In Silico and In Vitro Investigation of the Antifungal Activity of Isoeugenol against Penicillium citrinum

Ferreira, Sávio Benvindo; Dantas, Tassiana Barbosa; Silva, Daniele de Figuerêdo; Ferreira, Paula Benvindo; Melo, Thamara Rodrigues de; Lima, Edeltrudes de Oliveira

doi:10.2174/1568026619666181130141818

Cited by 11 publications

(20 citation statements)

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“…To evaluate the biological activities of cuminaldehyde, the Prediction of Activity Spectra for Substances (PASS) Online programme was used. This computational tool calculates the probability of a given organic molecule to present a biological activity by comparing the molecule structure to a database (www.way2drug.com/ passonline) composed of other organic molecules with defined biological activities [33,34]. Thus, the PASS online programme gives the probability of a compound of being active (Pa) or inactive (Pi) on a biological target.…”

Section: In Silico Analysismentioning

confidence: 99%

“…Information on the following properties were obtained: total polar surface area (TPSA), partition coefficient (water/ oil)-iLogP, molecular weight, number of hydrogen acceptors-nALH and number of hydrogen donors-nDLH of the compound. Then, an analysis based on the "Rule of Five" was performed as previously described [33,36]. By definition, to present a good estimated oral bioavailability, a molecule needs to meet the requirements for at least three of the analyzed parameters: i) total polar surface area (TPSA) <140 A 2 , ii) LogP � 5, iii) molecular weight <500 daltons, iv) number of acceptor hydrogen bonds (nALH) � 10, and v) number of donor hydrogen bonds (nDLH) � 5.…”

Section: In Silico Analysismentioning

confidence: 99%

“…Estimation of pharmacokinetic characteristics and toxic effects. For analysis of the possible toxic effects and the theoretical pharmacokinetic parameters (absorption, distribution, metabolism and excretion) of cuminaldehyde, the Osiris (www.organic-chemistry.org/prog/ peo/drugScore.html) [33] and SwissADME (http://www.swissadme.ch/index.php#) [35] programmes were used. These parameters and the toxicity were predicted by comparison of the cuminaldehyde chemical structure with a database containing commercially available drugs and commercially available compounds.…”

Section: In Silico Analysismentioning

confidence: 99%

“…These parameters and the toxicity were predicted by comparison of the cuminaldehyde chemical structure with a database containing commercially available drugs and commercially available compounds. Toxic effects were classified as mutagenic, tumorigenic, irritant, and effects on the reproductive system [33].…”

Section: In Silico Analysismentioning

confidence: 99%

“…Additionally, the probability of cuminaldehyde to becoming a commercial drug ("drugscore") was calculated by the Osiris programme (www.organic-chemistry.org/prog/peo/ drugScore.html), by combining the values obtained for iLogP, drug-likeness, solubility (Log S; the closer the score is to 0, the higher the solubility) [35], molar mass and toxicity in to a single value. A drug-score value of 0.1 to 1.0 was taken as an index of suitability for commercialization [33].…”

Section: In Silico Analysismentioning

confidence: 99%

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Cuminaldehyde potentiates the antimicrobial actions of ciprofloxacin against Staphylococcus aureus and Escherichia coli

et al. 2020

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Escherichia coli and Staphylococcus aureus are important agents of urinary tract infections that can often evolve to severe infections. The rise of antibiotic-resistant strains has driven the search for novel therapies to replace the use or act as adjuvants of antibiotics. In this context, plant-derived compounds have been widely investigated. Cuminaldehyde is suggested as the major antimicrobial compound of the cumin seed essential oil. However, this effect is not fully understood. Herein, we investigated the in silico and in vitro activities of cuminaldehyde, as well as its ability to potentiate ciprofloxacin effects against S. aureus and E. coli. In silico analyses were performed by using different computational tools. The PASS online and SwissADME programmes were used for the prediction of biological activities and oral bioavailability of cuminaldehyde. For analysis of the possible toxic effects and the theoretical pharmacokinetic parameters of the compound, the Osiris, SwissADME and PROTOX programmes were used. Estimations of cuminaldehyde gastrointestinal absorption, blood brain barrier permeability and skin permeation by using SwissADME; and drug likeness and score by using Osiris, were also evaluated The in vitro antimicrobial effects of cuminaldehyde were determined by using microdilution, biofilm formation and time-kill assays. In silico analysis indicated that cuminaldehyde may act as an antimicrobial and as a membrane permeability enhancer. It was suggested to be highly absorbable by the gastrointestinal tract and likely to cross the blood brain barrier. Also, irritative and harmful effects were predicted for cuminaldehyde if swallowed at its LD50. Good oral bioavailability and drug score were also found for this compound. Cuminaldehyde presented antimicrobial and anti-biofilm effects against S. aureus and E. coli.. When co-incubated with ciprofloxacin, it enhanced the antibiotic antimicrobial and anti-biofilm actions. We suggest that cuminaldehyde may be useful as an adjuvant therapy to ciprofloxacin in S. aureus and E. coli-induced infections.

