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PEST MANAGEMENT SCIENCE · 2024 · IF 3.8

Amphiphilic amidines as potential plasmic membrane-targeting antifungal agents: synthesis, bio-activities and QSAR

Guangyou Chen,Jing Bai,Xinyan Wu,Xinyi Huo,Yongqiang Li,Peng Lei,Zhiqing Ma

BACKGROUND Cationic antimicrobial peptides (AMPs) possess broad-spectrum biological activities with less inclination to inducing antibiotic resistance. Herein a battery of amphiphilic amidines were designed by mimicking the characteristics of AMPs. The antifungal activities and the effects to the hyphal morphology and membrane permeability were investigated. RESULTS The results indicated the inhibitory rates of ten compounds were over 80% to Botrytis cinerea and ten compounds over 90% to Valsa mali Miyabe et Yamada at 50 mg L −1 . The half maximal effective concentration (EC 50 ) values of compound 5g and 6g to V . mali were 1.21 and 1.90 mg L −1 respectively. The protective rate against apple canker of compound 5g reached 93.4% at 100 mg L −1 on twigs, superior to carbendazim (53.3%). When treated with 5g , the cell membrane permeability and leakage of content of V. mali increased, accompanied with the decrease of superoxide dismutase (SOD) and catalase (CAT) level. Concurrently, the mycelial hyphae contracted, wrinkled, and collapsed, providing evidence of membrane perturbation. A three-dimensional quantitative structure–activity relationship (3D-QSAR) between the topic compounds and the EC 50 to V . mali was established showing good predictability ( r 2 = 0.971). CONCLUSION Amphiphilic amidines can acquire antifungal activities by acting on the plasmic membrane. Compound 5g could be a promising lead in discovering novel fungicidal candidates. © 2024 Society of Chemical Industry.

研究领域: 药物化学 · 微生物学 · 真菌学 · 植物病理学 · 定量构效关系
✓ 已验证 DOI PubMed 高影响因子
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MOLECULES · 2023 ·Vol. 28 ·期 18 ·6713 · IF 4.6

Synthesis, Antioxidant, and Antifungal Activities of β-Ionone Thiazolylhydrazone Derivatives and Their Application in Anti-Browning of Freshly Cut Potato

Cong Huang,Yuan Zhong,Rong Zeng,Jie Wang,Qingwen Fang,Shuzhen Xiao,Ji Zhang,Zongde Wang,Shangxing Chen,Dayong Peng

In order to develop a new type of antioxidants with high efficiency, a series of β-ionone thiazolylhydrazone derivatives were designed and synthesized from β-ionone, and their structures were characterized by1H-NMR,13C-NMR, FT-IR, and HR-MS. The antioxidant test in vitro indicated that most of the target compounds had high biological activity. Among them, compound1kexhibited very strong DPPH (1,1-diphenyl-2-picrylhydrazyl radical)-scavenging activity with a half-maximal effective concentration (IC50) of 86.525 μM. Furthermore, in the ABTS (2,2-azinobis (3-ethylbenzothiazoline-6-sulfonate) diammonium salt)-scavenging experiment, compound1mexhibited excellent activity with an IC50of 65.408 μM. Their biological activities were significantly better than those of the positive control Trolox. These two compounds, which have good free-radical-scavenging activity in vitro, were used as representative compounds in the anti-browning experiment of fresh-cut potatoes. The results showed that1kand1mhad the same anti-browning ability as kojic acid, and they were effective browning inhibitors. In addition, it is well known that microbial infection is one of the reasons for food oxidation. Therefore, we investigated the antifungal activity of 25 target compounds against eight plant fungi at a concentration of 125 mg/L. The results indicated that these compounds all have some antifungal activity and may become new potential fungicides. Notably, compound 1u showed the best inhibitory effect againstPoria vaporaria, with an inhibition rate as high as 77.71%; it is expected to become the dominant structure for the development of new antifungal agents.Keywords:thiazolylhydrazone;synthesis;antioxidant;antifungal;anti-browning

研究领域: 食品科学 · 植物保护 · 有机化学
✓ 已验证 DOI PubMed 高影响因子
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INDUSTRIAL CROPS AND PRODUCTS · 2024 · IF 5.6

Lansiumamide B induced the degradation of polysaccharides and oligosaccharides showing antifungal activity against Rhizoctonia solani

