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Activation Energy of Light Induced Isomerization of Resveratrol

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Abstract

Isomerization of trans-stilbenes is known to be induced by light. The two isomers have distinct absorption, fluorescence excitation and emission spectra. Resveratrol, 3,4′,5-trihydroxystilbene, is a member of the stilbene family. The interest of the scientific community in resveratrol has increased over the last years due to its biomedical properties. Whereas there is a growing confidence that trans-resveratrol is non-toxic, very little is known about the pharmacology of cis-resveratrol. Of this very reason there is considerable interest in knowing the energetics of the trans-cis conversion. Cis-resveratrol is characterized by a large fluorescence quantum yield when compared to trans-resveratrol. In the present paper we report a detailed analysis of the spectral changes induced in trans-resveratrol upon 260 nm excitation for different time periods. Spectral changes have been monitored with UV-visible absorption and steady-state fluorescence spectroscopy at pH 4 at 20, 25, 30, 35, 40, 45 and 50 °C. Continuous 260 nm excitation induces a blue shift in the absorption and fluorescence excitation spectra of resveratrol and a 14 nm blue shift in its fluorescence emission. The photoisomerization yield is reported as a function of 260 nm excitation time. 330 min continuous excitation led to ~60% isomerization yield. The kinetics of trans-cis isomerization has been monitored following the increase in fluorescence quantum yield upon continuous 260 nm excitation of trans-resveratrol. The study was carried out at the above mentioned temperatures in order to obtain the Arrhenius activation energy of photoisomerization. Activation energy and pre-exponential factor were 3.7 ± 0.3 kcal.mol−1 and 10.6 ± 1.6 s−1, respectively. The activation energy is comparable with previously reported values for the photoisomerization of other stilbenes.

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Authors and Affiliations

  1. NanoBiotechnology Group, Department of Physics and Nanotechnology, Aalborg University, Skjernvej 4A, Aalborg, Denmark

    Teresa Sofia Figueiras

  2. Nanobiotechnology Group, Department of Biotechnology, Chemistry and Environmental Sciences, Aalborg University, Sohngaardsholmsvej 49, Aalborg, Denmark

    Maria Teresa Neves-Petersen

  3. Nanobiotechnology Group, Department of Health Science and Technology, Aalborg University, Frederik Bajers Vej 7D2, Aalborg, Denmark

    Steffen B. Petersen

  4. The Institute for Lasers, Photonics and Biophotonics, University at Buffalo, The State University of New York Buffalo, Buffalo, NY, 14260–3000, USA

    Steffen B. Petersen

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  1. Teresa Sofia Figueiras
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  2. Maria Teresa Neves-Petersen
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  3. Steffen B. Petersen
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Correspondence to Maria Teresa Neves-Petersen.

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Figueiras, T.S., Neves-Petersen, M.T. & Petersen, S.B. Activation Energy of Light Induced Isomerization of Resveratrol. J Fluoresc 21, 1897–1906 (2011). https://doi.org/10.1007/s10895-011-0886-3

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