Synthesis, Antifungal Evaluation, 3D-QSAR, and Preliminarily Mechanism Study of Novel Chiral Mandelic Acid Derivatives

Hou, Shuaitao; Shi, Huabin; Zhang, Hong; Wu, Zhibing; Hu, Deyu

doi:10.1021/acs.jafc.2c09006

Cited by 8 publications

(3 citation statements)

References 48 publications

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“…was measured by following the previously reported methods. [29,30] The mycelial cakes of P. sp. (5 mm) were placed in 30 mL of PDB liquid medium at 28 °C for 3 days with 140 rpm shaking.…”

Section: Determination Of Cytoplasmic Content Leakagementioning

confidence: 99%

Design, Synthesis and Antifungal Activity of Nootkatone Derivatives Containing Acylhydrazone and Oxime Ester

Liang,

Gao,

Jian

et al. 2024

Chemistry & Biodiversity

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In an attempt to search for new natural products‐based antifungal agents, fifty‐three nootkatone derivatives were designed, synthesized, and evaluated for their antifungal activity against Phytophthora parasitica var nicotianae, Fusarium oxysporum, Fusarium graminearum and Phomopsis sp. by the mycelium growth rate method. Nootkatone derivatives N17 exhibited good inhibitory activity against Phomopsis. sp. with EC50 values of 2.02 μM. The control effect of N17 against Phomopsis. sp. on kiwifruit showed that N17 exhibited a good curative effect in reducing kiwifruit rot at the concentration of 202 μM(100 × EC50 ), with the curative effect of 41.11% , which was better than commercial control of pyrimethanil at the concentration of 13437 μM(100 × EC50 ) with the curative effect of 38.65%. Phomopsis. sp. mycelium treated with N17 showed irregular surface collapse and shrinkage, and the cell membrane crinkled irregularly, vacuoles expanded significantly, mitochondria contracted, and organelles partially swollen by the SEM and TEM detected. Preliminary pharmacological experiments show that N17 exerted antifungal effects by altering release of cellular contents, and altering cell membrane permeability and integrity. The presented results implied that N17 may be as a potential antifungal agents for developing more efficient fungicides to control Phomopsis sp..

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“…was measured by following the previously reported methods. [29,30] The mycelial cakes of P. sp. (5 mm) were placed in 30 mL of PDB liquid medium at 28 °C for 3 days with 140 rpm shaking.…”

Section: Determination Of Cytoplasmic Content Leakagementioning

confidence: 99%

Design, Synthesis and Antifungal Activity of Nootkatone Derivatives Containing Acylhydrazone and Oxime Ester

Liang,

Gao,

Jian

et al. 2024

Chemistry & Biodiversity

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“…Sections were double-stained using uranyl acetate and lead citrate. The cell ultrastructure of F. graminearum was examined and photographed with TEM (JEOL, Tokyo, Japan) [34].…”

Section: Tem Observationmentioning

confidence: 99%

Effects of 2-Phenylethanol on Controlling the Development of Fusarium graminearum in Wheat

Sun,

Tang,

Han

et al. 2023

Microorganisms

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Applying plant-derived fungicides is a safe and sustainable way to control wheat scab. In this study, volatile organic compounds (VOCs) of wheat cultivars with and without the resistance gene Fhb1 were analyzed by GC-MS, and 2-phenylethanol was screened out. The biocontrol function of 2-phenylethanol on Fusarium graminearum was evaluated in vitro and in vivo. Metabolomics analysis indicated that 2-phenylethanol altered the amino acid pathways of F. graminearum, affecting its normal life activities. Under SEM and TEM observation, the mycelial morphology changed, and the integrity of the cell membrane was destroyed. Furthermore, 2-phenylethanol could inhibit the production of mycotoxins (DON, 3-ADON, 15-ADON) by F. graminearum and reduce grain contamination. This research provides new ideas for green prevention and control of wheat FHB in the field.

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“…The 1,3,4-oxadiazole skeleton, a class of heterocyclic compounds containing two N atoms, is widely utilized as a fundamental building block in natural products and pharmaceutical molecules due to its remarkable biological and pharmacological activities. − Therefore, the development of synthetic methodologies for 1,3,4-oxadiazole frameworks has consistently been a focal point of research in the chemical community. Notable commercially available pesticides containing a 1,3,4-oxadiazole moiety include oxadiazon and metoxadiazone.…”

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Compounds for Combating Rising Severity of Plant Diseases Caused by Fungi and Viruses

Pan,

Wang,

et al. 2023

ACS Omega

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In recent years, the severity of plant diseases caused by plant pathogenic fungi and viruses has been on the rise. However, there is a limited availability of pesticide chemicals in the market for effectively controlling both fungal and viral infections. To solve this problem, a series of novel pyrimidine derivatives containing a 1,3,4-oxadiazole thioether fragment were synthesized. Among them, compound 6s exhibited remarkable in vivo protection activity against tobacco mosaic virus, demonstrating the superior 50% effective concentration (EC50) value of 0.42 μM, outperforming ningnanmycin (0.60 μM). Meanwhile, compound 6s exhibited remarkable antifungal activity against Botrytis cinerea Pers. in postharvest blueberry in vitro, with an EC50 value of 0.011 μM, surpassing the inhibition rate of Pyrimethanil (0.262 μM). Additionally, compound 6s also demonstrated remarkable curative and protection activities against blueberry fruit gray mold in vivo, with control efficiencies of 54.2 and 60.4% at 200 μg/mL concentration, respectively, which were comparable to those of Pyrimethanil (49.3 and 63.9%, respectively). Scanning electron microscopy showed that the compound 6s-treated hyphae of B. cinerea Pers. in postharvest blueberry became abnormally collapsed and shriveled. Furthermore, the molecular docking simulation demonstrated that compound 6s formed hydrogen bonds with SER-17, ARG-43, and SER-39 of succinate dehydrogenase (SDH), providing a possible explanation for the mechanism of action between the target compounds and SDH. This study represents the first report on the antiviral and antifungal activities of novel pyrimidine derivatives containing a 1,3,4-oxadiazole thioether fragment.

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Synthesis, Antifungal Evaluation, 3D-QSAR, and Preliminarily Mechanism Study of Novel Chiral Mandelic Acid Derivatives

Cited by 8 publications

References 48 publications

Design, Synthesis and Antifungal Activity of Nootkatone Derivatives Containing Acylhydrazone and Oxime Ester

Design, Synthesis and Antifungal Activity of Nootkatone Derivatives Containing Acylhydrazone and Oxime Ester

Effects of 2-Phenylethanol on Controlling the Development of Fusarium graminearum in Wheat

Discovery of Novel Compounds for Combating Rising Severity of Plant Diseases Caused by Fungi and Viruses

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