Chemical Characterization, Antioxidant, Antimicrobial, Cytotoxicity and <i>in Silico</i> Studies of Hexane Extract and Essential Oils from <i>Citrus limon</i> Leaves

Riaz, Muhammad; Qadir, Rahman; Akhtar, Muhammad Tahir; Rehman, Muhammad Misbah ur; Anwar, Farooq; Eman, Rida; Rehman, Muhammad Fayyaz ur; Akram, Muhammad Safwan

doi:10.1002/cbdv.202200537

Cited by 5 publications

(2 citation statements)

References 42 publications

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“…The ligand–protein docking studies envisage the binding interactions of a ligand with a target protein. The dihydroorotase complexed with 2‐ oxo ‐1,2,3,6‐tetrahydropyrimidine‐4,6‐dicarboxylate (HDDP) of Escherichia coli is the target protein (PDB: 2eg7) [ 45–48 ] in case of bacterial infections. Compounds 7l and 7n bind to the abovementioned target and exhibit antibacterial activity.…”

Section: Resultsmentioning

confidence: 99%

Dihydrobenzothiazole coupled N‐piperazinyl acetamides as antimicrobial agents: Design, synthesis, biological evaluation and molecular docking studies

Bollikanda,

Nagineni,

Pranathi

et al. 2023

Archiv der Pharmazie

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Substituted saturated N‐heterocycles have gained momentum as effective scaffolds for the development of new drugs. In this study, we coupled partly saturated benzothiazoles with substituted piperazines and evaluated their antimicrobial activity. Following a three‐step reaction sequence from commercially available cyclic 1,3‐diones, a series of novel 2‐[4‐substituted‐1‐piperazinyl]‐N‐(7‐oxo‐4,5,6,7‐tetrahydrobenzo[d]thiazol‐2‐yl)acetamides (7a–af) were synthesised. 2‐Amino‐5,6‐dihydro‐benzo[d]thiazol‐7(4H)‐ones, obtained through the condensation of cyclohexane‐1,3‐diones with thiourea, were acetylated with chloroacetic chloride and then reacted with N‐substituted piperazines 6a–p to give the desired products 7a–af in excellent yields. All 32 new compounds were fully characterised by their 1H‐nuclear magnetic resonance (NMR), 13C‐NMR and high‐resolution mass spectrometry spectra. The synthetic compounds 7a–af were tested in vitro for their efficacy as antimicrobials against pathogenic strains of Gram‐positive and Gram‐negative bacteria, Streptococcus mutans and Salmonella typhi, respectively, as well as against fungal strains, including Candida albicans 3018 and C. albicans 4748. Ciprofloxacin and fluconazole served as the reference drugs. While compounds 7c and 7l showed inhibition against fungal strains with zones of inhibition of 11 and 1 mm, respectively, four analogues (7d, 7l, 7n, and 7r) demonstrated strong antibacterial action (zone of inhibition in the range of 10–15 mm). Three compounds (7j, 7l, and 7w) also exhibited moderate antitubercular activity (MIC: 6.25 µg/mL) against Mycobacterium tuberculosis H37Rv. Molecular docking investigations and the predicted physicochemical and ADMET (absorption, distribution, metabolism, excretion, and toxicity) properties for the potent compounds made this scaffold useful as a pharmacologically active framework for the development of potential antimicrobial hits.

