Name: Isogarcinol
Rating: 5 (10 reviews)

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HIT ID:HIT212732382
Cas No:71117-97-0
常用名:Isogarcinol
IUPAC:(1S,3S,9R,11R)-7-(3,4-dihydroxybenzoyl)-4,4,10,10-tetramethyl-3,9,11-tris(3-methylbut-2-en-1-yl)-5-oxatricyclo[7.3.1.0^{1,6}]tridec-6-ene-8,13-dione
IUPAC:(1S,3S,9R,11R)-7-(3,4-dihydroxybenzoyl)-4,4,10,10-tetramethyl-3,9,11-tris(3-methylbut-2-en-1-yl)-5-oxatricyclo[7.3.1.0^{1,6}]tridec-6-ene-8,13-dione
InChI key:KXTNVBQRLRYVCO-LPSZMIQCSA-N

分子式:C38H50O6
分子量:602.812
氢键供体数 (HBD):2
氢键受体数 (HBA):6
LogP:8.726593
SMILES:[#6]\[#6](-[#6])=[#6]\[#6]-[#6@H]1-[#6][C@@]23[#6]-[#6@@H](-[#6]\[#6]=[#6](\[#6])-[#6])C([#6])([#6])[C@@]([#6]\[#6]=[#6](\[#6])-[#6])([#6](=O)-[#6](-[#6](=O)-c4ccc(-[#8])c(-[#8])c4)=[#6]2-[#8]C1([#6])[#6])[#6]3=O |c:37|
SMILES:[#6]\[#6](-[#6])=[#6]\[#6]-[#6@H]1-[#6][C@@]23[#6]-[#6@@H](-[#6]\[#6]=[#6](\[#6])-[#6])C([#6])([#6])[C@@]([#6]\[#6]=[#6](\[#6])-[#6])([#6](=O)-[#6](-[#6](=O)-c4ccc(-[#8])c(-[#8])c4)=[#6]2-[#8]C1([#6])[#6])[#6]3=O |c:37|

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. 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. 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.

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