Startseite Larvicidal properties of essential oils of three Artemisia species against the chemically insecticide-resistant Nile fever vector Culex pipiens (L.) (Diptera: Culicidae): In vitro and in silico studies
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Larvicidal properties of essential oils of three Artemisia species against the chemically insecticide-resistant Nile fever vector Culex pipiens (L.) (Diptera: Culicidae): In vitro and in silico studies

  • Khalid Chebbac EMAIL logo , Oussama Abchir , Mohammed Chalkha EMAIL logo , Abdelfattah El Moussaoui , Mohammed El kasmi-alaoui , Soufyane Lafraxo , Samir Chtita , Mohammed M. Alanazi , Ashwag S. Alanazi , Mohamed Hefnawy , Otmane Zouirech , Zineb Benziane Ouaritini und Raja Guemmouh
Veröffentlicht/Copyright: 28. Oktober 2024
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Open Chemistry
Aus der Zeitschrift Open Chemistry Band 22 Heft 1

Abstract

The objective of this study is to determine the larvicidal activity of essential oils (EOs) extracted from three plants of the genus Artemisia against the mosquito Culex pipiens (C. pipiens) using in vitro and in silico studies. A total number of 20 third- and fourth-instar larvae were exposed to various concentrations of the three plants. The LC50 and LC90 values of the tested Artemisia EOs were determined using Probit analysis. In addition, the sensitivity of C. pipiens to these EOs was determined and compared against a standard insecticide, temephos, under laboratory conditions. Furthermore, in silico assessments were carried out on the major constituents to help understand and explain the acquired in vivo results. Gas chromatography analysis identified the major compounds as d-limonene and β-pinene for Artemisia flahaultii, camphor and borneol for Artemisia. aragonensis, and artemisia ketone and caryophyllene for Artemisia annua. A. flahaultii oil showed the highest efficacy against C. pipiens larvae, followed by A. annua oil with average larvicidal activity. In contrast, A. aragonensis EO, composed of a high percentage of monoterpenes, was the least active. Docking simulation indicated that several studied ligands had promising binding scores within the receptor’s binding site compared to the reference insecticide temephos. The obtained results allow us to conclude that A. flahaultii, a species endemic to Morocco, is an excellent means of controlling C. pipiens.

Keywords: Artemisia species; essential oil; Culex pipiens ; vector; bioassay larvicide; lethal concentration; endemic; in silico

1 Introduction

West Nile virus is an example of an emerging arbovirus transmitted by an arthropod vector (Culex sp.) to birds that causes West Nile fever [1,2]. It is one of the world’s major public health problems [3]. The disease is endemic and is widely distributed in sub-Saharan Africa [4]. Although its impact on human health has never been measured in sub-Saharan Africa, the West Nile virus has long been considered a low pathogenic arbovirus, with no significant public health consequences [5]. However, over the last 10 years or so, epidemics of several dozens to hundreds of cases have been reported in the Mediterranean basin [6]. Above all, following its introduction into the New World, the West Nile virus has spread in just a few years from Canada to Argentina [7]. In this new ecosystem, it has found vectors and hosts, enabling it to establish sustainable transmission cycles. Since then, it has caused thousands of cases every year, mainly in the United States [8].

In Morocco, the West Nile virus was first described in 1990, causing human diseases and equine epizootics for several successive years [9]. After 6 years of apparent absence, it caused a large-scale epizootic in 1996, 2003, and 2010, circulating regularly along the Mediterranean coast [10]. Horses are the main species affected by this virus. Birds, particularly crows and sparrows (on their way from Africa to Europe), are considered amplifying hosts, and mosquitoes of the Culex genus are vectors [11,12].

Culex pipiens Linnaeus, 1758 (C. pipiens) (Diptera: Culicidae) is the main biting species involved in the transmission of West Nile virus [13]. Its high density, which coincides in time and space with the date of detection of equine cases, makes it the most likely vector [14]. At present, this virus is not a public health problem in Morocco, but the American example prompts us to take the health risk associated with the West Nile virus seriously [15]. On the other hand, it poses a major veterinary problem in a region where cultural and tourist activities associated with horses are essential [16,17].

The World Health Organization (WHO, 2016) encourages the development of different approaches to achieve successful and sustainable vector control [18], including the use of biological technologies, physical and chemical, have been implemented [19]. A program of vector control is crucial for the prevention of certain vector-borne diseases [20]. In fact, synthetic pesticides with insecticidal properties are most frequently used to control C. pipiens [21,22].

However, these chemical pesticides have harmful effects on the environment, non-target organisms, and human health [23,24]. In addition, overexploitation of these chemicals induces the risk of Culicidae insects developing resistance to the insecticides used, which significantly reduces and diminishes the treatment efficacy [25,26]. Due to the enormous damage caused by synthetic insecticides, there is now a need to discover alternative mosquito control methods that have little or no negative impact on the environment or human health [27,28,29]. As part of its traditional medicine program, the WHO welcomes opportunities to collaborate with countries and scientific researchers to develop new alternative treatments and encourages this collaboration to develop safe and effective therapies that can be used in most African countries and other parts of the world [30,31].

This research also aims to investigate the in silico assessments on the major constituents in the essential oil (EO) studied to help understand and explain the acquired in vivo results, using molecular dynamics simulations. The EOs tested are from the genus of Artemisia: therein, two species are spontaneous, wild, and endemic to Morocco, A. flahaultii and A. aragonensis, while A. annua is cultivated.

2 Materials and methods

2.1 Plant collection and EO extraction of the Artemisia species studied

A. flahaultii, A. annua, and A. aragonensis plants were harvested between October and April 2021 in the Eastern Middle Atlas Mountains, Morocco. After harvesting, they were dried in the shade, away from light, in a dry, well-ventilated place. To extract the EOs, 100 g of leaves from each plant was ground to a powder and subjected to hydrodistillation for 2–3 h using a Clevenger apparatus. The EOs obtained after distillation were separated by decantation and then dried using anhydrous sodium sulfate to remove any residual moisture. Finally, the EOs were stored in small opaque bottles at a temperature of 4 ± 2°C.

2.2 Chemical study and identification of compounds of EOs

Chemical analysis of the EOs was carried out by gas chromatography coupled with mass spectrometry (GC/MS), enabling both chromatographic analysis of each oil and qualitative determination of the majority of compounds.

GC/MS was performed on a Shimadzu (Tokyo, Japan) GCMS-TQ8040 NX Triple Quadrupole GC/MS apparatus to determine the chemical components of the produced EOs. Helium was applied as a carrier gas during the analysis, which was conducted through an apolar capillary column (RTxi-5 Sil MS-30 m x 0.25 mm ID x 0.25 m). In our earlier research, the analytical settings were described in great detail.

A homologous sequence of n-alkanes was used to calculate the Kovats retention index (RI), which was then utilized to determine the compounds. Importantly, the estimated Kovats RI values were compared to those from the NIST 98 collection and the Adams database in order to identify the constituents [32].

2.3 Characteristics of the larval site

C. pipiens larvae were collected from a breeding site located in the urban area of the city of Fez in a small tributary of the El-Gaada dam (altitude, 407 m; 34 01 155 N and 004 57 213 W).

This site is established by a very high density of Culicidae larvae. It is located near an animal farm, which favors the proliferation of C. pipiens larvae.

