1. Academic Validation
  2. Synthesis of Deoxyradicinin, an Inhibitor of Xylella fastidiosa and Liberibacter crescens, a Culturable Surrogate for Candidatus Liberibacter asiaticus

Synthesis of Deoxyradicinin, an Inhibitor of Xylella fastidiosa and Liberibacter crescens, a Culturable Surrogate for Candidatus Liberibacter asiaticus

  • J Nat Prod. 2020 Jun 26;83(6):1810-1816. 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
Affiliations

Affiliations

  • 1 Department of Chemistry, Point Loma Nazarene University, San Diego, California 92106, United States.
  • 2 Department of Microbiology and Plant Pathology, University of California, Riverside, California 92521, United States.
  • 3 Pfizer Inc., La Jolla, California 92121, United States.
  • 4 Department of Botany and Plant Sciences, University of California, Riverside, California 92521, United States.
Abstract

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.

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