3,8-디하이드록시-6H-디벤조(b,d)피란-6-온

개요Urolithin A is a metabolite of ellagic acid. It is produced by the body after you ingest compounds found in particularly high concentration in pomegranates (particularly the bitter components such as the skin and seeds) and can help recycle defective mitochondria. Since it is a metabolite that results from the transformation of the tannins in pomegranate by gut bacteria, it can be classified as a postbiotic.It has been demonstrated to stimulate mitophagy and improve muscle health in old animals and in preclinical models of aging.

용도Urolithin A(UA) is a major metabolite of ellagitannin and exhibits anti-inflammatory and antioxidant properties. UA also has the ability to induce autophagy and apoptosis, inhibit cell cycle progression, and inhibit DNA synthesis. At the physiological level, UA improved muscle function in nematodes, young rodents, old mice, and muscle-wasting disorders such as Duchenne muscle dystrophy (DMD). Long-term intake of UA improves muscle endurance. In vitro studies, it has also been shown to inhibit the growth of human cancer cells in the colon, prostate and breast.

2-bromo-5-methoxybenzoic acid is coupled with resorcinol to yield the intermediate “methoxy” product (Intermediate A), which is then isolated via filtration and dried for use in step 2. The solvent methanol is utilized in this step.the intermediate product, "Intermediate A", is treated with the Lewis acid, AlCl3, in order to obtain a crude urolithin A. The ether cleavage of Intermediate A is accomplished by activation of the methyl ether through the addition of the Lewis acid, AlCl3, in toluene. The activated species is then hydrolyzed by the addition of water. Following hydrolysis, the crude product is filtered and dried.crude urolithin A is dissolved in dimethyl sulfoxide (DMSO) for a polish filtration and subsequently precipitated from this DMSO solution by the addition of water. The filter cake is rinsed by water, followed by methanol. The raw urolithin A is then triturated with acetic acid (HOAc) to further purify the product and then collected by filtration. Following filtration, the purified product is rinsed with HOAc followed by tert-butyl-methyl ether (TBME), then dried to yield the final product, urolithin A.Synthesis of Urolithin A