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Section: Resultsmentioning

confidence: 99%

Dihydrobenzothiazole coupled N‐piperazinyl acetamides as antimicrobial agents: Design, synthesis, biological evaluation and molecular docking studies

Bollikanda,

Nagineni,

Pranathi

et al. 2023

Archiv der Pharmazie

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“…The leaves of C×limon were found to contain compounds such as flavonoids, phenols, saponins, alkaloids, tannins and steroids/triterpenoids (Ehiobu et al, 2021;Grace et al, 2020;Mayasari & Laoli, 2018;Nsangou et al, 2021). The leaves of C×limon have been found to have antioxidant, has antimicrobial potential and cytotoxicity potential (Ehiobu et al, 2021;Riaz et al, 2023).…”

Section: Introductionmentioning

confidence: 99%

Chemical Composition Analysis of Citrus×limon (L) Osbeck Leaf Essential Oil and Its Activity as an Anti-Cervical Cancer Agent

Afif,

Suryati,

Santoni

2024

HJKK

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Cervical cancer is a life-threatening disease. The use of synthetic drugs for its treatment can have serious adverse effects on the body. Therefore, it is necessary to search for natural drugs that are safe for the body. One of the secondary metabolites contained in plants is essential oils (EO), EO are known to have activity as anti-cervical cancer. Genus Citrus is known for containing EO compounds, one of the species of the genus is Citrus×lemon (L) Osbeck. The purpose of this study is to identify the chemical components of the EO isolated from the leaves of C×limon and to evaluate its cytotoxic activity against cervical cancer. EO was isolated from C×limon leaves collected in Padang City, Indonesia using the hydrodistillation method. EO was then analyzed by GC-MS. To determine its cytotoxicity, BSLT was conducted, followed by molecular docking and MTT assays. The experiment yielded a yellow liquid with a density of 0,8684 g/mL and a yield of 0,181%. GC-MS analysis of the EO identified 56 chemical components, with the main compounds are (-)-β-pinene (7.32%), (-)-limonene (28.40%), geranial (5.54%), caryophyllene (5.22%). The EO showed high toxicity against Artemia salina L larvae, with an LC50 value of 3,697 µg/mL. Through molecular docking, it is known the (-)-limonene, geranial, (-)β-pinene and caryophyllene compounds as the main compounds in of EO are known to bind to form complexes with cervical cancer proteins (HPV18E6). MTT assay showed weak cytotoxic activity of EO against HeLa cells, with an IC50 of 218.9 µg/mL.

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In vitro Genotoxicity and In silico Docking Analyses of the Essential Oils of Thuja orientalis

BOZARI

2024

Chemistry & Biodiversity

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Two main objectives were pursued to assess the reliability of Thuja orientalis essential oils (TOEO). The first objective was to extract TOEO, analyze them by GC‐MS, and determine their in vitro genotoxicity against selected plants using the RAPD‐PCR method. The second objective was to evaluate the in‐silico toxicity of TOEO. The binding sites and energies of each content was calculated against B‐DNA. In‐silico analyses were performed using a simulation program, AutoDock Vina, and Toxicity Estimation Software Tools. 3‐carene, cedrol, and 2‐pinene were identified as the predominant components. In vitro studies showed that the TOEO had a more significant impact on reducing genomic stability in wheat compared to the amaranth. The lowest stability was determined as 39.78% in wheat and 53.58% in amaranth. Cedrol (‐5,7 kcal/mol) and selinene (‐5,6 kcal/mol) exhibited the highest binding affinity. The toxicity test indicated that components other than cyclohexene may have toxic effects, none of them were predicted to be mutagenic, and LD50 (mol/kg) values could vary between 1.33 and 1.55.

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Chemical Characterization, Antioxidant, Antimicrobial, Cytotoxicity and in Silico Studies of Hexane Extract and Essential Oils from Citrus limon Leaves

Cited by 5 publications

References 42 publications

Dihydrobenzothiazole coupled N‐piperazinyl acetamides as antimicrobial agents: Design, synthesis, biological evaluation and molecular docking studies

Dihydrobenzothiazole coupled N‐piperazinyl acetamides as antimicrobial agents: Design, synthesis, biological evaluation and molecular docking studies

Chemical Composition Analysis of Citrus×limon (L) Osbeck Leaf Essential Oil and Its Activity as an Anti-Cervical Cancer Agent

In vitro Genotoxicity and In silico Docking Analyses of the Essential Oils of Thuja orientalis

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