Dehydrozingerone Inspired Discovery of Potential Broad-Spectrum Fungicidal Agents as Ergosterol Biosynthesis Inhibitors

Song, Xiangmin; Zhu, Xiaodan; Li, Ting; Cai, Liang; Zhang, Meng; Shao, Yu; Tao, Jun; Sun, Ranfeng

doi:10.1021/acs.jafc.9b04231

Cited by 22 publications

(23 citation statements)

References 32 publications

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“…It is a chiral triazole fungicide employed to control plant pathogens. The fungicidal mechanism of such pesticides inhibits ergosterol biosynthesis and cell wall synthesis ( Song et al, 2019 ; Yang et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

Effect of Flutriafol Exposure on Residue Characteristics in Pig Muscle and Fat Tissue

Jeong¹,

Kim²,

Ji³

et al. 2022

Food Sci Anim Resour

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This study investigated the effect of exposure to flutriafol based on residues in pigs. Pigs were exposed to different concentrations (0.313, 0.625, 3.125, 6.25, and 12.5 mg/kg bw/d, n=20) for 4 wk in different treatment groups. Serum biochemical analysis, residue levels, and histological analysis were conducted using the VetTest chemistry analyzer, liquid chromatography mass spectrometry, and Masson’s trichrome staining, respectively. The body weight (initial and final) was not significantly different between groups. Parameters such as creatinine, blood urea nitrogen, alanine aminotransferase, and lipase levels were significantly different as compared to the control group. Flutriafol increased the residue limits in individual tissue of the pigs in a dose dependent manner. Flutriafol exposures indicated the presence of fibrosis, as confirmed from Masson’s trichrome staining. These results suggest that flutriafol affects the morphology and serum levels in pigs. The dietary flutriafol levels can provide a basis for maximum residue limits and food safety for pork and related products.

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Section: Introductionmentioning

confidence: 99%

Effect of Flutriafol Exposure on Residue Characteristics in Pig Muscle and Fat Tissue

Jeong¹,

Kim²,

Ji³

et al. 2022

Food Sci Anim Resour

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“…Synthesis of (E)-4-(2,4-Dichlorophenyl)-1,1,1-trifluorobut-3en-2-one (1). 23,27 A mixture of compound 2 (1 mmol) and 2iodoxybenzoic acid (IBX, 3 mmol) in ethyl acetate (3 mL) was stirred at room temperature. The mixture was refluxed for 30 h and then cooled to room temperature.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…In this work, it was found out that compound 1 had poor photostability in solution (detailed experimental data were shown in Figures S1 and S2 of the Supporting Information), which may be the reason for its weak antifungal activities in vivo. In this work, we will improve the photostability of trifluoromethyl dehydrozingerone derivatives in our previous work 23 to increase in vivo fungicidal activities.…”

Section: ■ Introductionmentioning

confidence: 99%

Photostable 1-Trifluoromethyl Cinnamyl Alcohol Derivatives Designed as Potential Fungicides and Bactericides

Zhang

Dou

Xia³

et al. 2021

J. Agric. Food Chem.

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In the current work, a series of 1-trifluoromethyl cinnamyl alcohol derivatives were designed and synthesized and their antifungal activities were evaluated. The bioassay result showed that most compounds exhibited excellent antifungal activity in vitro at 10 μg mL–1. Next, photostable and easily synthesized compound 2 with broad-spectrum antifungal activity in vitro was selected as a potential candidate to evaluate its antibacterial and antifungal activities. The EC50 values of compound 2 against eight fungal plant pathogens in vitro ranged from 3.806 to 17.981 μg mL–1; at the same time, compound 2 could effectively control Podosphaera xanthii, Odium heveae Steinm, Puccinia striiformis West, and Puccinia sorghi in pot experiments. In addition, compound 2 exhibited excellent antibacterial activities in vitro and in vivo against Xanthomonas oryzae pv. oryzae. Furthermore, the absorption and translocation of compound 2 in wheat plants were determined by the high-performance liquid chromatography method. The result showed that compound 2 could be translocated acropetally as well as basipetally in wheat plants. Finally, it was found that compound 2 had no cross-resistance with carbendazim, azoxystrobin, and boscalid.

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“…The fungicidal and insecticidal activities of the synthesized iridoid alkaloids were tested by means of our previously reported methods. − Detailed procedures are also provided in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Biomimetic Synthesis of Iridoid Alkaloids as Novel Leads for Fungicidal and Insecticidal Agents

Xia

Tian

et al. 2020

J. Agric. Food Chem.

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Monoterpenoid alkaloids are well known for their broad and excellent biological activities, but their extremely low content and complex chemical structure limit their practical application. This study used the biosynthetic precursor genipin as a basic material to conduct a biomimetic synthesis of iridoid alkaloids. The structures of the iridoid alkaloids were characterized by 1 H and 13 C NMR spectroscopy and high-resolution mass spectrometry, and their fungicidal and insecticidal activities were evaluated. Bioassay results indicated that iridoid alkaloids possess good to excellent activities against phytopathogenic fungi, diamondback moth, bean aphid, and spider mite. Compound 3s had the most promising activity against three important phytopathogenic fungi Fusarium graminearum (LC 50 value of 34.5 μg/mL with a 95% confidence interval of 33.4−35.5 μg/mL), Rhizoctonia solani (18 μg/ mL, 15.7−20.8 μg/mL), and Botrytis cinerea (26 μg/mL, 22.4−30.4 μg/mL), thereby emerging as a potential new fungicidal lead. The structure−activity relationship research has shown that the electrical property and steric hindrance sizes of iridoid alkaloids apparently influence fungicidal activity. Moreover, compound 3n exhibited good insecticidal activity against diamondback moth with an LC 50 (35.6 μg/mL, 95% confidence interval 19.0−66.6 μg/mL) comparable to that of the commercial insecticide rotenone (35.4 μg/mL, 95% confidence interval 22.2−56.4 μg/mL). This outcome indicates that this compound deserves further study as a potential lead for development of new insecticides.

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Dehydrozingerone Inspired Discovery of Potential Broad-Spectrum Fungicidal Agents as Ergosterol Biosynthesis Inhibitors

Cited by 22 publications

References 32 publications

Effect of Flutriafol Exposure on Residue Characteristics in Pig Muscle and Fat Tissue

Effect of Flutriafol Exposure on Residue Characteristics in Pig Muscle and Fat Tissue

Photostable 1-Trifluoromethyl Cinnamyl Alcohol Derivatives Designed as Potential Fungicides and Bactericides

Biomimetic Synthesis of Iridoid Alkaloids as Novel Leads for Fungicidal and Insecticidal Agents

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