title: Isolation and identification of 2,4,6-trihydroxyphenanthrene as a byproduct of trans-resveratrol photochemical isomerization and electrocyclization.
abstract: UV irradiation of trans-resveratrol leads to its photochemical isomerization and electrocyclization, giving rise to different byproducts. Preliminary attempts to purify and characterize these products were in the majority of cases unsuccessful. In the present work, the resveratrol photoreaction products were analyzed by HPLC, and one of these compounds, 2,4,6-trihydroxyphenanthrene (THP), was purified and unambiguously identified. The structure of THP was unequivocally characterized for the first time by combined GC-MS, ESI-MS/MS, NMR, and FT-IR analyses.
authors.affiliation: Department of Biochemical Sciences and ‡Department of Chemistry and Pharmaceutical Technology, Sapienza University , p.le Aldo Moro 5, 00185 Rome, Italy.
authors.forename: Antonio
authors.initials: A
authors.lastname: Francioso
authors.forename: Alberto
authors.initials: A
authors.lastname: Boffi
authors.forename: Claudio
authors.initials: C
authors.lastname: Villani
authors.forename: Lucio
authors.initials: L
authors.lastname: Manzi
authors.forename: Maria
authors.initials: M
authors.lastname: D'Erme
authors.forename: Alberto
authors.initials: A
authors.lastname: Macone
authors.forename: Luciana
authors.initials: L
authors.lastname: Mosca
mesh_terms: D002851:Chromatography, High Pressure Liquid; D004563:Electrochemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D010616:Phenanthrenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification*; D055668:Photochemical Processes; D000077185:Resveratrol; D017550:Spectroscopy, Fourier Transform Infrared; D013267:Stilbenes / Q000737:chemistry*
chemical_list: C000598149:2,4,6-trihydroxyphenanthrene; D010616:Phenanthrenes; D013267:Stilbenes; D000077185:Resveratrol