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1.
Chem Biodivers ; 21(6): e202301970, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38683904

ABSTRACT

New tranexamic acid (TXA) complexes of ferric(III), cobalt(II), nickel(II), copper(II) and zirconium(IV) were synthesized and characterized by elemental analysis (CHN), conductimetric (Λ), magnetic susceptibility investigations (µeff), Fourier transform infrared (FT-IR), proton nuclear magnetic resonance (1H-NMR), ultraviolet visible (UV-vis.), optical band gap energy (Eg) and thermal studies (TG/DTG and DTA). TXA complexes were established in 1 : 2 (metal: ligand) stoichiometric ratio according to CHN data. Based on FT-IR and 1H-NMR data the disappeared of the carboxylic proton supported the deprotonating of TXA and linked to metal ions via the carboxylate group's oxygen atom as a bidentate ligand. UV-visible spectra and magnetic moment demonstrated that all chelates have geometric octahedral structures. Eg values indicated that our complexes are more electro conductive. DTA revealed presence of water molecules in inner and outer spheres of the complexes. DTA results showed that endothermic and exothermic peaks were identified in the degradation mechanisms. The ligand and metal complexes were investigated for their antimicrobial and herbicidal efficacy. The Co(II) and Ni(II) complexes showed antimicrobial activity against some tested species. The obtained results showed a promising herbicidal effect of TXA ligand and its metal complexes particularly copper and zirconium against the three tested plants.


Subject(s)
Coordination Complexes , Microbial Sensitivity Tests , Tranexamic Acid , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemistry , Anti-Infective Agents/chemical synthesis , Antifungal Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/chemical synthesis , Coordination Complexes/pharmacology , Coordination Complexes/chemistry , Coordination Complexes/chemical synthesis , Fungi/drug effects , Molecular Structure , Structure-Activity Relationship , Tranexamic Acid/pharmacology , Tranexamic Acid/chemistry , Tranexamic Acid/chemical synthesis , Transition Elements/chemistry , Transition Elements/pharmacology , Ferric Compounds/chemical synthesis , Ferric Compounds/chemistry , Ferric Compounds/pharmacology
2.
Chem Biodivers ; 21(5): e202400274, 2024 May.
Article in English | MEDLINE | ID: mdl-38466647

ABSTRACT

The aim of the current study was to compare some biological activities of edible oils enriched with 10 % of cannabidiol (CBD samples) from the Slovak market. In addition, hemp, coconut, argan, and pumpkin pure oils were also examined. The study evaluated the fatty acids content, as well as antibacterial, antifungal, antioxidant, cytotoxic, and phytotoxic activities. The CBD samples presented antimicrobial activity against the tested bacterial strains at higher concentrations (10000 and 5000 mg/L) and antifungal activity against Alternaria alternata, Penicillium italicum and Aspergillus flavus. DPPH⋅ and FRAP assays showed greater activity in CBD-supplemented samples compared to pure oils and vitamin E. In cell lines (IPEC-J2 and Caco-2), a reduced cell proliferation and viability were observed after 24 hours of incubation with CBD samples. The oils showed pro-germinative effects. The tested activities were linked to the presence of CBD in the oils.


Subject(s)
Antioxidants , Cannabidiol , Cell Proliferation , Cannabidiol/pharmacology , Cannabidiol/chemistry , Humans , Cell Proliferation/drug effects , Antioxidants/pharmacology , Antioxidants/chemistry , Microbial Sensitivity Tests , Caco-2 Cells , Cell Survival/drug effects , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Plant Oils/pharmacology , Plant Oils/chemistry , Antifungal Agents/pharmacology , Antifungal Agents/chemistry , Penicillium/drug effects , Alternaria/drug effects , Aspergillus flavus/drug effects
3.
Int J Mol Sci ; 25(16)2024 Aug 06.
Article in English | MEDLINE | ID: mdl-39201258

ABSTRACT

The Middle Eastern prevalence of sickle cell anemia, a genetic disorder that affects red blood cells, necessitates additional research. On a molecular level, we sought to identify and sort the oral microbiota of healthy individuals and those with sickle cell anemia. Furthermore, it is crucial to comprehend how changes in the genetic makeup of the oral microbiota impact the state of sickle cell anemia. Using next-generation sequencing, the 16S rRNA amplicon was examined using saliva samples from 36 individuals with sickle cell anemia and healthy individuals. These samples were obtained from sickle cell anemia patients (18 samples) and healthy control participants (controls, 18 samples). Various analyses are conducted using bioinformatic techniques to identify distinct species and their relative abundance. Streptococcus, followed by Fusobacterium nucleatum, Prevotella, and Veillonella were the most prevalent genera of bacteria in the saliva of the SCA and non-SCA individuals according to our findings. Rothia mucilaginosa, Prevotella scoposa, and Veillonella dispar species were the dominant species in both sickle cell anemia and non-sickle cell anemia subjects. Streptococcus salivarius, Actinomyces graevenitzii, Actinomyces odontolyticus, and Actinomyces georgiae spp. were the most prevalent bacterial spp. in the studied SCA cases. The sequencing of the 16S rRNA gene yielded relative abundance values that were visualized through a heatmap analysis. Alterations in the oral microflora's constitution can significantly affect the susceptibility of sickle cell anemia patients to develop more severe health complications. Salivary diagnosis is a potential tool for predicting and preventing oral microbiome-related diseases in the future.


