The discovery of natural 4'-demethylepipodophyllotoxin from renewable Dysosma versipellis species as a novel bacterial cell division inhibitor for controlling intractable diseases in rice

Zhou, Xiang; Ye, Hao‐Jie; Gao, Xiuhui; Yang, Feng; Shao, Wu-Bin; Qi, Pu-Ying; Wu, Zhibing; Liu, Liwei; Wang, Peiyi; Yang, Song

doi:10.1016/j.indcrop.2021.114182

Cited by 27 publications

(31 citation statements)

References 68 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Further screening yielded 50% inhibitory concentrations (IC 50 s) of 159.4 µM and 225.0 µM for compound B 2 and berberine, respectively. Thus, although compound B 2 inhibited Xoo FtsZ GTPase activity with slightly higher potency than berberine and DMEP (IC 50 = 278.7 µM), as demonstrated in our previous study [ 23 ], compound B 2 was less potent than DMEP for inhibition of Xoo growth. One possible explanation for this apparent discrepancy may be the relatively poor aqueous solubility of compound B 2 compared with DMEP, which may have restricted the bactericidal activity of compound B 2 to a greater extent compared with its GTPase-inhibiting activity.…”

Section: Resultssupporting

confidence: 69%

“…Encouraged by our previous work [ 23 ], DMEP was currently certified as a promising scaffold of Xoo FtsZ inhibitors, but discovering how to guide and prepare higher active compounds derived from DMEP quickly and with high efficiency is a crucial purpose of our current work. To maximize the identification of derivatives that would be effective, safe to non-target organisms, and easily synthesizable, we employed a ligand-based approach followed by reranking of molecular docking scores using structure-based virtual screening.…”

Section: Resultsmentioning

confidence: 99%

“…For example, structural modification of DMEP has yielded many anticancer agents, including etoposide and teniposide [ 16 , 19 ], and various DMEP analogs and derivatives with insecticidal activity have been developed and shown to successfully control insect pests in recent years [ 20 , 21 , 22 ]. We recently employed the framework of DMEP to develop inhibitors of bacterial FtsZ, a tubulin homolog that possesses GTPase activity, that have bactericidal activity and control bacterial leaf blight of rice [ 23 ]. The results of that study suggested a new drug discovery strategy and application for DMEP to develop potent FtsZ-targeting compounds for controlling intractable bacterial diseases of plants.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Discovery of Epipodophyllotoxin-Derived B2 as Promising XooFtsZ Inhibitor for Controlling Bacterial Cell Division: Structure-Based Virtual Screening, Synthesis, and SAR Study

Song

Liu

Yang

et al. 2022

IJMS

Self Cite

View full text Add to dashboard Cite

The emergence of phytopathogenic bacteria resistant to antibacterial agents has rendered previously manageable plant diseases intractable, highlighting the need for safe and environmentally responsible agrochemicals. Inhibition of bacterial cell division by targeting bacterial cell division protein FtsZ has been proposed as a promising strategy for developing novel antibacterial agents. We previously identified 4′-demethylepipodophyllotoxin (DMEP), a naturally occurring substance isolated from the barberry species Dysosma versipellis, as a novel chemical scaffold for the development of inhibitors of FtsZ from the rice blight pathogen Xanthomonas oryzae pv. oryzae (Xoo). Therefore, constructing structure−activity relationship (SAR) studies of DMEP is indispensable for new agrochemical discovery. In this study, we performed a structure−activity relationship (SAR) study of DMEP derivatives as potential XooFtsZ inhibitors through introducing the structure-based virtual screening (SBVS) approach and various biochemical methods. Notably, prepared compound B2, a 4′-acyloxy DMEP analog, had a 50% inhibitory concentration of 159.4 µM for inhibition of recombinant XooFtsZ GTPase, which was lower than that of the parent DMEP (278.0 µM). Compound B2 potently inhibited Xoo growth in vitro (minimum inhibitory concentration 153 mg L−1) and had 54.9% and 48.4% curative and protective control efficiencies against rice blight in vivo. Moreover, compound B2 also showed low toxicity for non-target organisms, including rice plant and mammalian cell. Given these interesting results, we provide a novel strategy to discover and optimize promising bactericidal compounds for the management of plant bacterial diseases.