Yina Jia,Jianrong Tang,Yunfu Dang,Yizhou Yang,Shan He,Yue Jiang,Yong Wang,Juntao Feng,Zhiqing Ma,Xili Liu,He Yan

Lansiumamide B (LB) is a cinnamamide alkaloid isolated from Clausena lansium seeds. The compound is the main antifungal ingredient found in C. lansium . In this paper, the antifungal activity of LB against 10 plant pathogenic fungi was evaluated and found that it was the most effective to Rhizoctonia solani (EC 50 = 2.99 μg/mL). The compound also exhibits certain protective (53.06%) and curative (71.01%) activities against R. solani at 800 μg/mL. The mechanism of action of LB was further elucidated through physiological and biochemical experiments, mycelial morphology and ultrastructure observations, and transcriptomics studies with R. solani as the experimental strain. SEM and TEM observation showed that it caused abnormal mycelium growth, extravasation of contents and cell wall degradation. Physiological and biochemical tests showed that LB treatment had no significant effect on the cellular respiration of mycelium , but it could increase the membrane permeability , cause the leakage of intracellular electrolyte, reduce the content of extracellular polysaccharide and chitin in cell wall and increased the contents of intracellular reducing sugar. The results of transcriptome sequencing analysis showed that LB had significant effects on polysaccharide and oligosaccharide related metabolic pathways, such as starch and sucrose metabolic pathways, galactose metabolic pathways, and amino sugar metabolic pathways. Furthermore, LB treatment increased the specific enzyme activity of α-1, 4-glucanase, α-1,6-glucanase, cellulase and maltase of R. solani in vivo . Comprehensive analysis of the above experimental results shows that LB induces and regulates the degradation of polysaccharides and oligosaccharides of R. solani at the transcriptional level, thereby destroying the cell wall structure and ultimately leading to the death of fungi.

研究领域: 植物化学 · 真菌学 · 分子生物学
✓ 已验证 DOI 高影响因子
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INDUSTRIAL CROPS AND PRODUCTS · 2025 · IF 6.2

High foliar adhesion carvacrol-chitosan nanoparticles assist cotton against Fusarium oxysporum infection

Jing Zhou,Rourou Wang,Ming Niu,Zhenghua Zhang,Minrui Zhu,Lumei Pu,Weibing Xu,Runtian Ma

The infection caused by Fusarium oxysporum severely threatens cotton production. Herein, carvacrol-chitosan nanoparticles (CS@CAR) are facilely fabricated using tripolyphosphate as a crosslinker. When the initial mass ratio of chitosan to carvacrol is 1:0.4, the nanoparticles show the best stability and drug loading. Morphological analysis reveals that the CS@CAR nanoparticles possesses a uniform spherical structure with an average diameter of approximately 150 nm. About 51.23 % of total CAR is released within the 48 h in the simulated fungal infection environment. The contact angle of drug-loaded particles decreases by 12.2 and 6.6 ° compares with that of pure water and unloaded particles. The fluorescence intensity of leaves before and after rain erosion is 1.3 times and 1.2 times that of the pure water control group by fluorescence imaging analysis. The bacteriostatic activity of drug-loaded nanoparticles is 6–7 times that of non-drug-loaded nanoparticles. The contents of nucleic acid, protein, and malondialdehyde leaked by spores after treatment with drug-loaded particles are 1.4, 1.5 and 2.3 times those in the non-drug-loaded particle treatment group, respectively. The CS@CAR entirely prevents Fusarium oxysporum from infecting cotton leaves in spore inoculation experiments. The CS@CAR nanoparticles are expected to be used to prevent and control the infection of Fusarium oxysporum on cotton.

CAS / MDL: 499-75-2 9012-76-4
研究领域: 植物病理学 · 纳米生物学
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Antibiotics-Basel · 2025 ·Vol. 14 ·期 5 ·499 · IF 4.6

Antifungal Effects of the Phloroglucinol Derivative DPPG Against Pathogenic Aspergillus fumigatus

Liyang Wang,Junying He,Hanzhong Feng,Qian Li,Meirong Song,Haoran Gou,Yongxing He,Kui Zhu