Subject(s)
Anemia, Sickle Cell , Microbiota , Mouth , RNA, Ribosomal, 16S , Saliva , Humans , Anemia, Sickle Cell/microbiology , Anemia, Sickle Cell/genetics , Mouth/microbiology , Microbiota/genetics , RNA, Ribosomal, 16S/genetics , Female , Male , Adult , Saliva/microbiology , Bacteria/genetics , Bacteria/classification , Bacteria/isolation & purification , Young Adult , Case-Control Studies , Adolescent , High-Throughput Nucleotide Sequencing , Middle Aged
4.
Int J Mol Sci ; 24(4)2023 Feb 07.
Article in English | MEDLINE | ID: mdl-36834673

ABSTRACT

Natural products are compounds produced by living organisms and can be divided into two main categories: primary (PMs) and secondary metabolites (SMs). Plant PMs are crucial for plant growth and reproduction since they are directly involved in living cell processes, whereas plant SMs are organic substances directly involved in plant defense and resistance. SMs are divided into three main groups: terpenoids, phenolics and nitrogen-containing compounds. The SMs contain a variety of biological capabilities that can be used as flavoring agents, food additives, plant-disease control, strengthen plant defenses against herbivores and, additionally, it can help plant cells to be better adapted to the physiological stress response. The current review is mainly focusing on certain key elements related to the significance, biosynthesis, classification, biochemical characterization and medical/pharmaceutical uses of the major categories of plant SMs. In addition, the usefulness of SMs in controlling plant diseases, boosting plant resistance and as potential natural, safe, eco-friendly substitutes for chemosynthetic pesticides were also reported in this review.


Subject(s)
Biological Products , Pesticides , Plants/metabolism , Pesticides/metabolism , Biological Products/metabolism , Plant Diseases , Pharmaceutical Preparations/metabolism
5.
Molecules ; 28(23)2023 Nov 24.
Article in English | MEDLINE | ID: mdl-38067495

ABSTRACT

Increasing antimicrobial resistance to the action of existing antibiotics has prompted researchers to identify new natural molecules with antimicrobial potential. In this study, a green system was developed for biosynthesizing gold nanoparticles (BAuNPs) using sage (Salvia officinalis L.) leaf extract bioconjugated with non-toxic, eco-friendly, and biodegradable chitosan, forming chitosan/gold bioconjugates (Chi/BAuNPs). Characterization of the BAuNPs and Chi/BAuNPs conjugates takes place using transmission electron microscopy (TEM), X-ray spectra, Fourier transform infrared (FT-IR) spectroscopy, and zeta potential (Z-potential). The chemical composition of S. officinalis extract was evaluated via gas chromatography/mass spectrometry (GC/MS). This study evaluated the antioxidant and antimicrobial activities of human pathogenic multidrug-resistant (MDR) and multisensitive (MS) bacterial isolates using the agar diffusion method. Chi/BAuNPs showed inhibition of the MDR strains more effectively than BAuNPs alone as compared with a positive standard antibiotic. The cytotoxicity assay revealed that the human breast adenocarcinoma cancer cells (MCF7) were more sensitive toward the toxicity of 5-Fu + BAuNPs and 5-Fu + Chi/BAuNPs composites compared to non-malignant human fibroblast cells (HFs). The study shows that BAuNPs and Chi/BAuNPs, combined with 5-FU NPs, can effectively treat cancer at concentrations where the free chemical drug (5-Fu) is ineffective, with a noted reduction in the required dosage for noticeable antitumor action.


Subject(s)
Anti-Infective Agents , Antineoplastic Agents , Chitosan , Metal Nanoparticles , Salvia officinalis , Humans , Gold/chemistry , Chitosan/chemistry , Spectroscopy, Fourier Transform Infrared , Metal Nanoparticles/chemistry , Anti-Infective Agents/pharmacology , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Fluorouracil , Plant Extracts/pharmacology , Plant Extracts/chemistry , Green Chemistry Technology/methods
6.
Chem Biodivers ; 19(2): e202100785, 2022 Feb.
Article in English | MEDLINE | ID: mdl-35072322

