Urolithin B Specifications
| Name: | Urolithin B |
| Chemical Name: | 3-Hydroxy-6H-dibenzo[b,d]pyran-6-one |
| CAS: | 1139-83-9 |
| Chemical Formula: | C13H8O3 |
| Molecular Weight: | 212.2 g/mol |
| Color: | White powder |
| InChi Key: | WXUQMTRHPNOXBV-UHFFFAOYSA-N |
| SMILES Code: | O=C1C2=CC=CC=C2C3=CC=C(O)C=C3O1 |
| Function: | Urolithin B can improve mitochondrial and muscle function .
Urolithin B can improves muscle strength and endurance during aging. |
| Application: | Urolithin B is an intestinal microbial metabolite of ellagitannis and exhibits potent anti-oxidant and pro-oxidant activies depending on the assay system and conditions. Urolithin B can also display estrogenic and/or anti-estrogenic activity. |
| Solubility: | Easily soluble in N,N-dimethylformamide and dimethylmethylene. Sulfone, slightly soluble in methanol, ethanol, and ethyl acetate |
| Storage Temp: | Hygroscopic, -20°C Freezer, Under inert atmosphere |
| 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. |
Urolithin B NMR Spectrum
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Introduction to Urolithins
Urolithins are secondary metabolites of ellagic acid derived from ellagitannins. In humans ellagitannins are converted by the gut microflora into ellagic acid which is further transformed into urolithins A, urolithin B, urolithin C and urolithin D in the large intestines.
Urolithin A (UA) is the most prevalent metabolite of ellagitannins. However, urolithin A is not known to occur naturally in any dietary sources.
Urolithin B (UB) is an abundant metabolite produced in the gut through transformation of ellagitannins. Urolithin B is the last product after all the other urolithin derivatives are catabolized. Urolithin B is found in urine as urolithin B glucuronide.
Urolithin A 8-Methyl Ether is the intermediate product during the synthesis of Urolithin A. It is a significant secondary metabolite of ellagitannin and possess antioxidant and anti-inflammatory properties.
Mechanism of action of urolithin A and B
●Urolithin A induces mitophagy
Mitophagy is one form of autophagy that helps eliminate damaged mitochondrial for their optimal functioning. Autophagy refers to the general process in which cytoplasmic contents are degraded and consequently recycled while mitophagy is the degradation and recycling of mitochondria.
During aging a decrease in autophagy is one aspect leading to a decline in mitochondrial function. Further, oxidative stress could also lead to low autophagy. Urolithin A possess the ability to eliminate damaged mitochondria through selective autophagy.
●Antioxidant properties
Oxidative stress occurs when there is an imbalance between the free radicals and antioxidant in the body. These excess free radicals are often associated with many chronic illnesses such cardiac disorders, diabetes and cancer.
Urolithins A and B exhibit antioxidant effects through their ability to reduce the free radicals and specifically the intracellular reactive oxygen species (ROS) levels and also inhibit lipid peroxidation in certain cell types.
Further, urolithins are able to inhibit some oxidizing enzymes, including monoamine oxidase A and tyrosinase.
●Anti-inflammatory properties
Inflammation is a natural process in which our bodies fight against any fallen thing such as infections, injuries, and microbes. However, chronic inflammation can be harmful to the body as this is associated with various disorders such as asthma, heart issues, and cancer. Chronic inflammation could occur due to untreated acute inflammation, infections or even free radicals in the body.
Urolithins A and B exhibits anti-inflammation properties by inhibiting nitric oxide production. They specifically inhibit inducible nitric oxide synthase (iNOS) protein and mRNA expression which are responsible for inflammation.
●Anti-microbial effects
Microbes including bacteria, fungi and viruses occur naturally in the environment and even in the human body. However, a few microbes referred to as pathogens could cause infectious diseases such as flu, measles and malaria.
Urolithin A and B are able to exhibit antimicrobial activity by inhibiting quorum sensing. Quorum sensing is a mode of bacterial communication that enables bacteria to detect and control infection-related processes such as virulence and motility.
●Inhibiting protein glycation
Glycation refers to a non-enzymatic attachment of a sugar to a lipid or protein. It is a key biomarker in diabetes and other disorders as well as aging.
High protein glycation is a secondary effect of hyperglycemia has a major role in cardiovascular-related disorders such as diabetes and Alzheimer’s disease.
Urolithin A and B possess anti-glycative properties that are dose dependent that are independent of their antioxidant activity.
Urolithin B benefits
Urolithin B supplements also possess several health benefits and most of which are similar to urolithin A benefits.
