Synthesis and biological evaluation of pentacyclic triterpenoid derivatives as potential novel antibacterial agents

Wu, Panpan; Tu, Borong; Liang, Jianying; Guo, Shengzhu; Cao, Nana; Chen, Silin; Luo, Zhujun; Li, Jiahao; Zheng, Wende; Tang, Xiaowen; Li, Dongli; Xu, Xuetao; Liu, Wenfeng; Zheng, Xi; Sheng, Zhaojun; Roberts, Adam P.; Zhang, Kun; Hong, W. David

doi:10.1016/j.bioorg.2021.104692

Cited by 32 publications

(24 citation statements)

References 48 publications

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“…The antimicrobial of essential oils were determined according to the standard agar disk diffusion method with a slight modification ( Luangtongkum et al, 2007 ; Gaudreau et al, 2008 ; Benamrouche et al, 2014 ; Wu et al, 2018 ; Wu et al, 2021 ). A 0.5 McFarland (1 × 10 7 to 1 × 10 8 CFU/mL) concentration of the bacterial suspension was uniformly inoculated onto MHA solidified in 120 mm Petri dishes.…”

Section: Methodsmentioning

confidence: 99%

“…The dishes were incubated in a constant temperature incubator at 37°C for 24 h. The inhibition zone diameter was measured by a vernier caliper. All the experiments were performed in triplicate ( Wu et al, 2021 ).…”

Section: Methodsmentioning

confidence: 99%

“…The minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) were determined by a microdilution method in 96-well plates according to Clinical and Laboratory Standards Institute (CLSI), with a slight modification ( Sader et al, 2006 ; Meng et al, 2016 ; Wu et al, 2018 ; Wu et al, 2021 ). A series of diluted essential oils were prepared with DMSO as the solvent by two-fold serial dilution starting from a stock solution of 512 mg/mL.…”

Section: Methodsmentioning

confidence: 99%

“…Each well received 5 μL of a specific concentration of the essential oils and 195 μL of MHB inoculated with the test microorganism (1.5 × 10 5 CFU/mL); the final concentrations of the examined essential oils were reached. Gatifloxacin was used as positive control and DMSO was used as negative control ( Wu et al, 2021 ). The microplates were incubated in a bacteriological oven for 24 h at 37°C, and the susceptibility results of tested samples were monitored by measuring the absorbance at 600 nm using a Multimodel Plate Reader (Infinite 200).…”

Section: Methodsmentioning

confidence: 99%

“…The microplates were incubated in a bacteriological oven for 24 h at 37°C, and the susceptibility results of tested samples were monitored by measuring the absorbance at 600 nm using a Multimodel Plate Reader (Infinite 200). The lowest concentration without visible growth was defined as the MIC ( Wu et al, 2021 ).…”

Section: Methodsmentioning

confidence: 99%

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Chemical Composition, Antimicrobial and Insecticidal Activities of Essential Oils of Discarded Perfume Lemon and Leaves (Citrus Limon (L.) Burm. F.) as Possible Sources of Functional Botanical Agents

Tang

Jian

et al. 2021

Front. Chem.

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Two essential oils were isolated from discarded perfume lemon and leaves (Citrus limon (L.) Burm. F.) by hydro-distillation with good yield (0.044% for perfume lemon and 0.338% for leaves). Their biological activities were evaluated against five selected bacterial strains and Aedes albopictus (Ae. albopictus, Diptera: Culicidae). Chemical composition indicated that both essential oils were rich in essential phytochemicals including hydrocarbons, monoterpenes and sesquiterpene. These constituents revealed some variability among the oils displaying interesting chemotypes (R)-(+)-limonene (12.29–49.63%), citronellal (5.37–78.70%) and citronellol (2.98–7.18%). The biological assessments proved that the two essential oils had similar effect against bacterial (inhibition zones diameter ranging from 7.27 ± 0.06 to 10.37 ± 0.15 mm; MICs and MBCs ranging from 1.6 to 6.4 mg/mL); against Ae. albopictus larvae (LC50 ranging from 384.81 to 395.09 ppm) and adult mosquito (LD50 ranging from 133.059 to 218.962 μg/cm2); the activity of the two chemotypes ((R)-(+)-limonene and citronellal): larvae (LC50 ranging from 267.08 to 295.28 ppm), which were all presented in dose-dependent manners. Through this work, we have showcased that recycling and reusing of agriculture by-products, such as discarded perfume lemon and leaves can produce eco-friendly alternatives in bacterial disinfectants and mosquito control product.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Chemical Composition, Antimicrobial and Insecticidal Activities of Essential Oils of Discarded Perfume Lemon and Leaves (Citrus Limon (L.) Burm. F.) as Possible Sources of Functional Botanical Agents

