Discovery and Structural Optimization of 1,2,3,4-Tetrahydro-β-carbolines as Novel Reactive Oxygen Species Inducers for Controlling Intractable Plant Bacterial Diseases

Abstract

Nowadays, reactive oxygen species (ROS) have been acknowledged as promising bactericidal targets against pesticide-resistant bacteria. Herein, to further excavate more excellent ROS inducers, simple 1,2,3,4-tetrahydro-β-carboline derivatives containing a 3-aminopropanamide moiety were prepared and assessed for their antibacterial potency. Notably, three promising compounds displayed significant antibacterial potency. Compound I 29 exhibits excellent in vitro bioactivity, with an EC50 value of 5.73 μg/mL, and admirable in vivo activities (protective activity of 55.74% and curative activity of 65.50%) toward Xanthomonas oryzae pv. oryzae. Compound I 16 has good activity in vitro, with an EC50 of 3.43 μg/mL, and outstanding bioactivities in vivo (protective activity of 92.50% and curative activity of 59.68%) against Xanthomonas axonopodis pv. citri. Compound I 6 shows excellent in vitro bioactivity (EC50 = 2.86 μg/mL) and significant protective activity (94.02%) for preventing Pseudomonas syringae pv. actinidiae. Antibacterial mechanism investigations indicate that these compounds disrupt the balance of the redox system to kill bacteria. These simple 1,2,3,4-tetrahydro-β-carboline derivatives are promising leads to the discovery of bactericidal agents.

Recent Advances on the Synthesis and Application of Tetrahydro‐β‐Carbolines

“…Interestingly, piperidyl N-substituted tetrahydro-βcarbolines derivatives also have been developed for controlling intractable plant bacterial diseases. [62] The tetrahydro-β-carbolines featuring 3-aminopropanamide moiety were prepared as potential bactericidal agents, which showed excellent activity against three destructive phytopathogenic bacteria, including Xoo, Xac, and Psa.…”

Design, Synthesis, Antibacterial Activity, and Mechanisms of Novel Benzofuran Derivatives Containing Disulfide Moieties

“…In particular, rice leaf blight (BLB), rice bacterial streak (BLS), and citrus bacterial canker caused by Xanthomonas oryzae pv oryzae ( Xoo ), Xanthomonas oryzae pv oryzicola ( Xoc ), and Xanthomonas axonopodis pv citri ( Xac ), respectively, are extensively prevalent, highly contagious, rapidly progressing, and profoundly consequential bacterial ailments. − Typically, these bacterial pests result in a decrease in crop output ranging from 10 to 30%. In severe instances, they can lead to a fall in crop yield exceeding 50% or complete crop failure. − Unlike many fungal pathogens primarily restricted to the plant’s surface, bacterial pathogens can enter the plant’s vascular system, making them difficult to access and treat. , Moreover, fungicides are readily accessible and have efficacy against a diverse range of fungal diseases . Nevertheless, the limited availability of effective chemical interventions for the management of bacterial infections poses a more significant challenge, in terms of control.…”

Synthesis and Antifungal Activity of Coumarin Derivatives Containing Hydrazone Moiety

“…The use of fungicides is the preferred preventive measure for the effective control of most plant pathogens in agriculture. Many achievements were made for controlling plant diseases, such as 18β-glycyrrhetinic acid amide derivatives, [1] 1,2,3,4-Tetrahydro-β-carbolines, [2] ursolic acid derivatives, [3] 1,3,4-Oxadiazole-2-carbohydrazides SDH inhibitors, [4] eugenol derivatives, [5] phenothiazine analogues as mimics of host defense peptides (HDPs), [6] and the establishment of an intelligent photoresponsive pesticide delivery system based on β-cyclodextrin (β-CD) and azobenzene. [7] However, fungicides are facing some problems, such as antimicrobial resistance, residual pesticide, and the reduction of authorization in some countries.…”