Design and synthesis of eugenol/isoeugenol glycoconjugates and other analogues as antifungal agents against <i>Aspergillus fumigatus</i>

Goswami, Lakshmi; Gupta, Lovely; Paul, Sayantan; Vermani, Maansi; Vijayaraghavan, Pooja; Bhattacharya, Asish K.

doi:10.1039/d2md00138a

Cited by 14 publications

(10 citation statements)

References 38 publications

(54 reference statements)

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“…After completion of the reaction (TLC), the reaction mixture was evaporated in vacuo to obtain residue which was purified by flash chromatography using a RediSep column (SiO 2 , 12 g) with EtOAc‐petroleum ether mixture as eluent to furnish compound 2 a ‐ e . Spectral data of all the synthesized propargylated phenol were found to be consistent with the previous literature reports [7b,22] …”

Section: Methodssupporting

confidence: 88%

“…The homo coupled 1,3‐diynes were characterized from their corresponding NMR spectra. In 1 H NMR spectrum of 3 a , the absence of acetylenic proton of 2 a (δ H 2.48 ppm) [7b] indicates the coupling of two units of propargylated eugenol 2 a . All the synthesized products were identified by their 1 H, 13 C NMR spectra and HRMS.…”

Section: Resultsmentioning

confidence: 99%

“…The IC 50 of biofilm eradication concentration of compound 3 a on pre‐formed A. fumigatus biofilm was calculated by performing MTT assay in a 96‐well flat bottom microtiter plate. The MTT assay was applied according to our previous studies [7b] . Biofilm eradication property of compound 3 a was analysed on fully grown A. fumigatus biofilm on 12‐well polystyrene plate for 48 h. The biofilm was treated with IC 50 of compound 3 a for another 24 h [21,27] .…”

Section: Methodsmentioning

confidence: 99%

“…Eugenol 1a and isoeugenol 1b are the naturally occurring phenylpropanoids and has been traditionally isolated from the plants Syzygium aromaticum and Eugenia caryoplyllata , Myristica fragrans (Figure 2). [7] Eugenol and isoeugenol have shown antifungal activities against A. fumigatus with IC 50 value of 1900 μM [7b] . Both compounds exhibited antifungal activity against filamentous as well as non‐filamentous fungi [7c] .…”

Section: Introductionmentioning

confidence: 99%

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Design and Synthesis of 1,3‐Diynes as Potent Antifungal Agents against Aspergillus fumigatus

et al. 2023

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Eugenol and isoeugenol, secondary metabolites isolated from the plant Myristica fragrans have displayed antifungal activities against Aspergillus fumigatus (IC 50 1900 μM). Compounds having conjugated unsaturation have been of great use as antifungals i. e. amphotericin B, nystatin and terbinafine etc. Hence, in the present study, we have designed and synthesised 1,3-diynes by utilizing Glaser-Hay and Cadiot-Chodkiewicz coupling reactions to furnish possible antifungal agents. Synthesis of 1,6-diphenoxyhexa-2,4-diyne derivatives was achieved by Cu(I) catalysed coupling of propargylated eugenol, isoeugenol, guaiacol, vanillin and dihydrogenated eugenol or eugenol in good to excellent yields. All the synthesized compounds were evaluated against pathogenic fungus A. fumigatus. Among all the synthesized compounds, one of the compounds was found to be exhibiting promising antifungal activity with IC 50 value of 7.75 μM thereby suggesting that this type of scaffold could pave the way for developing new antifungal agents. The most active compound was found to be low cytotoxic when assayed against L-132 cancer cell line. Effect of the most active compound on ergosterol biosynthesis has also been studied. Also, the most active compound exhibited significant antibiofilm activity although the concentration was found to be higher than its anti-fungal activity. Morphological changes in the biofilm were remarkable under confocal laser scanning microscopy.

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Section: Methodssupporting

confidence: 88%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Design and Synthesis of 1,3‐Diynes as Potent Antifungal Agents against Aspergillus fumigatus

et al. 2023

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“…4-allyl-2-methoxyphenol, also known as eugenol, is a volatile naturally occurring phenolic bioactive constituent in clove oil, nutmeg, and basil ( Ferreira et al., 2017 ). It possesses significant antioxidant, antifungal, and anti-inflammatory properties, in addition to analgesic and local anaesthetic activity ( Huang et al., 2015 ; Marchese et al., 2017 ; Goswami et al, 2022 ). This compound offers a number of therapeutic benefits via inhibition of generative reactive oxygen and nitrogen species, scavenging of free radicals, and disruption of microbial biofilms ( Khalil et al., 2017 ).…”

Section: Introductionmentioning

confidence: 99%

4-Allyl-2-methoxyphenol modulates the expression of genes involved in efflux pump, biofilm formation and sterol biosynthesis in azole resistant Aspergillus fumigatus

Sen

Gupta

Vijay

et al. 2023

Front. Cell. Infect. Microbiol.

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IntroductionAntifungal therapy for aspergillosis is becoming problematic because of the toxicity of currently available drugs, biofilm formation on host surface, and increasing prevalence of azole resistance in Aspergillus fumigatus. Plants are rich source of bioactive molecules and antimicrobial activity of aromatic bioactive compounds draws attention because of its promising biological properties. The present study elucidated the antibiofilm activity of 4-allyl-2-methoxyphenol (eugenol) against azole-resistant environmental A. fumigatus isolates.MethodsSoil samples were collected from agricultural fields across India; azole-resistant A. fumigatus (ARAF) were isolated followed by their molecular identification. Antibiofilm activity of eugenol was calculated via tetrazolium based-MTT assay. The expression of the multidrug efflux pumps genes MDR1, MDR4, transporters of the MFS gene, erg11A gene encoding 14α demethylase, and transcription regulatory genes, MedA, SomA and SrbA, involved in biofilm formation of A. fumigatus were calculated by quantitative real time PCR.ResultsOut of 89 A. fumigatus isolates, 10 were identified as azole resistant. Eugenol exhibited antibiofilm activity against ARAF isolates, ranging from 312 to 500 µg/mL. Confocal laser scanning microscopy analysis revealed absence of extracellular matrix of ARAF biofilm after eugenol treatment. The gene expression indicated significantly low expression of efflux pumps genes MDR1, MDR4, erg11A and MedA in eugenol treated ARAF isolates when compared with untreated isolates.ConclusionsOur results demonstrate that eugenol effects the expression of efflux pump and biofilm associated genes as well as inhibits biofilm formation in azole resistant isolates of A. fumigatus.

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Antimicrobial Coatings for Fruits and Vegetables

Gupta,

Ghoshal,

Arya

2024

Functional Coatings for Biomedical, Energy, and Environmental Applications

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Design and synthesis of eugenol/isoeugenol glycoconjugates and other analogues as antifungal agents against Aspergillus fumigatus

Abstract: Glycoconjugates are biologically significant molecules as they tend to serve wide range of intra and extra cellular processes depending on their sizes and complexities. The secondary metabolites of the plant...

Cited by 14 publications

References 38 publications

Design and Synthesis of 1,3‐Diynes as Potent Antifungal Agents against Aspergillus fumigatus

Design and Synthesis of 1,3‐Diynes as Potent Antifungal Agents against Aspergillus fumigatus

4-Allyl-2-methoxyphenol modulates the expression of genes involved in efflux pump, biofilm formation and sterol biosynthesis in azole resistant Aspergillus fumigatus

Antimicrobial Coatings for Fruits and Vegetables

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