Synthesis and Antifungal Activity of Curcumol Derivatives

Gao, Fu-Tian; Jin, Jun; Jian, Jun-You; Chen, Liang; Gu, Wei; Yuan, Chunmao; Hao, Xiaojiang; Huang, Lie-jun

doi:10.1002/cbdv.202300442

Cited by 10 publications

(6 citation statements)

References 29 publications

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“…The inoculated PDA plates were incubated at 28±1 °C for 4–6 days. The EC50 was determined for compounds at five different concentrations [26–28] . Based on the test of in vitro antifungal activity, compound C17 against Phomopsis sp .…”

Section: Methodsmentioning

confidence: 99%

“…was further tested in vivo on kiwifruit. [29][30][31] Further understanding of the antimicrobial mechanism of compound C17 against Phomopsis sp. was obtained through the effect of extracellular polysaccharides (EPS) produced by Phomopsis sp., [32][33] alteration of Phomopsis sp.…”

Section: Fungimentioning

confidence: 99%

“…They have been discovered due to their conjugated double bonds and Michael receptor activity, and have excellent inhibitory against phytopathogenic fungi. [18] 2-(2-benzoxazolyl)-1-phenylethanone may be had three important antifungal roles, which was benzoxazole, α, βunsaturated ketone, and acetophenone (Figure 1). [19] However, the antifungal activities of these compounds had no reported, and the synthesis method of 2-(2-benzoxazolyl)-1-ethanone derivatives had more technology was further to be improved.…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, the compounds such as α,β‐unsaturated ketones, esters and amides are known as thiol alkylators. They have been discovered due to their conjugated double bonds and Michael receptor activity, and have excellent inhibitory against phytopathogenic fungi [18] …”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antifungal Activity of 2‐(2‐Benzoxazolyl)‐1‐arylethanone and 2‐(2‐Benzoxazolyl)‐1‐alkylethanone Derivatives

Che,

Jin,

Sun

et al. 2023

Chemistry & Biodiversity

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To discover more effective antifungal candidates, 33 benzoxazole derivatives, were designed, synthesized, and evaluated for their antifungal activity against seven phytopathogenic fungi by the mycelium growth rate method. Among 33 benzoxazole derivatives had thirteen derivatives no reported, and new derivatives C17 exhibited good inhibitory activity against Phomopsis sp. with EC50 values of 3.26 μM. Structure–activity relationship (SAR) of these derivatives analysis indicated that the substituent played a key role in antifungal activity in ortho‐, meta‐ and para‐ substituted acetophenones. The preliminary mechanistic exploration demonstrated that C17 might exert its antifungal activity by targeting the mycelia cell membrane, which was verified by the observed changes in mycelial morphology, the formation of extracellular polysaccharides, cellular contents, cell membrane permeability and integrity, among other effects. Furthermore, C17 had potent curative effect against Phomopsis sp. in vivo, which indicated that C17 may be as a novelty potent antifungal agent.

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Section: Methodsmentioning

confidence: 99%

Section: Fungimentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antifungal Activity of 2‐(2‐Benzoxazolyl)‐1‐arylethanone and 2‐(2‐Benzoxazolyl)‐1‐alkylethanone Derivatives

Che,

Jin,

Sun

et al. 2023

Chemistry & Biodiversity

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“…Effect on the Mycelial Morphology and Ultrastructure of P. nicotianae. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) were performed for studying effect on the mycelial morphology and ultrastructure of P. nicotianae according to the methods stated in a previous study, 37 and the experimental procedures are described in the Supporting Information.…”

Section: Antifungal Activity Assay In Vivomentioning

confidence: 99%

Isolating Antipathogenic Fungal Coumarins from Coriaria nepalensis and Determining Their Primary Mechanism In Vitro

Jian,

Fan,

Jin

et al. 2024

J. Agric. Food Chem.

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Through bioassay-guided isolation, eight undescribed coumarins (1−8), along with six reported coumarins (9−14), were obtained from Coriaria nepalensis. The new structures were determined by using IR, UV, NMR, HRESIMS, and ECD calculations. The results of the biological activity assays showed that compound 9 exhibited broad spectrum antifungal activities against all tested fungi in vitro and a significant inhibitory effect on Phytophthora nicotianae with an EC 50 value of 3.00 μg/mL. Notably, compound 9 demonstrated greater curative and protective effects against tobacco balack shank than those of osthol in vivo. Thus, 9 was structurally modified to obtain new promising antifungal agents, and the novel derivatives (17b, 17j, and 17k) exhibited better effects on Sclerotinia sclerotiorum than did lead compound 9. Preliminary mechanistic exploration illustrated that 9 could enhance cell membrane permeability, destroy the morphology and ultrastructure of cells, and reduce the exopolysaccharide content of P. nicotianae mycelia. Furthermore, the cytotoxicity results revealed that compound 9 exhibited relatively low cytotoxicity against HEK293 cell lines with an inhibition rate of 33.54% at 30 μg/mL. This research is promising for the discovery of new fungicides from natural coumarins with satisfactory ecological compatibility.

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Industrial Distillation Fractions of Garlic Essential Oil, Design, Synthesis, and Antifungal Activity Evaluation of Aliphatic Substituted Trisulfide Derivatives

Chen,

Wang,

Wang

et al. 2024

Chemistry & Biodiversity

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Garlic oil has a wide range of biological activities, and its broad‐spectrum activity against phytopathogenic fungi still has the potential to be explored. In this study, enzymatic treatment of garlic resulted in an increase of approximately 50 % in the yield of essential oil, a feasible GC‐MS analytical program for garlic oil was provided. Vacuum fractionation of the volatile oil and determination of its inhibitory activity against 10 fungi demonstrated that garlic oil has good antifungal activity. The antifungal activity levels were ranked as diallyl trisulfide (S‐3)>diallyl disulfide (S‐2)>diallyl monosulfide (S‐1), with an EC50 value of S‐3 against Botrytis cinerea reached 8.16 mg/L. Following the structural modification of compound S‐3, a series of derivatives, including compounds S‐4~7, were synthesized and screened for their antifungal activity. The findings unequivocally demonstrated that the compound dimethyl trisulfide (S‐4) exhibited exceptional antifungal activity. The EC50 of S‐4 against Sclerotinia sclerotiorum reached 6.83 mg/L. SEM, In vivo experiments, and changes in mycelial nucleic acids, soluble proteins and soluble sugar leakage further confirmed its antifungal activity. The study indicated that the trisulfide bond structure was the key to good antifungal activity, which can be developed into a new type of green plant‐derived fungicide for plant protection.

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Synthesis and Antifungal Activity of Curcumol Derivatives

Cited by 10 publications

References 29 publications

Synthesis and Antifungal Activity of 2‐(2‐Benzoxazolyl)‐1‐arylethanone and 2‐(2‐Benzoxazolyl)‐1‐alkylethanone Derivatives

Synthesis and Antifungal Activity of 2‐(2‐Benzoxazolyl)‐1‐arylethanone and 2‐(2‐Benzoxazolyl)‐1‐alkylethanone Derivatives

Isolating Antipathogenic Fungal Coumarins from Coriaria nepalensis and Determining Their Primary Mechanism In Vitro

Industrial Distillation Fractions of Garlic Essential Oil, Design, Synthesis, and Antifungal Activity Evaluation of Aliphatic Substituted Trisulfide Derivatives

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