2.4 Collecting larvae of C. pipiens

A rectangular plastic tray that was 45° angled toward the water’s surface was used to gather the larvae because the tension force it creates draws the plate toward the larvae. In the Faunistic Laboratory of the Scientific University of Fez, the obtained larvae were kept in breeding in rectangular trays at an average temperature of 22.6°C ± 2°C and a relative humidity of 70% ± 5%.

2.5 Identification of larvae

The Moroccan Culicidae identification key was used to identify the morphological characteristics of the larvae [33], and the Mediterranean African arthropod identification software was used to determine the scientific name of the vector to be tested (mosquitoes) [34].

2.6 Biocide tests

The biological tests were done following the standard protocol proposed by the WHO (2005, 2016) with slight modifications [35,36]. A stock solution (10%) of each EO was prepared by dissolving the particular EO in ethanol and diluting it with ethanol to obtain a range of concentrations: 7.812, 15.625, 31.25, 62.5, and 125 ppm for A. flahaultii; 62.5, 125, 250, 500, and 1,000 ppm for A. annua; 250, 500, 1,000, 3,000, and 6,000 ppm for A. aragonensis. A positive control (temephos) was also prepared with a range of concentrations: 0.0006, 0.0012, 0.0025, 0.05, and 0.0625 ppm. A total number of 20 third-instar larvae were placed in plastic beakers filled with distilled water at the designated concentration. For each concentration, three replicates were performed, and three controls were prepared for each test. The negative control comprised 99 ml of distilled water plus 1 ml of ethanol and received the same number of larvae. Mortality was counted after 24 h. LC50 and LC90 values were obtained using Log-Probit software. Three replicates were executed for each dilution and for the two controls. The beakers containing the larvae were placed in the laboratory under standard conditions (temperature, 26 ± 3°C; humidity, 70–80%). After 24 h of contact, live and dead larvae were counted.

The results of the bioassay test were expressed as % mortality in relation to the concentrations of EOs (biological insecticides) and controls used. If the % mortality in the controls was higher than 5%, the % mortality in the larvae exposed to the EO was corrected by the Abbott formula equation (1) [37]:

(1) % Corrected mortality = % Observed mortality − % Control mortality 100 − % Control mortality × 100 .

The test must be repeated if the control mortality exceeds 20%.

2.7 Data processing

The data were processed using Log-Probit analysis software (Windl, version 2.0). This software was developed by CIRAD-CA/MABIS (October 1999) [38]. ANOVA tests were also used to determine the analysis of mean values and standard deviation.

2.8 Insecticide-likeness

The insecticide-likeness of the compounds under analysis was evaluated by assessing various descriptors, including molecular weight (M W), hydrophobicity (log P), hydrogen bond acceptors (HBAs) and hydrogen bond donors (HBDs), rotatable bonds (RBs), and aromatic rings [39,40,41]. These descriptors, as recommended in previous studies, have specific ranges of values: an M W ranging from 150 to 500, <12 RBs, 1–8 HBAs, fewer than 2 HBDs, and a log P value < 5 [42,43]. The compounds that meet these criteria are deemed to possess significant potential for insecticidal activity. These descriptors were computed with the aid of the Molinspiration online tool [44]. The quantitative estimate of the insecticide-likeness (QEI) was calculated using QEPest, a free Java program addressing the field of agrochemicals. It allows the scoring of our molecules based on a function of previously reported descriptors [45].

2.9 Molecular docking study

The molecular docking analysis involved docking the studied ligands into the desired receptor using AutoDock Vina [46] to determine their optimal binding poses within the protein’s binding site [47]. The crystal structure of acetylcholinesterase from C. pipiens, obtained from the Protein Data Bank (PDB ID: 6v4c) [48], was prepared by subtracting water molecules, adding hydrogen bonds, and regulating the Kollman charges, following procedures outlined in our previous studies [49]. Additionally, a reference insecticide (temephos), known for its larvicidal activity, was docked to allow for a comparison of the interactions formed. Ligands were generated using Chem3D software, and optimized under the MMFF94 force field using Avogadro software [50]. A grid box with dimensions of 40 Å, positioned at coordinates x = 16.68 Å; y = −2.99 Å; and z = −27.44 Å, was employed for the docking simulations. The interactions between the ligands and the receptor were subsequently analyzed using Discovery Studio Visualizer [51].

2.10 Molecular dynamics simulations

The selected complexes from the docking results were subjected to 100 ns molecular dynamics simulations by using Maestro software [52]. Water molecules were excluded from all systems, and hydrogen atoms were added to the simulation beforehand [53]. The systems were then optimized and underwent energy minimization using the OPLS3e force field. Solvation was carried out using an orthorhombic box of TIP3P water molecules, and the systems were equilibrated with sodium and chloride ions [53]. The simulations began with a 1 ns run under NVT (constant number of particles, volume, and temperature) conditions, followed by a 100 ns run under NPT (constant number of particles, pressure, and temperature) conditions [54]. Throughout the simulations, parameters such as RMSD (root-mean-square deviation), RMSF (root-mean-squared fluctuation), and protein–ligand contacts were monitored to evaluate the stability of the complexes [55]. Additionally, the uncomplexed protein was simulated to compare structural changes upon binding with the docked ligands.

3 Results and discussion

3.1 Chemical analysis

After hydrodistillation, yellowish-brown oils were obtained in yields of 0.25% (w/w) (A. flahaultii), 0.30% (A. annua), and 1.19% (A. aragonensis), with a strong characteristic aroma. The composition of the EOs is presented in Table 1 and Figure 1, and chemical structures of the major components are shown in Figure 2. Based on the obtained findings, 25 chemical molecules were identified in A. flahaultii oil, making up 99.98% of the total oil. The A. flahaultii oil was dominated by d-limonene, which accounted for 22.09% of the total oil; the other main metabolites of the oil are β-pinene (15.22%), cymene (11.72%), and β-vinylnaphthalene (10.47%). A total of 12 compounds were identified in the A. annua oil, representing 100% of the oil. The most abundant constituents of A. annua were artemisia ketone (43.19%), caryophyllene (15.75%), β-selinene (10.32%), germacrene D (9.56%), and camphor (4.41%). In the A. aragonensis oil, 34 chemical molecules were identified by GC/MS. It was characterized by a predominance of monoterpenes (77.37%) with a low percentage of sesquiterpenes (15.13%), the main components of the oil being camphor (24.97%), borneol (13.20%), 1,8-cineole (10.88%), and fenchone (10.20%). The A. flahaultii oil had a medium monoterpene content (56.74%) and sesquiterpenes were also present in small amounts (13.43%), while A. annua oil continued to have a medium content of monoterpenes (55.35%) and hydrocarbon sesquiterpenes (43.03%) and was lower in oxygenated sesquiterpenes (1.62%) (Table 1).

