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A role for 3′-O-β-D-ribofuranosyladenosine in altering plant immunity
Phytochemistry ( IF 3.2 ) Pub Date : 2019-01-01 , DOI: 10.1016/j.phytochem.2018.10.016
Mikhail S Drenichev 1 , Mark Bennett 2 , Roman A Novikov 1 , John Mansfield 2 , Nick Smirnoff 3 , Murray Grant 4 , Sergey N Mikhailov 1
Affiliation  

Our understanding of how, and the extent to which, phytopathogens reconfigure host metabolic pathways to enhance virulence is remarkably limited. Here we investigate the dynamics of the natural disaccharide nucleoside, 3′-O-β-D-ribofuranosyladenosine, in leaves of Arabidopsis thaliana infected with virulent Pseudomonas syringae pv. tomato strain DC3000. 3′-O-β-D-ribofuranosyladenosine is a plant derived molecule that rapidly accumulates following delivery of P. syringae type III effectors to represent a major component of the infected leaf metabolome. We report the first synthesis of 3′-O-β-D-ribofuranosyladenosine using a method involving the condensation of a small excess of 1-O-acetyl-2,3,5-three-O-benzoyl-β-ribofuranose activated with tin tetrachloride with 2′,5′-di-O-tert-butyldimethylsilyladenosine in 1,2-dichloroethane with further removal of silyl and benzoyl protecting groups. Interestingly, application of synthetic 3′-O-β-D-ribofuranosyladenosine did not affect either bacterial multiplication or infection dynamics suggesting a major reconfiguration of metabolism during pathogenesis and a heavy metabolic burden on the infected plant.

中文翻译:

3'-O-β-D-呋喃核糖基腺苷在改变植物免疫中的作用

我们对植物病原体如何以及在多大程度上重新配置宿主代谢途径以增强毒力的理解非常有限。在这里,我们研究了感染毒力丁香假单胞菌 pv 的拟南芥叶片中天然二糖核苷 3'-O-β-D-呋喃糖基腺苷的动力学。番茄菌株 DC3000。3'-O-β-D-呋喃核糖基腺苷是一种植物来源的分子,在丁香假单胞菌 III 型效应物递送后迅速积累,代表受感染叶片代谢组的主要成分。我们报告了第一次合成 3'-O-β-D-呋喃核糖基腺苷,该方法涉及缩合少量过量的 1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-呋喃核糖活化1 中含有 2',5'-二-O-叔丁基二甲基甲硅烷基腺苷的四氯化锡,进一步去除甲硅烷基和苯甲酰基保护基团的 2-二氯乙烷。有趣的是,合成 3'-O-β-D-呋喃核糖基腺苷的应用不影响细菌繁殖或感染动力学,这表明发病过程中代谢的主要重新配置和受感染植物的沉重代谢负担。
更新日期:2019-01-01
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