Background:Fungal infections pose an increasingly predominant threat to human and animal health. Modified compounds derived from chemo-diverse natural products offer enhanced therapeutic efficacies and promising approaches to combat life-threatening fungal pathogens.Methods:We performed biosynthetic gene clusters analysis of 2,4-diacetylchloroglucoside (DAPG) in 4292 shotgun metagenomes samples from the healthy and diseased skin. Then, we assessed the antifungal activity of DAPG and the derivative 2,4-diproylphloroglucinol (DPPG) against pathogenic fungi by minimum inhibitory concentrations. The inhibitory effects of DPPG were measured using hyphal growth assay and spore germination assay. Concurrently, the mechanism of DPPG onAspergillus fumigatuswas investigated in membrane permeability and fluidity. The therapeutic efficacy was evaluated in aGalleria mellonellainfection model.Results:We observed a significantly higher abundance of bacteria harboring DAPG biosynthetic clusters on healthy skin compared to diseased skin. Further, we designed and synthesized a series of phloroglucinol derivatives based on DAPG and obtained an antifungal candidate DPPG. DPPG not only exhibited robust antifungal activity againstAspergillusspp. andCandidaspp. but also impaired hyphal growth and spore germination ofA. fumigatusin vitro. A mechanism study showed that DPPG reduced membrane fluidity and increased the leakage of cellular contents, resulting in membrane perturbation and fungal death. Lastly, the therapeutic efficacy of DPPG was confirmed in aG. mellonellainfection model.Conclusions:Our study demonstrates that DPPG is a potent scaffold to combat invasive fungal infections.

研究领域: 微生物学 · 药理学 · 感染病学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2025 · IF 5.4

In situ construction of antifungal surface on cellulose by ternary deep eutectic solvent and its application to Phyllostachys edulis

Qian Ao,Changhang Zhang,Xiaoyu Li,Yunchang He,Yu Zhang,Zhuo Zhao,Hailan Lian,Ying Zhou

Cellulosic materials have been widely applied in various fields such as construction, medicine, and new energy. However, the inherent structure of cellulose, composing of multiple hydroxyl groups, is highly susceptible to fungal degradation, thereby significantly limiting its high-value applications. Existing antifungal measures often fail to balance environmental friendliness and convenient preparation. Inspired by the antifungal properties of sulfated polysaccharides, this study utilized a deep eutectic solvent (DES) composed of sulfamic acid/1,3-propanediol/benzenesulfonic acid (S/P/B DES) to construct an intrinsically antifungal structure on cellulose via sulfation, making the preparation process more environmentally friendly and straightforward. Under the influence of the S/P/B DES, the hydroxyl groups at the C2, C3, and C6 positions of the cellulose pyranose ring underwent sulfation reactions, which imparted negative charge to the surface. The electrostatic interactions rendered the cellulose molecular chains more dispersed and amenable to rearrangement, combined with the acidolysis of the amorphous regions and the dissolution of the crystalline regions by the S/P/B DES, the cellulose chains spontaneously reorganized into a more compact structure. Using Material Studio demonstrated this structure would provide additional binding sites for fungi, thereby facilitating their adsorption and subsequent degradation, as a result, the antifungal performance of cellulose was significantly improved. Additionally, considering that Phyllostachys edulis contains over 50 wt% of cellulose and is highly susceptible to the degradation from fungal, which severely reduces its application value, this study further explored the potential surface application of the S/P/B DES in bamboo’s antifungal treatment.

CAS / MDL: 64-17-5
研究领域: 材料科学 · 微生物学 · 植物学
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Journal of Biomedical Research · 2018 · IF 0

Antifungal effects of BiOBr nanosheets carrying surfactant cetyltrimethylammonium bromide

Mei-qing Sun,Zhan-lin Ding,Hong Wang,Guang-ping Yu,Li,Ming-chun Li,Meng-meng Zhen

BiOBr nanosheets are important photocatalytic nanomaterials. However, their biological effects remain to be explored. In this study, we investigated the antifungal effect of BiOBr nanosheets on Candida albicans . Strikingly, the nanosheets strongly inhibited the growth of C. albicans [IC 50 =(96±4.7) mg/L], hyphal development and biofilm formation. Compareed to the antifungal effect of the cationic surfactant cetyltrimethylammonium bromide, the inhibitory effect of the nanosheets on fungal pathogen was attributed to cetyltrimethylammonium bromide adsorbed by the nanosheets. Thermal gravity analysis and cetyltrimethylammonium bromide release experiment indicated that only 0.42% cetyltrimethylammonium bromide on BiOBr nanosheets was released. Taken together, this study uncovers the contribution of surfactant released from the nanosheets to their antifungal activity.