Table 1

Phytochemical components identified in A. flahaultii, A. aragonensis, and A. annua EOs by GC/MS

RI Compound name A. flahaultii A. aragonensis A. annua
Peak Area (%) Peak Area (%) Peak Area (%)
933 α-Pinene 1 2.18 1 1.53 – —
949 Camphene — — 2 3.10 – —
952 Benzaldehyde 2 1.65 — — – —
979 β-Pinene 3 15.22 3 1.43 – —
999 Yamogi alcohol — — 4 2.75 – —
1026 Cymene 4 11.72 5 0.69 – —
1029 d-Limonene 5 22.09 — — — —
1032 1,8-Cineole — — 6 10.88 1 3.21
1045 (E)-β-Ocimene 6 2.18 — — — —
1048 Artemisia ketone — — — — 2 43.19
1068 Artemisia alcohol — — — — 3 1.48
1017 Terpinene 7 1.77 7 0.48 — —
1139 neo-allo-ocimene 8 0.62 — — — —
1086 Fenchone — — 8 10.20 — —
1102 α-Thujone — — 9 0.51 — —
1146 Camphor — — 10 24.97 4 4.41
1147 trans-pinocarveol — — 11 0.52 — —
1164 Pinocarvone — — 12 0.44 — —
1169 Borneol — — 13 13.20 5 3.07
1082 Terpinen-4-ol — — 14 1.39 — —
1173 Artemisia acetate — — 15 1.0 — —
1133 α-Terpineol — — 16 0.69 — —
1198 Myrtenol — — 17 2.73 — —
1206 Benzene, 2,4-pentadiynyl- 9 9.06 — — — —
1216 trans-Carveol — — 18 0.42 — —
1221 Copaene — — — — 6 3.52
1237 Pulegone — — 19 1.44 — —
1243 Cyclohexasiloxane, dodecamethyl- 10 0.71 — — — —
1288 Bornyl acetate — — 20 2.33 — —
1326 Myrtenyl acetate — — 21 0.83 — —
1335 Δ-Elemene 11 3.82 — — — —
1373 α-Copaene — — 22 0.75 — —
1403 Methyleugenol 12 0.93 — — — —
1435 γ-Cadinene — — — — 7 1.25
1447 Cinnamic acid, methyl ester 13 0.96 — — — —
1464 Caryophyllene 14 0.62 — — 8 15.75
1442 β-Farnesene — — — — 9 2.62
1446 Cycloheptasiloxane, tetradecamethyl- 15 0.43 — — — —
1485 Germacrene D — — 23 0.71 10 9.56
1490 β-Selinene 16 1.02 — — 11 10.32
1439 β-Vinylnaphthalene 17 10.47 — — — —
1555 2,4-Di-tert-butylphenol 18 1.07 — — — —
1556 Elemicin 19 3.59 — — — —
1570 Caryophyllene oxide 20 2.52 25 1.26 12 1.62
1578 Spathulenol 21 0.53 24 1.26 – —
1624 Isospathulenol 22 4.25 26 0.50 – —
1554 Cyclooctasiloxane, hexadecamethyl- 23 0.38 — — – —
1632 γ-Eudesmo — — 27 2.20 – —
1637 Capillin 24 1.56 — — – —
1600 Ledol 25 0.77 — — – —
1640 Cadinol — — 28 0.51 – —
1650 β-Eudesmo — — 29 1.30 – —
1658 Bisabolol oxide B — — 30 0.45 - —
1685 Bisabolone oxide A — 31 5.63 – —
1749 α-Bisabolol oxide A — — 32 0.56 – —
2500 Pentacosane — — 34 1.63 – —
2800 Octacosane — — 33 1.33 – —
Monoterpene (C10) 56.74% 77.37% 55.35%
Sesquiterpene (C15) 13.43% 15.13% 44.65%
Other compounds 29.83% 7.12% 00%
Total compounds identified 100% 99.62% 100%
Figure 1 Chromatographic profiles of A. annua (a), A. flahaultii (b), and A. aragonensis (c) EOs obtained by GC/MS [56,57,58].
Figure 1

Chromatographic profiles of A. annua (a), A. flahaultii (b), and A. aragonensis (c) EOs obtained by GC/MS [56,57,58].

Figure 2 Chemical structure of the main components: (1) d-limonene, (2) β-pinene, (3) p-cymene, (4) β-vinylnaphthalene, (5) artemisia ketone, (6) caryophyllene, (7) β-selinene, (8) germacrene D, (9) camphor, (10) borneol, (11) 1,8-cineole, and (12) fenchone.
Figure 2

Chemical structure of the main components: (1) d-limonene, (2) β-pinene, (3) p-cymene, (4) β-vinylnaphthalene, (5) artemisia ketone, (6) caryophyllene, (7) β-selinene, (8) germacrene D, (9) camphor, (10) borneol, (11) 1,8-cineole, and (12) fenchone.

3.2 Larvicidal activity of the EO of Artemisia plant on C. pipiens

The use of EOs from aromatic, medicinal, and biocide plants in vector control is an alternative method to minimize the side effects of chemical pesticides in the environment [59,60]. In recent research, some secondary plant metabolites have been found to act as botanical insecticides [61,62]. According to the biological results of this susceptibility test, the three EOs of Artemisia exerted significant larvicidal potential against C. pipiens. Figure 3 shows that the mortality rate of C. pipiens larvae increases with the concentration of EOs used. For example, with A. flahaultii, the mortality rate reaches 98.33% of larvae eliminated at 125 ppm. For A. annua, it rises from 11.67% mortality at 62.5 ppm to 98.33% mortality with a concentration of 1,000 ppm. For A. aragonensis, the percentage of mortality rises from 5% with a concentration of 250 ppm after 100% of larvae eliminated to a very high concentration of 6,000 ppm compared with the other two oils tested.

Figure 3 Mortality of C. pipiens larvae (%) due to the effect of EOs of A. flahaultii, A. annua, and A. aragonensis at different concentrations during 24 h of evaluation (negative control: ethanol; positive control: temephos).
Figure 3

Mortality of C. pipiens larvae (%) due to the effect of EOs of A. flahaultii, A. annua, and A. aragonensis at different concentrations during 24 h of evaluation (negative control: ethanol; positive control: temephos).

The LC50 [confidence intervals] values at the end of larval stage were 29.328 ± 0.316 [2.892; 297.414] ppm, 278.539 ± 0.187 [70.387; 1102.67] ppm, and 2373.75 ± 0.989 [1150.37; 4898.16] ppm for A. flahaultii, A. annua, and A. aragonensis oils, respectively (Table 2). Moreover, their LC90 [confidence intervals] values were 127.996 ± 0.175 [35.42; 462.525] ppm, 1089.21 ± 0.172 [307.572 ± 3857.21] ppm, and 5202.7 ± 0.12 [2150.43; 12587.3] ppm, respectively (Table 2). The Chi-square test was not significant at 5% for both EOs, indicating a good model fit.

Table 2

Lethal concentrations (LC50 and LC90) of A. flahaultii, A. annua, and A. argonensis oils after 24-h exposure

Essential oil Concentrations (ppm) LC50 (ppm) CI LC90 (ppm) CI Regression line equation Calculated Chi2 (χ 2) df
A. flahaultii (7.812; 15.625; 31.25; 62.5; 125) 29.328 ± 0.316 [2.892; 297.414] 127.996 ± 0.175 [35.42; 462.525] 2.00298 × X − 2.93895 15.092 3
A. annua (62.5; 125; 250; 500; 1000) 278.539 ± 0.187 [70.387; 1102.67] 1089.21 ± 0.172 [307.572 ± 3857.21] 2.16457 × X − 5.29232 15.016 3
A. aragonensis (250; 500; 1000; 3000; 6000) 2373.75 ± 0.989 [1150.37; 4898.16] 5202.7 ± 0.12 [2150.43; 12587.3] 3.76101 × X − 12.69505 18.979 3
Temephos (positive control) (0.0006; 0.0012; 0.0025; 0.05; 0.0625) 0.0055 ± 0.219 [0.0032; 0.212] 0.097 ± 0.41 [0.0149; 0.42] 1.03254 × X + 2.32702 22.368 3

CI: 95% confidence intervals; df: degree of freedom; LC90: lethal concentration that kills 90% of exposed larvae; LC50 lethal concentration that kills 50% of exposed larvae.

