Urolithin B
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MedKoo CAT#: 464699

CAS#: 1139-83-9

Description: Urolithin B is a metabolite of the polyphenolic antioxidant ellagic acid that has diverse biological activities. It is formed from ellagic acid via several intermediates by gut microbiota. Urolithin B reduces the levels of advanced glycation end products (AGEs) in a cell-free assay in a concentration-dependent manner. It inhibits aromatase activity in human placental microsomes and aromatase-sensitive MCF-7 (MCF-7aro) human breast cancer cells when used at concentrations of 47 and 4.7 µM, respectively. Urolithin B (1.18-4.7 nM) inhibits testosterone-induced proliferation of MCF-7aro cells. It also inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS), TNF-α, IL-6, IL-1β, and COX-2, as well as increases levels of IL-10, in BV-2 microglia when used at concentrations of 50 and 100 µM.

Chemical Structure

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Urolithin B
CAS# 1139-83-9
Instruction

Theoretical Analysis

MedKoo Cat#: 464699
Name: Urolithin B
CAS#: 1139-83-9
Chemical Formula: C13H8O3
Exact Mass: 212.05
Molecular Weight: 212.204
Elemental Analysis: C, 73.58; H, 3.80; O, 22.62

Price and Availability

Size Price Availability Quantity
500mg USD 295 2 Weeks
1g USD 550 2 Weeks
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Synonym: Urolithin B; Urolithin-B; NSC 94726; NSC94726; NSC-94726; 3-hydroxy Urolithin; 3 hydroxy Urolithin;

IUPAC/Chemical Name: 3-hydroxy-6H-benzo[c]chromen-6-one

InChi Key: WXUQMTRHPNOXBV-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H8O3/c14-8-5-6-10-9-3-1-2-4-11(9)13(15)16-12(10)7-8/h1-7,14H

SMILES Code: O=C1OC2=C(C=CC(O)=C2)C3=C1C=CC=C3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 141.37
DMSO 30.0 141.37
Ethanol 30.0 141.37

Preparing Stock Solutions

The following data is based on the product molecular weight 212.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Abdulrahman AO, Alzubaidi MY, Nadeem MS, Khan JA, Rather IA, Khan MI. Effects of urolithins on obesity-associated gut dysbiosis in rats fed on a high-fat diet. Int J Food Sci Nutr. 2021 Feb 22:1-12. doi: 10.1080/09637486.2021.1886255. Epub ahead of print. PMID: 33618593.

2: Abdulrahman AO, Kuerban A, Alshehri ZA, Abdulaal WH, Khan JA, Khan MI. Urolithins Attenuate Multiple Symptoms of Obesity in Rats Fed on a High-Fat Diet. Diabetes Metab Syndr Obes. 2020 Sep 25;13:3337-3348. doi: 10.2147/DMSO.S268146. PMID: 33061495; PMCID: PMC7524201.

3: Bobowska A, Granica S, Filipek A, Melzig MF, Moeslinger T, Zentek J, Kruk A, Piwowarski JP. Comparative studies of urolithins and their phase II metabolites on macrophage and neutrophil functions. Eur J Nutr. 2020 Sep 22. doi: 10.1007/s00394-020-02386-y. Epub ahead of print. PMID: 32960290.

4: Singh R, Chandrashekharappa S, Vemula PK, Haribabu B, Jala VR. Microbial Metabolite Urolithin B Inhibits Recombinant Human Monoamine Oxidase A Enzyme. Metabolites. 2020 Jun 19;10(6):258. doi: 10.3390/metabo10060258. PMID: 32575435; PMCID: PMC7345905.

5: Hassanein EHM, Sayed AM, Hussein OE, Mahmoud AM. Coumarins as Modulators of the Keap1/Nrf2/ARE Signaling Pathway. Oxid Med Cell Longev. 2020 Apr 22;2020:1675957. doi: 10.1155/2020/1675957. PMID: 32377290; PMCID: PMC7196981.

6: Cisneros-Zevallos L, Bang WY, Delgadillo-Puga C. Ellagic Acid and Urolithins A and B Differentially Regulate Fat Accumulation and Inflammation in 3T3-L1 Adipocytes While Not Affecting Adipogenesis and Insulin Sensitivity. Int J Mol Sci. 2020 Mar 18;21(6):2086. doi: 10.3390/ijms21062086. PMID: 32197417; PMCID: PMC7139477.

7: Cortés-Martín A, Selma MV, Tomás-Barberán FA, González-Sarrías A, Espín JC. Where to Look into the Puzzle of Polyphenols and Health? The Postbiotics and Gut Microbiota Associated with Human Metabotypes. Mol Nutr Food Res. 2020 May;64(9):e1900952. doi: 10.1002/mnfr.201900952. Epub 2020 Apr 9. PMID: 32196920.

8: Volpp L, Ferianec V, Ježovičová M, Ďuračková Z, Scherf-Clavel O, Högger P. Constituents and Metabolites of a French Oak Wood Extract (Robuvit®) in Serum and Blood Cell Samples of Women Undergoing Hysterectomy. Front Pharmacol. 2020 Feb 26;11:74. doi: 10.3389/fphar.2020.00074. PMID: 32174825; PMCID: PMC7054277.