show abstract

Section: Resultssupporting

confidence: 69%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Discovery of Epipodophyllotoxin-Derived B2 as Promising XooFtsZ Inhibitor for Controlling Bacterial Cell Division: Structure-Based Virtual Screening, Synthesis, and SAR Study

Song

Liu

Yang

et al. 2022

IJMS

Self Cite

View full text Add to dashboard Cite

show abstract

“…Plant diseases caused by pathogenic bacteria are a severe threat to food security because they lead to quality decline and significant yield losses in crops 1–3 . For example, Xanthomonas oryzae pv.…”

Section: Introductionmentioning

confidence: 99%

“…Plant diseases caused by pathogenic bacteria are a severe threat to food security because they lead to quality decline and significant yield losses in crops. [1][2][3] For example, Xanthomonas oryzae pv. oryzae (Xoo) can infect gramineous plants, including rice, causing bacterial blight and significant reduction in the yield and quality of rice ranging from 10% to 50%.…”

Section: Introductionmentioning

confidence: 99%

Discovery of novel rost‐4‐ene derivatives as potential plant activators for preventing phytopathogenic bacterial infection: Design, synthesis and biological studies

Wang

Liu

Zhang

et al. 2022

Pest Management Science

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Photo‐Stimuli Smart Supramolecular Self‐Assembly of Azobenzene/β‐Cyclodextrin Inclusion Complex for Controlling Plant Bacterial Diseases

Yang

Xiang

et al. 2023

Adv Funct Materials

Self Cite

View full text Add to dashboard Cite

Controllable and on‐demand delivery of supramolecular systems have received considerable attention in modern agricultural management, especially for managing intractable plant diseases. Here, an intelligent photoresponsive pesticide delivery system is reported based on β‐cyclodextrin (β‐CD) and azobenzene, which overcomes the resistance of phytopathogens caused by the irrational use of conventional pesticides. Antibacterial bioassays illustrated that designed azobenzene derivative 3a possesses the most efficient bioactivity with EC50 values of 0.52–25.31 µg mL−1 toward three typical phytopathogens. Moreover, the assembly of the supramolecular binary complex 3a@β‐CD is successfully elucidated and displays exceptional inhibitory activity on biofilm formation. Of note, this supramolecular binary complex significantly improves the water solubility, foliar surface wettability, and shows marked light‐responsive properties. In vivo anti‐Xoo assays reveal that 3a@β‐CD has excellent control efficiency (protective activity: 51.22%, curative activity: 48.37%) against rice bacterial blight pathogens, and their control efficiency can be elevated to values of 55.84% (protective activity) and 52.05% (curative activity) by UV–vis exposure. In addition, the 3a@β‐CD are non‐toxic toward various non‐target organisms. This study therefore offers new insights into the potential of host‐guest complexes as a feasible pesticide discovery strategy characterized by a safe, biocompatible, light‐responsive release, and antibiofilm properties for overcoming intractable plant bacterial diseases.

show abstract

The discovery of natural 4'-demethylepipodophyllotoxin from renewable Dysosma versipellis species as a novel bacterial cell division inhibitor for controlling intractable diseases in rice

Cited by 27 publications

References 68 publications

Discovery of Epipodophyllotoxin-Derived B2 as Promising XooFtsZ Inhibitor for Controlling Bacterial Cell Division: Structure-Based Virtual Screening, Synthesis, and SAR Study

Discovery of Epipodophyllotoxin-Derived B2 as Promising XooFtsZ Inhibitor for Controlling Bacterial Cell Division: Structure-Based Virtual Screening, Synthesis, and SAR Study

Discovery of novel rost‐4‐ene derivatives as potential plant activators for preventing phytopathogenic bacterial infection: Design, synthesis and biological studies

Photo‐Stimuli Smart Supramolecular Self‐Assembly of Azobenzene/β‐Cyclodextrin Inclusion Complex for Controlling Plant Bacterial Diseases

Contact Info

Product

Resources

About