Chemical composition and antimicrobial activity of essential oils and various extracts of endemic Onosma malatyana (Boraginaceae) from Anatolia.

The chemical contents of the endemic Onosma malatyana roots collected from Malatya/Türkiye were determined using the hydrodistillation and the soxhlet methods and antimicrobial activity analysis of the extracts was also performed. The hydrodistillation method applied to the roots of O.malatyana resulted in identifying 31 compounds according to their retention times in GC-MS analysis. Additionally, crude ethyl acetate and crude oil etheric extracts of O.malatyana roots contained 14 compounds each. This research identified that the main component of the essential oil obtained by the hydrodistillation method was palmitic acid comprising 56.48% of the total composition. Additionally, in the crude petroleum etheric extract, oleic acid methyl ester (31.22%); and palmitic acid (24.69%) were identified as the main components in the crude ethyl acetate extract. The results of the antimicrobial activities indicated that O.malatyana root extracts were particularly effective against Gram-positive bacteria, specifically S. aureus and B. subtilis.

The study, conducted for the first time, sheds detailed light on the chemical composition and antimicrobial activity of Onosma malatyana roots, highlighting the potential pharmacological importance of the plant.The research, carried out using hydrodistillation and Soxhlet extraction methods, emphasizes the chemical diversity of the plant by identifying various organic compounds, particularly prominent ones such as palmitic acid.Antimicrobial tests show strong inhibitory effects, especially against Gram-positive bacteria like S.aureus and B.subtilis. This indicates the potential of crude petroleum etheric extract as a natural antimicrobial agent.The findings allow for a better understanding of the chemical diversity and pharmacological potential of O. malatyana, enabling future research to target the plant's phytochemical profile, antimicrobial compound mechanisms, and optimization of cultivation practices.

A natural approach to breast cancer treatment: investigation of chemical features of aerial parts of endemic Onosma sintenisii Hausskn. ex Bornm and its antioxidant properties, in vitro cytotoxic and apoptosis induction on MCF-7 cells.

Onosma sintenisii Hausskn. ex Bornm. (O. sintenisii) belongs to the Boraginaceae family and it is an endemic species from Irano-turanian phytogeographical region (central and eastern Anatolia) that distributes in steppe areas. This study aimed to investigate the chemical composition, antioxidant, in vitro cytotoxic and apoptosis induction of methanol extract of aerial parts of O. sintenisii. As a result of GC/MS analysis, 14 components were identified, and the major compounds of the extracts are retronecine (13.94%), α.-D-Glucopyranosiduronic acid (10.86%), melaniline (7.5%) and 1,2-Butanediol (4.02%), respectively. Antioxidant properties of O. sintenisii were determined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, ferric reducing antioxidant power (FRAP) and superoxide radical scavenging activity methods. While the DPPH free radical scavenging activity results of O. sintenisii extract varied between 62.49% and 32.27%, reducing power activity and superoxide radical scavenging activity were found to be low. The result of the MTT assay revealed strong anticancer activity of O. sintenisii extract. The most significant cytotoxic effect was noted at a concentration of 1000 µg/mL after 48 hours. These findings together with flow cytometry analysis suggest that apoptosis can be the main mechanism underlying cell death after O. sintenisii extract treatment.

cis-Bis[N'-(4-bromo-benzo-yl)-N,N-dimethyl-thio-ureato-κO,S]copper(II).

The asymmetric unit of the title compound, [Cu(C(10)H(10)BrN(2)OS)(2)], contains two independent complex mol-ecules with almost identical conformations. Two S and two O atoms form the coordination environment of the Cu atom, resulting in a slightly distorted square-planar coordination. The S atoms are in a cis configuration. The crystal structure is stabilized by weak inter-molecular C-H⋯Br hydrogen-bonding inter-actions.

3-Chloro-N-(diphenyl-carbamothio-yl)benzamide.