9: Zheng D, Liu Z, Zhou Y, Hou N, Yan W, Qin Y, Ye Q, Cheng X, Xiao Q, Bao Y, Luo J, Wu X. Urolithin B, a gut microbiota metabolite, protects against myocardial ischemia/reperfusion injury via p62/Keap1/Nrf2 signaling pathway. Pharmacol Res. 2020 Mar;153:104655. doi: 10.1016/j.phrs.2020.104655. Epub 2020 Jan 26. PMID: 31996327.

10: Gao H, Huang X, Tong Y, Jiang X. Urolithin B improves cardiac function and reduces susceptibility to ventricular arrhythmias in rats after myocardial infarction. Eur J Pharmacol. 2020 Mar 15;871:172936. doi: 10.1016/j.ejphar.2020.172936. Epub 2020 Jan 17. PMID: 31958459.

11: Fallah A, Noshadi B, Gazi M, Gülcan HO. Urolithin A and B Derivatives as ON- OFF Selective Fluorescent Sensors for Iron(III). J Fluoresc. 2020 Jan;30(1):113-120. doi: 10.1007/s10895-019-02475-0. Epub 2020 Jan 2. PMID: 31897913.

12: García-Mantrana I, Calatayud M, Romo-Vaquero M, Espín JC, Selma MV, Collado MC. Urolithin Metabotypes Can Determine the Modulation of Gut Microbiota in Healthy Individuals by Tracking Walnuts Consumption over Three Days. Nutrients. 2019 Oct 16;11(10):2483. doi: 10.3390/nu11102483. PMID: 31623169; PMCID: PMC6835957.

13: Cortés-Martín A, Romo-Vaquero M, García-Mantrana I, Rodríguez-Varela A, Collado MC, Espín JC, Selma MV. Urolithin Metabotypes can Anticipate the Different Restoration of the Gut Microbiota and Anthropometric Profiles during the First Year Postpartum. Nutrients. 2019 Sep 3;11(9):2079. doi: 10.3390/nu11092079. PMID: 31484413; PMCID: PMC6769946.

14: Lv MY, Shi CJ, Pan FF, Shao J, Feng L, Chen G, Ou C, Zhang JF, Fu WM. Urolithin B suppresses tumor growth in hepatocellular carcinoma through inducing the inactivation of Wnt/β-catenin signaling. J Cell Biochem. 2019 Oct;120(10):17273-17282. doi: 10.1002/jcb.28989. Epub 2019 Jun 19. PMID: 31218741.

15: Mazumder MK, Choudhury S, Borah A. An in silico investigation on the inhibitory potential of the constituents of Pomegranate juice on antioxidant defense mechanism: Relevance to neurodegenerative diseases. IBRO Rep. 2019 May 9;6:153-159. doi: 10.1016/j.ibror.2019.05.003. PMID: 31193374; PMCID: PMC6527820.

16: Diop EHA, Queiroz EF, Marcourt L, Kicka S, Rudaz S, Diop T, Soldati T, Wolfender JL. Antimycobacterial activity in a single-cell infection assay of ellagitannins from Combretum aculeatum and their bioavailable metabolites. J Ethnopharmacol. 2019 Jun 28;238:111832. doi: 10.1016/j.jep.2019.111832. Epub 2019 Mar 23. PMID: 30914349.

17: Zhao W, Wang L, Haller V, Ritsch A. A Novel Candidate for Prevention and Treatment of Atherosclerosis: Urolithin B Decreases Lipid Plaque Deposition in apoE-/- Mice and Increases Early Stages of Reverse Cholesterol Transport in ox-LDL Treated Macrophages Cells. Mol Nutr Food Res. 2019 May;63(10):e1800887. doi: 10.1002/mnfr.201800887. Epub 2019 Apr 26. PMID: 30762936.

18: Lee G, Park JS, Lee EJ, Ahn JH, Kim HS. Anti-inflammatory and antioxidant mechanisms of urolithin B in activated microglia. Phytomedicine. 2019 Mar 1;55:50-57. doi: 10.1016/j.phymed.2018.06.032. Epub 2018 Jun 20. PMID: 30668443.

19: Gramec Skledar D, Tomašič T, Sollner Dolenc M, Peterlin Mašič L, Zega A. Evaluation of endocrine activities of ellagic acid and urolithins using reporter gene assays. Chemosphere. 2019 Apr;220:706-713. doi: 10.1016/j.chemosphere.2018.12.185. Epub 2018 Dec 26. PMID: 30611068.

20: Romo-Vaquero M, Cortés-Martín A, Loria-Kohen V, Ramírez-de-Molina A, García- Mantrana I, Collado MC, Espín JC, Selma MV. Deciphering the Human Gut Microbiome of Urolithin Metabotypes: Association with Enterotypes and Potential Cardiometabolic Health Implications. Mol Nutr Food Res. 2019 Feb;63(4):e1800958. doi: 10.1002/mnfr.201800958. Epub 2018 Dec 3. PMID: 30471188.