title: Photo-induced chemical reaction of trans-resveratrol.
abstract: Photo-induced chemical reaction of trans-resveratrol has been studied. UV B, liquid state and sufficient exposure time are essential conditions to the photochemical change of trans-resveratrol. Three principal compounds, cis-resveratrol, 2,4,6-phenanthrenetriol and 2-(4-hydroxyphenyl)-5,6-benzofurandione, were successively generated in the reaction solution of trans-resveratrol (0.25 mM, 100% ethanol) under 100 μW cm(-2) UV B radiation for 4h. cis-Resveratrol, originated from isomerization of trans-resveratrol, resulted in 2,4,6-phenanthrenetriol through photocyclisation reaction meanwhile loss of 2 H. 2,4,6-Phenanthrenetriol played a role of photosensitizer producing singlet oxygen in the reaction pathway. The singlet oxygen triggered [4+2] cycloaddition reaction of trans-resveratrol, and then resulted in the generation of 2-(4-hydroxyphenyl)-5,6-benzofurandione through photorearrangement and oxidation reaction. The singlet oxygen reaction was closely related to the substrate concentration of trans-resveratrol in solution.
authors.affiliation: Zhejiang University Tea Research Institute, Hangzhou 310058, China.
authors.forename: Yue
authors.initials: Y
authors.lastname: Zhao
authors.affiliation: Zhejiang University Tea Research Institute, Hangzhou 310058, China.
authors.forename: Meng
authors.initials: M
authors.lastname: Shi
authors.affiliation: Zhejiang University Tea Research Institute, Hangzhou 310058, China. Electronic address: jx0515@163.com.
authors.forename: Jian-Hui
authors.initials: JH
authors.lastname: Ye
authors.affiliation: Zhejiang University Tea Research Institute, Hangzhou 310058, China.
authors.forename: Xin-Qiang
authors.initials: XQ
authors.lastname: Zheng
authors.affiliation: Zhejiang University Tea Research Institute, Hangzhou 310058, China.
authors.forename: Jian-Liang
authors.initials: JL
authors.lastname: Lu
authors.affiliation: Zhejiang University Tea Research Institute, Hangzhou 310058, China.
authors.forename: Yue-Rong
authors.initials: YR
authors.lastname: Liang
mesh_terms: D002851:Chromatography, High Pressure Liquid; D005504:Food Analysis / Q000379:methods*; D005663:Furans / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D017319:Photosensitizing Agents / Q000737:chemistry; D000077185:Resveratrol; D026082:Singlet Oxygen / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013267:Stilbenes / Q000737:chemistry*; D014466:Ultraviolet Rays
chemical_list: D005663:Furans; D017319:Photosensitizing Agents; D013267:Stilbenes; D026082:Singlet Oxygen; D000077185:Resveratrol
keywords: Photochemistry; Photosensitizer; Singlet oxygen; UV B radiation; cis-Resveratrol; trans-Resveratrol