These results indicate that A. flahaultii EOs are very toxic to C. pipiens larvae, with an LC50 value below 100 ppm (Table 2). Previous studies by Cheng et al. and also by Dias and Moraes stated that a bio-insecticide product with an LC50 below 100 ppm was considered a promising product for mosquito control [63,64,65]. These toxicological parameters could be due to the chemical molecule of the EO of A. flahaultii composed mainly of limonene, belonging to the monoterpenes famous for their insecticidal effect against several species of insects [66,67].

Previous studies have indicated that the chemical molecule pinene (LC50 values between 36.53 and 66.52 ppm) and the chemical molecule limonene (LC50 values between 50.36 and 43.71 ppm) have a medium level of toxicity. In contrast, cymene is highly toxic, with an LD50 value close to 20 ppm, and terpinen-4-ol is non-toxic (LC50 value > 200 ppm). This reinforces our result, especially for A. flahaulti, which possesses all these molecules (15.22% pinenes, 22.09% limonene, and 11.72% cymene) [68,69].

To test and confirm the sensitivity of C. pipiens species to the EOs tested, we used temephos (positive control), which is considered as the most widely used insecticide locally (Morocco) in the control of mosquito larvae [70]. Table 2 shows that temephos has a very high insecticidal power compared to our oils, and it has the lowest LC50 which was 0.0055 ± 0.219 [0.0032; 0.212] ppm and a LC90 of 0.097 ± 0.41 [0.0149; 0.42] ppm. But the problem is that the C. pipiens species acquired resistance against this insecticide (temephos) and other insecticides such as malathion, fenitrothion, and fenthion [70,71].

Despite the differences in LC50 and LC90 between EOs and temephos (chemical insecticide) in relation to C. pipiens larvae, the larvicidal effect of EOs could be of great interest in the field of vector control. This is due to the problems associated with the use of synthetic insecticides (environmental pollution, resistance, risks to human health, etc.).

In general, EOs can be used in insecticides to target disease-carrying insects while having little or no impact on the surrounding insect population [72]. The potential biological activities of different EOs vary according to the plant, its origin, and its composition [73,74].

Regarding our results on larvicidal activity at stages 3 and 4, there were differences between the three EOs tested, with variations in LC50 and LC90 values. The data shown in Table 2 and Figure 3 show that the examined EOs have effective control over C. pipiens larvae, and the effect of sensitivity may be attributed to the interaction of many chemical molecules present in each essential oil, minor compounds, or mainly major components.

The secondary plant compounds in the EOs of A. flahaultii, A. annua, and A. aragonensis may act synergistically rather than individually, as previous studies have shown that the botanical insecticidal activity of EOs is stronger than that of their compounds studied individually [75].

Numerous studies have extracted and purified chemical compounds from the EOs of plants in the genus Artemisia to identify effective bioinsecticides with specific active components. For instance, EO extracts from A. absinthium, A. spicigera, and A. santonicum, containing 1,8-cineole, terpinen-4-ol, camphor, and alpha-terpineol, have proven effective against Lasioderma serricorne [76,77]. The EOs of A. negrei and A. aragonensis composed of camphor, β-thujone, 1,8-cineole, and borneol exhibit notable insecticidal potential against the stored product pest Callosobruchus maculatus Fab [75]. Additionally, A. rupestris contains α-terpinyl, α-terpineol, 4-terpineol, and linalool, which show high contact toxicity against Liposcelis bostrychophila. Furthermore, A. argyi and A. rupestris, composed of camphor, β-pinene, β-caryophyllene, eucalyptol, α-terpinyl acetate, and 4-terpineol, demonstrated significant toxicity against adult Lasioderma serricorne [78,79]. Collectively, these findings confirm that the chemical compounds present in the EOs of the Artemisia genus can serve as bioinsecticides, offering a safer alternative to harmful chemicals for the environment and human health.

The larvicidal activity of the chemical substances listed as main components of the tested EOs was examined to provide a solution to this final query, and the findings are shown in Table 2.

3.3 In silico studies

3.3.1 Insecticide-like activity of the major compounds

The outlined criteria for predicting insecticide-like compounds include a M W between 150 and 500, log P between 0 and 5, HBD ≤ 2, HBA 1–8, and RB ≤ 12. These criteria were applied to assess the insecticide potential of the analyzed compounds (Table 3). β-Pinene, cymene, d-limonene, benzene, 2,4-pentadiynyl, and camphene were disqualified due to their molecular weights being less than 150 and the absence of HBAs. Additionally, four other compounds had log P values greater than 5 and no HBAs; on the other hand, compounds like isospathulenol, 1,8-cineole, fenchone, camphor, borneol, bisabolone oxide A, and artemisia ketone met all the recommended criteria. However, the only exception was β-vinylnaphthalene, which had fewer than 1 HBA, violating one criterion. The quantitative estimate of the insecticide-likeness QEI of all compounds was calculated, and seven top-ranked compounds were suggested. These findings suggest that isospathulenol and bisabolone oxide A are promising insecticide candidates.

Table 3

Calculated descriptors of all compounds to determine the insecticide likeness by using Molinspiration

Name M W MLOGP nHBA nHBD nRB nAR QEI
β-Pinene 136.23 3.33 0 0 0 0 0.4043
Cymene 134.22 3.9 0 0 1 1 0.4189
d-Limone 136.23 3.62 0 0 1 0 0.427
Benzene 140.18 2.87 0 0 1 1 0.4176
β-Vinylnaphthalene 154.21 3.97 0 0 1 2 0.4279
Isospathulenol 220.35 3.96 1 1 0 0 0.5988
1,8-Cineole 154.25 2.72 1 0 0 0 0.4994
Fenchone 152.23 2.16 1 0 0 0 0.4795
Camphor 152.23 2.16 1 0 0 0 0.4795
Borneol 154.25 2.35 1 1 0 0 0.4081
Bisabolone oxide A 236.35 3.22 2 0 1 0 0.7606
Camphene 136.23 3.33 0 0 0 0 0.4043
Artemisia ketone 152.23 2.96 1 0 3 0 0.572
Caryophyllene 204.35 5.17 0 0 0 0 0.5974
Germacrene D 208.38 5.3 0 0 1 0 0.6326
β-Selinene 204.35 5.02 0 0 1 0 0.6275
Copaene 204.35 5.75 0 0 1 0 0.6107

3.3.2 Molecular docking study

As shown in Table 4, the docking results indicated that several studied ligands had promising binding scores within the receptor’s binding site compared to the reference insecticide temephos. Three compounds extracted from A. annua (caryophyllene, copaene, and β-selinene) were predicted to have a higher binding affinity than the temephos. From A. aragonensis, bisabolone oxide A was the only compound that showed a higher binding score than temephos. Additionally, compounds from A. flahaultii, including isospathulenol, benzene, 2,4-pentadiynyl, and β-vinylnaphthalene, exhibited good binding affinity compared to temephos.