研究领域: 微生物学 · 纳米医学 · 药物递送
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INDUSTRIAL CROPS AND PRODUCTS · 2019 · IF 4.191

Broad-spectrum antifungal activity of dichloromethane extract of Waltheria indica stems and isolated compounds

Cai Liang,Li Yang,Yu Shao,Xinyue Zhu,Hongliang Zhao,Biwei Chen,Wen Song,Xiangmin Song,Xiaofan Ding,Ranfeng Sun

The secondary metabolites produced by plants are important sources of fungicides with intriguing bioactivities and environmentally benign attributes (eg. low residual toxicity to mammals and readily biodegradable in soil). In this study, the dichloromethane extract of stems of Waltheria indica L. was found to exhibit broad-spectrum antifungal activity toward eight phytopathogenic fungi, particularly against carbendazim-resistant Sclerotinia sclerotiorum with inhibition rate of 100% at 500 μg/mL. Two quinoline alkaloids, antidesmone and waltherione C, were isolated and identified as fungicidal compounds by bioassay-guided isolation and spectroscopic analyses. Antidesmone displayed superior antifungal activities against eight phytopathogenic fungi to commercial botanical fungicides (osthole, carvacrol, and eugenol). Moreover, antidesmone was found to have significant negative cross-resistance with carbendazim to Sclerotinia sclerotiorum for the first time and exhibited much better antifungal activity (EC 50  = 0.60 μg/mL) against carbendazim-resistant strains than carbendazim-sensitive strain (EC 50  = 9.61 μg/mL) of Sclerotinia sclerotiorum , which was further supported by the molecular modelling result. In addition, the dichloromethane extract of the Waltheria indica stems could effectively control the development of eleven species of phytopathogenic fungi in vivo. These results suggest that Waltheria indica dichloromethane extract and antidesmone can be developed as promising broad-spectrum botanical fungicides.

CAS / MDL: 67-64-1
研究领域: 植物学 · 真菌学 · 农药科学
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PEST MANAGEMENT SCIENCE · 2014 ·Vol. 71 ·期 3 ·433-440 · IF 2.743

Synthesis and antifungal evaluation of a series of maleimides

Xiao-Long Chen,Li-Jun Zhang,Fu-Ge Li,Yong-Xian Fan,Wei-Ping Wang,Bao-Ju Li,Yin-Chu Shen

BACKGROUND Maleimides, both natural and synthesised, have good biological activities. In a continuous effort to discover new maleimides with good antifungal activities, the authors have synthesised a series of 3,4-dichloro-, 3-methyl and non-substituted maleimides based on previous studies. The compounds were biologically evaluated against the fungal pathogen Sclerotinia sclorotiorum. RESULTS Of the 63 compounds evaluated, 25 compounds had interesting inhibitory potency with EC 50 < 10 µg mL −1 . N -(3,5-Dichlorophenyl)-3,4-dichloromaleimide (EC 50 = 1.11 µg mL −1 ) and N -octyl-3-methylmaleimide (EC 50 = 1.01 µg mL −1 ) were more potent than the commercial fungicide dicloran (EC 50 = 1.72 µg mL −1 ). The results showed that compounds exhibiting log P values within the range 2.4–3.0 displayed the best results in terms of fungicidal activity, and this seemed, therefore, to be the optimum range for this physicochemical parameter. CONCLUSION The present work demonstrates that some maleimides can be used as potential lead compounds for developing novel antifungal agents against S. sclerotiorum . © 2014 Society of Chemical Industry

CAS / MDL: 616-02-4 108-31-6
研究领域: 药物化学 · 植物病理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF CULTURAL HERITAGE · 2022 · IF 3.229

PHMG-KH560 as antifungal and reinforcement media for paper materials

Minghao Jia,Xiaoxia Huang,Xiaogang Zhang,Gang Hu

Improving the strength decrease caused by fungal metabolites is still an arduous task in the field of paper materials protection. A set of damaged Kangxi Dictionary from Qing Dynasty was chosen as samples in this work. The main goal of this work is to develop high-efficiency and eco-friendly media with the characteristics of antifungal and reinforcement, to preserve paper materials and continue the historical and scientific research value of cultural heritage. PHMG as an efficient antifungal was used in this work. For better behavior, the epoxy group of KH560 can be induced by the amino group in PHMG by ring opening reaction to form PHMG-KH560 colloidal complex. Spraying PHMG-KH560 on paper could establish Si-O-C bonding and increased the hydrogen bond between polymeric material and paper fibers, which simultaneously inhibited fungi and improved mechanical strength of the original paper, even after the artificial aging. PHMG-KH560 had certain antifungal activity against five fungi, such as Aspergillus versicolor, and Aspergillus Niger , and had better inhibitory effect on Cladosporium herbarum, Trichoderma viride , and Penicillium expansum . The ancient writing ink on the paper sprayed with PHMG-KH560 did not affect its visual beauty, which also indicated that the complex reagent was expected to be applied to the antifungal and reinforcement of paper materials.

