A comprehensive phytochemical, biological, toxicological and molecular docking evaluation of Suaeda fruticosa (L.) Forssk.: An edible halophyte medicinal plant.

Suaeda fruticosa is an edible medicinal halophyte known for its traditional uses. In this study, methanol and dichloromethane extracts of S. fruticosa were explored for phytochemical, biological and toxicological parameters. Total phenolic and flavonoid constituents were determined by using standard aluminum chloride and Folin-Ciocalteu methods, and UHPLC-MS analysis of methanol extract was performed for tentative identification of secondary metabolites. Different standard methods like DPPH, ABTS, FRAP, CUPRAC, total antioxidant capacity (TAC), and metal chelation assays were utilized to find out the antioxidant potential of extracts. Enzyme inhibition studies of extracts against acetylcholinesterase, butyrylcholinesterase, tyrosinase, α-amylase and, α-glucosidase enzymes were also studied. Likewise, the cytotoxicity was also assessed against MCF-7, MDA-MB-231, and DU-145 cell lines. The higher phenolic and flavonoids contents were observed in methanol extracts which can be correlated to its higher radical scavenging potential. Similarly, 11 different secondary metabolites were tentatively identified by UHPLC profiling. Both the extract showed significant inhibition against all the enzymes except for α-glucosidase. Moreover, docking studies were also performed against the tested enzymes. In the case of cytotoxicity, both the samples were found moderately toxic against the tested cell lines. This plant can be explored further for its potential therapeutic and edible uses.

Chemical Composition and Pharmacological Evaluation and of Toddalia asiatica (Rutaceae) Extracts and Essential Oil by in Vitro and in Silico Approaches.

Toddalia asiatica (L.) Lam. is extensively used in traditional medicinal systems by various cultures. Despite its frequent use in traditional medicine, there is still a paucity of scientific information on T. asiatica growing on the tropical island of Mauritius. Therefore, the present study was designed to appraise the pharmacological and phytochemical profile of extracts (methanol, ethyl acetate and water) and essential oil obtained from aerial parts of T. asiatica. Biological investigation involved the evaluation of in vitro antioxidant and enzyme inhibitory potentials. The chemical profile of the EO was determined using gas chromatography coupled to mass spectrometry (GC/MS) analysis, while for the extracts, the total phenolic (TPC) and flavonoid content were quantified as well as their individual phenolic compounds by LC/MS/MS. Quinic acid, fumaric acid, chlorogenic acid, quercitrin and isoquercitrin were the main compounds in the extracts. Highest total phenolic (82.5±0.94 mg gallic acid equivalent (GAE/g)) and flavonoid (43.8±0.31 mg rutin equivalent (RE/g)) content were observed for the methanol extract. The GC/MS analysis has shown the presence of 26 compounds with linalool (30.9 %), linalyl acetate (20.9 %) and ß-phellandrene (7.9 %) being most abundant components in the EO. The extracts and EO showed notable antioxidant properties, with the methanol extract proved to be superior source of antioxidant compounds. Noteworthy anti-acetylcholinesterase (AChE) and anti-butyrylcholinesterase (BChE) effects were recorded for the tested samples, while only the methanol and ethyl acetate extracts were active against tyrosinase. With respect to antidiabetic effects, the extracts and EO were potent inhibitors of α-glucosidase, while modest activity was recorded against α-amylase. Docking results showed that linalyl acetate has the highest affinity to interact with the active site of BChE with docking score of -6.25 kcal/mol. The findings amassed herein act as a stimulus for further investigations of this plant as a potential source of bioactive compounds which can be exploited as phyto-therapeutics.

Identifying isomers of peroxy radicals in the gas phase: 1-C3H7O2vs. 2-C3H7O2.

The two isomers of the propylperoxy radical 1-C3H7O2 and 2-C3H7O2, together with their individual rotamers, are identified and assigned by threshold photoelectron spectroscopy with the aid of high-level theoretical computations, from which their accurate adiabatic ionization energies are derived. This study paves the way to probing elusive peroxy radicals and their isomers in advanced mass spectrometry analysis of combustion and atmospheric reactions.

Characterization of the simplest sulfenyl thiocyanate: isomers, spectroscopy and implications of astrophysical and biological relevance.

Sulfenyl thiocyanate compounds, RSSCN, are involved in the human immune system biochemical processes. They are also the routes for the synthesis of complex S-containing species such as polypeptides, or symmetrical (RSSR) and unsymmetrical disulfides (RSSR'). At present, we have characterized the stable forms of the simplest sulfenyl thiocyanate compound, HSSCN, at the coupled cluster level. We found twenty-three isomers, for which we determined a set of structural parameters, anharmonic frequencies and reaction energies for the formation of the corresponding diatomic + triatomic and atomic + tetratomic fragments. We also discussed the implications of the present findings for biological entities containing a disulfide bridge, where we identified three isomers that may serve as prototypes. Similarities and differences with other S/N hybrid bioactive molecules are also discussed. From an astrophysical point of view, we expect HSSCN isomers to be present in astrophysical media, since several of their molecular fragments have already been detected. In sum, the present set of data can be used for the identification of HSSCN compounds and understanding the physical chemistry of sulfur containing molecules in vivo, in the laboratory and in astrophysical media.

