ChemicalBook--->CAS DataBase List--->351416-47-2

351416-47-2

351416-47-2 Structure

351416-47-2 Structure
IdentificationBack Directory
[Name]

nemorosone
[CAS]

351416-47-2
[Synonyms]

nemorosone
[Molecular Formula]

C33H42O4
[MDL Number]

MFCD31579645
[MOL File]

351416-47-2.mol
[Molecular Weight]

502.68
Chemical PropertiesBack Directory
[Boiling point ]

608.9±55.0 °C(Predicted)
[density ]

1.077±0.06 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

DMF:30.0(Max Conc. mg/mL);59.68(Max Conc. mM)
DMSO:30.0(Max Conc. mg/mL);59.68(Max Conc. mM)
Ethanol:30.0(Max Conc. mg/mL);59.68(Max Conc. mM)
[form ]

A crystalline solid
[pka]

4.50±1.00(Predicted)
[color ]

White to off-white
Hazard InformationBack Directory
[Description]

Nemorosone is a polycyclic polyprenylated acylphloroglucinol (PPAP) originally isolated from C. rosea that has antiproliferative properties. 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). 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). 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. Nemorosone (50 mg/kg, i.p., per day) also reduces tumor growth in an MIA-PaCa-2 mouse xenograft model.
[Uses]

Nemorosone is the main component of the floral resin of Clusia rosea. Nemorosone has an antiproliferative effect on cancer cells. Nemorosone induces apoptosis in HT-29 and LoVo cells[1][2].
[in vivo]

Nemorosone (50 mg/kg; daily i.p. for 28 days) shows a significant growth-inhibitory effect in pancreatic cancer xenografts[2].

Animal Model:Athymic NMRI nu/nu nude mices (6 to 8 week old female), which had 100 mm3 MIA-PaCa-2 xenograft tumor[2]
Dosage:50 mg/kg
Administration:Daily i.p. injections for 28 days
Result:Showed a significant growth-inhibitory effect in pancreatic cancer xenografts[2].
[storage]

Store at -20°C
[References]

[1] Frión-Herrera Y, Gabbia D, Scaffidi M, et al. The Cuban Propolis Component Nemorosone Inhibits Proliferation and Metastatic Properties of Human Colorectal Cancer Cells. Int J Mol Sci. 2020;21(5):1827. Published 2020 Mar 6. DOI:10.3390/ijms21051827
[2] Wolf RJ, et al. In vivo activity and pharmacokinetics of nemorosone on pancreatic cancer xenografts. PLoS One. 2013;8(9):e74555. Published 2013 Sep 5. DOI:10.1371/journal.pone.0074555
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