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Rhapontigenin

Names

[ CAS No. ]:
500-65-2

[ Name ]:
Rhapontigenin

[Synonym ]:
trans-1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene
5-[(E)-2-(3-Hydroxy-4-methoxyphenyl)vinyl]-1,3-benzenediol
rhapontigenin
5-[(E)-2-(3-Hydroxy-4-methoxyphenyl)vinyl]benzene-1,3-diol
(E)-5-(3-Hydroxy-4-methoxystyryl)benzene-1,3-diol
1,3-Benzenediol, 5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-
3,3',5-Trihydroxy-4'-methoxy-trans-stilbene
5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol

Biological Activity

[Description]:

Rhapontigenin is a natural analog of resveratrol with anticancer, antioxidant, antifungal and antibacterial activities. Rhapontigenin is amechanism-based, potent and selective cytochrome P450 1A1 inactivator (IC50 = 400 nM). Rhapontigenin exhibits 400-fold and 23-fold selectivity for P450 1A1 over P450 1A2 and P450 1B1, respectively[1].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450
Research Areas >> Inflammation/Immunology

[Target]

CYP1A1:400 nM (IC50)


[In Vitro]

Rhapontigenin (0-250 μM; 24 hours) demonstrates concentration-dependent anti-cancer activity with an IC50 115μM in HEP G2 cells[1]. Rhapontigenin (20 μM; 20 hours) pre-treatment decreases TGF-β triggered increased snail expression in diverse cancer cells[2]. Rhapontigenin (0-20 μM; 6 hours) inhibits TGF-β-induced expression of N-cadherin, vimentin, and CA9 in a dose-dependent manner[2]. Rhapontigenin inhibits ADP- and collagen-induced platelet aggregation with IC50 values of 4 and 70 μg/ml, respectively[3]. Rhapontigenin demonstrates a strong inhibitory activity on the 13-hexosaminidase release induced by DNP-BSA, it exhibits IC50 value of 0.03 mM in RBL 2H3 cells[3]. Western Blot Analysis[2] Cell Line: HeLa, A549,769-P cells Concentration: 0 μM; 2.5 μM; 5 μM; 10 μM; 20 μM Incubation Time: 6 hours Result: Induced ubiquitination and degradation of HIF-1α.

[In Vivo]

Rhapontigenin (intraperitoneal injection; 25mg/kg) shows significant protection from death due to pulmonary thrombosis in mice, those samples are orally administered 90 min before tail vein injection of epinephrine and collagen[3]. Animal Model: ICR mice[3] Dosage: 25mg/kg Administration: 25mg/kg; intraperitoneal injection Result: Showed anti-thrombosis activity with 60% protection.

[References]

[1]. Roupe KA, et al. Preparative enzymatic synthesis and HPLC analysis of rhapontigenin: applications to metabolism, pharmacokinetics and anti-cancer studies.J Pharm Pharm Sci. 2005 Aug 22;8(3):374-86.

[2]. Yeh YH, et al. Rhapontigenin inhibits TGF-β-mediated epithelial‑mesenchymal transition via the PI3K/AKT/mTOR pathway and is not associated with HIF-1α degradation.Oncol Rep. 2016 May;35(5):2887-95.

[3]. Park EK, et al. Antithrombotic and antiallergic activities of rhaponticin from Rhei Rhizoma are activated by human intestinal bacteria.Arch Pharm Res. 2002 Aug;25(4):528-33.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
503.6±38.0 °C at 760 mmHg

[ Melting Point ]:
186-187ºC

[ Molecular Formula ]:
C15H14O4

[ Molecular Weight ]:
258.269

[ Flash Point ]:
258.4±26.8 °C

[ Exact Mass ]:
258.089203

[ PSA ]:
69.92000

[ LogP ]:
2.82

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.722

MSDS

Click to get detail MSDS

Related Compounds