Effect of Stereochemical Configuration on the Transport and Metabolism of Catechins from Green Tea across Caco-2 Monolayers
The transcellular transport and metabolism of eight green tea catechins (GTCs) were studied in Caco-2 monolayers, with the aim of investigating the effect of cis–trans isomerism on the membrane permeability and biotransformation of GTCs. The results showed that the catechin stereochemistry...
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MDPI AG
2019-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/6/1185 |
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| author | Zeyi Ai Shuyuan Liu Fengfeng Qu Haojie Zhang Yuqiong Chen Dejiang Ni |
| author_facet | Zeyi Ai Shuyuan Liu Fengfeng Qu Haojie Zhang Yuqiong Chen Dejiang Ni |
| author_sort | Zeyi Ai |
| collection | DOAJ |
| description | The transcellular transport and metabolism of eight green tea catechins (GTCs) were studied in Caco-2 monolayers, with the aim of investigating the effect of cis–trans isomerism on the membrane permeability and biotransformation of GTCs. The results showed that the catechin stereochemistry significantly affects the efflux transport rather than the absorption transport in the Caco-2 monolayers. The trans catechins showed a better transcellular permeability than their corresponding cis (epi) catechins in the efflux transport, as the efflux amount of trans catechins were all significantly higher than that of the cis (epi) catechins at each concentration and each time point tested. Moreover, the relative contents of the (+)-catechin (C)-<i>O</i>-sulfate, (+)-gallocatechin (GC)-<i>O</i>-sulfate, (−)-catechin gallate (CG)-<i>O</i>-sulfate, and (−)-gallocatechin gallate (GCG)-<i>O</i>-sulfate in the efflux transport were 2.67, 16.08, 50.48, and 31.54 times higher than that of the (−)-epicatechin (EC)-<i>O</i>-sulfate, (−)-epigallocatechin (EGC)-<i>O</i>-sulfate, (−)-epicatechin gallate (ECG)-<i>O</i>-sulfate, and (−)-epigallocatechin gallate (EGCG)-<i>O</i>-sulfate, respectively. It indicated that more metabolites were observed after the transcellular efflux of trans catechins. Furthermore, after two hours of incubation, the GTCs could significantly increase the expression of multidrug resistance-associated protein 2 (MRP2) and breast cancer-resistance protein (BCRP), and decrease the expression of <i>P</i>-glycoprotein in the Caco-2 cells. The regulation of GTCs on P-glycoprotein, MRP2, and BCRP could also be significantly influenced by the chemical and dimensional structure. In a conclusion, catechin stereochemistry significantly affects the transport and metabolism of GTCs when refluxed in the Caco-2 monolayers. |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T19:58:21Z |
| publishDate | 2019-03-01 |
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| spelling | doaj.art-b7176602a2934cc49e0c87b8e72484602022-12-22T00:52:35ZengMDPI AGMolecules1420-30492019-03-01246118510.3390/molecules24061185molecules24061185Effect of Stereochemical Configuration on the Transport and Metabolism of Catechins from Green Tea across Caco-2 MonolayersZeyi Ai0Shuyuan Liu1Fengfeng Qu2Haojie Zhang3Yuqiong Chen4Dejiang Ni5Key Laboratory of Horticultural Plant Biology, Ministry of Education, College of Horticulture and Forestry Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaKey Laboratory of Horticultural Plant Biology, Ministry of Education, College of Horticulture and Forestry Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaKey Laboratory of Horticultural Plant Biology, Ministry of Education, College of Horticulture and Forestry Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaKey Laboratory of Horticultural Plant Biology, Ministry of Education, College of Horticulture and Forestry Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaKey Laboratory of Horticultural Plant Biology, Ministry of Education, College of Horticulture and Forestry Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaKey Laboratory of Horticultural Plant Biology, Ministry of Education, College of Horticulture and Forestry Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaThe transcellular transport and metabolism of eight green tea catechins (GTCs) were studied in Caco-2 monolayers, with the aim of investigating the effect of cis–trans isomerism on the membrane permeability and biotransformation of GTCs. The results showed that the catechin stereochemistry significantly affects the efflux transport rather than the absorption transport in the Caco-2 monolayers. The trans catechins showed a better transcellular permeability than their corresponding cis (epi) catechins in the efflux transport, as the efflux amount of trans catechins were all significantly higher than that of the cis (epi) catechins at each concentration and each time point tested. Moreover, the relative contents of the (+)-catechin (C)-<i>O</i>-sulfate, (+)-gallocatechin (GC)-<i>O</i>-sulfate, (−)-catechin gallate (CG)-<i>O</i>-sulfate, and (−)-gallocatechin gallate (GCG)-<i>O</i>-sulfate in the efflux transport were 2.67, 16.08, 50.48, and 31.54 times higher than that of the (−)-epicatechin (EC)-<i>O</i>-sulfate, (−)-epigallocatechin (EGC)-<i>O</i>-sulfate, (−)-epicatechin gallate (ECG)-<i>O</i>-sulfate, and (−)-epigallocatechin gallate (EGCG)-<i>O</i>-sulfate, respectively. It indicated that more metabolites were observed after the transcellular efflux of trans catechins. Furthermore, after two hours of incubation, the GTCs could significantly increase the expression of multidrug resistance-associated protein 2 (MRP2) and breast cancer-resistance protein (BCRP), and decrease the expression of <i>P</i>-glycoprotein in the Caco-2 cells. The regulation of GTCs on P-glycoprotein, MRP2, and BCRP could also be significantly influenced by the chemical and dimensional structure. In a conclusion, catechin stereochemistry significantly affects the transport and metabolism of GTCs when refluxed in the Caco-2 monolayers.https://www.mdpi.com/1420-3049/24/6/1185stereochemical configurationcis–trans catechinsbidirectional transportefflux pumpsmetabolism |
| spellingShingle | Zeyi Ai Shuyuan Liu Fengfeng Qu Haojie Zhang Yuqiong Chen Dejiang Ni Effect of Stereochemical Configuration on the Transport and Metabolism of Catechins from Green Tea across Caco-2 Monolayers Molecules stereochemical configuration cis–trans catechins bidirectional transport efflux pumps metabolism |
| title | Effect of Stereochemical Configuration on the Transport and Metabolism of Catechins from Green Tea across Caco-2 Monolayers |
| title_full | Effect of Stereochemical Configuration on the Transport and Metabolism of Catechins from Green Tea across Caco-2 Monolayers |
| title_fullStr | Effect of Stereochemical Configuration on the Transport and Metabolism of Catechins from Green Tea across Caco-2 Monolayers |
| title_full_unstemmed | Effect of Stereochemical Configuration on the Transport and Metabolism of Catechins from Green Tea across Caco-2 Monolayers |
| title_short | Effect of Stereochemical Configuration on the Transport and Metabolism of Catechins from Green Tea across Caco-2 Monolayers |
| title_sort | effect of stereochemical configuration on the transport and metabolism of catechins from green tea across caco 2 monolayers |
| topic | stereochemical configuration cis–trans catechins bidirectional transport efflux pumps metabolism |
| url | https://www.mdpi.com/1420-3049/24/6/1185 |
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