Photochemical generation of a new, highly fluorescent compound from non-fluorescent resveratrol

Yang, Inho; Kim, Eunha; Kang, Jae Seong; Han, Hyouksoo; Sul, Soohwan; Park, Seung Bum; Kim, Seong Keun

doi:10.1039/c2cc30940h

Cited by 39 publications

(33 citation statements)

References 12 publications

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“…However, none of these authors could unequivocally characterize all the photoproducts [7][8][9][10][11][12]. Many of them started by indirect experiments aimed to compare the photochemical reaction kinetics of stilbenes to that of resveratrol.…”

Section: Photochemistry Of Resveratrol Iso-merizationmentioning

confidence: 99%

“…T íska et al and Baderschnider and Winterhalter isolated and characterized a novel highly fluorescent compound, the 2,4,6-trihydroxyphenanthrene-2-O-glucoside (Fig. Recently, Yang et al [11] generated a highly fluorescent novel compound by resveratrol irradiation, hypothesizing that the reaction steps of THDHP formation were similar to that of the stilbene. This latter work was incorrectly reported by Chen et al, who claimed that the authors isolated and characterized the THP instead of the glycosydic form of this compound [42].…”

Section: Photochemistry Of Resveratrol Iso-merizationmentioning

confidence: 99%

See 1 more Smart Citation

Chemistry, Stability and Bioavailability of Resveratrol

Francioso¹,

Mastromarino²,

Masci³

et al. 2014

154

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Resveratrol is a bioactive polyphenol found in many vegetables. It is well known for its multiple pharmacological activities, such as anti-inflammatory, antioxidant, antimicrobial, anticancer, neuroprotective and cardioprotective effects. In vitro evidence of resveratrol efficacy is widespread, however, many concerns regarding its effectiveness in vivo arise from its poor stability in vitro and bioavailability following oral ingestion. This review focuses on the in vitro stability, with special focus on the photochemical stability of resveratrol, and on the therapeutic perspectives of this molecule due to its low bioavailability.

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Section: Photochemistry Of Resveratrol Iso-merizationmentioning

confidence: 99%

Section: Photochemistry Of Resveratrol Iso-merizationmentioning

confidence: 99%

Chemistry, Stability and Bioavailability of Resveratrol

Francioso¹,

Mastromarino²,

Masci³

et al. 2014

154

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show abstract

“…Taking into account all these characteristics observed for the fluorescent product (absorption and emission spectra and the molecular weight), this compound was identified as (E)-4-(6,8-dihydroxynaphthalen-2-yl)but-3-en-2-one or resveratrone (RSVT), which has been previously characterized. [13] Our results point out that UV-A irradiation of cis-RSV leads to the formation of RSVT, and that this photochemical reaction takes place in ethanol, but not in water.…”

Section: Ethanolic Solutions Of Trans-rsvmentioning

confidence: 55%

“…[12] These results are contradictory to those that established that the RSV is an efficient antioxidant, and, therefore, the consumption of RSV, for cosmetic or dietary purposes, should be further evaluated. Additionally, a new yellow fluorescent product of the photodegradation of RSV was isolated and identified as resveratrone ((E)-4-(6,8dihydroxynaphthalen-2-yl)but-3-en-2-one, denoted hereafter as RSVT, figure 1), [13] and has been proposed for bio-imaging microscopy.…”

Section: Introductionmentioning

confidence: 99%

Clearing up the photochemistry of resveratrol: Effect of the solvent

Tosato

Vicendo

Thomas

et al. 2018

Journal of Photochemistry and Photobiology A: Chemistry

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Please cite this article as: Tosato MG, Vicendo P, Thomas AH, Lorente C, Clearing up the photochemistry of resveratrol: effect of the solvent, Journal of Photochemistry and amp; Photobiology, A: Chemistry (2018), https://doi. Graphical abstractHighlights  Resveratrol is a a natural polyphenolic substance with reported anti-inflammatory, antiviral and antioxidant properties.  The first step during UV absorption of trans-RSV is isomerization but after isomerization undergoes different photodegradation pathways depending on the solvent.  UV radiation of Resveratrol in ethanolic solutions leads to the formation of high fluorescent compound. Abstract Polyphenolic substances synthesized by plants are generally involved in protection against UV radiation and the attack of pathogenic microorganisms. Resveratrol (3,5,4'trihydroxystilbene, RSV) is synthesized in its trans-form (trans-RSV) in plants under stress conditions like infections or UV exposure and has attracted attention as an antioxidant agent. Trans-RSV was irradiated with both UV-A (MAX = 365 nm) and UV-B (MAX = 300 nm) radiation in aqueous and ethanolic solutions at room temperature. The reactions were followed by UV-Vis spectrophotometry, HPLC with UV and fluorescence detection, and UPLC coupled to mass spectrometry detection. In both solvents the irradiation caused the fast isomerization of trans-RSV to cis-RSV. In ethanolic solutions, a strong fluorescent compound, identified as resveratrone (RSVT) was detected independently on the irradiation wavelength. In aqueous solutions, RSVT was not detected in both irradiation conditions. However, in aqueous/ethanol mixtures the amount RSVT was found to be proportional to the amount of ethanol in the solution. Under UV-B irradiation, both in ethanolic or water solutions other products were detected. Our results demonstrated that RSV is photosensitive and its photochemistry depends on the solvent nature and on the irradiation wavelength.

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“…Resveratrol (3,5,4′ − trihydroxy − stilbene) is a natural phytoalexin produced by numerous plants, being an agent against injuries, fungal, or bacterial infection . Fluorescence properties from UV‐irradiated trans‐resveratrol compound have been reported . Considering its optical properties and nontoxic nature, resveratrol powder may function as a potential detection agent for latent fingerprint development on several kinds of surfaces.…”

Section: Experimental Details Results and Discussionmentioning

confidence: 99%

Fluorescence of a Natural Fluorophore as a Key to Improve Fingerprint Contrast Image

Oliveira

Leão

Balzuweit

et al. 2019

Journal of Forensic Sciences

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The optical and morphological properties of resveratrol were investigated. This nontoxic fluorescent natural material, emitting in the visible blue light, was used as an optical marker, enabling the enhancement of the image contrast coming from relief pictures marked on challenging surfaces. By applying appropriated imaging softwares, this marker was verified to be very useful in the latent fingerprint recognition deposited on different wood surface types, mainly those with high level of roughness, where conventional forensic materials do not allow effective fingerprint image visualization.

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Photochemical generation of a new, highly fluorescent compound from non-fluorescent resveratrol

Cited by 39 publications

References 12 publications

Chemistry, Stability and Bioavailability of Resveratrol

Chemistry, Stability and Bioavailability of Resveratrol

Clearing up the photochemistry of resveratrol: Effect of the solvent

Fluorescence of a Natural Fluorophore as a Key to Improve Fingerprint Contrast Image

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