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Juniperus thurifera L., a plant endemic to the Moroccan High Atlas Mountains, thrives in extreme climatic conditions, resulting in the production of valuable secondary metabolites. This study aims to elucidate the phytochemical diversity and biological activities of J. thurifera essential oil (JTEO) through a comparative analysis of samples from two distinct regions: Tensift-Al Haouz and Azilal, using both in vitro and in silico methods. Gas Chromatography-Mass Spectrometry (GC-MS) analysis revealed 21 components in the Tensift-Al Haouz JTEO (99.99 % of the oil) and 23 components in the Azilal JTEO (99.58 % of the oil), with oxygenated monoterpenes being the predominant compounds in both. The biological activities were assessed in vitro. Antioxidant properties, evaluated using DPPH, FRAP, and ABTS assays, showed significant activity in both oils. Antibacterial activity was tested against two strains of Gram-positive and two strains of Gram-negative bacteria, with both oils demonstrating notable bacterial growth inhibition. Enzymatic assays assessed the antidiabetic (α-amylase and α-glucosidase), dermo-protective (tyrosinase and elastase), and neuroprotective (AChE and BChE) activities. Both oils displayed substantial inhibitory effects across all tested activities, with variations attributed to their distinct chemical compositions. In silico analyses of six target enzymes confirmed significant binding affinities of the major compounds. Notably, 2,2'-Thiobis(6-tert-butyl-p-cresol) exhibited strong binding affinities with AChE, BChE, α-amylase, α-glucosidase, tyrosinase, and elastase, with binding energies ranging from -10.0 to -6.2 kcal/mol. These findings indicate that JTEO is a rich source of bioactive compounds with promising potential in pharmacological and cosmetic applications., (© 2024 Wiley-VHCA AG, Zurich, Switzerland.)

The present study aimed to comprehensively characterize the volatile compounds from the aerial parts of Origanum grosii and evaluate their potential as antioxidants and enzyme inhibitors through both in vitro and in silico approaches. The essential oil's volatile constituents were identified using Gas Chromatography-Mass Spectrometry (GC-MS) analysis, revealing carvacrol (31 %), p-cymene (18.59 %), thymol (12.31 %), and ɣ-terpinene (10.89 %) as the major compounds. The antioxidant capacity was measured using three distinct assays. Notably, Origanum grosii essential oil (OGEO) exhibited significant antioxidant activity, with IC 50 values of 55.40±2.23, 81.65±3.26, and 98.04±3.87 μg/mL in DPPH, ABTS, and FRAP assays, respectively. The antibacterial activity was evaluated against both Gram-positive and Gram-negative bacterial strains, including Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 29213, Pseudomonas aeruginosa IH, and Listeria monocytogenes ATCC 13932. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were determined using the broth microdilution method. The inhibitory effects of OGEO were also assessed against enzymes implicated in human pathologies, including α-glucosidase, α-amylase, tyrosinase, and acetylcholinesterase (AChE). OGEO demonstrated notable inhibitory activity with IC 50 values of 49.72±1.64, 60.28±2.13, 97.14±5.15, and 119.42±2.97 μg/mL against elastase, α-glucosidase, tyrosinase, and α-amylase, respectively. Additionally, OGEO exhibited anti-AChE and anti-BChE effects, with values of 7.49±0.83 and 1.91±0.77 mg GALAE/g, respectively. The MIC values were 0.125 μg/mL for E. coli, P. aeruginosa, and S. aureus, and 0.25 μg/mL for L. monocytogenes, while MBC values ranged from 0.25 to 0.5 μg/mL. Compared to chloramphenicol (MIC: 8-16 μg/mL, MBC: 32-64 μg/mL), OGEO showed significantly stronger antibacterial effects. In silico analysis further supported the strong binding affinities of the major compounds to the target enzymes. Overall, OGEO shows promise as a natural agent with potential applications in the food, pharmaceutical, and cosmetic industries., (© 2024 Wiley-VHCA AG, Zurich, Switzerland.)

