Mangostin Chemical Properties

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

pka

7.22±0.20(Predicted)

form 

powder

color 

faint yellow to yellow

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)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

1

RTECS 

ZD6122420

HS Code 

29329990

Hazardous Substances Data

6147-11-1(Hazardous Substances Data)

Mangostin Usage And Synthesis

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

It was isolated from Garcinia mangostana Linn (Guttiferae). It is an anti-inflammatory agent

Uses

antifungal, antilarval

Uses

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

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 -20°C

References

[1] MOHAN S, SYAM S, ABDELWAHAB S I, et al. 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[J]. Food & Function, 2018, 7: 3860-3871. DOI:10.1039/c8fo00439k
[2] DR. YIBO ZHANG. Identification of α-Mangostin as an Agonist of Human STING[J]. ChemMedChem, 2018, 13 19: 2057-2064. DOI:10.1002/cmdc.201800481
[3] DAHAE LEE. Alpha-Mangostin Improves Insulin Secretion and Protects INS-1 Cells from Streptozotocin-Induced Damage.[J]. International Journal of Molecular Sciences, 2018, 19 5. DOI:10.3390/ijms19051484
[4] CHIEN-MIN CHEN. Alpha-Mangostin Suppresses the Metastasis of Human Renal Carcinoma Cells by Targeting MEK/ERK Expression and MMP-9 Transcription Activity.[J]. Cellular Physiology and Biochemistry, 2017: 1460-1470. DOI:10.1159/000485582
[5] Y. XIA  J. S. Synergistic inhibition of cell proliferation by combined targeting with kinase inhibitors and dietary xanthone is a promising strategy for melanoma treatment[J]. Clinical and Experimental Dermatology, 2017, 43 2: 149-157. DOI:10.1111/ced.13283

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