Comparative Study of Fluorescence Emission of Fisetin, Luteolin and Quercetin Powders and Solutions: Further Evidence of the ESIPT Process

Comparative Study of Fluorescence Emission of Fisetin, Luteolin and Quercetin Powders and Solutions: Further Evidence of the ESIPT Process

Fisetin and Luteolin are important flavonoids produced in plants and known for their antioxidant, anti-inflammatory, neuroprotective, and analgesic properties. They are also good candidates for different types of biosensors. The model used to describe the fluorescence (FL) emission of these flavonoi...

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Bibliographic Details
Published in:Biosensors (Basel) Vol. 14; no. 9; p. 413
Main Authors: Deriabina, Alexandra, Prutskij, Tatiana, Morales Ochoa, Hector Daniel, Delgado Curiel, Esteban, Palacios Corte, Veranda
Format: Journal Article
Language:English
Published: Switzerland MDPI AG 26-08-2024
MDPI
Subjects:
Analgesics
Biosensors
Comparative analysis
Comparative studies
Emission measurements
Emission spectra
ESIPT
fisetin
Flavonoids
Flavonoids - analysis
Flavonoids - chemistry
Flavonols - analysis
Fluorescence
Isoflavones
luteolin
Luteolin - chemistry
Molecular structure
Neuroprotection
Photoexcitation
Powders
Protons
Quercetin
Quercetin - chemistry
Solutions
Solvents
Spectrometry, Fluorescence
TDDFT
Wavelengths
Mexico
St Louis Missouri
United States > US
luteolin
system of notation for flavonoids
fluorescence
fisetin
quercetin
ESIPT
TDDFT
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Summary:Fisetin and Luteolin are important flavonoids produced in plants and known for their antioxidant, anti-inflammatory, neuroprotective, and analgesic properties. They are also good candidates for different types of biosensors. The model used to describe the fluorescence (FL) emission of these flavonoids involves an excited-state intermolecular proton transfer (ESIPT) process that causes a change in the molecule configuration and a corresponding decrease in the emission energy. Due to the different molecular structures of Fisetin and Luteolin, only one possible proton transfer within the molecule is allowed for each of them: transfer of the H3 proton for Fisetin and of the H5 for Luteolin. Here, we compare their calculated emission wavelengths, obtained using TDDFT/M06-2X/6-31++G(d,p), with their FL emission spectra measured on the corresponding powders and solutions and show that the experimental data are consistent with the presence of the ESIPT process. We also compare the emission wavelengths found for Fisetin and Luteolin with those calculated and measured for Quercetin, where, under photoexcitation, the transfers of both H3 and H5 protons are possible. We analyze the difference in the processes associated with the H3 and H5 proton transfers and discuss the reason for the predominance of the H5 proton transfer in Quercetin. Additionally, a new system of notation for flavonoid molecules is developed.
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ISSN:2079-6374
2079-6374
DOI:10.3390/bios14090413