Promising Fungicides from Allelochemicals: Synthesis of Umbelliferone Derivatives and Their Structure–Activity Relationships

Pan, Le; Lei, Dongyu; Jin, Lu; He, Yang; Yang, Qing‐Qing

doi:10.3390/molecules23113002

Cited by 11 publications

(10 citation statements)

References 22 publications

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“…They not only participate in the scavenging process of plant reactive oxygen species, but also inhibit weeds and can be used to develop herbicides [24]. Umbelliferone can be used to develop new fungicides for natural products [25]. Rosmarinic acid can promote the attachment of beneficial bacteria to diatoms, while azelaic acid can promote the growth of beneficial bacteria and inhibit the growth of harmful bacteria [26].…”

Section: Introductionmentioning

confidence: 99%

Effect of Two Kinds of Fertilizers on Growth and Rhizosphere Soil Properties of Bayberry with Decline Disease

Ren

Wang

et al. 2021

Plants

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Decline disease causes severe damage to bayberry. However, the cause of this disease remains unclear. Interestingly, our previous studies found that the disease severity is related with the level of soil fertilizer. This study aims to explore the effect and mechanism of compound fertilizer (CF) and bio-organic fertilizer (OF) in this disease by investigating the vegetative growth, fruit characters, soil property, rhizosphere microflora and metabolites. Results indicated that compared with the disease control, CF and OF exhibited differential effect in plant healthy and soil quality, together with the increase in relative abundance of Burkholderia and Mortierella, and the reduction in that of Rhizomicrobium and Acidibacter, Trichoderma, and Cladophialophora reduced. The relative abundance of Geminibasidium were increased by CF (251.79%) but reduced by OF (13.99%). In general, the composition of bacterial and fungal communities in rhizosphere soil was affected significantly at genus level by exchangeable calcium, available phosphorus, and exchangeable magnesium, while the former two variables had a greater influence in bacterial communities than fungal communities. Analysis of GC-MS metabonomics indicated that compared to the disease control, CF and OF significantly changed the contents of 31 and 45 metabolites, respectively, while both fertilizers changed C5-branched dibasic acid, galactose, and pyrimidine metabolic pathway. Furthermore, a significant correlation was observed at the phylum, order and genus levels between microbial groups and secondary metabolites of bayberry rhizosphere soil. In summary, the results provide a new way for rejuvenation of this diseased bayberry trees.

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Section: Introductionmentioning

confidence: 99%

Effect of Two Kinds of Fertilizers on Growth and Rhizosphere Soil Properties of Bayberry with Decline Disease

Ren

Wang

et al. 2021

Plants

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“…Compound 9 (with a ten-carbon side chain) was inactive against all strains in the test. Pan et al 2018 made similar observations in their antifungal studies against phytopathogenic fungi with umbelliferone derivatives [44]. Chu et al 2017 indicated that the increase in lipophilicity arising from a methoxyl at the C-7 position of coumarin can influence the antimicrobial bioactivity of herniarin derivatives [45].…”

Section: Discussionmentioning

confidence: 81%

Synthesis of Coumarin and Homoisoflavonoid Derivatives and Analogs: The Search for New Antifungal Agents

et al. 2022

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A set of twenty-four synthetic derivatives, with coumarin and homoisoflavonoid cores and structural analogs, were submitted for evaluation of antifungal activity against various species of Candida. The broth microdilution test was used to determine the Minimum Inhibitory Concentration (MIC) of the compounds and to verify the possible antifungal action mechanisms. The synthetic derivatives were obtained using various reaction methods, and six new compounds were obtained. The structures of the synthesized products were characterized by FTIR spectroscopy: 1H-NMR, 13C-NMR, and HRMS. The coumarin derivative 8 presented the best antifungal profile, suggesting that the pentyloxy substituent at the C-7 position of coumarin ring could potentiate the bioactivity. Compound 8 was then evaluated against the biofilm of C. tropicalis ATCC 13803, which showed a statistically significant reduction in biofilm at concentrations of 0.268 µmol/mL and 0.067 µmol/mL, when compared to the growth control group. For a better understanding of their antifungal activity, compounds 8 and 21 were submitted to a study of the mode of action on the fungal cell wall and plasma membrane. It was observed that neither compound interacted directly with ergosterol present in the fungal plasma membrane or with the fungal cell wall. This suggests that their bioactivity was due to interaction involving other pharmacological targets. Compound 8 was also subjected to a molecular modeling study, which showed that its antifungal action mechanism occurred mainly through interference in the redox balance of the fungal cell, and by compromising the plasma membrane; not by direct interaction, but by interference in ergosterol synthesis. Another important finding was the antifungal capacity of homoisoflavonoids 23 and 24. Derivative 23 presented slightly higher antifungal activity, possibly due to the presence of the methoxyl substituent in the meta position in ring B.

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“…1 Data is in accordance with the literature except for the recorded melting point, which was measured after recrystallization from EtOH as per a literature precedent. 56 4-Chlorobenzyl (4-Methyl-2-oxo-2H-chromen-7-yl)carbamate (27). Compound 27 was prepared from 5 and 4-chlorobenzyl carbamate (42), according to the general procedure (0.02 equiv of catalyst was required, and the reaction time was 48 h), to give a beige solid.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Mp 208−210 °C (lit. 228−230 °C) 56. 1 H NMR (500 MHz, DMSO-d 6 ) δ 10.28 (s, 1H), 7.69 (d, J = 8.7 Hz, 1H), 7.55 (s, 1H), 7.45 (app.…”

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confidence: 99%

Cross-Coupling of Amide and Amide Derivatives to Umbelliferone Nonaflates: Synthesis of Coumarin Derivatives and Fluorescent Materials

et al. 2020

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The Buchwald−Hartwig cross-coupling reaction between 4-methylumbelliferone-derived nonaflates with amides, carbamates, and sulfonamides is described. A wide variety of Nsubstituted 7-amino coumarin analogues was prepared in good to excellent yields. The photophysical properties of aqueous-soluble derivatives were determined, and they displayed auxochrome-based variations. Gram-scale synthesis provided an acrylamide analogue, which was used to fabricate a fluorescent poly(2-hydroxylethyl methacrylate) (pHEMA) hydrogel that was resistant to leaching in ultrapure H 2 O. We envisage that our reported protocol to access 7amino-4-methylcoumarin derivatives will find use toward the development of new fluorescent coumarin-based probes by researchers in the field.

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Promising Fungicides from Allelochemicals: Synthesis of Umbelliferone Derivatives and Their Structure–Activity Relationships

Cited by 11 publications

References 22 publications

Effect of Two Kinds of Fertilizers on Growth and Rhizosphere Soil Properties of Bayberry with Decline Disease

Effect of Two Kinds of Fertilizers on Growth and Rhizosphere Soil Properties of Bayberry with Decline Disease

Synthesis of Coumarin and Homoisoflavonoid Derivatives and Analogs: The Search for New Antifungal Agents

Cross-Coupling of Amide and Amide Derivatives to Umbelliferone Nonaflates: Synthesis of Coumarin Derivatives and Fluorescent Materials

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