Urolithin B

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Urolithin B
Urolithin B.svg
Names
Preferred IUPAC name
3-Hydroxy-6H-dibenzo[b,d]pyran-6-one
Other names
Uro-B
3-Hydroxyurolithin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.236.446 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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
    Key: WXUQMTRHPNOXBV-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C3=C(C=C(C=C3)O)OC2=O
Properties
C13H8O3
Molar mass 212.204 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Urolithin B (UB) [1] is an urolithin, a type of phenolic compounds produced in the human gut after absorption of ellagitannins-containing food such as pomegranate, [2] strawberries, red raspberries, walnuts or oak-aged red wine. [3] Urolithin B is found in the urine in the form of urolithin B glucuronide. [ citation needed ]

Contents

See also

Related Research Articles

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<span class="mw-page-title-main">Ellagic acid</span> Natural phenol antioxidant

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<span class="mw-page-title-main">Castalagin</span> Chemical compound

Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of Anogeissus leiocarpus and Terminalia avicennoides.

The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds.

<span class="mw-page-title-main">Grandinin</span> Chemical compound

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<span class="mw-page-title-main">Miquelianin</span> Chemical compound

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<span class="mw-page-title-main">Punicalin</span> Chemical compound

Punicalin is an ellagitannin. It can be found in Punica granatum (pomegranate) or in the leaves of Terminalia catappa, a plant used to treat dermatitis and hepatitis. It is also reported in Combretum glutinosum, all three species being Myrtales, the two last being Combretaceae.

<span class="mw-page-title-main">Pedunculagin</span> Chemical compound

Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.

<span class="mw-page-title-main">Lambertianin C</span> Chemical compound

Lambertianin C is an ellagitannin.

<span class="mw-page-title-main">Sanguiin H-6</span> Chemical compound

Sanguiin H-6 is an ellagitannin.

<span class="mw-page-title-main">Urolithin</span> Group of chemical compounds

Urolithins are microflora metabolites of dietary ellagic acid derivatives, such as ellagitannins. They are produced in the gut, and found in the urine in the form of urolithin B glucuronide after absorption of ellagitannins-containing foods, such as pomegranate. During intestinal metabolism by bacteria, ellagitannins and punicalagins are converted to urolithins, which have unknown biological activity in vivo.

<span class="mw-page-title-main">Urolithin A</span> Chemical compound

Urolithin A is a metabolite compound resulting from the transformation of ellagitannins by the gut bacteria. It belongs to the class of organic compounds known as benzo-coumarins or dibenzo-α-pyrones. Its precursors – ellagic acids and ellagitannins – are ubiquitous in nature, including edible plants, such as pomegranates, strawberries, raspberries, walnuts, and others.

<span class="mw-page-title-main">Tellimagrandin I</span> Chemical compound

Tellimagrandin I is an ellagitannin found in plants, such as Cornus canadensis, Eucalyptus globulus, Melaleuca styphelioides, Rosa rugosa, and walnut. It is composed of two galloyl and one hexahydroxydiphenyl groups bound to a glucose residue. It differs from Tellimagrandin II only by a hydroxyl group instead of a third galloyl group. It is also structurally similar to punigluconin and pedunculagin, two more ellagitannin monomers.

References

  1. Ghosh N, Das A, Biswas N, Gnyawali S, Singh K, Gorain M, Polcyn C, Khanna S, Roy S, Sen CK (19 November 2020). "Urolithin A augments angiogenic pathways in skeletal muscle by bolstering NAD+ and SIRT1". Nature . 10 (1). Scientific Reports: 20184. doi:10.1038/s41598-020-76564-7. PMC   7678835 . PMID   33214614.
  2. Bialonska D, Kasimsetty SG, Khan SI, Ferreira D (11 November 2009). "Urolithins, intestinal microbial metabolites of Pomegranate ellagitannins, exhibit potent antioxidant activity in a cell-based assay". J Agric Food Chem. 57 (21): 10181–6. doi:10.1021/jf9025794. PMID   19824638.
  3. Cerdá B, Tomás-Barberán FA, Espín JC (2005). "Metabolism of Antioxidant and Chemopreventive Ellagitannins from Strawberries, Raspberries, Walnuts, and Oak-Aged Wine in Humans: Identification of Biomarkers and Individual Variability". Journal of Agricultural and Food Chemistry. 53 (2): 227–235. doi:10.1021/jf049144d. PMID   15656654.