ABSTRACT

String of vanadium (IV), zirconium (IV), palladium (II), platinum (IV) and uranium (VI) chelates of 2-cyano-2-[(2-nitrophenyl)hydrazono]thioacetamide (Cnphta) were prepared and characterized by physicochemical, spectroscopic and thermal analyses. The formulae of the isolated solid complexes were assigned as [VO(Cnphta)2 (H2 O)]SO4 ⋅ 5H2 O (1), [ZrO(Cnphta)2 (H2 O)]Cl2 ⋅ 4H2 O (2), [Pd(Cnphta)2 ]Cl2 (3), [Pt(Cnphta)2 Cl2 ]Cl2 (4) and [UO2 (Cnphta)2 ](NO3 )2 ⋅ 5H2 O (5). The infrared assignments clearly showed that Cnphta ligand coordinated as a bidentate feature through the hydrazono nitrogen and the thioacetamide nitrogen for V(IV), Zr(IV) and U(VI) but displayed different behavior for Pd(II) and Pt(IV). Results of the molar conductivities measurements showed that the metal complexes were electrolytes in contrast with Cnphta ligand. The interpretation, mathematical analysis and evaluation of kinetic parameters were also carried out. In addition, the studied ligand and its new chelates were tested for their antimicrobial activity against some human or phytopathogenic microorganisms. The new metal complexes explicated promising antibacterial activity against all tested bacteria especially Staphylococcus aureus and Bacillus subtilis. Regarding the antifungal activity, all metal complexes were able to inhibit the mycelium growth of both tested pathogenic fungi. In particular Zr(IV) and Pt(IV) complexes showed the highest significant fungicidal effect against A. fumigatus similar to positive control.


Subject(s)
Coordination Complexes , Anti-Bacterial Agents/pharmacology , Coordination Complexes/chemistry , Coordination Complexes/pharmacology , Fungi , Humans , Ligands , Microbial Sensitivity Tests , Spectrophotometry, Infrared
7.
Int J Mol Sci ; 23(4)2022 Feb 14.
Article in English | MEDLINE | ID: mdl-35216223

ABSTRACT

Four novel ligand-metal complexes were synthesized through the reaction of Fe(III), pleaseCo(II), Zn(II), and Zr(IV) with Schiff base gemifloxacin reacted with ortho-phenylenediamine (GMFX-o-phdn) to investigate their biological activities. Elemental analysis, FT-IR, 1H NMR, UV-visible, molar conductance, melting points, magnetic susceptibility, and thermal analyses have been carried out for insuring the chelation process. The antimicrobial activity was carried out against Monilinia fructicola, Aspergillus flavus, Penicillium italicum, Botrytis cinerea, Escherichia coli, Bacillus cereus, Pseudomonas fluorescens, and P. aeruginosa. The radical scavenging activity (RSA%) was in vitro evaluated using ABTS method. FT-IR spectra indicated that GMFX-o-phdn chelated with metal ions as a tetradentate through oxygen of carboxylate group and nitrogen of azomethine group. The data of infrared, 1H NMR, and molar conductivity indicate that GMFX-o-phdn reacted as neutral tetra dentate ligand (N2O2) with metal ions through the two oxygen atoms of the carboxylic group (oxygen containing negative charge) and two nitrogen atoms of azomethine group (each nitrogen containing a lone pair of electrons) (the absent of peak corresponding to ν(COOH) at 1715 cm-1, the shift of azomethine group peak from 1633 cm-1 to around 1570 cm-1, the signal at 11 ppm of COOH and the presence of the chloride ions outside the complex sphere). Thermal analyses (TG-DTG/DTA) exhibited that the decaying of the metal complexes exists in three steps with the final residue metal oxide. The obtained data from DTA curves reflect that the degradation processes were exothermic or endothermic. Results showed that some of the studied complexes exhibited promising antifungal activity against most of the tested fungal pathogens, whereas they showed higher antibacterial activity against E. coli and B. cereus and low activity against P. fluorescens and P. aeruginosa. In addition, GMFX-o-phdn and its metal complexes showed strong antioxidant effect. In particular, the parent ligand and Fe(III) complex showed greater antioxidant capacity at low tested concentrations than that of other metal complexes where their IC50 were 169.7 and 164.6 µg/mL, respectively.


Subject(s)
Anti-Infective Agents/pharmacology , Ferric Compounds/pharmacology , Gemifloxacin/pharmacology , Metals/pharmacology , Schiff Bases/pharmacology , Antifungal Agents/pharmacology , Bacteria/drug effects , Coordination Complexes/pharmacology , Humans , Ligands , Microbial Sensitivity Tests/methods
8.
Int J Mol Sci ; 23(14)2022 Jul 20.
Article in English | MEDLINE | ID: mdl-35887366

