Urolithin B

Last updated
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
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

<span class="mw-page-title-main">Berry</span> In the culinary sense, small edible fruit

A berry is a small, pulpy, and often edible fruit. Typically, berries are juicy, rounded, brightly colored, sweet, sour or tart, and do not have a stone or pit, although many pips or seeds may be present. Common examples are strawberries, raspberries, blueberries, blackberries, red currants, white currants and blackcurrants. In Britain, soft fruit is a horticultural term for such fruits.

<i>Rubus idaeus</i> Red raspberry

Rubus idaeus is a red-fruited species of Rubus native to Europe and northern Asia and commonly cultivated in other temperate regions.

<span class="mw-page-title-main">Strawberry</span> Edible fruit

The garden strawberry is a widely grown hybrid species of the genus Fragaria, collectively known as the strawberries, which are cultivated worldwide for their fruit. The fruit is widely appreciated for its characteristic aroma, bright red color, juicy texture, and sweetness. It is consumed in large quantities, either fresh or in such prepared foods as jam, juice, pies, ice cream, milkshakes, and chocolates. Artificial strawberry flavorings and aromas are also widely used in products such as candy, soap, lip gloss, perfume, and many others.

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

Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.

Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.

<span class="mw-page-title-main">Antioxidant effect of polyphenols and natural phenols</span>

A polyphenol antioxidant is a hypothetical type of antioxidant containing a polyphenolic substructure and studied in vitro. Numbering over 4,000 distinct species mostly from plants, polyphenols may have antioxidant activity in vitro, but are unlikely to be antioxidants in vivo. Hypothetically, they may affect cell-to-cell signaling, receptor sensitivity, inflammatory enzyme activity or gene regulation, although high-quality clinical research has not confirmed any of these possible effects in humans as of 2020.

<span class="mw-page-title-main">Anthocyanin</span> Class of chemical compounds

Anthocyanins, also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart gave the name Anthokyan to a chemical compound that gives flowers a blue color for the first time in his treatise “Die Farben der Blüthen”. Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

<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

Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves and in oaks species like the North American white oak and European red oak. It shows antioxydant activity. It is an astringent compound. It is also found in wine, red or white, aged in oak barrels.

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

Miquelianin is a flavonol glucuronide, a type of phenolic compound present in wine, in species of St John's wort, like Hypericum hirsutum, in Nelumbo nucifera or in green beans.

<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, and walnuts. Since the 2000s, urolithin A has been the subject of preliminary studies regarding its possible biological effects.

<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. "Urolithin A augments angiogenic pathways in skeletal muscle by bolstering NAD+ and SIRT1". Nature.com . Scientific Reports. 19 November 2020.
  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, Begoña; Tomás-Barberán, Francisco A.; Espín, Juan Carlos (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.