MedKoo Cat#: 574758 | Name: Isourolithin A

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Isourolithin A is an intestinal microbial metabolite of ellagitannins. It is also a potential inhibitor of 3-phosphoglycerate kinase.

Chemical Structure

Isourolithin A
Isourolithin A
CAS#174023-48-4

Theoretical Analysis

MedKoo Cat#: 574758

Name: Isourolithin A

CAS#: 174023-48-4

Chemical Formula: C13H8O4

Exact Mass: 228.0423

Molecular Weight: 228.20

Elemental Analysis: C, 68.42; H, 3.53; O, 28.04

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Synonym
Isourolithin A; 3,9-Dihydroxyurolithin; 3-Hydroxyisourolithin B
IUPAC/Chemical Name
3,9-Dihydroxy-6H-dibenzo[b,d]pyran-6-one
InChi Key
WDGSXHQNUPZEHA-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H8O4/c14-7-2-4-10-11(5-7)9-3-1-8(15)6-12(9)17-13(10)16/h1-6,14-15H
SMILES Code
O=C1C2=CC=C(O)C=C2C3=CC=C(O)C=C3O1
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Product Data
Biological target:
Isourolithin A is a potential inhibitor of 3-phosphoglycerate kinase.
In vitro activity:
Treatment of leukocytes with 15 μM Uro-A and IsoUro-A (isourolithin A) decreased formation of PGE2 (Fig. 3A). As expected, LPS treatment increased COX-2 levels in leukocytes, whereas in the presence of Uro-A or IsoUro-A (15 μM), this effect was attenuated (Figure 7A and B). Reference: Mol Nutr Food Res. 2020 Jun;64(11):e2000129. https://pubmed.ncbi.nlm.nih.gov/32306507/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 228.20 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:
1. Giménez-Bastida JA, González-Sarrías A, Espín JC, Schneider C. Inhibition of 5-Lipoxygenase-Derived Leukotrienes and Hemiketals as a Novel Anti-Inflammatory Mechanism of Urolithins. Mol Nutr Food Res. 2020 Jun;64(11):e2000129. doi: 10.1002/mnfr.202000129. Epub 2020 May 4. PMID: 32306507; PMCID: PMC7297467. 2. Selma MV, Beltrán D, Luna MC, Romo-Vaquero M, García-Villalba R, Mira A, Espín JC, Tomás-Barberán FA. Isolation of Human Intestinal Bacteria Capable of Producing the Bioactive Metabolite Isourolithin A from Ellagic Acid. Front Microbiol. 2017 Aug 7;8:1521. doi: 10.3389/fmicb.2017.01521. PMID: 28824607; PMCID: PMC5545574.
In vitro protocol:
1. Giménez-Bastida JA, González-Sarrías A, Espín JC, Schneider C. Inhibition of 5-Lipoxygenase-Derived Leukotrienes and Hemiketals as a Novel Anti-Inflammatory Mechanism of Urolithins. Mol Nutr Food Res. 2020 Jun;64(11):e2000129. doi: 10.1002/mnfr.202000129. Epub 2020 May 4. PMID: 32306507; PMCID: PMC7297467. 2. Selma MV, Beltrán D, Luna MC, Romo-Vaquero M, García-Villalba R, Mira A, Espín JC, Tomás-Barberán FA. Isolation of Human Intestinal Bacteria Capable of Producing the Bioactive Metabolite Isourolithin A from Ellagic Acid. Front Microbiol. 2017 Aug 7;8:1521. doi: 10.3389/fmicb.2017.01521. PMID: 28824607; PMCID: PMC5545574.
In vivo protocol:
TBD
1. Selma MV, Beltrán D, Luna MC, et al. Isolation of Human Intestinal Bacteria Capable of Producing the Bioactive Metabolite Isourolithin A from Ellagic Acid. Front Microbiol. 2017;8:1521. Published 2017 Aug 7. doi:10.3389/fmicb.2017.01521 2. Selma MV, Beltrán D, Luna MC, et al. Isolation of Human Intestinal Bacteria Capable of Producing the Bioactive Metabolite Isourolithin A from Ellagic Acid. Front Microbiol. 2017;8:1521. Published 2017 Aug 7. doi:10.3389/fmicb.2017.01521 3. Selma MV, Beltrán D, Luna MC, et al. Isolation of Human Intestinal Bacteria Capable of Producing the Bioactive Metabolite Isourolithin A from Ellagic Acid. Front Microbiol. 2017;8:1521. Published 2017 Aug 7. doi:10.3389/fmicb.2017.01521