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SCIENTIA HORTICULTURAE · 2022 · IF 4.342

Isolation and control of Botrytis cinerea in postharvest green pepper fruit

Luyao Wang,Jiepan Hu,Dongsheng Li,Okwong Oketch Reymick,Xiaoli Tan,Nengguo Tao

Botrytis cinerea is a necrotrophic fungus that causes severe losses of postharvest pepper fruit. Moreover, this fungus is indiscriminate, causing severe disease in a variety of plant species, thus isolation and identification of the individual strains are crucial for the development of strain specific antifungal agents. In this study, B. cinerea was isolated from naturally infected green pepper fruit and identified through morphological features, pathogenic symptoms and rDNA-ITS analysis. The antifungal potential of the food additive sodium dehydroacetate (SD) and plant natural product trans-2-hexenal (TH) against the isolated pathogen was then examined. Sequence alignment and phylogenetic tree analysis matched the isolated strain to B. cinerea strains previously isolated from infected sweet pepper in Pakistan, and homology alignment analysis showed that it was 100% homologous to strain NRCB07. In vitro and in vivo experiments showed that both SD and TH treatments strongly inhibited the growth of the isolated B. cinerea , SD had a concentration dependent effect, while TH had an obvious antifungal effect only at higher concentrations. Both SD and TH limited the progression of gray mold disease and reduced the weight loss and respiration rate of inoculated green peppers. Treated pepper retained higher levels of Vc, chlorophyll and total soluble solids. SD and TH also enhanced the activities of the antioxidant enzymes SOD, POD and CAT of pepper, which may be directly responsible for the delayed onset of gray mold disease. Taken together, these results suggest that SD and TH are potential antifungal agents against B. cinerea and can be considered for the health control of gray mold in postharvest green peppers.

CAS / MDL: 945-24-4
研究领域: 植物病理学 · 食品科学 · 分子生物学
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Pharmaceutics · 2023 ·Vol. 15 ·期 4 ·1219 · IF 5.4

Biocontrol Microneedle Patch: A Promising Agent for Protecting Citrus Fruits from Postharvest Infection

Ling Jiang,Huan Huang,Xingyu Shi,Jian Wu,Juexian Ye,Qian Xu,Shaobin Fang,Chuanbin Wu,Rui Luo,Chao Lu,Daojun Liu

With increasing human awareness of food safety, the replacement of highly toxic pesticides with biocompatible antimicrobials has become a trend. This study proposes a biocontrol microneedle (BMN) to expand the application of the food-grade preservative epsilon-poly-L-lysine (ε-PL) in fruit preservatives by utilizing a dissolving microneedle system. The macromolecular polymer ε-PL not only possesses broad-spectrum antimicrobial activity but also exhibits good mechanical properties. With the addition of a small amount of polyvinyl alcohol, the mechanical strength of the ε-PL-based microneedle patch could be further improved to achieve an enhanced failure force of needles at 1.6 N/needle and induce an approximately 96% insertion rate in citrus fruit pericarps. An ex vivo insertion test revealed that the microneedle tips could be effectively inserted into the citrus fruit pericarp, rapidly dissolve within 3 min, and produce inconspicuous needle holes. Moreover, the high drug loading capacity of BMN was observed to reach approximately 1890 μg/patch, which is essential for enhancing the concentration-dependent antifungal activity of ε-PL. The drug distribution study has confirmed the feasibility of mediating the local diffusion of EPL in the pericarp through BMN. Therefore, BMN has great potential to reduce the incidence of invasive fungal infections in local areas of citrus fruit pericarp.Keywords:biocontrol microneedle patch;antifungal agent;ε-poly-lysine;citrus fruit;postharvest infection

CAS / MDL: 9002-89-5 72-57-1
研究领域: 食品科学 · 农业生物技术 · 微生物学
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Scientific Reports · 2019 ·Vol. 9 ·期 1 ·1-9 · IF 4.011

Unusual Flavones from Primula macrocalyx as Inhibitors of OAT1 and OAT3 and as Antifungal Agents against Candida rugosa

Li Xue,Wang Xue,Li Caiyu,Khutsishvili Manana,Fayvush George,Atha Daniel,Zhang Youcai,Borris Robert P.