This research aimed to evaluate the antidiabetic, dermatoprotective, and antibacterial activities of Mentha viridis L. essential oil (MVEO) collected in the province of Ouezzane (Northwest Morocco). Gas chromatography-mass spectrometry (GC-MS) analysis revealed that the main constituents of MVEO were carvone (37.26 %), 1,8-cineole (11.82 %), limonene (5.27 %), α-terpineol (4.16 %), and β-caryophyllene (4.04 %). MVEO showed strong inhibitory effects on α-amylase and α-glucosidase activities, exceeding those of acarbose, but weak anti-elastase activity. The main compounds, β-caryophyllene (IC 50 =79.91±2.24 and 62.08±2.78 μg/mL) and limonene (IC 50 =90.73±3.47 and 68.98±1, 60 μg/mL), demonstrated the strongest inhibitory effects on both digestive enzymes (α-glucosidase and α-amylase, respectively). In silico investigations, using molecular docking, also showed the inhibitory potential of these bioactive compounds against the enzymes tested. In conclusion, MVEO, due to its main components such as limonene, 1,8-cineole, β-caryophyllene, carvone, and α-terpineol, shows promising prospects for drug discovery and natural therapeutic applications., (© 2024 Wiley-VHCA AG, Zurich, Switzerland.)

A mechanistic study was performed within the molecular electron density theory at the B3LYP/6-311G (d,p) computational level to explain the regioselectivity observed. An electron localization function analysis was also performed, and the results confirm the zwitterionic-type (zw-type) mechanism of the cycloaddition reactions between nitrile oxide and alkylated 4 H -chromene-2-carboxylate derivatives and shed more light on the obtained regioselectivity experimentally. In silico studies on the pharmacokinetics, ADME and toxicity tests of the compounds were also performed, and it was projected that compounds 5a , 5b , 5c and 5d are pharmacokinetic and have favorable ADME profiles. Moreover, docking and molecular dynamics investigations were conducted to evaluate the interactions, orientation and conformation of the target compounds on the active sites of four distinct enzymes. The results of this investigation showed that two compounds, 5a and 5c , interacted effectively with the S. aureus active site while maintaining acceptable binding energy.Communicated by Ramaswamy H. Sarma.

This study investigated the molecular, phytochemical, and biological aspects of ten local Moroccan traditional landrace Cannabis seeds. Genetic polymorphisms were analyzed using DNA barcode determination, revealing two distinct molecular profiles: " Cannabis , species sativa, subspecies indica " and " Cannabis , species sativa , subspecies sativa ". Furthermore, a new sequence was identified by sequencing of the THCA synthase coding gene. Chemical profiling via HPLC-ESI-FULL-MS and GC-MS-MS of AMSD1 maceration extracts revealed 13 non-volatile chemicals, including 3 inactive cannabinoids and 3 polyphenols, and 24 intriguing volatile compounds, including 7 previously unreported in Cannabis seed extracts. Moreover, the in vitro/in silico analysis provision of biological activities through their antioxidant power, antimicrobial effect, and cytotoxicity potency, as well as antiviral activity, were realized. These results contribute to a thorough comprehension of Moroccan Cannabis seeds, illuminating their molecular, phytochemical, and biological features. Furthermore, they highlight the seeds as a potential source of nutritious components with antioxidant properties, offering valuable insights for future research.