研究领域: 文物保护 · 材料科学 · 微生物学
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PEST MANAGEMENT SCIENCE · 2023 · IF 4.1

Efficacy and toxic action of the natural product natamycin against Sclerotinia sclerotiorum

Yuxuan Cao,Xu Zhang,Xiaoning Song,Wenkui Li,Zheng Ren,Juntao Feng,Zhiqing Ma,Xili Liu,Yong Wang

BACKGROUND Sclerotinia stem rot caused by Sclerotinia sclerotiorum seriously endangers oilseed rape production worldwide, and the occurrence of fungicide-resistant mutants of S. sclerotiorum leads to control decline. Thus, it is critical to explore new green substitutes with different action mechanisms and high antifungal activity. Herein, the activity and the action mechanism of natamycin against S. sclerotiorum were evaluated. RESULTS Natamycin showed potent inhibition on the mycelial growth of S. sclerotiorum , and half-maximal effective concentration (EC 50 ) values against 103 S. sclerotiorum strains ranged from 0.53 to 4.04 μg/mL (mean 1.44 μg/mL). Natamycin also exhibited high efficacy against both carbendazim- and dimethachlone-resistant strains of S. sclerotiorum on detached oilseed rape leaves. No cross-resistance was detected between natamycin and carbendazim. Natamycin markedly disrupted hyphal form, sclerotia formation, integrity of the cell membrane, and reduced the content of oxalic acid and ergosterol, whereas it increased the reactive oxygen species (ROS) and malondialdehyde content. Interestingly, exogenous addition of ergosterol could reduce the inhibition of natamycin against S. sclerotiorum . Importantly, natamycin significantly inhibited expression of the Cyp51 gene, which is contrary to results for the triazole fungicide flusilazole, indicating a different action mechanism from triazole fungicides. CONCLUSION Natamycin is a promising effective candidate for the resistance management of S. sclerotiorum . © 2023 Society of Chemical Industry.

CAS / MDL: 85509-19-9 7681-93-8
研究领域: 植物病理学 · 真菌学 · 农业科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FOOD HYDROCOLLOIDS · 2020 · IF 7.053

Development of antifungal gelatin-based nanocomposite films functionalized with natamycin-loaded zein/casein nanoparticles

Xiepeng Mo,Xinling Peng,Xianrui Liang,Sheng Fang,Hujun Xie,Jie Chen,Yuecheng Meng

In this study, natamycin-loaded zein/casein composite nanoparticles (Nata-Z/C NPs) were fabricated and incorporated into gelatin film to improve the film's physicochemical and antifungal properties. The mean particle diameter (MPD) and zeta potential (ZP) values of the Nata-Z/C NPs were characterized by dynamic light scattering (DLS) with 68.5 ± 1.2 nm and −33.1 ± 0.8 mV, respectively. The Nata-Z/C NPs were well dispersed in the gelatin film and improved its mechanical properties, including the tensile strength (from 30.5 ± 3.2 MPa to 51.4 ± 3.0 MPa) and percentage elongation at break (from 0.225 ± 0.087 to 0.685 ± 0.103). The NPs as hydrophobic filler also improved the water barrier properties to 0.335 × 10 −9  g ˑ m/m 2 ˑ Pa ˑ s and water contact angle to 122.55 ± 1.54° of the gelatin film. The possible interactions between the Nata-Z/C NPs and gelatin were studied by differential scanning calorimetry (DSC), Fourier-transform infrared spectroscopy (FTIR), and scanning electron microscopy (SEM) techniques. The sustained release of natamycin from the film was achieved by its encapsulation, and the release kinetics were assessed with the Avrami model. Furthermore, the nanocomposite films exhibited strong antifungal activities against Aspergillus niger , Botrytis cinerea , and Penicillium citrinum . This study revealed that the Nata-Z/C NPs could be used as both nanofillers and functional additives to improve the physicochemical and bacteriostatic properties of gelatin films.

研究领域: 材料科学 · 食品科学 · 纳米技术 · 生物技术
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