A bioactivity guided program exploring the interaction of phytochemicals in the entire plant Primula macrocalyx with the organic anion transporters (OAT1 and OAT3) and microorganisms led to the elucidation of ten known flavones ( 1 – 4 , 6 – 10 , 12 ) and two previously undescribed flavones ( 5 , 11 ). The structures of the compounds were determined by extensive analysis of spectroscopic data, as well as by comparison with data from previous reports. Two known flavones ( 9 , 12 ) are reported for the first time from the family Primulaceae. All compounds were evaluated for inhibition of OAT1 and OAT3. Six flavones ( 2 , 3 , 6 – 8 , 12 ) showed potent inhibitory activity on OAT1, while seven flavones ( 2 , 3 , 6 – 9 , 12 ) showed marked inhibitory activity on OAT3, with IC 50  ≤ 10.0  µ M. Antimicrobial activities of crude fractions against sixteen microorganisms were tested to give a target yeast strain Candida rugosa for further evaluation of MICs on the isolates. Three flavones ( 7 , 8 , 12 ) showed marked antifungal activity with MIC < 2.0  µ M. To our knowledge, this study is the first to evaluate these flavones as inhibitors of the OAT1 and OAT3, and as antifungal agents.

CAS / MDL: 3301-79-9
研究领域: 药理学 · 生物化学 · 植物科学 · 微生物学
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PEST MANAGEMENT SCIENCE · 2024 · IF 3.8

3D-QSAR model-oriented optimization of Pyrazole β-Ketonitrile derivatives with diphenyl ether moiety as novel potent succinate dehydrogenase inhibitors

Liangliang Cheng,Cong Zhou,Qinglong Yuan,Letian Zhang,Xusheng Shao,Xiaoyong Xu,Zhong Li,Jiagao Cheng

BACKGROUND Succinate dehydrogenase inhibitor (SDHI) fungicides play important roles in the control of plant fungal diseases. However, they are facing serious challenges from issues with resistance and cross-resistance, primarily attributed to their frequent application and structural similarities. There is an urgent need to design and develop SDHI fungicides with novel structures. RESULTS Aiming to discover novel potent SDHI fungicides, 31 innovative pyrazole β -ketonitrile derivatives with diphenyl ether moiety were rationally designed and synthesized, which were guided by a 3D-QSAR model from our previous study. The optimal target compound A23 exhibited not only outstanding in vitro inhibitory activities against Rhizoctonia solani with a half-maximal effective concentration (EC 50 ) value of 0.0398 μg mL −1 comparable to that for fluxapyroxad (EC 50 = 0.0375 μg mL −1 ), but also a moderate protective efficacy in vivo against rice sheath blight. Porcine succinate dehydrogenase (SDH) enzymatic inhibitory assay revealed that A23 is a potent inhibitor of SDH, with a half-maximal inhibitory concentration of 0.0425 μ m . Docking study within R. solani SDH indicated that A23 effectively binds into the ubiquinone site mainly through hydrogen-bonds, and cation–π and π–π interactions. CONCLUSION The identified β -ketonitrile compound A23 containing diphenyl ether moiety is a potent SDH inhibitor, which might be a good lead for novel fungicide research and optimization. © 2024 Society of Chemical Industry.

CAS / MDL: 75-05-8
研究领域: 植物保护学 · 药物化学 · 分子生物学
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Letters in Drug Design & Discovery · 2020 ·Vol. 17 ·期 3 ·300-311 · IF 1.169

Novel Strobilurin Derivatives Containing Carboxylate Unit as Potential Antifungal Agents

Bao Longzhu,Wang Shuangshuang,Song Di,Wang Jingjing,Yue Xiali,Cao Xiufang

Background: Due to the extensive use of a single fungicide to control crop diseases, the increase of resistant individuals leads to control failures. The search for molecules with fungicidal activity is still ongoing. Strobilurin is one of the most popularly used fungicides in the agrochemical field. A large number of strobilurin derivatives with both high activity and low toxicity have been developed. Methods: In the present study, a series of novel ortho-substituted benzyl carboxylates were efficiently synthesized by the reaction of (E)-methyl 2-(2-(bromom-ethyl)phenyl)-2-methox-yiminoaceta with various carboxylic acids. Their structures were confirmed and characterized by 1H NMR, 13C NMR, and ESI-MS analysis. Their fungicidal activities against common phytopathogenic fungi from six major cash crops were screened based on the pesticides guidelines for the laboratory bioactivity tests. Results: The primary fungicidal activity test results indicate that all compounds showed a certain inhibitory effect on the growth of 13 plants pathogenic fungi at a concentration of 100 ppm, and Compd. 3 has the most obvious inhibitory effect on all fungi. Further fungicidal activity studies indicate that some of these novel strobilurin derivatives containing carboxylate unit exhibited potential in vitro fungicidal activities at the dosage of 6.25 mg/L-1. Conclusion: A series of the ortho-substituted benzyl carboxylates derivatives containing β- methoxyacrylate moiety were designed and synthesized by modifying the side chain of traditional strobilurin fungicide. Compd. 3, Compd. 2 and Compd. 16 were identified as the most promising candidates for further study.