Table 4

Binding score of the complexes obtained by molecular docking

Plants Main compounds Score (kcal/mol)
A. annua Artemisia ketone −6.3
Camphor −5.1
Caryophyllene −9.4
Copaene −8
Germacrene D −6.1
β-Selinene −7.6
A. aragonensis 1,8-Cineole −5.8
Bisabolone oxide A −7.2
Borneol −5.1
Camphene −6
Camphor −5.1
Fenchone −6.4
A. flahaultii Benzene, 2,4-pentadiynyl −7.1
Cymene −6.3
d-Limonene −6
Isospathulenol −9.3
β-Pinene −6.2
β-Vinylnaphthalene −7.7
(Standard insecticide) Temephos −6.7

Three lead compounds were chosen based on the outcomes of molecular docking and the insecticide-likeness prediction. Their molecular interactions with key protein residues are detailed in Table 5 and were analyzed to determine their influence on the desired activity.

Table 5

2D and 3D visualization of the best selected complexes, the created interactions, distances, and the participated residues

Complex Residues Interaction type Distances (Å)
6v4c–isospathulenol Arg262 Conventional hydrogen bond 2.11
Ile25 Alkyl 4.88
Phe13 Pi–Alkyl 4.29
6v4c–bisabolone oxide A Arg192 Alkyl 4.58
Lys195 Alkyl 4.53
Lys196 Alkyl 4.29
Arg192 Alkyl 4.48
Lys196 Alkyl 4.06
6v4c–caryophyllene Phe13 Pi–Sigma 3.77
Ile259 Alkyl 4.95
6v4c–temephos Asp7 Attractive charge 3.97
Glu9 Attractive charge 4.40
Glu14 Attractive charge 4.78
Glu9 Conventional hydrogen bond 3.52
Gln142 Carbon–hydrogen bond 3.56
Ser4 Carbon–hydrogen bond 3.72
Ala55 Carbon–hydrogen bond 3.50
Glu10 Pi–anion 4.09
Arg192 Pi–alkyl 4.84
Lys196 Pi–alkyl 3.99

For the caryophyllene–6v4c complex, the interactions included a conventional hydrogen bond with Arg262 at a distance of 2.11 Å, an alkyl interaction with Ile25 at 4.88 Å, and a pi–alkyl interaction with Phe13 at 4.29 Å. In the 6v4c–bisabolone oxide A complex, six alkyl bonds were observed with Arg192, Lys195, and Lys196 at distances ranging from 4.06 to 4.58 Å.

The 6v4c–isospathulenol complex featured Pi–sigma and alkyl bonds with Phe13 and Ile259 at distances of 3.77 and 4.95 Å, respectively.

The standard insecticide formed multiple interactions: attractive charges, conventional hydrogen bonds, carbon–hydrogen bonds, Pi–anion, and Pi–alkyl interactions with residues Asp7, Glu9, Glu14, Gln142, Ser4, Ala55, Glu10, Arg192, and Lys196, at distances ranging from 3.50 to 4.84 Å.

3.3.3 Molecular dynamics simulations

Molecular dynamics simulations were done on the three best-chosen compounds to provide insights into the structural changes affecting the protein and ligands upon complex formation, as well as the molecular interactions created between them. Key parameters such as RMSD, RMSF, and protein–ligand contacts were analyzed.

The RMSD values for both the protein and ligands in each system were calculated and plotted to facilitate the interpretation of the results. Figure 4 shows the protein RMSD of the three best-selected complexes in addition to the apo-protein, indicating stability throughout the entire simulation period. Conversely, Figure 5, which presents the ligand RMSD of the analyzed complexes, exhibited significant deviations during the first 30 ns of the simulation, followed by stability for the remainder of the simulation.

Figure 4 Protein RMSD plot of the best selected complexes in comparison with the apo-protein.
Figure 4

Protein RMSD plot of the best selected complexes in comparison with the apo-protein.

Figure 5 Ligand RMSD of the best selected complexes during the 100 ns of simulation.
Figure 5

Ligand RMSD of the best selected complexes during the 100 ns of simulation.

The RMSF of the protein, calculated and plotted in Figure 6, demonstrated minor fluctuations, in the protein residues for all complexes. These results indicate that the protein maintained its structural integrity throughout the simulations, and the ligands achieved stable binding after an initial adjustment period.

Figure 6 Protein RMSF plot of the simulated complexes.
Figure 6

Protein RMSF plot of the simulated complexes.

3.3.4 Protein–ligand contact

The created molecular interactions between the protein and candidate ligands are presented in Figure 7 to display their influences on the stability of the obtained complexes. In the 6v4c–caryophyllene complex, only hydrophobic bonds were detected with the following residues: Phe12, Ala16, Met191, Ala204, Ile259, and Tyr266. While in the 6v4c–bisabolone oxide A complex, two hydrophobic bonds were observed with Ile150 and Phe153, along with two hydrogen bonds with Gln157 and Arg189. Additionally, water bridges were formed with Asp7, Gln142, Lys144, Gln157, and Arg189 residues. Meanwhile, the isospathulenol complex formed hydrogen bonds with Glu20, Arg207, and Arg262, hydrophobic bonds with Phe13, Ala16, Ile259, and Tyr266, and water bridges with Ala16, Glu20, Arg262, Asn265, and Tyr268 residues.

Figure 7 Protein–ligand contact of the best selected compounds (violet: hydrophobic bonds, green: hydrogen bonds, and blue: water bridges).
Figure 7

Protein–ligand contact of the best selected compounds (violet: hydrophobic bonds, green: hydrogen bonds, and blue: water bridges).

4 Conclusions

To sum up, this study reports the chemical composition and larvicidal activity of the EOs extracted from three plants of the genus Artemisia. The extracted EOs were yellowish-brown in color, with yields of 0.25% for A. flahaultii, 0.30% for A. annua, and 1.19% for A. aragonensis, all possessing a strong characteristic aroma. The EOs exhibited varying compositions of mono- and sesquiterpenes, as determined by GC/MS analysis. The EOs of the three Artemisia species show good larvicidal efficacy against the C. pipiens. In addition, we examined, using in silico tools, the larvicidal activity of the major chemical compounds identified in the EOs of plants of Artemisia.

Molecular docking analysis and molecular dynamics simulations revealed that the major chemical compounds of the studied EOs exhibited strong interactions with the target proteins, suggesting their potential role in insecticidal activity. Also, ADMET (absorption, distribution, metabolism, excretion, and toxicity) studies of the main chemical compounds indicated acceptable drug-like properties. Altogether, the present study shows the importance of using EOs of A. flahaultii, A. annua, and A. aragonensis in the control of C. pipiens mosquitoes, vectors of the West Nile virus, due to their larvicidal properties. It could therefore represent a less costly alternative for its application in the production of bioinsecticides.

Acknowledgements

The authors extend their appreciation to Princess Nourah bint Abdulrahman University researcher supporting project number (PNURSP2024R342) and Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia, for supporting this work. The authors also extend their appreciation to the Researchers Supporting Project number (RSPD2024R754), King Saud University, Riyadh 11451, Saudi Arabia, for supporting this research.

  1. Funding information: This research was supported by the researchers supporting project number (PNURSP2024R342), Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia, and also by the Researchers Supporting Project number (RSPD2024R754), King Saud University, Riyadh 11451, Saudi Arabia.

