RESUMEN
BACKGROUND: Plant pathogens have led to large yield and quality losses in crops worldwide. The discovery and study of novel agrochemical alternatives based on the chemical modification of bioactive natural products is a highly efficient approach. Here, two series of novel cinnamic acid derivatives incorporating diverse building blocks with alternative linking patterns were designed and synthesized to identify their antiviral capacity and antibacterial activity. RESULTS: The bioassay results demonstrated that most cinnamic acid derivatives had excellent antiviral competence toward tobacco mosaic virus (TMV) in vivo, especially compound A5 (median effective concentration [EC50 ] = 287.7 µg mL-1 ), which had a notable protective effect against TMV when compared with the commercial virucide ribavirin (EC50 = 622.0 µg mL-1 ). In addition, compound A17 had a protective efficiency of 84.3% at 200 µg mL-1 against Xac in plants. Given these outstanding results, the engineered title compounds could be regarded as promising leads for controlling plant virus and bacterial diseases. Preliminary mechanistic studies suggest that compound A5 could enhance the host's defense responses by increasing the activity of defense enzymes and upregulating defense genes, thereby suppressing phytopathogen invasion. CONCLUSION: This research lays a foundation for the practical application of cinnamic acid derivatives containing diverse building blocks with alternative linking patterns in pesticide exploration. © 2023 Society of Chemical Industry.
Asunto(s)
Infecciones Bacterianas , Virus de Plantas , Virus del Mosaico del Tabaco , Humanos , Agroquímicos/farmacología , Antivirales/farmacología , Antivirales/química , Relación Estructura-Actividad , Diseño de Fármacos , Enfermedades de las Plantas/prevención & controlRESUMEN
Discovering new anti-virulent agents to control plant bacterial diseases by preventing bacterial pathogenesis/pathogenicity rather than affecting bacterial growth is a sensible strategy. However, the effects of compound-manipulated bacterial virulence factors on host response are still not clear. In this work, 35 new 1,3,4-oxadiazole derivatives were synthesized and systematically evaluated for their anti-phytopathogenic activities. Bioassay results revealed that compound C7 possessed outstanding antibacterial activity in vitro (half-maximal effective concentration: 0.80 µg/mL) against Xanthomonas oryzae pv. oryzae (Xoo) and acceptable bioactivity in vivo toward rice bacterial leaf blight. Furthermore, virulence factor-related biochemical assays showed that C7 was a promising anti-virulent agent. Interestingly, C7 could indirectly reduce the inducible expression of host SWEET genes and thereby alleviate nutrient supply in the infection process of phytopathogenic bacteria. Our results highlight the potential of 1,3,4-oxadiazole-based agrochemicals for manipulating type III secretion system-induced phytopathogenic bacteria starvation mechanisms to prevent plant bacterial diseases.
Asunto(s)
Infecciones Bacterianas , Oryza , Xanthomonas , Sistemas de Secreción Tipo III/genética , Enfermedades de las Plantas/prevención & control , Enfermedades de las Plantas/microbiología , Oxadiazoles/farmacología , Oxadiazoles/química , Factores de Virulencia/metabolismo , Xanthomonas/genética , Oryza/metabolismo , Antibacterianos/químicaRESUMEN
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-ß-carboline derivatives containing a 3-aminopropanamide moiety were prepared and assessed for their antibacterial potency. Notably, three promising compounds displayed significant antibacterial potency. Compound I29 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 I16 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 I6 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-ß-carboline derivatives are promising leads to the discovery of bactericidal agents.
Asunto(s)
Infecciones Bacterianas , Oryza , Xanthomonas , Especies Reactivas de Oxígeno , Pruebas de Sensibilidad Microbiana , Enfermedades de las Plantas/microbiología , Antibacterianos/farmacología , Antibacterianos/química , Oryza/microbiología , Oxadiazoles/químicaRESUMEN
BACKGROUND: Gradually aggravated disease caused by phytopathogenic bacteria severely restricts food security and crop yield, and few pesticides can relieve this severe situation. Thus, development and excavation of new agrochemicals with high bioactivity and novel action mechanism may be a feasible strategy to control intractable bacterial diseases. As a privileged molecular framework, steroid molecules exhibit diversiform bioactivities. Herein, a series of novel androst-4-ene derivatives were designed, synthesised and investigated for their antibacterial behaviour to excavate novel agrochemicals on the base of steroid molecules. RESULTS: Bioassay results indicated that target compounds displayed high bioactivities toward three destructive phytopathogenic bacteria, including Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas axonopodis pv. citri (Xac) and Pseudomonas syringae pv. actinidiae (Psa). Compound III19 displayed excellent in vitro antibacterial profiling (EC50 = 2.37 mg L-1 towards Xoo, EC50 = 2.10 mg L-1 towards Xac, EC50 = 9.50 mg L-1 towards Psa). Furthermore, compound III19 showed outstanding in vivo protective activities, with values of 81.81% and 58.75% towards kiwifruit bacterial canker and rice bacterial leaf blight, respectively. Analysis of the antibacterial mechanism disclosed that compound III19 enhanced host defence enzyme activities superoxide dismutase (SOD), peroxidase (POD), phenylalanine ammonia lyase (PAL), polyphenol oxidase (PPO), and catalase (CAT) and increased the salicylate synthase content to induce host resistance. In addition, compound III19 increased the membrane permeability, destroyed the cell membrane and killed the bacteria. CONCLUSION: Given these profiles of target compounds, we highlight a new strategy for controlling intractable plant bacterial diseases by inducing plant resistance and targeting the bacterial cell membrane. © 2022 Society of Chemical Industry.
