Georg Petroianu, Eva Szoke, Huba Kalász, Péter Szegi, Rudolf Laufer, Bernadett Benko, Ferenc Darvas, Kornélia Tekes
{"title":"Monitoring by HPLC of chamomile flavonoids exposed to rat liver microsomal metabolism.","authors":"Georg Petroianu, Eva Szoke, Huba Kalász, Péter Szegi, Rudolf Laufer, Bernadett Benko, Ferenc Darvas, Kornélia Tekes","doi":"10.2174/1874104500903010001","DOIUrl":null,"url":null,"abstract":"<p><p>Three major flavonoid chamomile components (quercetin, apigenin-7-O-glucoside and rutin) were subjected to oxidative metabolism by cytochrome P-450 of rat liver microsomal preparations. Changes over time in their respective concentrations were followed using reversed-phase HPLC with UV detection. No clean-up had to be applied as only the specific flavonoid had to be separated from the background components originating from the rat liver microsome.Neither the concentration of apigenin-7-O-glucoside nor that of the diglycoside rutin decreased during one hour of exposure to rat microsomal treatment. In contrast, the concentration of quercetin, a lipophilic aglycon, decreased.Our analytical HPLC results complement the in silico calculated lipophilicity (logP) of these compounds; the relatively high lipophilicity of quercetin appears to predispose it to oxidative metabolism in order to decrease its fat solubility. In contrast the much less lipophilic compounds apigenin-7-O-glucoside and rutin were resistant in vitro to microsomal treatment.</p>","PeriodicalId":39133,"journal":{"name":"Open Medicinal Chemistry Journal","volume":"3 ","pages":"1-7"},"PeriodicalIF":0.0000,"publicationDate":"2009-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/b0/ec/TOMCJ-3-1.PMC2729991.pdf","citationCount":"6","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Open Medicinal Chemistry Journal","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2174/1874104500903010001","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Pharmacology, Toxicology and Pharmaceutics","Score":null,"Total":0}
引用次数: 6
Abstract
Three major flavonoid chamomile components (quercetin, apigenin-7-O-glucoside and rutin) were subjected to oxidative metabolism by cytochrome P-450 of rat liver microsomal preparations. Changes over time in their respective concentrations were followed using reversed-phase HPLC with UV detection. No clean-up had to be applied as only the specific flavonoid had to be separated from the background components originating from the rat liver microsome.Neither the concentration of apigenin-7-O-glucoside nor that of the diglycoside rutin decreased during one hour of exposure to rat microsomal treatment. In contrast, the concentration of quercetin, a lipophilic aglycon, decreased.Our analytical HPLC results complement the in silico calculated lipophilicity (logP) of these compounds; the relatively high lipophilicity of quercetin appears to predispose it to oxidative metabolism in order to decrease its fat solubility. In contrast the much less lipophilic compounds apigenin-7-O-glucoside and rutin were resistant in vitro to microsomal treatment.
研究了大鼠肝微粒体制剂细胞色素P-450对三种黄酮类成分槲皮素、芹菜素-7- o -葡萄糖苷和芦丁的氧化代谢作用。采用反相高效液相色谱法(HPLC)和紫外检测法,观察其浓度随时间的变化。不需要进行清理,因为只有特定的类黄酮必须从源自大鼠肝微粒体的背景成分中分离出来。暴露于大鼠微粒体治疗一小时后,芹菜素-7- o -葡萄糖苷和二糖苷芦丁的浓度均未下降。相反,槲皮素(一种亲脂多糖)的浓度下降。我们的HPLC分析结果与计算机计算的这些化合物的亲脂性(logP)相辅相成;槲皮素相对较高的亲脂性似乎使其易于氧化代谢,从而降低其脂溶性。相比之下,亲脂性较低的化合物芹菜素-7- o -葡萄糖苷和芦丁对微粒体治疗有体外抗性。