title: Chemistry of trans-resveratrol with singlet oxygen: [2+2] addition, [4+2] addition, and formation of the phytoalexin moracin M.
abstract: Resveratrol (1) reacts with singlet oxygen by two major pathways: A [2+2] cycloaddition forming a transient dioxetane that cleaves into the corresponding aldehydes and a [4+2] cycloaddition forming an endoperoxide that, upon heating, undergoes a rearrangement to moracin M. The rate constant by which singlet oxygen is removed by 1 (k(T)) was determined by time-resolved infrared luminescence spectroscopy to be 1.5 × 10(6) M(-1) sec(-1) in CD(3)OD, smaller than previously reported values. Chemical reaction accounts for ca. 25% of k(T).
authors.affiliation: Department of Chemistry and Biochemistry, California State University, Los Angeles, Los Angeles, California 90032, USA.
authors.forename: Jeff A
authors.initials: JA
authors.lastname: Celaje
authors.forename: Dong
authors.initials: D
authors.lastname: Zhang
authors.forename: Angela M
authors.initials: AM
authors.lastname: Guerrero
authors.forename: Matthias
authors.initials: M
authors.lastname: Selke
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D012118:Resorcinols / Q000138:chemical synthesis* / Q000737:chemistry; D000077185:Resveratrol; D026082:Singlet Oxygen / Q000737:chemistry*; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry*
chemical_list: D001572:Benzofurans; D012118:Resorcinols; D013267:Stilbenes; D026082:Singlet Oxygen; C568020:moracin M; D000077185:Resveratrol