Interaction of chrysin and its main conjugated metabolites chrysin-7-sulfate and chrysin-7-glucuronide with serum albumin

Violetta Mohos, Eszter Fliszár-Nyúl, Gabriella Schilli, C. Hetényi, Beáta Lemli, S. Kunsági-Máté, Balázs Bognár, Miklós Poór

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Article number4073
JournalInternational Journal of Molecular Sciences
Volume19
Issue number12
DOIs
Publication statusPublished - Jan 1 2018

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metabolites
Glucuronides
Metabolites
albumins
Serum Albumin
serums
Sulfates
sulfates
Dietary supplements
Flavonoids
interactions
supplements
affinity
Ultrafiltration
chrysin
drugs
Fluorescence
Ligands
fluorescence
Dietary Supplements

Keywords

  • Albumin-ligand complexes
  • Chrysin
  • Chrysin-7-glucuronide
  • Chrysin-7-sulfate
  • Fluorescence spectroscopy
  • Serum albumin

ASJC Scopus subject areas

  • Catalysis
  • Molecular Biology
  • Spectroscopy
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Interaction of chrysin and its main conjugated metabolites chrysin-7-sulfate and chrysin-7-glucuronide with serum albumin. / Mohos, Violetta; Fliszár-Nyúl, Eszter; Schilli, Gabriella; Hetényi, C.; Lemli, Beáta; Kunsági-Máté, S.; Bognár, Balázs; Poór, Miklós.

In: International Journal of Molecular Sciences, Vol. 19, No. 12, 4073, 01.01.2018.

Research output: Contribution to journalArticle

Mohos, Violetta ; Fliszár-Nyúl, Eszter ; Schilli, Gabriella ; Hetényi, C. ; Lemli, Beáta ; Kunsági-Máté, S. ; Bognár, Balázs ; Poór, Miklós. / Interaction of chrysin and its main conjugated metabolites chrysin-7-sulfate and chrysin-7-glucuronide with serum albumin. In: International Journal of Molecular Sciences. 2018 ; Vol. 19, No. 12.
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AU - Mohos, Violetta

AU - Fliszár-Nyúl, Eszter

AU - Schilli, Gabriella

AU - Hetényi, C.

AU - Lemli, Beáta

AU - Kunsági-Máté, S.

AU - Bognár, Balázs

AU - Poór, Miklós

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N2 - 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.

AB - 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.

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KW - Chrysin-7-sulfate

KW - Fluorescence spectroscopy

KW - Serum albumin

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