Theoretical and experimental exploration of the photochemistry of resveratrol: beyond the simple double bond isomerization

Rodríguez, Roi Álvarez; Lahoz, Inmaculada R.; Faza, Olalla Nieto; Cid, Marı́a Magdalena; López, Carlos Silva

doi:10.1039/c2ob26241j

Cited by 35 publications

(22 citation statements)

References 63 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%

“…However, in spite of the absence of unequivocal spectral data, the formation of THDHP intermediate during resveratrol photochemical oxidation-reaction is accepted by the scientific community and supported by UV-Vis, fluorescence data and spectral studies on stilbenes [9,12]. Firstly, in the case of resveratrol the solvent applied for the reaction should be less hydrophobic than those utilized for stilbene photoconversion, due to the presence of the three -OH groups on the aromatic rings that give an important contribution to the solubility of resveratrol in more polar solvents.…”

Section: Photochemistry Of Resveratrol Iso-merizationmentioning

confidence: 99%

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Chemistry, Stability and Bioavailability of Resveratrol

Francioso¹,

Mastromarino²,

Masci³

et al. 2014

158

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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

158

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“…The formation of a trihydroxy phenanthrene was supported also by Tříska et al [17] Yang et al [18] showed that the UV irradiation of trans-resveratrol leads to the formation of a highly fluorescent compound, resveratrone, which was properly characterized by UV, MS and NMR. Computational exploration by Rodríguez et al [19] uncovered the feasibility of singlet oxygen addition to cis or trans-resveratrol to furnish a dioxetane intermediate which spontaneously cycloreverts to benzaldehydes. Recently, Francioso et al [20] showed that upon UV-exposure resveratrol in red wine can isomerise from the trans to the cis-isomer, which may further cyclise to 2,4,6-trihydroxyphenanthrene.…”

Section: Introductionmentioning

confidence: 99%

Stability and Photoisomerization of Stilbenes Isolated from the Bark of Norway Spruce Roots

et al. 2021

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Stilbenes or stilbenoids, major polyphenolic compounds of the bark of Norway spruce (Picea abies L. Karst), have potential future applications as drugs, preservatives and other functional ingredients due to their antioxidative, antibacterial and antifungal properties. Stilbenes are photosensitive and UV and fluorescent light induce trans to cis isomerisation via intramolecular cyclization. So far, the characterizations of possible new compounds derived from trans-stilbenes under UV light exposure have been mainly tentative based only on UV or MS spectra without utilizing more detailed structural spectroscopy techniques such as NMR. The objective of this work was to study the stability of biologically interesting and readily available stilbenes such as astringin and isorhapontin and their aglucones piceatannol and isorhapontigenin, which have not been studied previously. The effects of fluorescent and UV light and storage on the stability of trans stilbenes were assessed and the identification and characterisation of new compounds formed during our experiments were carried out by chromatographic (HPLC, GC) and spectroscopic techniques (UV, MS, NMR). The stilbenes undergo a trans to cis isomerisation under extended UV irradiation by intramolecular cyclisation (by the formation of a new C-C bond and the loss of two hydrogens) to phenanthrene structures. The characterised compounds are novel and not described previously.

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“…There is evidence for photoinduced trans - cis isomerization of resveratrol. Moreover, once the cis -isomer is formed it is possible to form the phenanthrene-derivative by energy-consuming ring closure, a chemical-quenching mechanism ( Figure 5 B) [ 58 , 59 , 60 ]. The cis -isomers of a series of chlorine substituted stilbenes have been prepared by irradiating solutions of the trans -isomers [ 61 ].…”

Section: Discussionmentioning

confidence: 99%

Triplet-Energy Quenching Functions of Antioxidant Molecules

et al. 2022

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UV-like DNA damage is created in the dark by chemiexcitation, in which UV-activated enzymes generate reactive oxygen and nitrogen species that create a dioxetane on melanin. Thermal cleavage creates an electronically excited triplet-state carbonyl whose high energy transfers to DNA. Screening natural compounds for the ability to quench this energy identified polyenes, polyphenols, mycosporine-like amino acids, and related compounds better known as antioxidants. To eliminate false positives such as ROS and RNS scavengers, we then used the generator of triplet-state acetone, tetramethyl-1,2-dioxetane (TMD), to excite the triplet-energy reporter 9,10-dibromoanthracene-2-sulfonate (DBAS). Quenching measured as reduction in DBAS luminescence revealed three clusters of 50% inhibitory concentration, ~50 μM, 200–500 μM, and >600 μM, with the former including sorbate, ferulic acid, and resveratrol. Representative triplet-state quenchers prevented chemiexcitation-induced “dark” cyclobutane pyrimidine dimers (dCPD) in DNA and in UVA-irradiated melanocytes. We conclude that (i) the delocalized pi electron cloud that stabilizes the electron-donating activity of many common antioxidants allows the same molecule to prevent an electronically excited species from transferring its triplet-state energy to targets such as DNA and (ii) the most effective class of triplet-state quenchers appear to operate by energy diversion instead of electron donation and dissipate that energy by isomerization.

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Theoretical and experimental exploration of the photochemistry of resveratrol: beyond the simple double bond isomerization

Cited by 35 publications

References 63 publications

Chemistry, Stability and Bioavailability of Resveratrol

Chemistry, Stability and Bioavailability of Resveratrol

Stability and Photoisomerization of Stilbenes Isolated from the Bark of Norway Spruce Roots

Triplet-Energy Quenching Functions of Antioxidant Molecules

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