165393-06-6Relevant articles and documents
Urolithin C, a gut metabolite of ellagic acid, induces apoptosis in PC12 cells through a mitochondria-mediated pathway
Yin, Peipei,Zhang, Jianwei,Yan, Linlin,Yang, Lingguang,Sun, Liwei,Shi, Lingling,Ma, Chao,Liu, Yujun
, p. 17254 - 17263 (2017/03/27)
Urolithins (Uros), metabolites of ellagitannins (ET) and ellagic acid (EA) produced by gut microbiota, showed better bioavailability and extensive bioactivity, and were considered as the active compounds responsible for the health benefits exerted by ET-containing foodstuffs. Here, we chemically synthesized three Uros including Uros A, B, and C and compared their anti-proliferative activities with that of EA in PC12 cells. MTT assay showed that EA significantly promoted, while Uros significantly inhibited the proliferation of PC12 cells, among which UroC showed the strongest anti-proliferation. UroC treatment actively increased the lactate dehydrogenase (LDH) release and lipid peroxidation malondialdehyde (MDA), stimulated reactive oxygen species (ROS) formation and mitochondrial membrane depolarization, and caused calcium dyshomeostasis. Furthermore, flow cytometry analysis showed that UroC treatment induced apoptosis and S phase cell cycle arrest with increasing UroC concentrations. Consequently, UroC also induced imbalance in the Bcl-2/Bax ratio, which triggered the caspase cascade, thereby shifting the balance in favor of apoptosis, as evidenced by western blotting and real-time PCR. These observations indicated that UroC possessed significantly different anti-proliferation activities from EA, and actively induced cell apoptosis through a mitochondria-mediated pathway.
Cu(I)-mediated lactone formation in subcritical water: A benign synthesis of benzopyranones and urolithins A-C
Nealmongkol, Prattya,Tangdenpaisal, Kassrin,Sitthimonchai, Somkid,Ruchirawat, Somsak,Thasana, Nopporn
, p. 9277 - 9283 (2013/10/01)
Benzopyranones were successfully synthesized using Cu(I)-mediated C-O bond formation in subcritical water. A number of benzopyranone derivatives including polymethoxy benzopyranones, benzopyranopyridones, chromenoindolones, and furochromenones were synthesized in satisfactory yield. This methodology was further applied to synthesize the intestinal microbial metabolites, urolithins A, B, and C, which were found to exhibit potent antioxidant activity.
Identification of urinary and intestinal bacterial metabolites of ellagitannin geraniin in rats
Ito, Hideyuki,Iguchi, Ayumu,Hatano, Tsutomu
experimental part, p. 393 - 400 (2009/04/10)
Hydrolyzable tannins, including ellagitannins, occur in foods such as berries and nuts. Various biological activities, including antioxidant, antiviral, and antitumor activities, have been noted and reported for ellagitannins, but the absorption and metabolism of purified ellagitannins are poorly understood. We describe herein the characterization of urinary and intestinal microbial metabolites in rats after the ingestion of ellagitannins. Urine samples were collected after oral administration of ellagitannins such as geraniin (1), corilagin (2), and their related polyphenols. The suspension of rat intestinal microflora was anaerobically incubated with ellagitannins. Each sample was separated by column chromatography and/or preparative HPLC to give seven metabolites, M1-M7. The structures of these metabolites were determined on the basis of spectroscopic data and chemical evidence. These compounds, except for M1, were characterized as ellagitannin metabolites for the first time. Furthermore, among four major metabolites (M1-M4) in urine, M2 showed an antioxidant activity comparable to intact geraniin and related polyphenols.
