Characterization and bioactive potentials of secondary metabolites from Fusarium chlamydosporum

Abstract

A search for bioactive secondary metabolites from the endophytic fungus Fusarium chlamydosporum, isolated from the root of Suaeda glauca, led to the isolation of three indole derivatives (1–3), three cyclohexadepsipeptides (4–6), and four pyrones (7–10). The structures of new (1) and known compounds (2–10) were elucidated on the basis of extensive spectroscopic analysis. All these compounds were evaluated for phytotoxic, antimicrobial activities, and brine shrimp lethality. Compound 1 showed significant phytotoxic activity against the radicle growth of Echinochloa crusgalli, even better than the positive control of 2,4-D. Cyclohexadepsipeptides (4–6) and pyrones (7–10) exhibited brine shrimp lethality, especially 4 and 7 with the LD₅₀ values of 2.78 and 7.40?μg mL^?1, respectively, better than the positive control.     

Evaluation of the cytotoxicity on breast cancer cell of extracts and compounds isolated from Hyptis pectinata (L.) poit

Abstract

Hyptis pectinata is a herb popularly used in Brazil for the treatment of inflammations, pain, bacterial infections and cancer. In the present study, inflorescences (MPIn), leaves (MPL), branches (MPB), root (MPR) extracts and three compounds isolated from MPIn were assayed against breast tumor cell lines. The structures of the three compounds (pectinolide J, hyptolide and pectinolide E) were determined by means of spectroscopic analysis. Pectinolide J was isolated for the first time. The MPIn, MPL and MPR exhibited specific antiproliferative activity on tumor cell lines when compared to normal cell lines with IC₅₀ of 52.01?±?0.64, 45.91?±?0.02?μg/mL and 82.84?±?0.03?μg/mL, respectively. Although the isolated substances did not present good antiproliferative activity, when the three were associated, a greater biological effect was observed, suggesting a synergistic effect. Hyptolide (5.6?±?0.4?μg/mL) showed IC₅₀ sufficiently low to be considered as a drug prototype.     

Design and nonlinear optical properties (NLO) using DFT approach of new Cr(III), VO(II), and Ni(II) chelates incorporating tri-dentate imine ligand for DNA interaction,antimicrobial, anticancer activities and molecular docking studies

In recent years, metals based antitumor complexes have played a vital role in chemotherapy. Therefore, in this study, some new imine Cr(III), VO(II) and Ni(II) complexes incorporating ESAP imine ligand (2-Ethoxy-6-((2-hydroxy-phenylimino)-methyl)-phenol were designed and synthesized. The investigated complexes were fully characterized by micro analysis, infrared, electronic spectra, thermal analysis (TGA), conductivity as well as magnetic susceptibility measurements. Moreover, the stability constants of the prepared complexes were determined spectrophotometrically. The results suggest that the titled ESAP imine ligand serves as tri-dentate moiety through deprotonated two phenolic oxygen and azomethene nitrogen atoms for coordination to Cr(III) in octahedral geometry, tetrahedral to Ni(II) and distorted square pyramidal to VO(II). The electronic structure and nonlinear optical parameters NLO of the newly synthesized complexes are investigated theoretically at the B3LYP/GEN level of theory. The studied complexes show promising optical properties. Indeed, the prepared compounds were evaluated for antimicrobial effect against some types of bacteria and fungi. The investigated complexes exhibit a stronger antimicrobial efficiency compared to its ligand. Moreover, the interaction of the complexes with CT-DNA was monitored using spectral studies, viscosity and gel electrophoreses measurements. Furthermore, the cytotoxic activity of the prepared imine complexes on human colon carcinoma cells, hepatic cellular carcinoma cells and breast carcinoma cells have shown promising results and enhancement of the anti-proliferative activity compared to its ligand. The molecular docking into TRK (PDB: 1t46) was done for the optimization of the investigated compounds as potential TRK inhibitors.     

