIKey]
GNRIZKKCNOBBMO-UHFFFAOYSA-N | [SMILES]
C1(=O)C2=C(C=C(O)C(OC)=C2C/C=C(/C)\C)OC2=C1C(O)=C(C/C=C(/C)\C)C(O)=C2 | [CAS DataBase Reference]
6147-11-1(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
α-Mangostin (6147-11-1) is a xanthone natural product that has historically been used in traditional folk medicine.1 It is a potent agonist of human STING (Stimulator of Interferon Genes) and also weakly activates mouse STING.2 Induces IFN-β production and repolarizes human monocyte-derived M2 macrophages to M1. Improves insulin secretion and protects INS-1 cells from streptozotocin-induced damage.3 Suppresses the metastasis of human renal carcinoma cells.4 Synergizes with kinase inhibitors in suppression of proliferation of SK-MEL-2 malignant melanoma cells.5 | [Chemical Properties]
Yellow Crystalline Solid | [Uses]
antifungal, antilarval | [Uses]
It was isolated from Garcinia mangostana Linn (Guttiferae). It is an anti-inflammatory agent | [Definition]
ChEBI: Alpha-mangostin is a member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities. It has a role as an antineoplastic agent, an antimicrobial agent, an antioxidant and a plant metabolite. It is a member of xanthones, a member of phenols and an aromatic ether. | [General Description]
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG | [Biochem/physiol Actions]
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. | [storage]
Store at 2-8°C | [References]
1) Mohan et al. (2018), An anti-inflammatory molecular mechanism of action of α-mangostin, the major xanthone from the pericarp of Garcinia mangostana: an in silico, in vitro and in vivo approach; Food Funct., 9 3860
2) Zhang et al. (2018), Identification of α-Mangostin as an Agonist of Human STING; Chem. Med. Chem.,?13 2057
3) Lee et al. (2018), Alpha-Mangostin Improves Insulin Secretion and Protects INS-1 Cells from Streptozotocin-induced Damage; J. Mol. Sci., 19 E1484
4) Chen et al. (2017), Alpha-Mangostin Suppresses the Metastasis of Human renal Carcinoma Cells by Targeting MEK/ERK Expression and MMP-9 Transcription Activity; Cell Physiol. Biochem., 44 1460
5) Xia and Sun (2018), Synergistic inhibition of cell proliferation by combined targeting with kinase inhibitors and dietary xanthone is a promising strategy for melanoma treatment; Clin. Exp. Dermatol., 43 149 |
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