Department of Pharmacognosy and Molecular Basis of Phytotherapy, Faculty of Pharmacy, Medical University of Warsaw , Banacha 1, 02-097 Warsaw, Poland.
Department of Pharmaceutical Microbiology, CePT, Medical University of Warsaw , Banacha 1B, 02-097 Warsaw, Poland.
J Nat Prod. 2016 Dec 23;79(12):3022-3030. doi: 10.1021/acs.jnatprod.6b00602. Epub 2016 Nov 23.
Ellagitannin-rich plant materials are used as popular remedies in the treatment of various inflammatory diseases. Urolithins are gut microbiota metabolites of ellagitannins and are considered responsible for in vivo health effects. Various natural products have been studied that are known sources of urolithins. However, few studies have focused on the metabolism of ellagitannin molecules. The aim of the study was to examine the metabolic fate of select ellagitannins using ex vivo cultures of human gut microbiota. Fifteen monomeric and dimeric ellagitannins, 1-O-galloyl-4,6-(S)-HHDP-β-d-glucose (2), pedunculagin (3), potentillin (4), casuarictin (5), coriariin B (6), vescalagin (7), castalagin (8), stachyurin (9), casuarinin (10), stenophyllinin A (11), stenophyllanin A (12), salicarinin A (13), gemin A (14), agrimoniin (15), and oenothein B (16), and ellagic acid (1) were studied. The formation of the metabolites in ex vivo human microbiota cultures was monitored using UHPLC-DAD-MS/MS. Ellagitannins possessing hexahydroxydiphenoyl moieties were metabolized to 6H-dibenzo[b,d]pyran-6-one derivatives, i.e., urolithins. The observed differences in amounts of produced urolithins indicated that the individual microbiota composition and type of ingested ellagitannins could determine the rate of urolithin production. When the oral ingestion of natural products containing ellagitannins with hexahydroxydiphenoyl groups is considered, the formation of urolithins and their bioactivity should be addressed.
富含鞣花单宁的植物材料被用作治疗各种炎症性疾病的流行疗法。尿石素是鞣花单宁的肠道微生物群代谢物,被认为是体内健康影响的原因。已经研究了各种天然产物,它们是尿石素的已知来源。然而,很少有研究关注鞣花单宁分子的代谢。本研究旨在使用体外培养的人类肠道微生物群来研究选择的鞣花单宁的代谢命运。研究了 15 种单体和二聚鞣花单宁,包括 1-O-没食子酰基-4,6-(S)-HHDP-β-d-葡萄糖(2)、鞣云实精(3)、鞣花酸(4)、柯里拉京(5)、柯里里亚因 B(6)、维斯卡林(7)、鞣花丹宁(8)、原花青素(9)、casuarictin(10)、stenophyllinin A(11)、stenophyllanin A(12)、salicarinin A(13)、gemin A(14)、agrimoniin(15)和 oenothein B(16)以及鞣花酸(1)。使用 UHPLC-DAD-MS/MS 监测在体外人类微生物群培养物中代谢物的形成。具有六羟基二苯甲酰基部分的鞣花单宁被代谢为 6H-二苯并[b,d]吡喃-6-酮衍生物,即尿石素。所观察到的产生的尿石素的量的差异表明,个体微生物群落组成和摄入的鞣花单宁的类型可以决定尿石素产生的速度。当考虑口服含有六羟基二苯甲酰基的天然产物时,应该注意尿石素的形成及其生物活性。