A series of new isoxazolederivatives incorporating the sulfonate ester function has been synthesized from 2-benzylidenebenzofuran-3(2 H)-one, known as aurone. The synthesis of the target compounds was carried out following an efficient methodology that allows access to the desired products in a reproducible way and with good yield. The structures of the synthesized compounds were established using NMR ( 1 H and 13 C) spectroscopy and mass spectrometry. A theoretical study was performed to optimize the geometrical structures and to calculate the structural and electronic parameters of the synthesized compounds. The calculations were also carried out to understand the influence and the effect of substitutions on the chemical reactivity of the studied compounds. The synthesized isoxazoles were screened for their antioxidant and antibacterial activities. The findings demonstrate that the studied compounds exhibit good to moderate antibacterial activity against the tested bacteria (Staphylococcus aureus, Bacillus subtilis, and Escherichia coli). Moreover, a number of the tested isoxazole derivatives exhibit high effectiveness against DPPH free radicals. Besides that, molecular docking studies were carried out to predict binding affinity and identify the most likely binding interactions between the active molecules and the target microorganisms' proteins. A 100 ns molecular dynamics study was then conducted to examine the dynamic behavior and stability of the highly potent isoxazole 4e in complex with the target bacterial proteins. Finally, the ADMET analyses suggest that all the synthesized isoxazoles have good pharmacokinetic profiles and non-toxicity and non-carcinogenicity in biological systems., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Ltd. All rights reserved.)

The aim of this study was the determination of the chemical compounds of Lavandula stoechas essential oil from Aknol (LSEO A ), Khenifra (LSEO K ), and Beni Mellal (LSEO B ), and the in vitro investigation of their antibacterial, anticandidal, and antioxidant effects, and in silico anti-SARS-CoV-2 activity. The chemical profile of LSEO was determined using GC-MS-MS analysis, the results of which showed a qualitative and quantitative variation in the chemical composition of volatile compounds including L-fenchone, cubebol, camphor, bornyl acetate, and τ-muurolol; indicating that the biosynthesis of essential oils of Lavandula stoechas (LSEO) varied depending on the site of growth. The antioxidant activity was evaluated using the ABTS and FRAP methods, our results showed that this tested oil is endowed with an ABTS inhibitory effect and an important reducing power which varies between 4.82 ± 1.52 and 15.73 ± 3.26 mg EAA/g extract. The results of antibacterial activity of LSEO A , LSEO K and LSEO B , tested against Gram-positive and Gram-negative bacteria, revealed that B. subtilis (20.66 ± 1.15-25 ± 4.35 mm), P. mirabilis (18.66 ± 1.15-18.66 ± 1.15 mm), and P. aeruginosa (13.33 ± 1.15-19 ± 1.00 mm) are the most susceptible strains to LSEO A , LSEO K and LSEO B of which LSEO B exhibits bactericidal effect against P. mirabilis . furthermore The LSEO exhibited varying degrees of anticandidal activity with an inhibition zones of 25.33 ± 0.5, 22.66 ± 2.51, and 19 ± 1 mm for LSEO K , LSEO B , and LSEO A , respectively. Additionally, the in silico molecular docking process, performed using Chimera Vina and Surflex-Dock programs, indicated that LSEO could inhibit SARS-CoV-2. These important biological properties of LSEO qualify this plant as an interesting source of natural bioactive compounds with medicinal actions.

