尿石素A
| 中文名称 | 尿石素A |
|---|---|
| 中文同义词 | 3,8-二羟基-6H-二苯并[B,D]吡喃-6-酮;尿石素A;3,8-二羟基-6H-苯并[C]苯并吡喃-6-酮;T24和CACO-2细胞抑制剂(UROLITHIN A);3,8-二羟基-6H-苯并[C]色烯-6-酮;3,8-二羟基-6H-二苯并(二,四)吡喃-6-酮;尿石素-A (MITOUROLITHIN);T24和CACO-2细胞抑制剂(UROLCHEMICALBOOKITHINA) |
| 英文名称 | Urolithin A |
| 英文同义词 | 3,8-dihydroxy-6H-dibenzo(b,d)pyran-6-one;3,8-DIHYDROXYDIBENZO-(B,D)PYRAN-6-ONE;3, 8-Dihydroxy-6H-benzo[c]chromen-6-one;Castoreum pigment I;Urolithin A;6H-Dibenzo(B,D)pyran-6-one, 3,8-dihydroxy-;3,8-dihydroxy-6H-dibenzopyran-6-one);urolithin-A(UA |
| CAS号 | 1143-70-0 |
| 分子式 | C13H8O4 |
| 分子量 | 228.2 |
| EINECS号 | 1592732-453-0 |
| 相关类别 | 细胞生物学试剂;对照品;新品;黄金产品;产品2;novel chemicals;化工原料;原料;高定高含量产品;医药保健品原料;带图片的产品 |
| Mol文件 | 1143-70-0.mol |
| 结构式 |  |
尿石素A 性质
| 熔点 | 340-345 °C |
|---|---|
| 沸点 | 527.9±43.0 °C(Predicted) |
| 密度 | 1.516±0.06 g/cm3(Predicted) |
| 储存条件 | 2-8°C |
| 溶解度 | 可溶于DMSO（轻微）、甲醇（非常轻微） |
| 形态 | 粉末 |
| 酸度系数(pKa) | 9.07±0.20(Predicted) |
| 形态 | 固体/粉末 |
| 颜色 | 白色至米色 |
| 颜色 | 米色至黄色 |
| InChI | InChI=1S/C13H8O4/c14-7-1-3-9-10-4-2-8(15)6-12(10)17-13(16)11(9)5-7/h1-6,14-15H |
| InChIKey | RIUPLDUFZCXCHM-UHFFFAOYSA-N |
| SMILES | C12=CC(O)=CC=C1C1=CC=C(O)C=C1C(=O)O2 |
| LogP | 2.311 (est) |
|
Human Endogenous Metabolite
|
Micromolar urolithin A concentrations induces both autophagy and apoptosis. Urolithin A suppresses cell cycle progression and inhibited DNA synthesis in human sw620 colorectal cancer cells.
Urolithin A shows antiproliferative effects and inhibits T24 and Caco-2 cell growth with IC
50
s of 43.9 and 49 μM, respectively.
Urolithin A exerts a dose- and time-dependent significant arrest at G2/M and S phases after treatments with 50 and 100 μM at 24 and 48 h compared to control cells. It induces cell apoptosis with 50 and 100 μM .
Urolithin A shows potent antiproliferative activity on HepG2 cells. When cell death is induced by Urolithin A, the expression of β-catenin, c-Myc and Cyclin D1 are decreased and TCF/LEF transcriptional activation is notably down-regulated. Urolithin A also increases protein expression of p53, p38-MAPK and caspase-3, but suppresses expression of NF-κB p65 and other inflammatory mediators.
The volume of paw edema is reduced at 1 h after oral administration of urolithin A. In addition, plasma in treated mice exhibited significant oxygen radical antioxidant capacity (ORAC) scores with high plasma levels of the unconjugated form at 1 h after oral administration of urolithin A.