In-vitro cytotoxicity of synthesized phthalide-fused indoles and indolines against HL-60 and HepG2 cells

Phthalide derivatives bearing indole or indoline moieties were successfully synthesized via eco-friendly method and were evaluated for their antiproliferative activity on HL-60 and HepG2 cell lines in vitro. At a final concentration of 100 μM, most of the compounds showed moderate potency on both the cell lines tested. Compound 3b bearing 5-chloro substituted indoline had the best potency against HL-60 and HepG2 cell lines with IC₅₀ values of 45.4 and 57.7 μM, respectively. It was also found that replacement of a conjugated indoline to indole moiety gave better antiproliferative activity on HL-60 cells by almost two-fold. Morphological observation demonstrated numerous fragmented nuclei which are indicative of apoptosis. Molecular docking studies predicted non-covalent interactions and H-bonding of selected compounds with the P2 binding hot spot of the anti-apoptotic protein, Bcl-2, formed by Asp108, Phe109, Met112, Leu134, Arg143, Ala146 and Val153. Overall, our work highlights the potential of synthesized phthalide-fused indoles or indolines as antitumor agents.     

Visible light driven photocatalytic activity of ZnO/CuO nanocomposites coupled with rGO heterostructures synthesized by solid-state method for RhB dye degradation

Metal oxide frame works along with carbon materials have been attracting tremendous attention of researches as the potential materials for energy and environmental remediation. In the present work heterostructures of (ZnO/CuO)/rGO ternary nanocomposites were synthesized by solid-state method. The crystalline structure of the nanoparticles was obtained from the XRD analysis. Optical band gap of the ZnO nanoparticles (3.1 eV) is tuned to 2.8 eV in the synthesized (ZnO/CuO)/rGO ternary nanocomposites. Field emission scanning electron microscope images of the (ZnO/CuO)/rGO ternary nanocomposites revealed formation of well-developed flowers like morphology of (ZnO/CuO) nanoparticles on rGO sheets. Photoluminescence spectroscopy analysis of (ZnO/CuO)/rGO ternary nanocomposites show enhancement in the electron-hole pair separation and thereby diminishing electron-hole pairs recombination rates effectively. In the present work, the photocatalytic activity of the ZC₃G₁₅ ternary nanocomposites show 99% and 93% of degradation efficiency respectively against RhB dye and 4-chlorophenol for 20 min under visible light irradiation. Thus, the simple solid-state method provides the effective ternary nanocomposites heterostructures light harvesting material for energy and environmental remediation.     

Chemical composition variations,allelopathic, and antioxidant activities of Symphyotrichum squamatum (Spreng.) Nesom essential oils growing in heterogeneous habitats

The present study aimed to analyze the chemical composition of Symphyotrichum squamatum EOs growing in two different habitats to explore the ecological implication on the EOs production and evaluate their antioxidant and allelopathic potentialities. The EOs from the aerial parts collected from coastal Mediterranean belt and inland abandoned habitats in the Nile Delta of Egypt, were extracted and analyzed using gas chromatography-mass spectrometry. Sixty compounds were characterized as overall constituents of EOs from both samples. Sesquiterpenes were the main component and represented by 69.77% and 88.68% from coastal and inland sample, respectively. The coastal sample attained a relatively high content of monoterpenes compared to the inland sample. Major compounds from the EOs of the coastal habitat sample, were humulene epoxide, (-)-spathulenol, (-)-caryophyllene oxide, germacrene D, and α-humulene representing 59.72%. However, β-pinene, germacrene D, α-humulene, α-muurolene, humulene epoxide, (-)-caryophyllene oxide, and β-cadinene were the major compounds of EOs of the inland habitat sample, representing 63.70%. The correlation analysis revealed more correlation between the Egyptian inland S. squamatum and the Japanese ecospecies. However, the Egyptian coastal S. squamatum and Turkish ecospecies were more correlated to each other. The present data suggested that chemotypes of S. squamatum maintain their typical pattern despite ecological or climatic differences. The EOs of S. squamatum showed moderate antioxidant activity, wherein coastal and inland EOs have an IC₅₀ value of 382.53 and 559.63 μL L⁻¹, respectively. Also, the EOs from both habitats showed moderate allelopathic activity against the noxious weed Bidens pilosa. However, the activity of the coastal sample was more than inland one and could be attributed to the content of the major compounds, especially the oxygenated terpenes.     