Food is always subjected to microbial infection and lipid peroxidation, which frequently leads to serious food intoxications. In the present study, essential oils (EOs) extracted from Lavandula dentata Moroccan species and its major component (linalool) were chemically characterized and their antioxidant potential and antibacterial properties against foodborne pathogenic bacteria were examined. EOs phytochemical profile was carried out using gas chromatography-mass spectrometry analysis (GC-MS). The antioxidant potential was evaluated, in vitro , by use of the β -carotene discoloration assay and in silico vs. NADPH oxidase enzymatic complex as an antioxidant marker. The antibacterial proprieties were assessed by use of minimal inhibitory concentration (MIC) and disc diffusion methods, against Gram (-) bacteria ( Pseudomonas aeruginosa , Salmonella enterica , and Escherichia coli ) and Gram (+) bacteria ( Bacillus subtilis and Staphylococcus aureus ). Linalool (49.71%) was the major component among the eighteen components identified in Lavandula dentate EO, followed by camphor (14.36%) and borneol (8.21%). The studied EO and linalool compounds showed important antioxidant activity through the β -carotene discoloration test with IC 50 values of 35.72 ± 1.21 mg/mL and 30.32 ± 1.23 mg/mL, respectively. Among all the analyzed compounds of lavender EOs, thymol, carvacrol, and α -terpineol were the most active compounds against NADPH oxidase with a glide score of -6.483, -6.17, and -4.728 kcal/mol, respectively. 2D and 3D views showed the formation of hydrogen bonds between the most active compounds and the active site of NADPH oxidase. The antibacterial data showed a significant activity of Lavandula dentata essences against tested foodborne pathogenic bacteria, especially against S. aureus and B. subtilis . Linalool proved active toward the same bacteria and had closer activity to that of lavender essential oil. In light of the obtained findings, the essential oil of Lavandula dentata Moroccan species can be used in the packaging sector as a promising natural food conservative to limit lipid oxidation and treat foodborne infections., Competing Interests: The authors declare that they have no conflicts of interest., (Copyright © 2023 Youness El Abdali et al.)

A series of new heterocycle hybrids incorporating pyrazole and isoxazoline rings was successfully synthesized, characterized, and evaluated for their antimicrobial responses. The synthesized compounds were obtained utilizing N -alkylation and 1,3-dipolar cycloaddition reactions, as well as their structures were established through spectroscopic methods and confirmed by mass spectrometry. To get more light on the regioselective synthesis of new hybrid compounds, mechanistic studies were performed using DFT calculations with B3LYP/6-31G(d,p) basis set. Additionally, the results of the preliminary screening indicate that some of the examined hybrids showed potent antimicrobial activity, compared to standard drugs. The results confirm that the antimicrobial activity is strongly dependent on the nature of the substituents linked pyrazole and isoxazoline rings. Furthermore, molecular docking studies were conducted to highlight the interaction modes between the investigated hybrid compounds and the Escherichia coli and Candida albicans receptors. Notably, the results demonstrate that the investigated compounds have strong protein binding affinities. The stability of the formed complexes by the binding between the hybrid compound 6c , and the target proteins was also confirmed using a 100 ns molecular dynamics simulation. Finally, the prediction of ADMET properties suggests that almost all hybrid compounds possess good pharmacokinetic profiles and no signs of observed toxicity, except for compounds 6e , 6f , and 6g ., Competing Interests: The authors declare no competing financial interest., (© 2022 The Authors. Published by American Chemical Society.)

Juniperus thurifera is a native species to the mountains of the western Mediterranean region. It is used in traditional medicine as a natural treatment against infections. The present study aimed to carry out the chemical analysis and evaluate the antioxidant, antimicrobial, as well as in silico inhibition studies of the essential oils from Juniperus thurifera bark (EOEJT). Chemical characterization of EOEJT was done by gas chromatography (GC-MS). We have performed three antioxidant assays (Reducing power (FRAP), 2, 2-diphenylpicrylhydrazyl (DPPH), and total antioxidant capacity (TAC)) of the EOEJT. We next evaluated the antimicrobial activity against in silico study, which was carried out to help evaluate the inhibitory effect of EOEJT against NADPH oxidase. Results of the GC/MS analysis revealed seven major compounds in EOEJT wherein muurolol (36%) and elemol (26%) were the major components. Moreover, EOEJT possessed interesting antioxidant potential with an IC 50 respectively of 21.25 ± 1.02  μ g/mL, 481.02 ± 5.25  μ g/mL, and 271  μ g EAA/mg in DPPH, FRAP, and total antioxidant capacity systems. Molecular docking of EOEJT in NADPH oxidase active site showed inhibitory activity of α -cadinol and muurolol with a glide score of -6.041 and -5.956 Kcal/mol, respectively. As regards the antibacterial and antifungal capacities, EOEJT was active against all tested bacteria and all fungi, notably, against Escherichia coli K12 with an inhibition diameter of 21 mm and a MIC value of 0.67 mg/mL, as well as against Proteus mirabilis ATCC 29906 with an inhibition diameter of 18.33 ± 1.15 mm and a MIC value of 1.34 mg/mL. A more pronounced effect was recorded for the fungal pathogens Fusarium oxysporum MTCC 9913 with inhibition of 37.44 ± 0.28% and MIC value of 6.45 mg/mL, as well as against Candida albicans ATCC 10231 with an inhibition diameter of 20.33 ± 1.15 mm and a MIC value of 0.67 ± 0.00 mg/mL. Altogether, these results highlight the importance of EOEJT as a source of natural antibacterial and antioxidant drugs to fight clinically important pathogenic strains., Competing Interests: The authors declare that they have no conflicts of interest., (Copyright © 2022 Soufyane Lafraxo et al.)

