每周分子 | Molecule of the Week
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每周分子：鞣花酸
Molecule of the Week: Ellagic acid
鞣花酸是一种天然的稠环多酚，pKa为5.5。它存在于水果、坚果、橡树瘿和桉树的树胶中。其名称源自法语acide ellagique，由反向拼写的galle(gall)一词创造。
自19世纪上半叶以来，鞣花酸一直被认作制革材料的一种成分。早在1868年它就出现在化学文献报道中，当时的德国化学家和实业家Julius Löwe以砷酸或氧化银氧化没食子酸1来合成它。1905年，英国利兹大学的Arthur George perkin2和Maximilian Nierenstein通过使用过硫酸钠作为氧化剂改进了该合成工艺。
鞣花酸长期被吹捧为天然抗氧化剂，并作为膳食补充剂销售，声称它可以预防或治疗癌症和心脏病。2008年至2021年间，美国食品药品监督管理局就该分子在保健方面的虚假声明向制药公司和公众发出了警告。
但鞣花酸的确可能对健康有益。2006年，来自CEBAS−CSIC3(西班牙，穆尔西亚)的Juan Carlos Espin及其同事发现，两种结肠微生物菌群鞣花酸代谢物(尿石素A4和B5)神奇地同时具有雌激素和抗雌激素活性。他们认为尿石素可能对治疗乳腺癌具有意义。随后，Espin和及其团队研究了尿石素多方面的活性，包括其抗炎特性。
让我们快进到2022年9月：在Espin工作的基础上，四川大学的Jian Zhao及其同事使用小鼠研究确定尿石素A可减轻幽门螺杆菌诱导的体内损伤。尿石素A不仅可以减少肠道炎症，而且还减少了幽门螺杆菌毒力因子的分泌、组织损伤以及在感染小鼠粪便中幽门螺杆菌属的相对丰度。
1. CAS 登记号：149-91-7
2. 期刊Perkin Transactions 即以他的名字命名。
3. 西班牙国家研究委员会，塞古拉土壤生态学和应用生物学中心。土壤生态学是土壤科学中的一种。
4. CAS 登记号：1143-70-0
5. CAS 登记号：1139-83-9
鞣花酸信息速览
鞣花酸危害信息
【关于每周分子】
自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社 (CAS) 提供的CAS SciFindern中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子吧。
Ellagic acid is a natural fused-ring polyphenol with a pKa of 5.5. It is found in fruits, nuts, the galls of oak trees, and the kino (gum) of eucalyptus trees. Its name comes from the French acide ellagique, coined from the word galle (gall) spelled backward.
Ellagic acid has been known since the first half of the 19th century as a component of tanning materials. It was mentioned in the chemical literature as early as 1868, when German chemist and industrialist Julius Löwe synthesized it by oxidizing gallic acid1 with arsenic acid or silver oxide. In 1905, Arthur George Perkin2 and Maximilian Nierenstein at the University of Leeds (UK) refined the process by using sodium persulfate as the oxidant.
Ellagic acid has been touted as a natural antioxidant and marketed as a dietary supplement with claims that it can prevent or treat cancer and heart disease. From 2008 to 2021, the US Food and Drug Administration issued warnings to drug companies and the public about false health claims about the molecule.
But ellagic acid may have some health benefits. In 2006, Juan Carlos Espin and colleagues at CEBAS−CSIC3 (Murcia, Spain) found that two colonic microflora ellagic acid metabolites (urolithins A4 and B5) have, oddly, both estrogenic and antiestrogenic activity. The authors suggested that the urolithins may have implications for treating breast cancer. Espin and his group subsequently investigated several aspects of urolithin activity, including its anti-inflammatory properties.
Fast forward to September 2022: Building on Espin’s work, Jian Zhao and co-workers at Sichuan University, used mouse studies to determine that urolithin A attenuates Helicobacter pylori-induced damage in vivo. Urolithin A not only decreased inflammation in the gut, but it also reduced H. pylori virulence factor secretion, tissue injuries, and the relative abundance of Helicobacter spp. In feces of H. pylori-infected mice.
1. CAS Reg. No. 149-91-7
2. For whom the Perkin Transactions journals were named.
3. Center for Edaphology and Applied Biology of Segura, Spanish National Research Council. Edaphology is a type of soil science.
4. CAS Reg. No. 1143-70-0.
5. CAS Reg. No. 1139-83-9.
Ellagic acidfast facts
Ellagic acidhazard information
About Molecule of the Week
MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using CAS SciFindern. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.
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