  2. Author contributions: Conceptualization, K.C.; methodology, K.C. and M.E.K.A.; software, O.A. and S.C.; validation, MEKA and S.C.; investigation, EA-F.; resources, K.C. and O.Z.; data curation, S.L.; writing – original draft preparation, Z.B. and M.C.; writing – review and editing, K.C., EA-F., and M.C.; project administration, R.G.; supervision, R.G.; funding acquisition, M.M.A., M.H., and A.S.A. All authors have read and agreed to the published version of the manuscript.

  3. Conflict of interest: The authors declare no conflict of interest.

  4. Ethical approval: The conducted research is not related to either human or animal use.

  5. Data availability statement: All data generated or analyzed during this study are included in this published article.

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Received: 2024-06-12
Revised: 2024-10-01
Accepted: 2024-10-04
Published Online: 2024-10-28

© 2024 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Regular Articles
  2. Porous silicon nanostructures: Synthesis, characterization, and their antifungal activity
  3. Biochar from de-oiled Chlorella vulgaris and its adsorption on antibiotics
  4. Phytochemicals profiling, in vitro and in vivo antidiabetic activity, and in silico studies on Ajuga iva (L.) Schreb.: A comprehensive approach
  5. Synthesis, characterization, in silico and in vitro studies of novel glycoconjugates as potential antibacterial, antifungal, and antileishmanial agents
  6. Sonochemical synthesis of gold nanoparticles mediated by potato starch: Its performance in the treatment of esophageal cancer
  7. Computational study of ADME-Tox prediction of selected phytochemicals from Punica granatum peels
  8. Phytochemical analysis, in vitro antioxidant and antifungal activities of extracts and essential oil derived from Artemisia herba-alba Asso
  9. Two triazole-based coordination polymers: Synthesis and crystal structure characterization
  10. Phytochemical and physicochemical studies of different apple varieties grown in Morocco
  11. Synthesis of multi-template molecularly imprinted polymers (MT-MIPs) for isolating ethyl para-methoxycinnamate and ethyl cinnamate from Kaempferia galanga L., extract with methacrylic acid as functional monomer
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  13. Evaluation of influence of Butea monosperma floral extract on inflammatory biomarkers
  14. Cannabis sativa L. essential oil: Chemical composition, anti-oxidant, anti-microbial properties, and acute toxicity: In vitro, in vivo, and in silico study
  15. The effect of gamma radiation on 5-hydroxymethylfurfural conversion in water and dimethyl sulfoxide
  16. Hollow mushroom nanomaterials for potentiometric sensing of Pb2+ ions in water via the intercalation of iodide ions into the polypyrrole matrix
  17. Determination of essential oil and chemical composition of St. John’s Wort
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  19. Anti-parasitic activity and computational studies on a novel labdane diterpene from the roots of Vachellia nilotica
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  27. pH-based colorimetric detection of monofunctional aldehydes in liquid and gas phases
  28. Investigating the effect of resveratrol on apoptosis and regulation of gene expression of Caco-2 cells: Unravelling potential implications for colorectal cancer treatment
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https://doi.org/10.1515/chem-2024-0108
Schlagwörter für diesen Artikel
Artemisia species; essential oil; Culex pipiens; vector; bioassay larvicide; lethal concentration; endemic; in silico
Creative Commons
BY 4.0

