A xanthone with diverse biological activities
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Isomer(s)
364843-Isomangostin
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α-Mangostin

Item No. 29108

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-buten-1-yl)-9H-xanthen-9-one
CAS Number
6147-11-1
Synonyms
  • NSC 27593
  • NSC 139154
Molecular Formula
C24H26O6
Formula Weight
410.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 10 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
245, 318 nm
SMILES
OC1=C2C(OC(C=C(O)C(OC)=C3C/C=C(C)/C)=C3C2=O)=CC(O)=C1C/C=C(C)/C
InChi Code
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
Origin
Plant/Garcinia mangostana L.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    10 mg

    $49

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    25 mg

    $97

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    50 mg

    $171

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    100 mg

    $315

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    Product Description

    α-Mangostin is a xanthone that has been found in G. mangostana and has diverse biological activities.1,2,3,4,5 It inhibits fatty acid synthase and HIV-1 protease (IC50s = 5.54 and 5.12 μM, respectively).2,3 α-Mangostin is active against methicillin-sensitive and -resistant S. aureus strains (MICs = 1.57-12.5 μg/ml).1 It inhibits nitric oxide and prostaglandin E2 (PGE2; Item No. 14010) production in LPS-stimulated RAW 264.7 cells (IC50s = 12.4 and 11.08 μM, respectively).4 α-Mangostin is an agonist of stimulator of interferon genes (STING) that binds to the C-terminal domain of STING (H232 variant) with a Kd value of 137 μM and induces expression of an IFN-β-luciferase reporter in HEK293T cells transfected with human STING (H232 variant) to a greater extent than cells expressing murine STING or human STING (R232 variant) when used at a concentration of 25 μM.6 α-Mangostin (20 mg/kg) prevents carrageenan-induced paw edema in mice. It decreases the viability of LNCaP, 22Rv1, DU145, and PC3 prostate cancer cells in vitro (IC50s = 5.9, 6.9, 22.5, and 12.7 μM, respectively) and reduces tumor growth in a 22Rv1 mouse xenograft model when administered at a dose of 100 mg/kg.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Iinuma, M., Tosa, H., Tanaka, T., et al. Antibacterial activity of xanthones from guttiferaeous plants against methicillin-resistant Staphylococcus aureus. J. Pharm. Pharmacol. 48(8), 861-865 (1996).

    2. Jiang, H.Z., Quan, X.F., Tian, W.X., et al. Fatty acid synthase inhibitors of phenolic constituents isolated from Garcinia mangostana. Bioorg. Med. Chem. Lett. 20(20), 6045-6047 (2010).

    3. Chen, S.-X., Wan, M., and Loh, B.-N. Active constituents against HIV-1 protease from Garcinia mangostana. Planta Med. 62(4), 381-382 (1996).

    4. Chen, L.-G., Yang, L.-L., and Wang, C.-C. Anti-inflammatory activity of mangostins from Garcinia mangostana. Food Chem. Toxicol. 46(2), 688-693 (2008).

    5. Johnson, J.J., Petiwala, S.M., Syed, D.N., et al. α-Mangostin, a santhone from mangosteen fruit, promotes cell cycle arrest in prostate cancer and decreases xenograft tumor growth. Carcinogenesis 33(2), 413-419 (2012).

    6. Zhang, Y., Sun, Z., Pei, J., et al. Identification of α-mangostin as an agonist of human STING. ChemMedChem 13(19), 2057-2064 (2018).