punicalgin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: punicalgin
• 英文别名: punicalagin；(α/β)-punicalagin；Punicalagin, Technical grade；(1R,35R,38R,55S)-6,7,8,11,12,23,24,27,28,29,37,43,44,45,48,49,50-heptadecahydroxy-2,14,21,33,36,39,54-heptaoxaundecacyclo[33.20.0.04,9.010,19.013,18.016,25.017,22.026,31.038,55.041,46.047,52]pentapentaconta-4,6,8,10,12,16,18,22,24,26,28,30,41,43,45,47,49,51-octadecaene-3,15,20,32,40,53-hexone
• 化学式: C₄₈H₂₈O₃₀
• 分子量: 1084.73
• InChiKey: ZJVUMAFASBFUBG-UYMKNUMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  78
• 可旋转键数：
  0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  511
• 氢给体数：
  17
• 氢受体数：
  30

ADMET

代谢

石榴，一种原产于中东的水果，已经作为一种功能食品和营养保健源在全球范围内获得了广泛的流行。关于整个石榴、及其果汁和提取物的健康效果，已经针对多种慢性疾病进行了研究。来自人类临床试验的结果显示，石榴在对抗心血管疾病、糖尿病和前列腺癌方面具有前景。石榴的体外抗氧化活性归功于其高多酚含量，尤其是石榴酸、石榴素、没食子酸和鞣花酸。这些化合物在消化过程中被代谢成鞣花酸和尿石素，这表明提供体内抗氧化活性的生物活性化合物可能与全食物中存在的化合物不同……

Pomegranate, a fruit native to the Middle East, has gained widespread popularity as a functional food and nutraceutical source. The health effects of the whole fruit, as well as its juices and extracts, have been studied in relation to a variety of chronic diseases. Promising results against cardiovascular disease, diabetes, and prostate cancer have been reported from human clinical trials. The in vitro antioxidant activity of pomegranate has been attributed to its high polyphenolic content, specifically punicalagins, punicalins, gallagic acid, and ellagic acid. These compounds are metabolized during digestion to ellagic acid and urolithins, suggesting that the bioactive compounds that provide in vivo antioxidant activity may not be the same as those present in the whole food...

来源:Hazardous Substances Data Bank (HSDB)

代谢

石榴已被证明含有124种不同的植物化学物质，其中一些共同作用，对癌细胞发挥抗氧化和抗炎效果。鞣花单宁是石榴中存在的生物活性多酚。通过挤压整个果实获得的石榴汁比任何常见消费的果汁含有更高的鞣花单宁浓度，并且含有独特的鞣花单宁，即安石榴苷。安石榴苷是已知分子量最大的多酚。石榴鞣花单宁不会完整地被血液吸收，而是在肠道中被水解为鞣花酸，需要几个小时。鞣花单宁还通过肠道菌群转化为尿石素，这些尿石素在肝脏中结合并随尿液排出。这些尿石素也具有生物活性，并能抑制前列腺癌细胞的生长...

Pomegranates have been shown to contain 124 different phytochemicals, and some of them act in concert to exert antioxidant and anti-inflammatory effects on cancer cells. Ellagitannins are bioactive polyphenols present in pomegranate. Pomegranate juice obtained by squeezing the whole fruit has the highest concentration of ellagitannins than any commonly consumed juice and contains the unique ellagitannin, punicalagin. Punicalagin is the known largest molecular weight polyphenol. Pomegranate ellagitannins are not absorbed intact into the blood stream but are hydrolyzed to ellagic acid over several hours in the intestine. Ellagitannins are also metabolized into urolithins by gut flora, which are conjugated in the liver and excreted in the urine. These urolithins are also bioactive and inhibit prostate cancer cell growth...

来源:Hazardous Substances Data Bank (HSDB)

代谢

腹膜内和口服合成的尿石素A导致前列腺组织中摄取尿石素A及其结合物，且相对于其他器官，前列腺、结肠和肠组织的水平较高。目前尚不清楚为什么石榴鞣花单宁代谢物在前列腺、结肠和肠组织中的水平相对于研究中其他器官更高。重要的是，生物活性的石榴鞣花单宁代谢物倾向于定位于前列腺组织，结合临床数据表明石榴汁具有抗癌效果，这表明石榴产品在前列腺癌化学预防中可能发挥作用。尿石素在人体前列腺组织中是否可以作为长期服用石榴汁或石榴提取物后的生物标志物仍有待确定。

Intraperitoneal and oral administration of synthesized urolithin A led to uptake of urolithin A and its conjugates in prostate tissue, and levels were higher in prostate, colon, and intestinal tissues relative to other organs. It is unclear why pomegranate ellagitannins metabolites localize at higher levels in the prostate, colon, and intestinal tissues relative to the other organs studied. Importantly, the predilection of bioactive pomegranate ellagitannins metabolites to localize in prostate tissue, combined with clinical data demonstrating the anticancer effects of pomegranate juice, suggests the potential for pomegranate products to play a role in prostate cancer chemoprevention. Whether uro-lithins in human prostate tissue can be used as a biomarker following the long-term administration of pomegranate juice or pomegranate extract remains to be determined. /pomegranate extract/

来源:Hazardous Substances Data Bank (HSDB)