Artikel in diesem Heft

  1. Regular Articles
  2. Porous silicon nanostructures: Synthesis, characterization, and their antifungal activity
  3. Biochar from de-oiled Chlorella vulgaris and its adsorption on antibiotics
  4. Phytochemicals profiling, in vitro and in vivo antidiabetic activity, and in silico studies on Ajuga iva (L.) Schreb.: A comprehensive approach
  5. Synthesis, characterization, in silico and in vitro studies of novel glycoconjugates as potential antibacterial, antifungal, and antileishmanial agents
  6. Sonochemical synthesis of gold nanoparticles mediated by potato starch: Its performance in the treatment of esophageal cancer
  7. Computational study of ADME-Tox prediction of selected phytochemicals from Punica granatum peels
  8. Phytochemical analysis, in vitro antioxidant and antifungal activities of extracts and essential oil derived from Artemisia herba-alba Asso
  9. Two triazole-based coordination polymers: Synthesis and crystal structure characterization
  10. Phytochemical and physicochemical studies of different apple varieties grown in Morocco
  11. Synthesis of multi-template molecularly imprinted polymers (MT-MIPs) for isolating ethyl para-methoxycinnamate and ethyl cinnamate from Kaempferia galanga L., extract with methacrylic acid as functional monomer
  12. Nutraceutical potential of Mesembryanthemum forsskaolii Hochst. ex Bioss.: Insights into its nutritional composition, phytochemical contents, and antioxidant activity
  13. Evaluation of influence of Butea monosperma floral extract on inflammatory biomarkers
  14. Cannabis sativa L. essential oil: Chemical composition, anti-oxidant, anti-microbial properties, and acute toxicity: In vitro, in vivo, and in silico study
  15. The effect of gamma radiation on 5-hydroxymethylfurfural conversion in water and dimethyl sulfoxide
  16. Hollow mushroom nanomaterials for potentiometric sensing of Pb2+ ions in water via the intercalation of iodide ions into the polypyrrole matrix
  17. Determination of essential oil and chemical composition of St. John’s Wort
  18. Computational design and in vitro assay of lantadene-based novel inhibitors of NS3 protease of dengue virus
  19. Anti-parasitic activity and computational studies on a novel labdane diterpene from the roots of Vachellia nilotica
  20. Microbial dynamics and dehydrogenase activity in tomato (Lycopersicon esculentum Mill.) rhizospheres: Impacts on growth and soil health across different soil types
  21. Correlation between in vitro anti-urease activity and in silico molecular modeling approach of novel imidazopyridine–oxadiazole hybrids derivatives
  22. Spatial mapping of indoor air quality in a light metro system using the geographic information system method
  23. Iron indices and hemogram in renal anemia and the improvement with Tribulus terrestris green-formulated silver nanoparticles applied on rat model
  24. Integrated track of nano-informatics coupling with the enrichment concept in developing a novel nanoparticle targeting ERK protein in Naegleria fowleri
  25. Cytotoxic and phytochemical screening of Solanum lycopersicum–Daucus carota hydro-ethanolic extract and in silico evaluation of its lycopene content as anticancer agent
  26. Protective activities of silver nanoparticles containing Panax japonicus on apoptotic, inflammatory, and oxidative alterations in isoproterenol-induced cardiotoxicity
  27. pH-based colorimetric detection of monofunctional aldehydes in liquid and gas phases
  28. Investigating the effect of resveratrol on apoptosis and regulation of gene expression of Caco-2 cells: Unravelling potential implications for colorectal cancer treatment
  29. Metformin inhibits knee osteoarthritis induced by type 2 diabetes mellitus in rats: S100A8/9 and S100A12 as players and therapeutic targets
  30. Effect of silver nanoparticles formulated by Silybum marianum on menopausal urinary incontinence in ovariectomized rats
  31. Synthesis of new analogs of N-substituted(benzoylamino)-1,2,3,6-tetrahydropyridines
  32. Response of yield and quality of Japonica rice to different gradients of moisture deficit at grain-filling stage in cold regions
  33. Preparation of an inclusion complex of nickel-based β-cyclodextrin: Characterization and accelerating the osteoarthritis articular cartilage repair
  34. Empagliflozin-loaded nanomicelles responsive to reactive oxygen species for renal ischemia/reperfusion injury protection
  35. Preparation and pharmacodynamic evaluation of sodium aescinate solid lipid nanoparticles
  36. Assessment of potentially toxic elements and health risks of agricultural soil in Southwest Riyadh, Saudi Arabia
  37. Theoretical investigation of hydrogen-rich fuel production through ammonia decomposition
  38. Biosynthesis and screening of cobalt nanoparticles using citrus species for antimicrobial activity
  39. Investigating the interplay of genetic variations, MCP-1 polymorphism, and docking with phytochemical inhibitors for combatting dengue virus pathogenicity through in silico analysis
  40. Ultrasound induced biosynthesis of silver nanoparticles embedded into chitosan polymers: Investigation of its anti-cutaneous squamous cell carcinoma effects
  41. Copper oxide nanoparticles-mediated Heliotropium bacciferum leaf extract: Antifungal activity and molecular docking assays against strawberry pathogens
  42. Sprouted wheat flour for improving physical, chemical, rheological, microbial load, and quality properties of fino bread
  43. Comparative toxicity assessment of fisetin-aided artificial intelligence-assisted drug design targeting epibulbar dermoid through phytochemicals
  44. Acute toxicity and anti-inflammatory activity of bis-thiourea derivatives
  45. Anti-diabetic activity-guided isolation of α-amylase and α-glucosidase inhibitory terpenes from Capsella bursa-pastoris Linn.
  46. GC–MS analysis of Lactobacillus plantarum YW11 metabolites and its computational analysis on familial pulmonary fibrosis hub genes
  47. Green formulation of copper nanoparticles by Pistacia khinjuk leaf aqueous extract: Introducing a novel chemotherapeutic drug for the treatment of prostate cancer
  48. Improved photocatalytic properties of WO3 nanoparticles for Malachite green dye degradation under visible light irradiation: An effect of La doping
  49. One-pot synthesis of a network of Mn2O3–MnO2–poly(m-methylaniline) composite nanorods on a polypyrrole film presents a promising and efficient optoelectronic and solar cell device
  50. Groundwater quality and health risk assessment of nitrate and fluoride in Al Qaseem area, Saudi Arabia
  51. A comparative study of the antifungal efficacy and phytochemical composition of date palm leaflet extracts
  52. Processing of alcohol pomelo beverage (Citrus grandis (L.) Osbeck) using saccharomyces yeast: Optimization, physicochemical quality, and sensory characteristics
  53. Specialized compounds of four Cameroonian spices: Isolation, characterization, and in silico evaluation as prospective SARS-CoV-2 inhibitors
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  56. FMS-like tyrosine kinase 3 inhibitory potentials of some phytochemicals from anti-leukemic plants using computational chemical methodologies
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  63. Study of phytochemical compound and antipyretic activity of Chenopodium ambrosioides L. fractions
  64. Investigating the adsorption mechanism of zinc chloride-modified porous carbon for sulfadiazine removal from water
  65. Performance repair of building materials using alumina and silica composite nanomaterials with electrodynamic properties
  66. Effects of nanoparticles on the activity and resistance genes of anaerobic digestion enzymes in livestock and poultry manure containing the antibiotic tetracycline
  67. Effect of copper nanoparticles green-synthesized using Ocimum basilicum against Pseudomonas aeruginosa in mice lung infection model
  68. Cardioprotective effects of nanoparticles green formulated by Spinacia oleracea extract on isoproterenol-induced myocardial infarction in mice by the determination of PPAR-γ/NF-κB pathway
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  70. Curcumin conjugated zinc nanoparticles for the treatment of myocardial infarction
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  72. Exploring the phytochemical profile and antioxidant evaluation: Molecular docking and ADMET analysis of main compounds from three Solanum species in Saudi Arabia
  73. Unveiling the molecular composition and biological properties of essential oil derived from the leaves of wild Mentha aquatica L.: A comprehensive in vitro and in silico exploration
  74. Analysis of bioactive compounds present in Boerhavia elegans seeds by GC-MS
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  76. LncRNA MIR17HG alleviates heart failure via targeting MIR17HG/miR-153-3p/SIRT1 axis in in vitro model
  77. Development and validation of a stability indicating UPLC-DAD method coupled with MS-TQD for ramipril and thymoquinone in bioactive SNEDDS with in silico toxicity analysis of ramipril degradation products
  78. Biosynthesis of Ag/Cu nanocomposite mediated by Curcuma longa: Evaluation of its antibacterial properties against oral pathogens
  79. Development of AMBER-compliant transferable force field parameters for polytetrafluoroethylene
  80. Treatment of gestational diabetes by Acroptilon repens leaf aqueous extract green-formulated iron nanoparticles in rats
  81. Development and characterization of new ecological adsorbents based on cardoon wastes: Application to brilliant green adsorption
  82. A fast, sensitive, greener, and stability-indicating HPLC method for the standardization and quantitative determination of chlorhexidine acetate in commercial products
  83. Assessment of Se, As, Cd, Cr, Hg, and Pb content status in Ankang tea plantations of China
  84. Effect of transition metal chloride (ZnCl2) on low-temperature pyrolysis of high ash bituminous coal
  85. Evaluating polyphenol and ascorbic acid contents, tannin removal ability, and physical properties during hydrolysis and convective hot-air drying of cashew apple powder
