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Urolithin C

Names

[ CAS No. ]:
165393-06-6

[ Name ]:
Urolithin C

[Synonym ]:
Urolithin C
Uro C
3,8,9-thihydroxy-6H-benzo[c]chromen-6-one
6H-Dibenzo[b,d]pyran-6-one, 3,8,9-trihydroxy-
3,8,9-Thihydroxybenzo[c]chromen-6-one
3,8,9-Trihydroxy-6H-benzo[c]chromen-6-one
3,8,9-trihydroxy-6H-dibenzo[b,d]pyran-6-one

Biological Activity

[Description]:

Urolithin C, a gut-microbial metabolite of Ellagic acid, is a glucose-dependent activator of insulin secretion. Urolithin C is a L-type Ca2+ channel opener and enhances Ca2+ influx. Urolithin C induces cell apoptosis through a mitochondria-mediated pathway and also stimulates reactive oxygen species (ROS) formation[1][2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel
Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Metabolic Disease

[Target]

Insulin secretion[1] L-type Ca2+ channel[1] Reactive oxygen species (ROS)[2] Apoptosis[2]


[In Vitro]

Urolithin C (20-100 μM; 1 hour; INS-1 cells) treatment enhances glucose-induced extracellular signal-regulated kinases 1/2 (ERK1/2) activation in INS-1 β-cells[1]. Urolithin C significantly inhibits the proliferation of PC12 cells. Urolithin C treatment actively increases the lactate dehydrogenase (LDH) release and lipid peroxidation malondialdehyde (MDA), stimulates reactive oxygen species (ROS) formation and mitochondrial membrane depolarization, and caused calcium dyshomeostasis[2]. Urolithin C treatment induces apoptosis and S phase cell cycle arrest[2]. Western Blot Analysis[1] Cell Line: INS-1 cells Concentration: 20 μM, 100 μM Incubation Time: 1 hour Result: Enhanced glucose-induced extracellular signal-regulated kinases 1/2 (ERK1/2) activation.

[In Vivo]

The pharmacokinetics of Urolithin C (10 mg/kg; intraperitoneal administration) in male Wistar rat (140-160 g) are studied. The half-life of the terminal part is 11.3 h and the total clearance (CL/F) is 3.41 L/h/kg. The initial volume of distribution (V1/F) and the steady-state volume of distribution (Vss/F) are 0.831 L/kg and 55.6 L/kg, respectively[3].

[References]

[1]. Slimane Toubal, et al. Urolithin C Increases Glucose-Induced ERK Activation Which Contributes to Insulin Secretion. Fundam Clin Pharmacol. 2020 Feb 21.

[2]. Peipei Yin, et al. Urolithin C, a gut metabolite of ellagic acid, induces apoptosis in PC12 cells through a mitochondria-mediated pathway. RSC Advances. Issue 28, 2017.

[3]. Morgane Bayle, et al. Development and Validation of a Liquid Chromatography-Electrospray Ionization-Tandem Mass Spectrometry Method for the Determination of Urolithin C in Rat Plasma and Its Application to a Pharmacokinetic Study. J Pharm Biomed Anal. 2016 Nov 30;131:33-39.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
605.4±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C13H8O5

[ Molecular Weight ]:
244.200

[ Flash Point ]:
243.6±25.0 °C

[ Exact Mass ]:
244.037170

[ PSA ]:
90.90000

[ LogP ]:
1.88

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.758

Related Compounds