ABSTRACT

Coumarin is highly distributed in nature, notably in higher plants. The biological features of coumarin include antibacterial, anticancer and antioxidant effects. It is well known that metal ions present in complexes accelerate the drug action and the efficacy of organic therapeutic agents. The main aim of the current study is the synthesis of different complexes of the interaction between ciprofloxacin hydrochloride (CIP) and coumarin derivative 7-hydroxy-4-methylcoumarin (HMC) with Zr(IV). The chelates of CIP with Zr(IV) were prepared and characterized by elemental analysis, melting point, conductance measurements, spectroscopic techniques involving IR, UV-Vis, 1H NMR, and thermal behavior (TG-DTG) in the presence of HMC, dimethylformamide (DMF), pyridine (Py), and triethylamine (Et3N). Results of molar conductivity tests showed that the new synthesized complexes are electrolytes with a 1:1 or 1:2 electrolyte ratio, with the chloride ions functioning as counter ions. According to IR spectra, CIP acts as a neutral bidentate ligand with Zr(IV) through one carboxylato oxygen and the carbonyl group, HMC as a monodentate through the carbonyl group, and DMF through the oxygen atom of the carbonyl group and the N atom of Py and Et3N. The thermal behavior of the complexes was carefully investigated using TG and DTG techniques. TG findings signal that water molecules are found as hydrated and coordinated. The thermal decomposition mechanisms proposed for CIP, HMC, and Zr(IV) complexes are discussed and the activation energies (Ea), Gibbs free energies (∆G*), entropies (∆S*), and enthalpies (∆H*) of thermal decomposition reactions have been calculated using Coats-Redfern (CR) and Horowitz-Metzeger (HM) methods. The studied complexes were tested against some human pathogens and phytopathogens, including three Gram-positive bacteria (Bacillus subtilis, B. cereus, Brevibacterium otitidis) and three Gram-negative bacteria (Escherichiacoli, Pseudomonas aeruginosa and Klebsiella pneumoniae), and compared to the free CIP and HMC parent compounds.


Subject(s)
Ciprofloxacin , Coordination Complexes , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacteria , Ciprofloxacin/pharmacology , Coordination Complexes/chemistry , Coumarins/pharmacology , Humans , Ions/pharmacology , Ligands , Microbial Sensitivity Tests , Oxygen/pharmacology , Spectrophotometry, Infrared
9.
Chem Biodivers ; 18(9): e2100365, 2021 Sep.
Article in English | MEDLINE | ID: mdl-34288421

ABSTRACT

String of Fe(III), Cu(II), Zn(II) and Zr(IV) complexes were synthesized with tetradentateamino Schiff base ligand derived by condensation of ethylene diamine with gemifloxacin. The novel Schiff base (4E,4'E)-4,4'-(ethane-1,2-diyldiazanylylidene)bis{7-[(4Z)-3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid} (GMFX-en) and its metal complexes were identified and confirmed by elemental analyses, FT-IR, UV/VIS, 1 H-NMR spectra, magnetic susceptibility, conductometric measurements and thermal analyses. The FT-IR spectral data showed the chelation behavior of GMFX-en toward the metal ions through oxygen of carboxylate group and nitrogen of azomethine group. In the light of all spectral data, these complexes presumably have octahedral geometry configurations. Thermal analysis specified that the decaying of the metal complexes exist in two or three steps with the final residue metal oxides. Antimicrobial activity of the new prepared metal complexes was screened against some common phytopathogens and their mode of action has been also discussed. The potential phytotoxic effectiveness of the new complexes was furthermore inspected on two commonly experimental plants. The complexes showed significant antimicrobial and phytotoxic effects against the majority of tested phytopathogens and the two tested plants, respectively. The potential antimicrobial activity of the complexes proved their possibility to be used successfully in agropharmacutical industry to control many serious phytopathogens. The phytotoxicity of the studied complexes also indicated their possibility as potential bio-based herbicides alternatives to weed control in crop fields.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Coordination Complexes/pharmacology , Gemifloxacin/pharmacology , Metals, Heavy/pharmacology , Schiff Bases/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Bacteria/drug effects , Coordination Complexes/chemical synthesis , Coordination Complexes/chemistry , Fungi/drug effects , Gemifloxacin/chemistry , Lepidium sativum/drug effects , Solanum lycopersicum/drug effects , Metals, Heavy/chemistry , Microbial Sensitivity Tests , Schiff Bases/chemistry
10.
Molecules ; 26(5)2021 Mar 09.
Article in English | MEDLINE | ID: mdl-33803210

