Flavonoid Deactivation of Excited State Flavins: Reaction Monitoring by Mass Spectrometry
Flavonoid Deactivation of Excited State Flavins: Reaction Monitoring by Mass Spectrometry
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DOI：
10.1021/jf301823h
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发表时间：
2012-09-12
影响因子：
6.1
通讯作者：
Skibsted, Leif H.
中科院分区：
文献类型：
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作者：
Huvaere, Kevin;Sinnaeve, Bart;Skibsted, Leif H.
黄素单核苷酸（FMN，作为B-2维生素模型）显示诱导类黄酮二聚化（黄烷酮、芹菜素、柚皮素、圣草酚、花旗松素、儿茶素、山奈酚、毛地黄黄酮、槲皮素、芦丁和七种较小的模型酚）作为主要的光反应，当水溶液暴露于可见光时，通过LC-MS和MS 2分析支持的实时电喷雾电离质谱（ESI-MS）技术。亲电中间体，如瞬态自由基阳离子，邻醌，对醌甲基化物被提出参与耦合过程。黄酮-3-醇中的C-3-OH产生非典型化合物，如缩酚酸或二氧杂环己烷连接的二聚体。在光照条件下储存过程中添加到食品中的植物提取物中形成的黄酮二聚体，其结构基于MS和MS 2进行了分析，可能会影响胶体稳定性、颜色、涩味和抗氧化能力。
Flavin mononucleotide (FMN, as a B-2 vitamin model) was shown to induce dimerization of flavonoids (flavanone, apigenin, naringenin, eriodictyol, taxifolin, catechin, kaempferol, luteolin, quercetin, rutin, and seven smaller model phenols studied) as the major photoreaction, when aqueous solutions were exposed to visible light using a new, real-time electrospray ionization mass-spectrometric (ESI-MS) technique supported by LC-MS and MS2 analysis. Electrophilic intermediates such as transient radical cations, o-quinones, and p-quinone methide were proposed to be involved in the coupling process. The C-3-OH in flavon-3-ols gave rise to atypical compounds such as a depside or a dioxane-linked dimer. Flavonoid dimers, formed in vegetal extracts added to food during storage in light and for which structures are proprosed based on MS and MS2, may affect colloidal stability, color, astringency, and antioxidative capacity.