(1) Anti-cancer potential
The anti-inflammatory properties of urolithin B make it a good candidate for fighting cancer. Some researchers have reported these potential in fibroblasts, microphages and endothelial cells.
Studies have reported that UB inhibits different types of cancer such as prostate, colon and bladder cancer.
In a study involving human colon cancer cells, ellagitannins, ellagic acid and urolithins A and B were evaluated for their anti-cancer potential. They reported that all the treatments were able to inhibit growth of the cancer cells. They inhibited the cancer cells proliferation through cell cycle arrest at different phases and also by inducing apoptosis.
(2) Can help fight against oxidative stress
Urolithin B possess excellent antioxidant properties through reducing reactive oxygen species levels and lipid peroxidation in certain cell types. The high levels of ROS are associated with many disorders such as Alzheimer’s disease.
In a study with neuronal cells exposed to oxidative stress, urolithin B supplement as well as urolithin A were found to protect the cells against oxidation hence increased the cell survival.
(3) Urolithin B in memory enhancement
Urolithin b has been reported to improve the blood-barrier permeability. This enhances cognitive functioning.
Studies show that urolithin B can be a potential memory enhancer by improving the general cognitive functioning.
(4) Prevents muscle loss
Muscle loss can occur due to various reasons such as disorders, aging and deficiency of protein in the diet. Several measures to stop, limit or better prevent muscle loss including, exercise, drugs and amino acids as well as polyphenols can be employed.
Urolithins can be classified as polyphenols and play role in preventing muscle loss by activating muscle protein synthesis and also slowing down degradation.
In a study with mice, Urolithin B supplements administered over a period of time was found to enhance their muscle development as the muscles were seen to become larger.
(5) Urolithin B fights against inflammation
Urolithin B possess anti-inflammation properties by reducing most inflammation markers.
In a study of rats with induced renal fibrosis, urolithin B was found to ameliorate the kidney injury. It enhanced the renal function, the morphology of the kidney as well as reduced the renal injury markers. This indicates that UB was able to mitigate renal inflammation.
(6) Synergistic benefits of urolithin A and B
Synergistic effects have also been reported in a combination of urolithin A and B in cognitive function and capacity. The study stated that this combination can be used in treating or preventing dementia-related disorders such as anxiety or Alzheimer’s disorder.
Other benefits associated with urolithins are;
- Neuroprotection
- Ameliorates metabolic syndrome
Urolithin A and B food sources
Urolithins are not known to be found naturally in any dietary sources. They are a product of transformation of ellagic acids which are derived from ellagitannins. Ellagitannins are transformed into ellagic acids by the gut microbiota and the ellagic acid is further converted into its metabolites (urolithins) in the large intestines.
Ellagitannins occur naturally in food sources such as pomegranates, berries including strawberries, raspberries, cloudberries and blackberries, muscadine grapes, almonds, guavas, tea, and nuts such as walnuts and chestnuts as well as oak-aged beverages for instance red wine and whiskey from oak barrels.
We can therefore conclude urolithin A foods and urolithin B foods are ellagitannin-rich foods. It is worth noting that ellagitannin bioavailability is very limited while its secondary metabolites (urolithins) are readily bioavailable.
Urolithins excretion and production vary widely among individuals since the conversion from ellagitannins rely on microbiota in the gut. There are specific bacteria involved in these conversion and vary among individuals where some have high, low or no available appropriate microbiota. The food sources also vary in their ellagitannins levels. Hence the potential benefits of ellagitannins vary from one individual to the other.
Urolithin A and B Supplements
Urolithin A supplements as well as Urolithin B supplements are readily found in the market as ellagitannin-rich food source supplements. Urolithin A supplements are also readily available. Majorly the pomegranates supplements have been widely sold and used with success. These supplements are synthesized from the fruits or nuts and formulated into liquid or powder form.
Due to variations in ellagitannins concentration in different foods, customers of urolithin a buy it putting into consideration the food source. The same applies when sourcing for urolithin B powder or liquid supplements.
The few human clinical studies conducted with urolithin A powder or B have not reported any serious side effects from administration of these supplements.
Reference
- Garcia-Muñoz, Cristina; Vaillant, Fabrice (2014-12-02). “Metabolic Fate of Ellagitannins: Implications for Health, and Research Perspectives for Innovative Functional Foods”. Critical Reviews in Food Science and Nutrition.
- 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.
- Bodwell, Graham; Pottie, Ian; Nandaluru, Penchal (2011). “An Inverse Electron-Demand Diels-Alder-Based Total Synthesis of Urolithin M7”.
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