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Synthesis of Deoxyradicinin, an Inhibitor of Xylella fastidiosa and Liberibacter crescens, a Culturable Surrogate for Candidatus Liberibacter asiaticus.
Journal of Natural Products ( IF 5.1 ) Pub Date : 2020-06-08 , DOI: 10.1021/acs.jnatprod.9b01207
Connor A Brandenburg 1 , Claudia A Castro 2 , Alex A Blacutt 2 , Elizabeth A Costa 3 , Kyler C Brinton 1 , Diana W Corral 1 , Christopher L Drozd 2 , M Caroline Roper 2 , Philippe E Rolshausen 4 , Katherine N Maloney 1 , Jonathan W Lockner 1
Affiliation  

Pierce’s disease of grapevine and citrus huanglongbing are caused by the bacterial pathogens Xylella fastidiosa and Candidatus Liberibacter asiaticus (CLas), respectively. Both pathogens reside within the plant vascular system, occluding water and nutrient transport, leading to a decrease in productivity and fruit marketability and ultimately death of their hosts. Field observations of apparently healthy plants in disease-affected vineyards and groves led to the hypothesis that natural products from endophytes may inhibit these bacterial pathogens. Previously, we showed that the natural product radicinin from Cochliobolus sp. inhibits X. fastidiosa. Herein we describe a chemical synthesis of deoxyradicinin and establish it as an inhibitor of both X. fastidiosa and Liberibacter crescens, a culturable surrogate for CLas. The key to this three-step route is a zinc-mediated enolate C-acylation, which allows for direct introduction of the propenyl side chain without extraneous redox manipulations.

中文翻译:

Deoxyradicinin 的合成,Xylella fastidiosa 和 Liberibacter crescens 的抑制剂,Candidatus Liberibacter asiaticus 的可培养替代物。

葡萄皮尔斯病和柑橘黄龙病分别是由病原菌Xylella fastidiosaCandidatus Liberibacter asiaticus ( C Las)引起的。这两种病原体都存在于植物维管系统中,阻碍水和养分的运输,导致生产力和果实适销性下降,最终导致宿主死亡。对受疾病影响的葡萄园和小树林中明显健康的植物进行实地观察,得出的假设是,来自内生菌的天然产物可能会抑制这些细菌病原体。以前,我们发现,从天然产物radicinin旋孢腔菌藻。抑制X. fastidiosa. 在本文中,我们描述了脱氧放射菌素的化学合成,并将其确定为X. fastidiosaLiberibacter crescensC Las的可培养替代品)的抑制剂。这个三步路线的关键是锌介导的烯醇C-酰化,它允许直接引入丙烯基侧链,而无需额外的氧化还原操作。
更新日期:2020-06-26
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