Tang

Jian

et al. 2021

Front. Chem.

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Exploration of 1,2,3‐triazolo fused triterpenoids as inhibitors of human coronavirus 229E targeting the viral nsp15 protein

Wang,

Stevaert,

Truong

et al. 2023

Archiv der Pharmazie

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The coronavirus disease‐19 (COVID‐19) pandemic has raised major interest in innovative drug concepts to suppress human coronavirus (HCoV) infections. We previously reported on a class of 1,2,3‐triazolo fused betulonic acid derivatives causing strong inhibition of HCoV‐229E replication via the viral nsp15 protein, which is proposedly related to compound binding at an intermonomer interface in hexameric nsp15. In the present study, we further explored the structure–activity relationship (SAR), by varying the substituent at the 1,2,3‐triazolo ring as well as the triterpenoid skeleton. The 1,2,3‐triazolo fused triterpenoids were synthesized by a multicomponent triazolization reaction, which has been developed in‐house. Several analogs possessing a betulin, oleanolic acid, or ursolic acid core displayed favorable activity and selectivity (EC50 values for HCoV‐229E: 1.6–3.5 μM), but neither of them proved as effective as the lead compound containing betulonic acid. The 18β‐glycyrrhetinic acid‐containing analogs had low selectivity. The antiviral findings were rationalized by in silico docking in the available structure of the HCoV‐229E nsp15 protein. The new SAR insights will aid the further development of these 1,2,3‐triazolo fused triterpenoid compounds as a unique type of coronavirus inhibitors.

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Application of Chalcone in the Structural Modification of Natural Products: An Overview

Quan,

Liu,

Wang

et al. 2024

Chemistry & Biodiversity

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Natural products frequently display a range of biological activities, yet many exhibit only moderate efficacy during initial evaluations. Often, these natural substances necessitate structural alterations to yield promising lead compounds. Chalcones, characterized by their β‐unsaturated carbonyl aromatic ketone structure, are prevalent in plant life and serve as fundamental scaffolds for the biosynthetic precursors of flavonoids and isoflavones. Due to their straightforward synthesis and extensive spectrum of biological effects, chalcones have found extensive application in medicinal chemistry. Chalcone analogs have demonstrated significant potential for drug discovery and development, as structural modifications can both amplify pharmacological efficacy and effectively mitigate toxic side effects. This paper endeavors to delve into the applications of chalcones in the structural modification of natural products, providing a theoretical foundation for future endeavors in derivatization and drug development. The full paper is organized into categories based on the biological activities of the derivatives, including anti‐dyslipidemic, antibacterial, antimalarial, anti‐inflammatory, anticancer, anti‐Alzheimer, and α‐glucosidase inhibitory activities.

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Synthesis and biological evaluation of pentacyclic triterpenoid derivatives as potential novel antibacterial agents

Cited by 32 publications

References 48 publications

Chemical Composition, Antimicrobial and Insecticidal Activities of Essential Oils of Discarded Perfume Lemon and Leaves (Citrus Limon (L.) Burm. F.) as Possible Sources of Functional Botanical Agents

Chemical Composition, Antimicrobial and Insecticidal Activities of Essential Oils of Discarded Perfume Lemon and Leaves (Citrus Limon (L.) Burm. F.) as Possible Sources of Functional Botanical Agents

Exploration of 1,2,3‐triazolo fused triterpenoids as inhibitors of human coronavirus 229E targeting the viral nsp15 protein

Application of Chalcone in the Structural Modification of Natural Products: An Overview

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