研究领域: 植物保护学 · 农药化学
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APPLIED MICROBIOLOGY AND BIOTECHNOLOGY · 2021 ·Vol. 105 ·期 12 ·5147-5158 · IF 4.813

o-Vanillin, a promising antifungal agent, inhibits Aspergillus flavus by disrupting the integrity of cell walls and cell membranes

Li Qian,Zhu Xiaoman,Xie Yanli,Zhong Yue

Abstract o -Vanillin is a natural product that has been widely applied in the food and pharmaceutical industries. In this study, we determined that o -vanillin can strongly inhibit the growth of Aspergillus flavus mycelia. However, the inhibition mechanism of o -vanillin is still elusive. The ultrastructural morphology of mycelia was injured, and the cell walls were destroyed. The OH functional groups on cell walls were altered, and the content of protein in mycelial cell walls was reduced by o -vanillin. The content of β-1,3-glucan in cell walls was significantly ( P < 0.05) reduced by o -vanillin in a dose-dependent manner, while chitin was not markedly affected. Moreover, o -vanillin led to an increase in the permeability of cell membranes. o -Vanillin also exhibited a promising antifungal effect on contaminated corn kernels. Therefore, o -vanillin inhibited the growth of mycelia by disrupting the integrity of cell walls and cell membranes. This study not only sheds light on the antifungal mechanism of o -vanillin but also indicates that it is a promising agent for the control of A. flavus infection. Key points o -Vanillin has strong inhibitory effects on A. flavus. o -Vanillin destroyed the integrity of cell walls and cell membranes. o -Vanillin could effectively inhibit the growth of A. flavus on corn kernels.

CAS / MDL: 121-33-5 148-53-8
研究领域: 药理学 · 微生物学 · 食品科学
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POLYMER ENGINEERING AND SCIENCE · 2025 · IF 3.2

Green Synthetic Xylan-Based Antifungal Polymer for Wood Preservation

Zhanpeng Jiang,Zeqi Cheng,Chuanpeng Li,Jiuyin Pang

Since commercially available metal ion antifungal agents face the problems of polluting the environment and endangering human health, the development of environmentally friendly antifungal agents has become a top priority. Xylan nanoparticles with an average particle size of 500 nm were extracted from a biomass resource, corn kernel, by secondary alkali treatment. Hyperbranched polymers with terminal hydroxyl groups (HBP-OH) were synthesized using maleic anhydride and diethanolamine in a “one-step melting method”. New reactive functional groups were introduced on the hydroxyl group of HBP-OH by a quaternization reaction. The successful preparation of the quaternary ammonium cationic hyperbranched polymer (HBP-L) was demonstrated by IR and 1 HNMR. Cross-linking of HBP-L with xylan nanoparticles via glutaraldehyde conferred new antifungal properties to the xylan nanoparticles. Infrared spectroscopy and nuclear magnetic hydrogen spectroscopy proved the attachment of the polymer to the nanoparticles. The synthesized antifungal agent showed class I inhibition of both fungi, with weight loss reduced to 5%. The innovative application of modified nano-xylan in wood provides new ideas for the commercialization of polysaccharide-based antifungal agents.

CAS / MDL: 1310-73-2 64-17-5
研究领域: 高分子科学 · 林产化工 · 生物材料 · 绿色化学 · 纳米技术 · 天然产物化学 · 木材科学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2023 · IF 6.1

Liverwort-Derived Metabolites Retard Endophyte Growth and Inspire Antifungal Application

Mingzhu Zhu,Chen He,Jinchuan Zhou,Yi Li,Lilin Qian,Jiaozhen Zhang,Yanan Qiao,Wenqiang Chang,Hongxiang Lou

Liverwort secondary metabolites play an important role in the peaceful relationship between liverwort endophytic fungi and the host. This study identified potential antifungal agents based on interactions between host plants and endophytic fungi. Two endophytic fungi strains and 25 metabolites, including nine new compounds, were isolated from the Chinese liverwort Herbertus herpocladioides. Endophytic fungi were identified using internal transcribed spacer and whole-genome sequencing, and the compound structures were determined using comprehensive spectroscopic analysis coupled with electronic circular dichroism calculations. Among these compounds, compounds 10–13 exhibited potent antifungal activities. Compound 10, the most potent antifungal agent, disrupted fungal mitochondrial respiration by inhibiting the activity of mitochondrial complexes I and IV and resulted in the intracellular ATP content of endophytic fungi being significantly reduced. The in vivo results show that compound 10 protected fruits and animals from infection by phytopathogen Alternaria citriarbusti and human pathogen Candida albicans, respectively.