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Section: In Silico Analysismentioning

confidence: 99%

Section: In Silico Analysismentioning

confidence: 99%

Section: In Silico Analysismentioning

confidence: 99%

Section: In Silico Analysismentioning

confidence: 99%

Section: In Silico Analysismentioning

confidence: 99%

See 3 more Smart Citations

Cuminaldehyde potentiates the antimicrobial actions of ciprofloxacin against Staphylococcus aureus and Escherichia coli

et al. 2020

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Isolation and Chemical Characterization of Antifungal, Antioxidant, and Anti‐Inflammatory Compounds from Centrosema coriaceum using GC/MS, UFLC‐QTOF‐MS, and FACE

Lemos

Campos

Freitas

et al. 2022

Chemistry & Biodiversity

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In recent years, natural products with biological activities have been increasingly researched. The elucidation of phytoconstituents is necessary for the development of drugs as a natural alternative for the treatment of various diseases. The work aimed to evaluate in vitro and in silico bioactivities of hexane (CCHE) and methanol (CCME) fractions of ethanolic extract from Centrosema coriaceum Benth (Fabaceae) leaves and elucidate their phytoconstituents. CCHE and CCME showed antifungal activity for Candida glabrata (MIC of 1000 μg/mL) with fungistatic effect and action in cell envelope by sorbitol and ergosterol assays. CCHE and CCME presented promising antioxidant activity against the DPPH radical with IC 50 of 13.61 � 0.50 and 6.31 � 0.40 μg/mL, respectively, and relative antioxidant activity (RAA%) of 45.77 � 3.61/ 28.53 � 2.25 % for CCHE and 82.18 � 2.25/ 51.99 � 3.23 % for CCME when compared to rutin and quercetin, respectively. Moreover, these fractions demonstrated promising results for the inhibition of lipid peroxidation by β-carotene/linoleic acid assay. For antiinflammatory and cytotoxicity activities, CCHE and CCME significantly inhibited the production of nitric oxide and TNF-α, without toxicity on murine intraperitoneal macrophages, respectively. Esters, alkanes, steroids, tocopherols, and terpenes were identified in CCHE by GC/MS. Flavonoids, phenolic acids, and disaccharides were detected in CCME by UFLC-QTOF-MS and FACE. Furthermore, rutin was purified from CCME. In silico predictions evidenced that compounds present in both fractions have high affinity to the fungal membrane besides antioxidant and anti-inflammatory activities. Based on these observations, CCHE and CCME have a noteworthy potential for the design of novel antifungal and anti-inflammatory agents that should be explored in future studies.

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Isoeugenol affects expression pattern of conidial hydrophobin gene RodA and transcriptional regulators MedA and SomA responsible for adherence and biofilm formation in Aspergillus fumigatus

et al. 2022

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Aspergillus fumigatus is one of the major pathogenic fungal species, causing life-threatening infections. Due to a limited spectrum of available antifungals, exploration of new drug targets as well as potential antifungal molecules has become pertinent. Rodlet layer plays an important role in adherence of fungal conidia to hydrophobic cell surfaces in host, which also leads to A. fumigatus biofilm formation, contributing factor to fungal pathogenicity. From decades, natural sources have been known for the development of new active molecules. The present study investigates effect of isoeugenol on genes responsible for hydrophobins ( RodA ), adhesion as well as biofilm formation ( MedA and SomA ) of A. fumigatus . Minimum inhibitory concentrations (MIC and IC 50 ) of isoeugenol against A. fumigatus were determined using broth microdilution assay. The IC 50 results showed reduced hydrophobicity and biofilm formation as well as eradication after treatment with the compound and electron micrograph data corroborated these findings. The qRT-PCR showed a significant downregulation of genes RodA, MedA, SomA and pksP involved in hydrophobicity and biofilm formation. SwissADME studies potentiated drug-like propensity for isoeugenol which formed four hydrogen bonds with low binding energy (− 4.54 kcal/mol) at the catalytic site of RodA protein studied via AutoDock4. Hence, the findings conclude that isoeugenol inhibits conidial hydrophobicity and biofilm formation of A. fumigatus and further investigations are warranted in this direction. Supplementary Information The online version contains supplementary material available at 10.1007/s00203-022-02817-w.

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In Silico and In Vitro Investigation of the Antifungal Activity of Isoeugenol against Penicillium citrinum

Cited by 11 publications

References 0 publications

Cuminaldehyde potentiates the antimicrobial actions of ciprofloxacin against Staphylococcus aureus and Escherichia coli

Cuminaldehyde potentiates the antimicrobial actions of ciprofloxacin against Staphylococcus aureus and Escherichia coli

Isolation and Chemical Characterization of Antifungal, Antioxidant, and Anti‐Inflammatory Compounds from Centrosema coriaceum using GC/MS, UFLC‐QTOF‐MS, and FACE

Isoeugenol affects expression pattern of conidial hydrophobin gene RodA and transcriptional regulators MedA and SomA responsible for adherence and biofilm formation in Aspergillus fumigatus

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