Complex formation of flavonoids fisetin and geraldol with β-cyclodextrins

Nikolett Sali, Rita Csepregi, Tamás Kőszegi, Sándor Kunsági-Máté, Lajos Szente, Miklós Poór

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Fisetin (FIS) is a flavonoid aglycone which is widely distributed in several fruits and vegetables. Based on its complex biochemical action in the body, FIS seems a promising candidate for the treatment of neurodegenerative diseases, diabetes, or cancer. During the 3′-O-methylation of FIS by catechol-O-methyltransferase geraldol (GER) is formed which is also pharmacologically active. Similarly to other flavonoids, FIS and GER are poorly soluble in water. Microcapsulation of flavonoids can enhance their aqueous solubility and may improve their pharmacokinetic properties. Since both FIS and GER are fluorescent molecules, the interaction of these flavonoids by native and chemically modified β-cyclodextrins was investigated by fluorescence spectroscopy. Both FIS-CD and GER-CD complexes show considerable emission with maxima at 475 and 540 nm reflecting the two conformers of the complexes. Thereafter, fluorescence enhancement of each tautomer by cyclodextrins and binding constants of flavonoid-cyclodextrin complexes were determined. Chemically modified cyclodextrins were stronger fluorescence enhancers of flavonoids and formed more stable complexes with FIS and GER than the native β-cyclodextrin. Finally, influence of cyclodextrins on the cellular impact of FIS and GER was tested on HepG2 tumor cell line.

Original languageEnglish
Pages (from-to)82-90
Number of pages9
JournalJournal of Luminescence
Volume194
DOIs
Publication statusPublished - Feb 1 2018

Fingerprint

Cyclodextrins
Flavonoids
fluorescence
vegetables
methylation
fruits
tautomers
cultured cells
tumors
solubility
cancer
augmentation
Fluorescence
Neurodegenerative diseases
Catechol O-Methyltransferase
water
spectroscopy
Methylation
Pharmacokinetics
3,4',7-trihydroxy-3'-methoxyflavone

Keywords

  • Cyclodextrin
  • Fisetin
  • Fluorescence spectroscopy
  • Geraldol
  • Host-guest interaction

ASJC Scopus subject areas

  • Biophysics
  • Atomic and Molecular Physics, and Optics
  • Chemistry(all)
  • Biochemistry
  • Condensed Matter Physics

Cite this

Complex formation of flavonoids fisetin and geraldol with β-cyclodextrins. / Sali, Nikolett; Csepregi, Rita; Kőszegi, Tamás; Kunsági-Máté, Sándor; Szente, Lajos; Poór, Miklós.

In: Journal of Luminescence, Vol. 194, 01.02.2018, p. 82-90.

Research output: Contribution to journalArticle

Sali, Nikolett ; Csepregi, Rita ; Kőszegi, Tamás ; Kunsági-Máté, Sándor ; Szente, Lajos ; Poór, Miklós. / Complex formation of flavonoids fisetin and geraldol with β-cyclodextrins. In: Journal of Luminescence. 2018 ; Vol. 194. pp. 82-90.
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