Solvent effects on the formation of Resveratrone

PATRICIA VICENDO; LORENTE, CAROLINA; NATHALIE MARTIN-FROMENT; THOMAS, ANDRÉS H.; GASPAR TOSATO, MAIRA

Encuentro; XIII Latin-American Meeting on Photochemistry and Photobiology; 2017

Cosmeceuticals skin products and pills containing antioxidants are getting more popular every day. The enormous therapeutic potential of RSV in treatments of a wide variety of diseases have been postulated and/or demonstrated [1]. However, most of the adverse effects under UV radiation are unknown. Moreover, recent articles mencioned the generation of 4-(6,8-dihydroxynaphthalen-2-yl)but-3-en-2-one, known as resveratrone (RSVT), when trans-resveratrol (t-RSV) and/or cis-resveratrol (c-RSV) are exposed to UV radiation. In this work, the photodegradation of t-RSV and c-RSV in aqueous and ethanol solutions were investigated employing high pressure liquid chromatography (HPLC) coupled to UV-spectrophotometry and mass spectrometry detectors. The solutions were irradiated with UVB and UVA for different irradiation times at 298 K.Several products were identified, both in the presence and the absence of oxygen. One of the products obtained was the RSVT (Figure 1). Structure of molecule consists of two fused aromatic rings with two hidroxyl groups linked to a linear chain containing a carbonyl group. This novel compound was recently characterized, and it is highly fluorescent with a fluorescence quantum yield up to 0.5 in some solvents. This characteristic is being analyzed to be used as organic fluorophore in bio-imaging [2][3]. The phenantrene-like photoproducts can acts as photosensitizer producing singlet oxygen [4] promoting the oxidation of macromolecules.