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尿石素葡萄糖醛酸苷的新型区域选择性合成——鞣花单宁和鞣花酸的人体肠道微生物共代谢产物

Novel Regioselective Synthesis of Urolithin Glucuronides─Human Gut Microbiota Cometabolites of Ellagitannins and Ellagic Acid.

作者信息

Villalgordo Jose M, Trulli Laura, García-Villalba Rocío, García Victor, Althobaiti Yusuf, Tomás-Barberán Francisco A

机构信息

Eurofins-VillaPharma Research S.L., Parque Tecnológico de Fuente Alamo, E-30320 Fuente Alamo, Murcia, Spain.

CEBAS-CSIC, Research Group on Quality, Safety, and Bioactivity of Plant-Derived Foods, P.O. Box 164, Espinardo, Murcia 30100, Spain.

出版信息

J Agric Food Chem. 2022 May 18;70(19):5819-5828. doi: 10.1021/acs.jafc.2c00170. Epub 2022 May 9.

DOI:10.1021/acs.jafc.2c00170
PMID:35533350
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9121390/
Abstract

Urolithins (dibenzo-pyran-[,]-6 one derivatives) are human gut microbiota metabolites produced from the natural food antioxidant ellagic acid. Urolithins are better absorbed than ellagic acid and demonstrate biological activities that suggest that they are responsible for the health effects observed after consuming ellagitannin- and ellagic acid-containing foods. Urolithins occur in the systemic circulation as glucuronide conjugates following phase II metabolism. These phase II conjugates are essential for testing the urolithin mechanisms of action in human cell line bioassays. Urolithin glucuronides are not commercially available, and their biosynthesis leads to mixtures of regional isomers. This study describes a novel and regioselective synthesis of urolithin A (3,8-dihydroxy urolithin) 3- and 8-glucuronides and isourolithin A (3,9-dihydroxy urolithin) 3- and 9-glucuronides. The metabolites were characterized using H and C NMR spectroscopy and UV spectrophotometry. The presence of these metabolites in human subjects belonging to different urolithin metabotypes was also investigated.

摘要

尿石素（二苯并 - 吡喃 - [,] - 6 - 酮衍生物）是由天然食物抗氧化剂鞣花酸产生的人体肠道微生物群代谢产物。尿石素比鞣花酸更容易被吸收，并表现出生物活性，这表明它们对食用含鞣花单宁和鞣花酸的食物后观察到的健康影响负责。尿石素在II期代谢后以葡萄糖醛酸苷共轭物的形式出现在体循环中。这些II期共轭物对于在人类细胞系生物测定中测试尿石素的作用机制至关重要。尿石素葡萄糖醛酸苷没有商业供应，并且它们的生物合成会导致区域异构体的混合物。本研究描述了尿石素A（3,8 - 二羟基尿石素）3 - 和8 - 葡萄糖醛酸苷以及异尿石素A（3,9 - 二羟基尿石素）3 - 和9 - 葡萄糖醛酸苷的一种新颖的区域选择性合成方法。使用氢谱和碳谱核磁共振光谱以及紫外分光光度法对这些代谢产物进行了表征。还研究了这些代谢产物在属于不同尿石素代谢型的人类受试者中的存在情况。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd2b/9121390/5e198d5013fd/jf2c00170_0004.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd2b/9121390/7342272605b1/jf2c00170_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd2b/9121390/3ab7fad9bd13/jf2c00170_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd2b/9121390/700b90492e40/jf2c00170_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd2b/9121390/ec3c5954e0dc/jf2c00170_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd2b/9121390/dd6969f2918c/jf2c00170_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd2b/9121390/9c31e79a1c07/jf2c00170_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd2b/9121390/5e198d5013fd/jf2c00170_0004.jpg

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