研究领域: 植物学 · 药理学 · 微生物学 · 植物科学
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ChemMedChem · 2017 ·Vol. 12 ·期 4 ·319-326 · IF 3.225

Synthesis and Biological Evaluation of Novel 2-Aminonicotinamide Derivatives as Antifungal Agents

Tingjunhong Ni,Ran Li,Fei Xie,Jing Zhao,Xin Huang,Maomao An,Chengxu Zang,Zhan Cai,Dazhi Zhang,Yuanying Jiang

Graphical Infections unanchored ! A series of novel 2-aminonicotinamide derivatives were designed, synthesized, and evaluated for in vitro antifungal activity. Compounds 11 g and 11 h have excellent activity against Candida albicans , with MIC 80 values of 0.0313 μg mL −1 , and exhibit broad-spectrum antifungal activity against fluconazole-resistant C. albicans , C. parapsilosis , C. glabrata , and Cryptococcus neoformans , with a MIC 80 range of 0.0313–2.0 μg mL −1 . Further investigation suggested that compound 11 g targets the cell wall and decreases glycosylphosphatidylinositol anchor content on the cell surface of C. albicans . Based on the structures of the reported compounds G884 [ N -(3-(pentan-2-yloxy)phenyl)nicotinamide], E1210 [3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-amine], and 10 b [2-amino- N -((5-(3-fluorophenoxy)thiophen-2-yl)methyl)nicotinamide], which inhibit the biosynthesis of glycosylphosphatidylinositol (GPI)-anchored proteins in fungi, a series of novel 2-aminonicotinamide derivatives were designed, synthesized, and evaluated for in vitro antifungal activity. Most of these compounds were found to exhibit potent in vitro antifungal activity against Candida albicans , with MIC 80 values ranging from 0.0313 to 4.0 μg mL −1 . In particular, compounds 11 g [2-amino- N -((5-(((2-fluorophenyl)amino)methyl)thiophen-2-yl)methyl)nicotinamide] and 11 h [2-amino- N -((5-(((3-fluorophenyl)amino)methyl)thiophen-2-yl)methyl)nicotinamide] displayed excellent activity against C. albicans , with MIC 80 values of 0.0313 μg mL −1 , and exhibited broad-spectrum antifungal activity against fluconazole-resistant C. albicans , C. parapsilosis , C. glabrata , and Cryptococcus neoformans , with a MIC 80 range of 0.0313–2.0 μg mL −1 . Further studies by electron microscopy and laser confocal microscopy indicated that compound 11 g targets the cell wall and decreases GPI anchor content on the cell surface of C. albicans .

研究领域: 药理学 · 微生物学 · 化学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2018 ·Vol. 99 ·期 7 ·3343-3349 · IF 2.379

Synergistic effect of natural antifungal agents for postharvest diseases of blackberry fruits

Hongxia Liu,Huifang Zhao,Lianfei Lyu,Zhengjin Huang,Sufan Fan,Wenlong Wu,Weilin Li

BACKGROUND Blackberry postharvest diseases are caused by fungal pathogens, and treatment of fruits with edible, natural products could reduce the postharvest losses and contribute to food sustainability. Based on the hypothesis that inhibition of fungal pathogens will significantly extend the shelf-life of food products, the effects of natural antifungal agents on fungal pathogens were tested. RESULTS Two pathogenic fungal isolates, Aspergillus japonicus and Gilbertella persicaria , from infected blackberry fruits were identified morphologically using scanning electron microscopy and confirmed by DNA sequence analysis. The inhibitory effects and synergistic action of natural antifungal agents against the two fungal isolates were investigated. The results obtained demonstrated that the natamycin, chitosan and ferulic acid exhibited significant antifungal activities against the tested strains based on the calculated minimum inhibitory concentration. The best antifungal activity was obtained using a combination of ferulic acid and natamycin, which generated a total synergistic effect on both tested strains with a fractional inhibitory concentration index of 0.281. Application of the selected agents on postharvest blackberry fruits reduced the rot ratio and weight loss and also increased fruit firmness. In addition, the shelf-life of fresh blackberry fruits was extended up to 12–15 days at 4 °C and 90 ± 5% relative humidity. CONCLUSION The combined utilization of ferulic acid and natamycin showed synergistic antifungal activity against two pathogenic fungal isolates, and extended the shelf life of fresh blackberry fruits up to 12–15 days. © 2018 Society of Chemical Industry