ABSTRACT

Recently, the design of new biological metal-ligand complexes has gained a special interest all over the world. In this research, new series of mixed ligand complexes from meloxicam (H2mel) and glycine (Gly) were synthesized. Structures of the compounds were investigated employing elemental analyses, infrared, electronic absorption, 1H NMR, thermal analyses, effective magnetic moment and conductivity. The estimated molar conductivity of the compounds in 1 × 10-3 M DMF solution indicates the non-electrolyte existence of the examined complexes. Additionally, the effective magnetic moment values refer to the complexes found as octahedral molecular geometry. The data of the infrared spectra showed the chelation of H2mel and Gly with metal ions from amide oxygen and nitrogen of the thyizol groups of H2mel and through nitrogen of the amide group and oxygen of the carboxylic group for Gly. Thermal analyses indicated that the new complexes have good thermal stability and initially lose hydration water molecules followed by coordinated water molecules, Gly and H2mel. The kinetic parameters were calculated graphically using Coats-Redfern and Horowitz-Metzeger methods at n = 1 and n ≠ 1. The density functional theory (DFT) calculations were performed at B3LYP levels. The optimized geometry of the ligand and its complexes were obtained based on the optimized structures. The data indicated that the complexes are soft with η value in the range 0.114 to 0.086, while η = 0.140 for free H2mel. The new prepared complexes were investigated as antibacterial and antifungal agents against some phyto- and human pathogens and the minimum inhibitory concentration (MIC) data showed that complex (A) has the lowest MIC for Listeria and E. coli (10.8 µg/mL).


Subject(s)
Meloxicam/chemistry , Meloxicam/pharmacology , Anti-Bacterial Agents/pharmacology , Anti-Infective Agents/pharmacology , Bacteria/drug effects , Coordination Complexes/chemistry , Escherichia coli/drug effects , Ions , Kinetics , Ligands , Magnetic Resonance Spectroscopy/methods , Meloxicam/chemical synthesis , Metals/chemistry , Microbial Sensitivity Tests , Molecular Structure , Schiff Bases/chemistry , Spectrophotometry, Infrared/methods , Thermodynamics
12.
Molecules ; 25(5)2020 Feb 25.
Article in English | MEDLINE | ID: mdl-32106569

ABSTRACT

In the present work, tenoxicam (H2Ten) reacted with Mn(II), Co(II), Ni(II), Cu(II) and Zn (II) ions in the presence of 1.10-phenthroline (Phen), forming new mixed ligand metal complexes. The properties of the formed complexes were depicted by elemental analyses, infrared, electronic spectra, proton nuclear magnetic resonance (1H NMR), mass spectrometry, thermogravimetric (TGA) and differential thermogravimetric (DTG) analysis, molar conductance and magnetic moment. IR spectra demonstrated that H2Ten acted as a neutral bidentate ligand, coordinated to the metal ions via the pyridine-N and carbonyl group of the amide moiety, and Phen through the nitrogen atoms. Kinetic thermodynamics parameters activation energy (E*), enthalpy of activation (ΔH*), entropy of activation (ΔS*), Gibbs, free energy (ΔG*) associated to the complexes have been evaluated. Antibacterial screening of the compounds was carried out in vitro against Clavibacter michiganensis, Xanthomonas campestris and Bacillus megaterium. Antifungal activity was performed in vitro against Monilinia fructicola, Penicillium digitatum and Colletotrichum acutatum. The possible phytotoxic effect of the studied compounds was also investigated on Solanum lycopersicum (tomatoes) and Lepidium sativum (garden cress) seeds. The anticancer activity was screened against cell cultures of HCT-116 (human colorectal carcinoma), HepG2 (human hepatocellular carcinoma) and MCF-7 (human breast adenocarcinoma).


Subject(s)
Anti-Bacterial Agents/chemistry , Antifungal Agents/chemistry , Coordination Complexes/chemistry , Piroxicam/analogs & derivatives , Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Bacillus megaterium/drug effects , Cobalt/chemistry , Coordination Complexes/pharmacology , Copper/chemistry , Humans , Ligands , Magnetic Resonance Spectroscopy , Manganese/chemistry , Microbial Sensitivity Tests , Molecular Structure , Nickel/chemistry , Piroxicam/chemistry , Piroxicam/pharmacology , Schiff Bases , Spectrophotometry, Infrared , Thermodynamics , Xanthomonas campestris/drug effects , Zinc/chemistry
13.
Molecules ; 25(3)2020 Jan 29.
Article in English | MEDLINE | ID: mdl-32013272

ABSTRACT

Searching for new bio-based herbicides is crucial for decreasing chemical pollution, protecting the environment, and sustaining biodiversity. Origanum vulgare is considered a promising source of essential oil with herbicidal effect. The mode of action is not known. The present study focused on (1) comparison of phytotoxic activity of Origanum vulgare EO on monocot (Triticum aestivum and Hordeum vulgare) and dicot species (Lepidium sativum and Sinapis alba); (2) and evaluating other antimicrobial biological activities against phytopatogen bacteria (Clavibacter michiganensis, Pseudomonas syringae pv. phaseolicola, Pseudomonas savastanoi, and Xanthomonas campestris); antifungal activity against Monilinia fructicola, Aspergillus niger, Penicillium expansum, and Botrytis cinerea; cytotoxic activity and antioxidant activity. According to the GC/MS analyses, the EO belongs to the thymol chemotype O. vulgare with its high content of thymol (76%). Germination of all four species was not influenced by EO. The phytotoxic effect was statistically significant in the monocot species, while in the dicot species the opposite was observed-a stimulation effect, which was also statistically significant. Strong biological activity of O. vulgare EO was noted on all phytopatogen bacteria and fungi in the highest dose. Cytotoxic activity showed an IC50 = 50.5 µg/mL. Antioxidant activity showed an IC50 = 106.6 µg/mL after 45 min experimental time. Based on the presented results, it is possible to conclude that thymol chemotype O. vulgare essential oil could be potentially used as a herbicide with selective effects on monocot plant species.


