Interaction of Chrysin and Its Main Conjugated Metabolites Chrysin-7-Sulfate and Chrysin-7-Glucuronide with Serum Albumin
Chrysin (5,7-dihydroxyflavone) is a flavonoid aglycone, which is found in nature and in several dietary supplements. During the biotransformation of chrysin, its conjugated metabolites chrysin-7-sulfate (C7S) and chrysin-7-glucuronide (C7G) are formed. Despite the fact that these conjugates appear i...
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doaj-685f46f0a59243cf8d123fae68c8d90b2020-11-24T20:44:36ZengMDPI AGInternational Journal of Molecular Sciences1422-00672018-12-011912407310.3390/ijms19124073ijms19124073Interaction of Chrysin and Its Main Conjugated Metabolites Chrysin-7-Sulfate and Chrysin-7-Glucuronide with Serum AlbuminVioletta Mohos0Eszter Fliszár-Nyúl1Gabriella Schilli2Csaba Hetényi3Beáta Lemli4Sándor Kunsági-Máté5Balázs Bognár6Miklós Poór7Department of Pharmacology, University of Pécs, Faculty of Pharmacy, Szigeti út 12, H-7624 Pécs, HungaryDepartment of Pharmacology, University of Pécs, Faculty of Pharmacy, Szigeti út 12, H-7624 Pécs, HungaryDepartment of Pharmacology and Pharmacotherapy, University of Pécs, Medical School, Szigeti út 12, H-7624 Pécs, HungaryDepartment of Pharmacology and Pharmacotherapy, University of Pécs, Medical School, Szigeti út 12, H-7624 Pécs, HungaryJános Szentágothai Research Center, University of Pécs, Ifjúság útja 20, H-7624 Pécs, HungaryJános Szentágothai Research Center, University of Pécs, Ifjúság útja 20, H-7624 Pécs, HungaryDepartment of Organic and Pharmacological Chemistry, University of Pécs, Medical School, Honvéd utca 1, H-7624 Pécs, HungaryDepartment of Pharmacology, University of Pécs, Faculty of Pharmacy, Szigeti út 12, H-7624 Pécs, HungaryChrysin (5,7-dihydroxyflavone) is a flavonoid aglycone, which is found in nature and in several dietary supplements. During the biotransformation of chrysin, its conjugated metabolites chrysin-7-sulfate (C7S) and chrysin-7-glucuronide (C7G) are formed. Despite the fact that these conjugates appear in the circulation at much higher concentrations than chrysin, their interactions with serum albumin have not been reported. In this study, the complex formation of chrysin, C7S, and C7G with human (HSA) and bovine (BSA) serum albumins was investigated employing fluorescence spectroscopic, ultrafiltration, and modeling studies. Our major observations/conclusions are as follows: (1) Compared to chrysin, C7S binds with a threefold higher affinity to HSA, while C7G binds with a threefold lower affinity; (2) the albumin-binding of chrysin, C7S, and C7G did not show any large species differences regarding HSA and BSA; (3) tested flavonoids likely occupy Sudlow’s Site I in HSA; (4) C7S causes significant displacement of Sudlow’s Site I ligands, exerting an even stronger displacing ability than the parent compound chrysin. Considering the above-listed observations, the high intake of chrysin (e.g., through the consumption of dietary supplements with high chrysin contents) may interfere with the albumin-binding of several drugs, mainly due to the strong interaction of C7S with HSA.https://www.mdpi.com/1422-0067/19/12/4073chrysinchrysin-7-sulfatechrysin-7-glucuronideserum albuminfluorescence spectroscopyalbumin–ligand complexes |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Violetta Mohos Eszter Fliszár-Nyúl Gabriella Schilli Csaba Hetényi Beáta Lemli Sándor Kunsági-Máté Balázs Bognár Miklós Poór |
spellingShingle |
Violetta Mohos Eszter Fliszár-Nyúl Gabriella Schilli Csaba Hetényi Beáta Lemli Sándor Kunsági-Máté Balázs Bognár Miklós Poór Interaction of Chrysin and Its Main Conjugated Metabolites Chrysin-7-Sulfate and Chrysin-7-Glucuronide with Serum Albumin International Journal of Molecular Sciences chrysin chrysin-7-sulfate chrysin-7-glucuronide serum albumin fluorescence spectroscopy albumin–ligand complexes |
author_facet |
Violetta Mohos Eszter Fliszár-Nyúl Gabriella Schilli Csaba Hetényi Beáta Lemli Sándor Kunsági-Máté Balázs Bognár Miklós Poór |
author_sort |
Violetta Mohos |
title |
Interaction of Chrysin and Its Main Conjugated Metabolites Chrysin-7-Sulfate and Chrysin-7-Glucuronide with Serum Albumin |
title_short |
Interaction of Chrysin and Its Main Conjugated Metabolites Chrysin-7-Sulfate and Chrysin-7-Glucuronide with Serum Albumin |
title_full |
Interaction of Chrysin and Its Main Conjugated Metabolites Chrysin-7-Sulfate and Chrysin-7-Glucuronide with Serum Albumin |
title_fullStr |
Interaction of Chrysin and Its Main Conjugated Metabolites Chrysin-7-Sulfate and Chrysin-7-Glucuronide with Serum Albumin |
title_full_unstemmed |
Interaction of Chrysin and Its Main Conjugated Metabolites Chrysin-7-Sulfate and Chrysin-7-Glucuronide with Serum Albumin |
title_sort |
interaction of chrysin and its main conjugated metabolites chrysin-7-sulfate and chrysin-7-glucuronide with serum albumin |
publisher |
MDPI AG |
series |
International Journal of Molecular Sciences |
issn |
1422-0067 |
publishDate |
2018-12-01 |
description |
Chrysin (5,7-dihydroxyflavone) is a flavonoid aglycone, which is found in nature and in several dietary supplements. During the biotransformation of chrysin, its conjugated metabolites chrysin-7-sulfate (C7S) and chrysin-7-glucuronide (C7G) are formed. Despite the fact that these conjugates appear in the circulation at much higher concentrations than chrysin, their interactions with serum albumin have not been reported. In this study, the complex formation of chrysin, C7S, and C7G with human (HSA) and bovine (BSA) serum albumins was investigated employing fluorescence spectroscopic, ultrafiltration, and modeling studies. Our major observations/conclusions are as follows: (1) Compared to chrysin, C7S binds with a threefold higher affinity to HSA, while C7G binds with a threefold lower affinity; (2) the albumin-binding of chrysin, C7S, and C7G did not show any large species differences regarding HSA and BSA; (3) tested flavonoids likely occupy Sudlow’s Site I in HSA; (4) C7S causes significant displacement of Sudlow’s Site I ligands, exerting an even stronger displacing ability than the parent compound chrysin. Considering the above-listed observations, the high intake of chrysin (e.g., through the consumption of dietary supplements with high chrysin contents) may interfere with the albumin-binding of several drugs, mainly due to the strong interaction of C7S with HSA. |
topic |
chrysin chrysin-7-sulfate chrysin-7-glucuronide serum albumin fluorescence spectroscopy albumin–ligand complexes |
url |
https://www.mdpi.com/1422-0067/19/12/4073 |
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