CAS / MDL: 20283-92-5
研究领域: 食品科学 · 植物病理学 · 药理学
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PEST MANAGEMENT SCIENCE · 2024 · IF 3.8

Discovery of novel piperidine-containing thymol derivatives as potent antifungal agents for crop protection

Xiaoqun Yang,Shichun Jiang,Meng Zhang,Tingting Li,Zhichao Jin,Xingxing Wu,Yonggui Robin Chi

BACKGROUND Plant fungal diseases pose a significant threat to crop production. The extensive use of chemical pesticides has led to growing environmental safety risks and pesticide resistance of various plant pathogens. Therefore, it is an urgent task to explore novel eco-friendly fungicidal agents with high efficacy to combat fungal infection. RESULTS In this study, we rationally designed a series of novel thymol derivatives by incorporation of the sulfonamide moiety and evaluated their biological activities against plant pathogenic fungi. The bioassay results underscored the remarkable in vitro antifungal activity of compounds 5m and 5t against Phytophthora capsici ( P. capsici ), with EC 50 values of 8.420 and 8.414 μ g/mL, respectively. Their efficacies were superior to that of widely used commercial fungicides azoxystrobin (AZO, 20.649 μ g/mL) and cabendazim (CAB, 251.625 μ g/mL). Furthermore, compound 5v exhibited excellent in vitro antifungal activity against Sclerotinia sclerotiorum ( S. sclerotiorum ), with an EC 50 value of 12.829 μ g/mL, significantly outperforming AZO (63.629 μ g/mL). In vivo bioassays demonstrated the impactful activity of compound 5v against S. sclerotiorum , achieving over 98% curative and protective efficacies at the concentration of 200 μ g/mL. Further mechanistic investigations unveiled that compound 5v induced mycelial shrinkage and collapse in S. sclerotiorum , resulting in organelle damage and the accumulation of antioxidant enzyme activity. CONCLUSION The significant antifungal efficacy of the prepared thymol derivatives shall encourage further exploration of compound 5v as a promising candidate to develop novel fungicides for crop protection. © 2024 Society of Chemical Industry.

研究领域: 农业科学 · 植物病理学 · 化学生物学
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PEST MANAGEMENT SCIENCE · 2023 · IF 4.1

Natural products in crop protection: thiosemicarbazone derivatives of 3-acetyl-N-benzylindoles as antifungal agents and their mechanism of action

Tianze Li,Min Lv,Houpeng Wen,Jiawei Du,Zhen Wang,Shaoyong Zhang,Hui Xu

Background Phytopathogenic fungi can cause a direct loss in economic value of agriculture. Especially Valsa mali Miyabe et Yamada, a devastating phytopathogenic disease especially threatening global apple production, is very difficult to control and manage. To discover new potential antifungal agents, a series of thiosemicarbazone derivatives of 3-acetyl- N -benzylindoles were prepared. Their antifungal activities were first tested against six typically phytopathogenic fungi including Curvularia lunata , Valsa mali , Alternaria alternate , Fusarium graminearum , Botrytis cinerea and Fusarium solani . Then their mechanism of action against V. mali was investigated. Results Derivatives displayed potent antifungal activity against V. mali . Notably, 3-acetyl- N -benzylindole thiosemicarbazone (IV-1: EC 50 : 0.59 μ g mL −1 ), whose activity was comparable to that of a commercial fungicide carbendazim (EC 50 : 0.33 μ g mL −1 ), showed greater than 98-fold antifungal activity of the precursor indole. Moreover, compound IV-1 displayed good protective and therapeutic effects on apple Valsa canker disease. By scanning electron microscope (SEM) and RNA-Seq analysis, it was demonstrated that compound IV-1 can destroy the hyphal structure and regulate the homeostasis of metabolism of V. mali via the ergosterol biosynthesis and autophagy pathways. Conclusion 3-Acetyl- N -(un)substituted benzylindoles thiosemicarbazones (IV-1–IV-5) can be studied as leads for further structural modification as antifungal agents against V. mali . Particularly, these ergosterol biosynthesis and autophagy pathways can be used as target receptors for design of novel green pesticides for management of congeneric phytopathogenic fungi. © 2023 Society of Chemical Industry.

研究领域: 农业科学 · 植物病理学 · 化学
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