Combination of phenolic profiles, pharmacological properties and in silico studies to provide new insights on Silene salsuginea from Turkey.

The genus Silene is renowned in Turkey for its traditional use as food and medicine. Currently, there are 138 species of Silene in Turkey, amongst which have been several studies for possible pharmacological potential and application in food industry. However, there is currently a paucity of data on Silene salsuginea Hub.-Mor. This study endeavours to access its antioxidant, enzyme inhibitory, and anti-inflammatory properties. Besides, reversed-phase high-performance liquid chromatography-diode array detector (RP-HPLC-DAD) was used to detect phenolic compounds, and molecular docking was performed to provide new insights for tested enzymes and phenolics. High amounts of apigenin (534 µg/g extract), ferulic acid (452 µg/g extract), p-coumaric acid (408 µg/g extract), and quercetin (336 µg/g extract) were detected in the methanol extract while rutin (506 µg/g extract) was most abundant in the aqueous extract. As for their biological properties, the methanol extract exhibited the best antioxidant effect in the DPPH and CUPRAC assays, and also the highest inhibition against tyrosinase. The aqueous extract was the least active enzyme inhibitor but showed the highest antioxidant efficacy in the ABTS, FRAP, and metal chelating assays. At a concentration of 15.6 µg/mL, the methanol extract resulted in a moderate decrease (25.1%) of NO production in lipopolysaccharide-stimulated cells. Among the phenolic compounds, epicatechin, (+)-catechin, and kaempferol showed the highest binding affinity towards the studied enzymes in silico. It can be concluded that extracts of S. salsuginea are a potential source of functional food ingredients but need further analytical experiments to explore its complexity of chemical compounds and pharmacological properties as well as using in vivo toxicity models to establish its maximum tolerated dose.

Diaminobenzene schiff base, a novel class of DNA minor groove binder.

Molecules that target the deoxyribonucleic acid (DNA) minor groove are relatively sequence specific and they can be excellent carrier structures for cytotoxic chemotherapeutic compounds which can help to minimize side effects. Two novel isomeric derivatives of diaminobenzene Schiff base [N,N'-bis (2-hydroxy-3-methoxybenzylidene)-1,2-diaminobenzene (2MJ) and N,N'-bis(2-hydroxy-3-methoxybenzylidene)-1,3-diaminobenzene (2MH)] were analyzed for their DNA minor groove binding (MGB) ability using viscometry, UV and fluorescence spectroscopy, computational modeling and clonogenic assay. The result shows that 2MJ and 2MH are strong DNA MGBs with the latter being more potent. 2MH can form interstrand hydrogen bond linkages at its oxygens with N3 of adenines. Changing the 2-hydroxy-3-methoxybenzylidene binding position to the 1,3 location on the diaminobenzene structure (2MJ) completely removed any viable hydrogen bond formation with the DNA and caused significant decrease in binding strength and minor groove binding potency. Neither compound showed any significant cytotoxicity towards human breast, colon or liver cancer cell lines.

Chemical reaction of soybean flavonoids with DNA: a computational study using the implicit solvent model.

Genistein, daidzein, glycitein and quercetin are flavonoids present in soybean and other vegetables in high amounts. These flavonoids can be metabolically converted to more active forms, which may react with guanine in the DNA to form complexes and can lead to DNA depurination. We assumed two ultimate carcinogen forms of each of these flavonoids, diol epoxide form and diketone form. Density functional theory (DFT) and Hartree-Fock (HF) methods were used to study the reaction thermodynamics between active forms of flavonoids and DNA guanine. Solvent reaction field method of Tomasi and co-workers and the Langevin dipoles method of Florian and Warshel were used to calculate the hydration free energies. Activation free energy for each reaction was estimated using the linear free energy relation. Our calculations show that diol epoxide forms of flavonoids are more reactive than the corresponding diketone forms and are hence more likely flavonoid ultimate carcinogens. Genistein, daidzein and glycitein show comparable reactivity while quercetin is less reactive toward DNA.

Density functional theory and ab initio studies of the structure and energetics of digallium tetraoxide, Ga2O4, in the gas phase.

