A natural benzophenone that has immunosuppressant actions
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Isomer(s)
10566Garcinol
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Isogarcinol

Item No. 21164

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,4aS,6R,8R)-10-(3,4-dihydroxybenzoyl)-3,4,5,6,7,8-hexahydro-2,2,7,7-tetramethyl-3,6,8-tris(3-methyl-2-buten-1-yl)-9H-4a,8-methano-2H-cycloocta[b]pyran-9,11-dione
CAS Number
71117-97-0
Synonyms
  • Cambogin
Molecular Formula
C38H50O6
Formula Weight
602.8
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlDMSO:PBS (pH 7.2) (1:10): 0.1 mg/mlEthanol: 20 mg/ml
λmax
228, 230, 276 nm
SMILES
CC([C@H](C/C=C(C)/C)C[C@]1(C[C@H](C/C=C(C)/C)C(C)(C)O2)C2=C3C(C4=CC(O)=C(O)C=C4)=O)(C)[C@](C/C=C(C)\C)(C1=O)C3=O
InChi Code
InChI=1S/C38H50O6/c1-22(2)11-14-26-20-37-21-27(15-12-23(3)4)36(9,10)44-33(37)30(31(41)25-13-16-28(39)29(40)19-25)32(42)38(34(37)43,35(26,7)8)18-17-24(5)6/h11-13,16-17,19,26-27,39-40H,14-15,18,20-21H2,1-10H3/t26-,27+,37+,38+/m1/s1
InChi Key
KXTNVBQRLRYVCO-LPSZMIQCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Isogarcinol is a natural polyisoprenylated benzophenone first isolated from plant species in the genus Garcinia. It has immunosuppressant actions, inhibiting the protein phosphatase calcineurin (IC50 = 36 µM) and suppressing the proliferation of T cells.1 Oral administration of isogarcinol in mice decreases delayed type hypersensitivity, prolongs graft survival in allogeneic skin transplants, suppresses inflammation in collagen-induced arthritis, and reduces clinical symptoms in experimental autoimmune encephalomyelitis.1,2,3 Isogarcinol inhibits the proliferation of HL-60 and PC-3 cancer cells (IC50s = 4 and 8 µg/ml, respectively) through cell cycle arrest and apoptosis.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cen, J., Shi, M., Yang, Y., et al. Isogarcinol is a new immunosuppressant. PLoS One 8(6), e66503 (2013).

    2. Fu, Y., Zhou, H., Wang, M., et al. Immune regulation and anti-inflammatory effects of isogarcinol extracted from Garcinia mangostana L. against collagen-induced arthritis. J. Agric. Food Chem. 62(18), 4127-4134 (2014).

    3. Wang, M., Xie, Y., Xhong, Y., et al. Amelioration of experimental autoimmune encephalomyelitis by isogarcinol extracted from Garcinia mangostana L. Mangosteen. J. Agric. Food Chem. 64(47), 9012-9021 (2016).

    4. Pieme, C.A., Ambassa, P., Yankep, E., et al. Epigarcinol and isogarcinol isolated from the root of Garcinia ovalifolia induce apoptosis of human promyelocytic leukemia (HL-60 cells). BMC Res. Notes 8, 700 (2015).