A xanthone with diverse biological activities
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Isomer(s)
29108α-Mangostin
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3-Isomangostin

Item No. 36484

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,4-dihydro-5,9-dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-butenyl)-2H,6H-pyrano[3,2-b]xanthen-6-one
CAS Number
19275-46-8
Molecular Formula
C24H26O6
Formula Weight
410.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetone: solubleChloroform: solubleDichloromethane: solubleDMSO: solubleEthyl Acetate: soluble
SMILES
O=C1C2=C(OC3=CC(O)=C(C(C/C=C(C)\C)=C13)OC)C=C(OC(C)(CC4)C)C4=C2O
InChi Code
InChI=1S/C24H26O6/c1-12(2)6-7-14-19-17(10-15(25)23(14)28-5)29-18-11-16-13(8-9-24(3,4)30-16)21(26)20(18)22(19)27/h6,10-11,25-26H,7-9H2,1-5H3
InChi Key
KJCDBAVVDILRMP-UHFFFAOYSA-N
Origin
Plant/Garcinia mangostana L.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    3-Isomangostin is a xanthone and α-mangostin (Item No. 29108) derivative that has been found in G. mangostana and has diverse biological activities.1,2,3,4,5,6 It is an inhibitor of mutT homolog 1 (MTH1; IC50 = 52 nM).1 3-Isomangostin also inhibits aldose reductase (IC50 = 3.48 µM), acetylcholinesterase (AChE; IC50 = 2.36 µg/ml), and butyrylcholinesterase (BChE; IC50 = 5.32 µg/ml).2,3 It inhibits the growth of P. falciparum strains D6 and W2 in isolated and infected red blood cells (IC50s = 3.23 and 2.52 µg/ml, respectively).4 3-Isomangostin inhibits cyclin D2/Cdk4 and cyclin E1/Cdk2 (EC50s = 15.6 and 34.92 µM, respectively) and reduces viability of HCC1937 and HCT116 cells (IC50s = 59.9 and 47.4 µM, respectively).5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yokoyama, T., Kitakami, R., and Mizuguchi, M. Discovery of a new class of MTH1 inhibitor by X-ray crystallographic screening. Eur. J. Med. Chem. 167, 153-160 (2019).

    2. Khaw, K.Y., Choi, S.B., Tan, S.C., et al. Prenylated xanthones from mangosteen as promising cholinesterase inhibitors and their molecular docking studies. Phytomedicine 21(11), 1303-1309 (2014).

    3. Fatmawati, S., Ersam, T., and Shimizu, K. The inhibitory activity of aldose reductase in vitro by constituents of Garcinia mangostana Linn. Phytomedicine 22(1), 49-51 (2015).

    4. Lyles, J.T., Negrin, A., Khan, S.I., et al. In vitro antiplasmodial activity of benzophenones and xanthones from edible fruits of Garcinia species. Planta Med. 80(8-9), 676-681 (2014).

    5. Vemu, B., Nauman, M.C., Veenstra, J.P., et al. Structure activity relationship of xanthones for inhibition of cyclin dependent kinase 4 from mangosteen (Garcinia mangostana L.). Int. J. Nutr. 4(2), 38-45 (2019).

    6. Nauman, M.C., Tocmo, R., Vemu, B., et al. Inhibition of CDK2/CyclinE1 by xanthones from the mangosteen (Garcinia mangostana): A structure-activity relationship study. Nat. Prod. Res. 35(23), 5429-5433 (2021).