Urolithin A powder

Urolithin A powder Specifications

Name:	Urolithin A
Chemical Name:	3,8-Dihydroxybenzo[c]chromen-6-one
CAS:	1143-70-0
Chemical Formula:	C13H8O4
Molecular Weight:	228.2
Color:	White to off-white solid powder
InChi Key:	RIUPLDUFZCXCHM-UHFFFAOYSA-N
SMILES Code:	O=C1C2=CC(O)=CC=C2C3=C(O1)C=C(O)C=C3
Function:	Urolithin A, a gut-microbial metabolite of ellagic acid, exerts anti-inflammatory, antiproliferative, and antioxidant properties. Urolithin A induces autophagy and apoptosis, suppresses cell cycle progression, and inhibits DNA synthesis.
Application:	Urolithin A is a metabolite of ellagitannin; Pharmaceutical Intermediates
Solubility:	Soluble in DMSO (3 mg/mL).
Storage Temp:	Dry, dark and at 0 – 4 C for short term (days to weeks) or -20 C for long term (months to years).
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 A 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 A benefits

(1)Can extends lifespan
Urolithin A induces mitophagy by selectively eliminating damaged mitochondria. This also ensures recycling of mitochondria for optimal functioning. Mitochondria often get damaged with age and also due to stress. Getting rid of damaged mitochondria plays role in extending the lifespan.

In a study of worms, urolithin A supplement administered at 50 µM from the egg stage till death was found to extend their lifespan by 45.4%.

In another study conducted in 2019 using senescent human fibroblasts, urolithin A supplement was found to exhibit anti-aging potential. It was able to increase type 1 collagen expression and also reduce the expression of matrix metalloproteinase 1.

A small human study also show that UA was able to improve the mitochondrial function and skeletal health in elderly individuals when administered orally at 500-1000mg for a period of four weeks.

(2)Help prevent prostate cancer
The urolithins and their precursor, ellagitannins, possess anti-cancer properties. They are able to inhibit cancer-cell proliferation through cell cycle arrest and inducing apoptosis. Apoptosis refers to a programmed cell death in which the body eliminates potential cancer-cells and also other infected cells.

In a study of mice injected with human cancerous cells, ellagitannins metabolites (Urolithin A) were found to inhibit the growth of prostate cancer. The study further reported higher concentration of the metabolites in the prostate gland, colon and intestinal tissues.

(3)Cognitive enhancement
Urolithin A is able to protect neurons from death and can also trigger neurogenesis through anti-inflammatory signaling.

In a study of mice with memory impairment, urolithin A was found to ameliorate cognitive impairment and protect neurons from apoptosis. This suggest that UA can be used in treating Alzheimer’s disease (AD).

(4)Anti-obesity potential
Research show that ellagitannins are able to inhibit lipid accumulation and also adipogenic markers such as early growth response protein 2 as well as enhancer-binding protein through cell cycle arrest.

Urolithin A has been specifically found to improve insulin sensitivity thus prevents the development of obesity.

In a study of mice with induced obesity, urolithin A supplementation was found to prevent diet-induced obesity and metabolic impairment in mice. The study showed that UA treatment increased energy expenditure thus a lower body mass.

 

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

1. 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.
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.
3. Bodwell, Graham; Pottie, Ian; Nandaluru, Penchal (2011). “An Inverse Electron-Demand Diels-Alder-Based Total Synthesis of Urolithin M7”.

 

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