  86. Development and characterization of functional low-fat frozen dairy dessert enhanced with dried lemongrass powder
  87. Scrutinizing the effect of additive and synergistic antibiotics against carbapenem-resistant Pseudomonas aeruginosa
  88. Preparation, characterization, and determination of the therapeutic effects of copper nanoparticles green-formulated by Pistacia atlantica in diabetes-induced cardiac dysfunction in rat
  89. Antioxidant and antidiabetic potentials of methoxy-substituted Schiff bases using in vitro, in vivo, and molecular simulation approaches
  90. Anti-melanoma cancer activity and chemical profile of the essential oil of Seseli yunnanense Franch
  91. Molecular docking analysis of subtilisin-like alkaline serine protease (SLASP) and laccase with natural biopolymers
  92. Overcoming methicillin resistance by methicillin-resistant Staphylococcus aureus: Computational evaluation of napthyridine and oxadiazoles compounds for potential dual inhibition of PBP-2a and FemA proteins
  93. Exploring novel antitubercular agents: Innovative design of 2,3-diaryl-quinoxalines targeting DprE1 for effective tuberculosis treatment
  94. Drimia maritima flowers as a source of biologically potent components: Optimization of bioactive compound extractions, isolation, UPLC–ESI–MS/MS, and pharmacological properties
  95. Estimating molecular properties, drug-likeness, cardiotoxic risk, liability profile, and molecular docking study to characterize binding process of key phyto-compounds against serotonin 5-HT2A receptor
  96. Fabrication of β-cyclodextrin-based microgels for enhancing solubility of Terbinafine: An in-vitro and in-vivo toxicological evaluation
  97. Phyto-mediated synthesis of ZnO nanoparticles and their sunlight-driven photocatalytic degradation of cationic and anionic dyes
  98. Monosodium glutamate induces hypothalamic–pituitary–adrenal axis hyperactivation, glucocorticoid receptors down-regulation, and systemic inflammatory response in young male rats: Impact on miR-155 and miR-218
  99. Quality control analyses of selected honey samples from Serbia based on their mineral and flavonoid profiles, and the invertase activity
  100. Eco-friendly synthesis of silver nanoparticles using Phyllanthus niruri leaf extract: Assessment of antimicrobial activity, effectiveness on tropical neglected mosquito vector control, and biocompatibility using a fibroblast cell line model
  101. Green synthesis of silver nanoparticles containing Cichorium intybus to treat the sepsis-induced DNA damage in the liver of Wistar albino rats
  102. Quality changes of durian pulp (Durio ziberhinus Murr.) in cold storage
  103. Study on recrystallization process of nitroguanidine by directly adding cold water to control temperature
  104. Determination of heavy metals and health risk assessment in drinking water in Bukayriyah City, Saudi Arabia
  105. Larvicidal properties of essential oils of three Artemisia species against the chemically insecticide-resistant Nile fever vector Culex pipiens (L.) (Diptera: Culicidae): In vitro and in silico studies
  106. Design, synthesis, characterization, and theoretical calculations, along with in silico and in vitro antimicrobial proprieties of new isoxazole-amide conjugates
  107. The impact of drying and extraction methods on total lipid, fatty acid profile, and cytotoxicity of Tenebrio molitor larvae
  108. A zinc oxide–tin oxide–nerolidol hybrid nanomaterial: Efficacy against esophageal squamous cell carcinoma
  109. Research on technological process for production of muskmelon juice (Cucumis melo L.)
  110. Physicochemical components, antioxidant activity, and predictive models for quality of soursop tea (Annona muricata L.) during heat pump drying
  111. Characterization and application of Fe1−xCoxFe2O4 nanoparticles in Direct Red 79 adsorption
  112. Torilis arvensis ethanolic extract: Phytochemical analysis, antifungal efficacy, and cytotoxicity properties
  113. Magnetite–poly-1H pyrrole dendritic nanocomposite seeded on poly-1H pyrrole: A promising photocathode for green hydrogen generation from sanitation water without using external sacrificing agent
  114. HPLC and GC–MS analyses of phytochemical compounds in Haloxylon salicornicum extract: Antibacterial and antifungal activity assessment of phytopathogens
  115. Efficient and stable to coking catalysts of ethanol steam reforming comprised of Ni + Ru loaded on MgAl2O4 + LnFe0.7Ni0.3O3 (Ln = La, Pr) nanocomposites prepared via cost-effective procedure with Pluronic P123 copolymer
  116. Nitrogen and boron co-doped carbon dots probe for selectively detecting Hg2+ in water samples and the detection mechanism
  117. Heavy metals in road dust from typical old industrial areas of Wuhan: Seasonal distribution and bioaccessibility-based health risk assessment
  118. Phytochemical profiling and bioactivity evaluation of CBD- and THC-enriched Cannabis sativa extracts: In vitro and in silico investigation of antioxidant and anti-inflammatory effects
  119. Investigating dye adsorption: The role of surface-modified montmorillonite nanoclay in kinetics, isotherms, and thermodynamics
  120. Antimicrobial activity, induction of ROS generation in HepG2 liver cancer cells, and chemical composition of Pterospermum heterophyllum
  121. Study on the performance of nanoparticle-modified PVDF membrane in delaying membrane aging
  122. Impact of cholesterol in encapsulated vitamin E acetate within cocoliposomes
  123. Review Articles
  124. Structural aspects of Pt(η3-X1N1X2)(PL) (X1,2 = O, C, or Se) and Pt(η3-N1N2X1)(PL) (X1 = C, S, or Se) derivatives
  125. Biosurfactants in biocorrosion and corrosion mitigation of metals: An overview
  126. Stimulus-responsive MOF–hydrogel composites: Classification, preparation, characterization, and their advancement in medical treatments
  127. Electrochemical dissolution of titanium under alternating current polarization to obtain its dioxide
  128. Special Issue on Recent Trends in Green Chemistry
  129. Phytochemical screening and antioxidant activity of Vitex agnus-castus L.
  130. Phytochemical study, antioxidant activity, and dermoprotective activity of Chenopodium ambrosioides (L.)
  131. Exploitation of mangliculous marine fungi, Amarenographium solium, for the green synthesis of silver nanoparticles and their activity against multiple drug-resistant bacteria
  132. Study of the phytotoxicity of margines on Pistia stratiotes L.
  133. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part III
  134. Impact of biogenic zinc oxide nanoparticles on growth, development, and antioxidant system of high protein content crop (Lablab purpureus L.) sweet
  135. Green synthesis, characterization, and application of iron and molybdenum nanoparticles and their composites for enhancing the growth of Solanum lycopersicum
  136. Green synthesis of silver nanoparticles from Olea europaea L. extracted polysaccharides, characterization, and its assessment as an antimicrobial agent against multiple pathogenic microbes
  137. Photocatalytic treatment of organic dyes using metal oxides and nanocomposites: A quantitative study
  138. Antifungal, antioxidant, and photocatalytic activities of greenly synthesized iron oxide nanoparticles
  139. Special Issue on Phytochemical and Pharmacological Scrutinization of Medicinal Plants
  140. Hepatoprotective effects of safranal on acetaminophen-induced hepatotoxicity in rats
  141. Chemical composition and biological properties of Thymus capitatus plants from Algerian high plains: A comparative and analytical study
  142. Chemical composition and bioactivities of the methanol root extracts of Saussurea costus
  143. In vivo protective effects of vitamin C against cyto-genotoxicity induced by Dysphania ambrosioides aqueous extract
  144. Insights about the deleterious impact of a carbamate pesticide on some metabolic immune and antioxidant functions and a focus on the protective ability of a Saharan shrub and its anti-edematous property
  145. A comprehensive review uncovering the anticancerous potential of genkwanin (plant-derived compound) in several human carcinomas
  146. A study to investigate the anticancer potential of carvacrol via targeting Notch signaling in breast cancer
  147. Assessment of anti-diabetic properties of Ziziphus oenopolia (L.) wild edible fruit extract: In vitro and in silico investigations through molecular docking analysis
  148. Optimization of polyphenol extraction, phenolic profile by LC-ESI-MS/MS, antioxidant, anti-enzymatic, and cytotoxic activities of Physalis acutifolia
  149. Phytochemical screening, antioxidant properties, and photo-protective activities of Salvia balansae de Noé ex Coss
  150. Antihyperglycemic, antiglycation, anti-hypercholesteremic, and toxicity evaluation with gas chromatography mass spectrometry profiling for Aloe armatissima leaves
  151. Phyto-fabrication and characterization of gold nanoparticles by using Timur (Zanthoxylum armatum DC) and their effect on wound healing
  152. Does Erodium trifolium (Cav.) Guitt exhibit medicinal properties? Response elements from phytochemical profiling, enzyme-inhibiting, and antioxidant and antimicrobial activities
  153. Integrative in silico evaluation of the antiviral potential of terpenoids and its metal complexes derived from Homalomena aromatica based on main protease of SARS-CoV-2
  154. 6-Methoxyflavone improves anxiety, depression, and memory by increasing monoamines in mice brain: HPLC analysis and in silico studies
  155. Simultaneous extraction and quantification of hydrophilic and lipophilic antioxidants in Solanum lycopersicum L. varieties marketed in Saudi Arabia
  156. Biological evaluation of CH3OH and C2H5OH of Berberis vulgaris for in vivo antileishmanial potential against Leishmania tropica in murine models
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Heruntergeladen am 21.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2024-0108/html?srsltid=AfmBOooUryLSbf1m4Hd7YSKDXl-9hJ_wvCFFAf-VSCFNu5bgapvkwope
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