Resveratrol improves fungal ribosylation capacity through a unique mechanism
Resveratrol improves fungal ribosylation capacity through a unique mechanism
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DOI：
10.1039/c4ra12851f
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发表时间：
2015
期刊：
影响因子：
3.9
通讯作者：
G. Zhao;Jing-Yang Fan;Cheng-Pin Hua;Wei Yan;Chao-Jun Chen;Yanhua Lu;R. Jiao;R. Tan
中科院分区：
文献类型：
--
作者：
G. Zhao;Jing-Yang Fan;Cheng-Pin Hua;Wei Yan;Chao-Jun Chen;Yanhua Lu;R. Jiao;R. Tan
核糖基化是赋予化合物新的复杂和拓宽的细胞作用的重要修饰，但小的有机分子很少被核糖基化。本文报道了白藜芦醇的3-O-和4′-O-α-核糖基化反应。白藜芦醇是一种植物抗毒素，对真菌黑炭层壳（Daldinia eschscholzii IFB-TL 01）是外源性的。核糖基化的机制是由于白藜芦醇激活的沉默或活性较低的真菌基因的表达，控制非真菌植物酚的核糖基化。白藜芦醇诱导的核糖基化的特征还在于核糖基转移酶的表达增加，这与使用烟酰胺单核苷酸（NMN）作为核糖供体的罕见核糖基化反应一致。核糖基化降低了白藜芦醇对D. Eschschscholzii，沿着至少两个β-糖蛋白参与糖基化，表明这种糖基化过程可能是真菌对酚类化学物质解毒的一般策略。这些发现提出了小分子核糖基化的最新观点，并提供了直接的化学发生学证据，有助于理解植物酚如白藜芦醇在植物，微生物和动物王国中的不同功能。
Ribosylation is a significant modification conferring new complex and broadened cellular roles of compounds, but small organic molecules are rarely ribosylated. Here, we report the 3-O- and 4′-O-α-ribosylation of resveratrol, a phytoalexin that is exogenous to the fungus Daldinia eschscholzii IFB-TL01. The ribosylation is mechanistically due to the resveratrol-activated expression of the silent or less active fungal genes governing the ribosylation of non-fungal phytophenols. The resveratrol-induced ribosylation is also characterized by an increased expression of ribosyltransferases in concert with a rare ribosylating reaction using nicotinamide mononucleotide (NMN) as a ribose donor. The ribosylation-reduced toxicity of resveratrol to D. eschscholzii, along with the involvement of at least two p-glycoproteins in the glycosylation, suggests that such a glycosylation process may be a general strategy for the fungal detoxification of phenolic chemicals. The findings present an updated view of the ribosylation of small molecules, and provide direct chemogenetic evidence that will aid understanding of how phytophenols such as resveratrol function differently in the plant, microbial and animal kingdoms.