A systematic investigation on the neutral and anionic digallium tetraoxide, Ga(2)O(4) has been carried out by using density functional theory (DFT), second-order Møller-Plesset perturbation theory (MP2), and the coupled cluster approach with single and double substitutions and a perturbative treatment of the triple excitations [CCSD(T)]. The geometry of neutral Ga(2)O(4) has been proposed earlier, from an experimental study, to adopt a D(2d) symmetry (J. Phys. Chem. 1979, 83, 656). However, the current research reveals that, out of the several isomers considered for neutral and anionic digallium tetraoxide, the (3)B(1u) and (2)B(3g) of the planar D(2h) geometry (7a-D(2h)) are the lowest-energy states for Ga(2)O(4) and Ga(2)O(4)(-). Our computations rule out the D(2d) geometry (3-D(2d)) as a viable contender for neutral Ga(2)O(4). The (3)B(2) (3-D(2d)) state is located above the (3)B(1u) (7-D(2h)) state by at least 4.26 eV. The energies of the low lying states, geometrical parameters, and energetic features (VEDE, AEDE, and AEA) are reported. The AEA of Ga(2)O(4) is calculated to be 3.94 eV (B3LYP), 3.24 eV (MP2), 3.42 eV [CCSD(T)//B3LYP], and 3.38 eV [CCSD(T)//MP2], respectively. In addition, the dissociation energy, D(e), for the process Ga(2)O(4) ((3)B(1u)) → 2GaO(2) ((2)A(2)) is 3.59 eV (B3LYP), 5.08 eV (MP2), 4.82 eV [CCSD(T)//B3LYP], and 4.80 eV [CCSD(T)//MP2]. The results obtained in this work are critically analyzed, discussed, and compared with those of the analogous metal oxides.

Gas-phase Acidity and Liquid Phase pKa Calculations of Some Cyclic Oxocarbon Acids (CnOnH2 (n = 3, 4, 5, 6)): A Theoretical Investigation.

The gas-phase acidity and the pKa values of the organic acids have been attracting a lot of attention from organic and analytical chemists. The gas-phase acidity and pKa calculations for some oxocarbon acids were investigated under B3LYP/6-311+G(d,p) level of theory. In this study, four oxocarbon acids, CnOnH2 were selected, namely deltic acid (n = 3), squaric acid (n = 4), croconic acid (n = 5) and rhodizonic acids (n = 6). The calculations in gas phase show that the gas-phase acidity of the acids increases as the ring size increases due to the formation of resonance-stabilized monoanions and dianions. Solvation free energy is required in pKa calculation. However, there is significant uncertainty in calculating the solvation free energy using theoretical methods. Therefore, three methods to calculate the free energy of solvation were adopted for comparison, which are the (i) solvent reaction field (SCRF) method using the Simple United Atom Topological Model (UA0); (ii) SCRF using the United Atom Topological Model (UAHF) optimized for HF/6-31G(d) level of theory; and (iii) Langevin dipoles (LD) method. From the results obtained, it was shown that SCRF method with UAHF atomic radii has the potential of reproducing the experimental values. The calculated pKa values were in good agreement with experimental results and have shown that the croconic acid, C5O5H2 is found to be the most acidic in aqueous phase.

Poly[µ(2)-aqua-(µ(3)-2,5-dichloro-benzene-sulfonato)sodium].

In the title compound, [Na(C(6)H(3)Cl(2)O(3)S)(H(2)O)](n), the Na(I) ion is penta-coordinated by three dichloro-benzene-sulfonate anions and two water mol-ecules, forming a distorted trigonal-bipyramidal geometry. The Na(I) ions are bridged by the sulfonate groups and the water mol-ecules, leading to a polymeric layer structure parallel to the bc plane in which O-H⋯O hydrogen bonds are observed.

Triethyl-ammonium 4-nitro-benzene-sulfonate.

In the anion of the title molecular salt, C(6)H(16)N(+)·C(6)H(4)O(5)S(-), the nitro group is twisted slightly from the benzene ring, making a dihedral angle of 3.16 (10)°. In the crystal structure, the cations and anions are linked into a two-dimensional network parallel to the ab plane by C-H⋯O and N-H⋯O hydrogen bonds.

1,3-Bis[(3-allyl-imidazol-3-ium-1-yl)meth-yl]benzene bis-(hexa-fluoridophosphate).

In the title compound, C(20)H(24)N(4) (2+)·2PF(6) (-), the ethene and 3-allyl-imidazolium moieties of the cation are disordered over two positions with refined site occupancies of 0.664 (19):0.336 (19) and 0.784 (7):0.216 (7), respectively, whereas four F atoms of one hexa-fluoridophosphate anion and all atoms in the other hexa-fluoridophosphate anion are disordered over two positions with refined site occupancies of 0.764 (5):0.2365) and 0.847 (9):0.153 (9), respectively. The benzene ring is inclined at angles of 78.2 (3), 81.3 (4) and 73.9 (12)° with the 1H-imidazol-3-ium ring and the major and minor components of the disordered 1H-imidazol-3-ium ring, respectively. In the crystal, the hexa-fluoridophosphate anions link the cations into two-dimensional networks parallel to (001) via inter-molecular C-H⋯F hydrogen bonds. The crystal structure is further consolidated by π-π [centroid-centroid distance = 3.672 (3) Å] and C-H⋯π inter-actions.