Chemistry of trans- Resveratrol with Singlet Oxygen: [2 + 2] Addition, [4 + 2] Addition, and Formation of the Phytoalexin Moracin M
2011; American Chemical Society; Volume: 13; Issue: 18 Linguagem: Inglês
10.1021/ol201922u
ISSN1523-7060
AutoresJeff Joseph A. Celaje, Dong Zhang, Angela Guerrero, Matthias Selke,
Tópico(s)Bioactive natural compounds
ResumoResveratrol (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 (kT) was determined by time-resolved infrared luminescence spectroscopy to be 1.5 × 106 M–1 sec–1 in CD3OD, smaller than previously reported values. Chemical reaction accounts for ca. 25% of kT.
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