Synthesis and in vitro antimycobacterial potential of novel hydrazones of eugenol

Fifty one hydrazone derivatives of eugenol were designed and docked with 2NSD and 2X22 (enzymes of H37Rv strain) using Schrodinger v7.4. The selective ten hydrazone derivatives (4, 5, 11, 18, 30, 34, 35, 37, 42, and 45) of eugenol were synthesized via esterification, hydrazination and treatment with different aldehydes. Synthesized compounds were characterized by IR, ¹H NMR, and LCMS data. The compounds were evaluated for their antitubercular potential against H37Rv using microplate alamar blue assay (MABA). The study revealed that all synthesized compounds were significantly active at concentration 50 and 100 μg/ml, whereas compound 11 exhibited activity at 25 μg/ml. Present study showed that antitubercular activity of novel hydrazone derivatives of eugenol is strongly connected with the position of the substituent on aromatic aldehyde or ketones.     

Evaluation of structural,spectral characterization and in vitro cytotoxic activity studies of some polycyclic aromatic compounds

The present study aims to introduce three known and three new stable polycyclic aromatic compounds synthesized. With MALDI-Mass, ¹H and ¹³C NMR spectroscopy, all new compounds were characterized. In the DMF solution were carried out the electrochemical and photophysical properties of the polyaromatic compounds. The compounds are highly fluorescent showing green-red emission when excited at one single wavelength. For the compound 3, it was shown that the highest Stokes Shift (191 nm) appeared which may be due to the excited state energy transfer. The compounds also indicated the blue-orange region of the electromagnetic spectrum strong emission bands. Additionally, compounds 1, 3, 4, and 5 were investigated for their in vitro cytotoxic activities against PC-3 prostate cancer cells, L-929 non-cancerous cells, and MDA-MB-231 breast cancer for 24 h, 48 h and 72 h. The results obtained from the experiment demonstrated that compounds had different cytotoxic activity against cell lines. Compound 3 was indicated to be inactive against L-929 cells and MDA-MB-231 cancer cells, whereas compounds 1, 4 and 5 indicated a dose and time-dependent cytotoxic activity against PC-3, MDA-MB-231, and L-929 cell lines. It was found that the most sensitive cells to compound 5 were MDA-MB-231 human breast cancer cells. Additionally, it became clear that compounds 1 and 3 had significant selectivity for human PC-3 prostate cancer cells, and compounds 1, 4 and 5 had considerable selectivity for human MDA-MB-231 breast cancer cells. Also, the quantum chemical examinations of six organic compounds were conducted at the B3LYP/6-31G level in the gas phase and water. According to calculated results, compound 5 was found to be the best candidate for NLO applications.     

Phytochemical profiling and antimicrobial activity of ginger (Zingiber officinale) essential oils against important phytopathogens

The objectives of this study were to profile ginger essential oils (EOs) phytochemical constituents and antimicrobial activity against important phytopathogens. Ginger EOs was extracted using a modified Clevenger-type apparatus by hydro-distillation then followed by GCMS and headspace analysis of its phytochemical constituents. The phytoconstituents identified were monoterpenes and sesquiterpene hydrocarbons. Food poisoned and disc diffusion techniques were applied to determine the percentage inhibition of fungal mycelial and bacterial growth respectively. The EOs produced mycelial growth inhibition in all the test fungal pathogens after five days of incubation. The MIC and MFC of the EOs on the tested fungi were in the range of 1 μl/ml and 5–6 μl/ml, respectively. The bacterial growth of all the tested isolates was also affected by EOs at 100–500 µl/ml, from weak to strong antibacterial activity. The EOs affected the Xanthomonas oryzae pv. oryzae-strain A isolate most at a higher concentration of 400–500 μl/ml with mean inhibition of 20.66 mm and 22.66 mm respectively, which are found to be effective. The MIC values on the bacterial pathogens were at100 μl/ml. The inhibition zone of positive control (streptomycin) at 15 µg/disc was 25.00 mm and appeared to be efficient. Metabolomics analysis to concurrently quantify variability among multiple compounds in the data sets and identify such compounds responsible for the X. oryzae pv. oryzae-strain-A inhibition were determined. The cross-validated PLS model has shown a strong correlation between ginger EOs and bioactivity. The action of ginger EOs on the cell structure was fully identified using SEM by observing the changes in morphology and integrity of X. oryzae pv. oryzae-strain-A cells. The DMSO treatment (control) showed a normal rod shape cell, while treatment with the ginger EOs showed irregular shape with sunken surfaces, and treatment with antibiotics display abnormal growth of the cells. These findings can, therefore, propose that the ginger EOs could be used as a new antimicrobial agent in suppressing the growth of phytopathogens and as possible new alternatives to synthetic fungicides and bactericides.