Subject(s)
Herbicides/pharmacology , Oils, Volatile/pharmacology , Origanum/chemistry , Plant Oils/pharmacology , Plants/drug effects , Thymol/pharmacology , Anti-Infective Agents/isolation & purification , Anti-Infective Agents/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Cytotoxins/isolation & purification , Cytotoxins/pharmacology , Drug Screening Assays, Antitumor , Free Radical Scavengers , Gas Chromatography-Mass Spectrometry , Herbicides/isolation & purification , Hordeum/drug effects , Humans , Lepidium sativum/drug effects , Oils, Volatile/chemistry , Oils, Volatile/isolation & purification , Plant Oils/chemistry , Plant Oils/isolation & purification , Sinapis/drug effects , Species Specificity , Thymol/chemistry , Thymol/isolation & purification , Triticum/drug effects
14.
Chem Biodivers ; 16(3): e1800633, 2019 Mar.
Article in English | MEDLINE | ID: mdl-30629800

ABSTRACT

Two novel ligand-metal complexes were prepared through the reaction of Zn(II) and Sn(II) with moxifloxacin (MOX) in the presence of glycine (Gly) to investigate their biological activities. IR, UV/VIS and 1 H-NMR analysis have been carried out for insuring the chelation process. Results suggested that MOX and Gly react with the metal ions through the carbonyl oxygen atom and the oxygen atom of the carboxylic group of MOX and Gly. The antimicrobial activity was carried out against some common bacterial and fungal pathogens and the radical scavenging activity (RSA%) was evaluated using DPPH and ABTS methods. Phytotoxic effect of the prepared complexes was evaluated in vitro against Raphanus raphanistrum and Lepidium sativum. Hemolytic activity was tested against cell membrane of erythrocytes. Results showed that the two prepared complexes exhibited high antimicrobial activity against all tested phytopathogens and no significant phytotoxic effect has been observed. Only MOX-Zn(II) complex showed moderate hemolysis at 100 % concentration.


Subject(s)
Antioxidants/pharmacology , Cell Membrane/drug effects , Coordination Complexes/pharmacology , Erythrocytes/drug effects , Lepidium sativum/drug effects , Raphanus/drug effects , Antioxidants/chemical synthesis , Antioxidants/chemistry , Benzothiazoles/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Coordination Complexes/chemical synthesis , Coordination Complexes/chemistry , Glycine/chemistry , Glycine/pharmacology , Humans , Magnetic Resonance Spectroscopy , Molecular Structure , Moxifloxacin/chemistry , Moxifloxacin/pharmacology , Picrates/antagonists & inhibitors , Spectrophotometry, Ultraviolet , Sulfonic Acids/antagonists & inhibitors , Tin/chemistry , Tin/pharmacology , Zinc/chemistry , Zinc/pharmacology
15.
Molecules ; 24(14)2019 Jul 16.
Article in English | MEDLINE | ID: mdl-31315175

ABSTRACT

There is a growing interest in a potential use of essential oils (EOs) as a replacement for traditional pesticides and herbicides. The aims of this study were to: (i) Identify the chemical composition of the two EOs derived from Origanum heracleoticum L. and O. majorana L., (ii) evaluate the in vitro antifungal activity of the EOs against some postharvest phytopathogens (Botrytis cinerea, Penicillium expansum, Aspergillus niger and Monilinia fructicola), (iii) evaluate the in vitro antibacterial activity against Bacillus megaterium, Clavibacter michiganensis, Xanthomonas campestris, Pseudomonas fluorescens and P. syringae pv. phaseolicola, (iv) evaluate the effect of both studied EOs on the spore germination percentage and their minimum inhibitory concentration (MIC) against M. fructicola, and (v) study the possible phytotoxicity of the two EOs and their major constituents, carvacrol for O. heracleoticum and terpinen-4-ol for O. majorana, against tha germination and initial radicle growth of radish, lettuce, garden cress and tomato. The two EOs demonstrated promising in vitro antimicrobial and antifungal activities against all tested microorganisms. EOs showed high inhibition of spore germination percentage at the minimal inhibitory concentration of 500 and 2000 µg/mL, respectively. Moreover, both germination and radical elongation of selected plant species were sensitive to the oils.


