Chemistry of trans-Resveratrol with Singlet Oxygen: [2+2] Addition, [4+2] Addition, and Formation of the Phytoalexin Moracin M

被引：59

作者：

Celaje, Jeff A. ^{[1
]}

Zhang, Dong ^{[1
]}

Guerrero, Angela M. ^{[1
]}

Selke, Matthias ^{[1
]}

机构：

[1] Calif State Univ Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90032 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 18期

关键词：

ALPHA-TOCOPHEROL; MORUS-ALBA; VITAMIN-E; DERIVATIVES; PHOTOOXIDATION; DEACETYLASE; PRODUCTS; MOLECULE; SURVIVAL; CELLS;

D O I：

10.1021/ol201922u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 x 10(6) M-1 sec(-1) in CD3OD, smaller than previously reported values. Chemical reaction accounts for ca. 25% of k(T).

引用

页码：4846 / 4849

页数：4

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