In the title compound, C28H27NO3, the cyclo-hexa-none and isoxazole rings have envelope conformations, with the methyl-ene and spiro C atoms as the flaps, respectively. The mean plane of the isoxazole ring is inclined slightly to the p-tolyl ring, making a dihedral angle of 14.20 (9)°, and is nearly perpendicular to the mean plane through the tetra-lone moiety and to the meth-oxy-phenyl ring [dihedral angles = 83.41 (8) and 72.12 (9)°, respectively]. The crystal packing is stabilized mainly by van der Waals forces.

In the title compound, C20H20O2, the exocyclic C=C double bond has an E conformation. The ethyl substituent on the cyclo-hexa-none ring is in an axial orientation. The cyclo-hexa-none ring adopts a screw-boat conformation, with the methyl-ene C atom and the C atom bearing the 4-meth-oxy-benzyl-idene group displaced from the other atoms by 0.812 (1) and 0.334 (1) Å, respectively. The dihedral angle between the planes of the benzene rings is 42.20 (8)°. In the crystal, no directional inter-actions beyond van der Waals contacts are observed.

In the title compound, C(30)H(31)NO(2), the cyclo-hexa-none ring in the naphthalene fused-ring system adopts a half-chair conformation, presumably due to conjugation of the benzene ring. The naphthalene ring system makes dihedral angles of 86.63 (7), 65.15 (8) and 63.18 (8)° with respect to the two methyl-benzene planes and the 1,2-oxazole ring system. Inter-molecular C-H⋯O and C-H⋯N hydrogen bonding and C-H⋯π inter-actions stabilize the crystal structure. The H atoms of the two methyl groups of the methyl-phenyl groups are disordered over two positions with equal occupancies.

In the title compound C(22)H(24)O(2), the exocyclic C=C double bond is in an E configuration and the tert-butyl group is in an axial position on the cyclo-hexa-none ring. The cyclo-hexa-none ring in the dihydro-naphthalene fused-ring system adopts a half-chair conformation in both independent two mol-ecules in the asymetric unit. The benzene ring system is oriented angles of 43.97 (12) and 39.24 (12)° with respect to the naphthyl ring system in the two independent mol-ecules. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

In the title compound, C(19)H(18)O, the exocyclic C=C double bond has an E configuration. The ethyl substituent on the cyclo-hexa-none ring is in an axial position. The cyclo-hexa-none ring adopts a half-chair conformation, presumably due to conjugation in the benzene ring.

The title compound C(20)H(20)O(2), has the exocyclic C=C double bond in an E configuration. The two benzene rings form a dihedral angle of 72.92 (6)°.

In the title compound, C(30)H(31)NO(3), the tolyl ring is almost coplanar with the isoxazole ring [dihedral angle = 12.51 (7)°], whereas the meth-oxy-phenyl ring is almost perpendicular to the isoxazole ring [dihedral angle = 89.77 (5)°]. In the crystal, mol-ecules are connected through C-H⋯O hydrogen bonds, forming chains running along the a axis.