Subject(s)
Anti-Infective Agents/chemistry , Oils, Volatile/chemistry , Origanum/chemistry , Spores/drug effects , Anti-Infective Agents/pharmacology , Cymenes/pharmacology , Lepidium sativum/growth & development , Lepidium sativum/microbiology , Lactuca/growth & development , Lactuca/microbiology , Solanum lycopersicum/growth & development , Solanum lycopersicum/microbiology , Microbial Sensitivity Tests , Oils, Volatile/pharmacology , Plant Diseases/microbiology , Plant Diseases/prevention & control , Plant Oils/chemistry , Plant Oils/pharmacology , Raphanus/growth & development , Raphanus/microbiology , Terpenes/pharmacology
16.
Molecules ; 24(7)2019 Mar 27.
Article in English | MEDLINE | ID: mdl-30934783

ABSTRACT

Plant essential oils (EOs) are one of the most relevant natural products due to their biological, medicinal, and nutritional properties. The promising biological effects of many plants EOs encourage researchers to study their biochemical properties to be used as possible natural alternatives for commercial pesticides and not only as herbal medicines. The current research has been conducted to study the microbicide effect of Solidago canadensis L. EO to control some common plant diseases caused by several postharvest phytopathogenic fungi (Monilinia fructicola, Botrytis cinerea, Aspergillus niger, and Penicillium expansum) in comparison with Azoxystrobin as a large spectrum fungicide. The antibacterial activity has been carried out against some phytopathogenic bacteria (Bacillus megaterium and Clavibacter michiganensis (G+ve) and Xanthomonas campestris, Pseudomonas fluorescens, and Pseudomonas syringae pv. phaseolicola (G-ve)) compared to the synthetic antibiotic Tetracycline. Minimum inhibitory concentration was carried out to determine the lowest effective EO dose using a 96-well microplate. The cell membrane permeability was also evaluated by measuring the electric conductivity (EC) to examine the possible mechanisms of action of S. canadensis EO. Chemical characterization of EO has been carried out using gas chromatography and mass spectrometry (GC-MS). Thirty-two identified components in S. canadensis EO presented 97.7% of total compounds in EO. The principal compounds were identified as germacrene D (34.9%), limonene (12.5%), α-pinene (11.6%), ß-elemene (7.1%), and bornyl acetate (6.3%). In addition, S. canadensis EO demonstrated promising in vitro antimicrobial activities against the majority of tested phytopathogens at all tested concentrations.


Subject(s)
Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Oils, Volatile/chemistry , Oils, Volatile/pharmacology , Phytochemicals/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Solidago/chemistry , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Bacteria/drug effects , Cell Membrane Permeability/drug effects , Fungi/drug effects , Gas Chromatography-Mass Spectrometry , Microbial Sensitivity Tests
17.
Molecules ; 23(5)2018 May 15.
Article in English | MEDLINE | ID: mdl-29762531

ABSTRACT

Three novel mixed ligand metal complexes have been synthesized by the reaction of Zn(II), Sn(II), and Ce(III) with gemifloxacin (GMFX) in the presence of glycine (Gly) (1:1:1 molar ratio). The coordination possibility of the two ligands toward metal ions has been proposed in the light of elemental analysis, molar conductance, spectral infrared (IR), ultraviolet-visible (UV-Vis) and proton-nuclear magnetic resonance (¹H NMR), and magnetic studies. Results suggest that GMFX and Gly interact with the metal ions as bidentate ligands. Electronic and magnetic data proposed the octahedral structure for all complexes under investigation. Antibacterial screening of the compounds was carried out in vitro against two Gram-positive bacteria, Clavibacter michiganensis and Bacillus megaterium, and two Gram-negative bacteria, Escherichia coli and Xanthomonas campestris. Antifungal activity was performed in vitro against Rhizoctonia solani, Sclerotinia sclerotiorum, Aspergillus niger, Botrytis cinerea, and Penicillium digitatum. The ligands and their complexes were also screened for their antioxidant activity. Results showed that some metal complexes showed more biological efficiency than the parent GMFX drug.


Subject(s)
Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/pharmacology , Fluoroquinolones/chemical synthesis , Fluoroquinolones/pharmacology , Glycine/chemistry , Naphthyridines/chemical synthesis , Naphthyridines/pharmacology , Zinc/chemistry , Anti-Bacterial Agents/chemistry , Fluoroquinolones/chemistry , Gemifloxacin , Ions/chemistry , Ligands , Magnetic Resonance Spectroscopy , Metals/chemistry , Microbial Sensitivity Tests , Molecular Structure , Naphthyridines/chemistry , Spectroscopy, Fourier Transform Infrared , Spectrum Analysis
18.
Molecules ; 22(9)2017 Aug 30.
Article in English | MEDLINE | ID: mdl-28867805