Asunto(s)
Infecciones Bacterianas , Oryza , Xanthomonas , Agroquímicos , Antibacterianos , Pruebas de Sensibilidad Microbiana , Oxadiazoles/química , Enfermedades de las Plantas/prevención & controlRESUMEN
Plant bacterial diseases can potentially damage agricultural products around the world, and few effective bactericides can manage these infections. Herein, to sequentially explore highly effective antibacterial alternatives, 1,2,3-triazole-tailored carbazoles were rationally fabricated. These compounds could suppress the growth of three main intractable pathogens including Xanthomonas oryzae pv oryzae (Xoo), X. axonopodis pv citri (Xac), and Pseudomonas syringae pv actinidiae (Psa) with lower EC50 values of 3.36 (3p), 2.87 (3p), and 4.57 µg/mL (3r), respectively. Pot experiments revealed that compound 3p could control the rice bacterial blight with protective and curative efficiencies of 53.23% and 50.78% at 200 µg/mL, respectively. Interestingly, the addition of 0.1% auxiliaries such as organic silicon and orange oil could significantly enhance the surface wettability of compound 3p toward rice leaves, resulting in improved control effectiveness of 65.50% and 61.38%, respectively. Meanwhile, compound 3r could clearly reduce the white pyogenic exudates triggered by Psa infection and afforded excellent control efficiencies of 79.42% (protective activity) and 78.74% (curative activity) at 200 µg/mL, which were quite better than those of commercial pesticide thiodiazole copper. Additionally, a plausible apoptosis mechanism for the antibacterial behavior of target compounds was proposed by flow cytometry, reactive oxygen species detection, and defensive enzyme (e.g., catalase and superoxide dismutase) activity assays. The current work can promote the development of 1,2,3-triazole-tailored carbazoles as prospective antibacterial alternatives bearing an intriguing mode of action.
Asunto(s)
Oryza , Xanthomonas , Antibacterianos/farmacología , Carbazoles , Pruebas de Sensibilidad Microbiana , Enfermedades de las Plantas , Estudios Prospectivos , Triazoles/farmacologíaRESUMEN
BACKGROUND: Induced apoptosis is an effective technique that can reprogram cellular physiological and pathological processes to eradicate undesirable cells using their innate systems. Inspired by this, numerous apoptosis inducers have been developed to treat animal diseases, especially in the anticancer field. However, few studies have reported on the development of inductive agents that attack plant pathogens by activation of apoptosis. With the aim of exploring and discovering apoptosis inducers that target phytopathogens, a cluster of piperazine-tailored ursolic acid (UA) hybrids was systematically fabricated. RESULTS: In vitro testing showed that the title molecules could inhibit the growth of two intractable bacterial strains, defined as Xanthomonas oryzae pv. oryzae and X. axonopodis pv. citri. The corresponding lowest EC50 values were 0.37 and 1.08 µg mL-1 , which exceed those of UA (>400 µg mL-1 ) and positive controls. Moreover, compounds 5u and 5v could manage bacterial blight in vivo using pot experiments. Flow cytometer analysis indicted that the title compounds could induce distinct apoptotic behaviors on tested bacteria. In-depth study revealed that the introduction of designed compounds could reduce the enzyme activities of catalase and superoxide dismutase, subsequently leading to the accumulation of reactive oxygen species. CONCLUSION: This study promoted the development of apoptosis initiators for managing bacterial infections in agriculture by an innovative mode of action. © 2020 Society of Chemical Industry.
Asunto(s)
Oryza , Xanthomonas , Antibacterianos , Apoptosis , Piperazina , Enfermedades de las Plantas , Triterpenos , Ácido UrsólicoRESUMEN
In recent years, naturally occurring tetrahydro-ß-carboline (THC) alkaloids and their derivatives have been of biological interest. However, few studies and developments have reported the use of such structures in managing plant bacterial diseases. Herein, an array of novel THC derivatives containing an attractive 1,3-diaminopropan-2-ol pattern were prepared to evaluate the antiphytopathogen activity in vitro and in vivo and explore innovative antibacterial frameworks. Notably, target compounds exhibited excellent activities against three rebellious phytopathogens, namely, Pseudomonas syringae pv. actinidiae (Psa), Xanthomonas axonopodis pv. citri, and Xanthomonas oryzae pv. oryzae, at related optimal EC50 values of 2.39 (II9), 2.06 (I23), and 1.69 (II9) µg/mL, respectively. These effects were superior to those of the parent structure 1,2,3,4-THC and positive controls. In vivo assays showed that II9 exhibited excellent control efficiencies of 51.89 and 65.45% at 200 µg/mL against rice bacterial blight and kiwifruit bacterial canker, respectively, and I23 substantially relieved the citrus canker on the leaves. Antibacterial mechanisms indicated that these THC compounds could induce the increment of reactive oxygen species and subsequently endow the tested bacteria with distinct apoptotic behavior. In addition, II9 could alleviate the hypersensitive response and pathogenicity of Psa. Overall, these simple THC derivatives can be further developed as versatile antibacterial agents.