Name: Nemorosone
Rating: 5 (10 reviews)

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HIT ID:HIT214321396
Cas No:351416-47-2
常用名:Nemorosone
IUPAC:(1R,5R,7S)-1-benzoyl-4-hydroxy-8,8-dimethyl-3,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione
IUPAC:(1R,5R,7S)-1-benzoyl-4-hydroxy-8,8-dimethyl-3,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione
InChI key:SYKFHCWMZKYPEA-RFQWPUQQSA-N

分子式:C33H42O4
分子量:502.695
氢键供体数 (HBD):
氢键受体数 (HBA):
LogP:
SMILES:[#6]\[#6](-[#6])=[#6]\[#6]-[#6@H]1-[#6][C@]2([#6]\[#6]=[#6](\[#6])-[#6])[#6](-[#8])=[#6](-[#6]\[#6]=[#6](\[#6])-[#6])-[#6](=O)[C@@]([#6](=O)-c3ccccc3)([#6]2=O)C1([#6])[#6] |t:14|
SMILES:[#6]\[#6](-[#6])=[#6]\[#6]-[#6@H]1-[#6][C@]2([#6]\[#6]=[#6](\[#6])-[#6])[#6](-[#8])=[#6](-[#6]\[#6]=[#6](\[#6])-[#6])-[#6](=O)[C@@]([#6](=O)-c3ccccc3)([#6]2=O)C1([#6])[#6] |t:14|

Nemorosone is a polycyclic polyprenylated acylphloroglucinol (PPAP) originally isolated from C. rosea that has antiproliferative properties.1 Nemorosone inhibits growth of NB69, Kelly, SK-N-AS, and LAN-1 neuroblastoma cells (IC50s = 3.1-6.3 μM), including several drug-resistant clones, but not MRC-5 human embryonic fibroblasts (IC50 = >40 μM).2 It increases DNA fragmentation in LAN-1 cells in a dose-dependent manner, and decreases N-Myc protein levels and phosphorylation of ERK1/2 by MEK1/2. Nemorosone also inhibits growth of Capan-1, AsPC-1, and MIA-PaCa-2 pancreatic cancer cells (IC50s = 4.5-5.0 μM following a 72-hour treatment) but not human dermal and foreskin fibroblasts (IC50s = >35 μM).1 It induces apoptosis, abolishes the mitochondrial membrane potential, and increases cytosolic calcium concentration in pancreatic cancer cells in a dose-dependent manner. Nemorosone activates the caspase cascade in a dose-dependent manner and inhibits cell cycle progression, increasing the proportion of cells in the G0/G1 phase, in both neuroblastoma and pancreatic cancer cells.1,2 Nemorosone (50 mg/kg, i.p., per day) also reduces tumor growth in an MIA-PaCa-2 mouse xenograft model.3

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