ABSTRACT

The potential of plant essential oils (EOs) in anticancer treatment has recently received many research efforts to overcome the development of multidrug resistance and their negative side effects. The aims of the current research are to study (i) the cytotoxic effect of the crude EO extracted from Origanum vulgare subsp hirtum and its main constituents (carvacrol, thymol, citral and limonene) on hepatocarcinoma HepG2 and healthy human renal cells HEK293; (ii) the antibacterial and phytotoxic activities of the above EO and its main constituents. Results showed that cell viability percentage of treated HepG2 by EO and its main constituents was significantly decreased when compared to untreated cells. The calculated inhibition concentration (IC50) values for HepG2 were lower than healthy renal cells, indicating the sort of selectivity of the studied substances. Citral is not potentially recommended as an anticancer therapeutic agent, since there are no significant differences between IC50 values against both tested cell lines. Results showed also that oregano EO and its main constituents have a significant antibacterial activity and a moderate phytotoxic effect. The current research verified that oregano EO and its main constituents could be potentially utilized as anticancer therapeutic agents.


Subject(s)
Carcinoma, Hepatocellular/drug therapy , Carcinoma, Hepatocellular/pathology , Liver Neoplasms/drug therapy , Liver Neoplasms/pathology , Origanum/chemistry , Plant Extracts/therapeutic use , Anti-Bacterial Agents/pharmacology , Bacillus megaterium/drug effects , Cell Death/drug effects , Cell Shape/drug effects , Cell Survival/drug effects , Germination/drug effects , HEK293 Cells , Hep G2 Cells , Humans , Microbial Sensitivity Tests , Oils, Volatile/chemistry , Oils, Volatile/pharmacology , Plant Extracts/pharmacology , Plant Weeds/drug effects
19.
Chem Biodivers ; 11(4): 639-51, 2014 Apr.
Article in English | MEDLINE | ID: mdl-24706631

ABSTRACT

The chemical composition of the essential oils of Origanum vulgare ssp. hirtum, growing wild in three different localities in the Southern Apennines, was studied by GC-FID and GC/MS analyses. In total, 103 compounds were identified. The oils were mainly composed of phenolic compounds and all oils belonged to the chemotype carvacrol/thymol. The three essential oils were evaluated for their in vitro phytotoxic activity by determining their influence on the germination and initial radicle elongation of Sinapis arvensis L., Phalaris canariensis L., Lepidium sativum L., and Raphanus sativus L. The seed germination and radicle growth were affected in various degrees. Moreover, the antifungal activity of the three essential oils was assayed against three species causing pre- and postharvest fruit decay (Monilinia laxa, M. fructigena, and M. fructicola). At 1000 ppm, the three oils completely inhibited fungal growth. The hemolytic activity of the oils was assayed and showed no effect on the cell membranes of bovine erythrocytes.


Subject(s)
Oils, Volatile/analysis , Oils, Volatile/chemistry , Oils, Volatile/toxicity , Origanum/chemistry , Animals , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Ascomycota , Cattle , Cymenes , Erythrocytes/drug effects , Gas Chromatography-Mass Spectrometry , Germination/drug effects , Italy , Lepidium sativum/drug effects , Monoterpenes/analysis , Raphanus/drug effects , Sinapis/drug effects , Thymol/analysis
20.
Plants (Basel) ; 13(18)2024 Sep 17.
Article in English | MEDLINE | ID: mdl-39339573

ABSTRACT

Chitin (Ct) is a crucial biopolymer present in fungi, algae, arthropods, and is usually obtained from crustacean shells. Chitosan (Cs) is a derivative from Ct deacetylation, and possesses numerous uses in various agro-industrial fields. Research on fungal-derived Ct and Cs is mostly focused on pharmaceutical uses, however their uses for plant disease control remain less explored. The main objective of the current study is to evaluate the possibility of using chitosan obtained from mushroom Pleurotus eryngii (Cs-Pe) for controlling some phytopathogens compared to commercial chitosan (C.Cs). This study is focused on the following key areas: (i) extracting Ct from P. eryngii mycelium and converting it to Cs through deacetylation, using both bleaching and non-bleaching methods; (ii) conducting a physico-chemical characterization and in vitro evaluation of the antimicrobial activity of the obtained Cs; (iii) performing an in vivo assessment of the phytotoxic and cytotoxic effects of Cs; and (iv) investigating in vivo the impact of the studied chitosan on fruit quality and its biocontrol efficacy against Monilinia laxa infections in plum fruits. Results showed that Cs-Pe, especially the unbleached one, displayed promising in vitro antimicrobial activity against the majority of tested pathogens. Regarding the cytotoxicity, the highest significant increase in cell abnormality percentage was observed in the case of C.Cs compared to Cs-Pe. In the in vivo study, Cs-Pe acted as a protective barrier, lowering and/or preventing moisture loss and firmness of treated plums. The studied Cs-Pe demonstrated notable efficacy against M. laxa which decreased the fruits' percentage decline. These results strongly suggest that Cs derived from P. eryngii is a potential candidate for increasing plums' shelf-life. This research shed light on the promising applications of P. eryngii-derived Cs in the agri-food field.

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