In the title compound, C(20)H(15)ClN(2)OS, the bond lengths and angles in the thio-urea group are typical of thio-urea derivatives. The C-N bond lengths in the center of the mol-ecule are shorter than the normal C-N single bond due to the resonance effects in this part of the mol-ecule. The conformation of the title mol-ecule with respect to the thio-carbonyl and carbonyl groups is twisted, as reflected by the C-N-C-O and C-N-C-N torsion angles of -4.4 (6) and -53.3 (5)°, respectively. Pairs of the mol-ecules are linked into centrosymmetric dimers, stacked along the c axis via inter-molecular N-H⋯S inter-actions. There are also weak inter-molecular C-H⋯O and C-H⋯S contacts in the structure.

N-(Diphenyl-carbamothio-yl)-3-methyl-benzamide.

The synthesis of the title compound, C(21)H(18)N(2)OS, involves the reaction of 3-methyl-benzoyl chloride with potassium thio-cyanate in dry acetone followed by condensation of the 3-methyl-benzoyl isothio-cyanate with diphenyl-amine. The carbonyl [C-O = 1.215 (2) Å] and thio-carbonyl [C-S = 1.6721 (17) Å] distances indicate that these correspond to double bonds. The short C-N bonds at the center of the mol-ecule reveal the effects of resonance in this part of the mol-ecule. The conformation of the mol-ecule with respect to the thio-carbonyl and carbonyl groups is twisted. The 3-methyl-phenyl and two phenyl rings are also twisted, with dihedral angles of 75.67 (9) and 14.91 (9)°. The phenyl rings are rotated out of the mean plane of the N-C-S-N atoms by 66.87 (8) and 78.40 (9)°. Pairs of mol-ecules are linked into centrosymmetric dimers via inter-molecular N-H⋯S inter-actions and a C-H⋯O link also occurs. The dimers are stacked along the a axis.

4-Bromo-N-(diethyl-carbamothio-yl)-benzamide.

The synthesis of the title compound, C(12)H(15)BrN(2)OS, involves the reaction of 4-bromo-benzoyl chloride with potassium thio-cyanate in dry acetone, followed by condensation of 4-bromo-benzoyl isothio-cyanate with diethyl-amine. The carbonyl and thio-carbonyl bond lengths indicate that these correspond to double bonds. The short C-N bond lengths reveal the effects of resonance in this part of the mol-ecule. The conformation of the mol-ecule with respect to the thio-carbonyl and carbonyl units is twisted, with torsion angles of -5.7 (3) and 87.2 (2)°. The N atom of the diethyl-amine group is sp(2)-hybridized: the sum of the angles around the N atom is 359.97 (14)°. The two diethyl groups are twisted in + and - anti-periplanar conformations with angles of -179.89 and 179.92°. In the crystal structure, the mol-ecules form infinite chains via an inter-molecular N-H⋯O inter-action.

4-Bromo-N-(di-n-propyl-carbamothioyl)-benzamide.

The synthesis of the title compound, C(14)H(19)BrN(2)OS, involves the reaction of 4-bromo-benzoyl chloride with potassium thio-cyanate in acetone followed by condensation of the resulting 4-bromo-benzoyl isothio-cyanate with di-n-propyl-amine. Typical thio-urea carbonyl and thio-carbonyl double bonds, as well as shortened C-N bonds, are observed in the title compound. The short C-N bond lengths in the centre of the mol-ecule reveal the effects of resonance in this part of the mol-ecule. The asymmetric unit of the title compound contains two crystallographically independent mol-ecules, A and B. There is very little difference between the bond lengths and angles of these mol-ecules. In mol-ecule B, one di-n-propyl group is twisted in a -anti-periplanar conformation with C-C-C-H = -179.1 (3)° and the other adopts a -synclinal conformation with C-C-C-H = -56.7 (4)°; in mol-ecule A the two di-n-propyl groups are twisted in + and -anti-periplanar conformations, with C-C-C-H = -179.9 (3) and 178.2 (3)°, respectively. In the crystal, the mol-ecules are linked into dimeric pairs via pairs of N-H⋯S hydrogen bonds.

The molecular structure and vibrational spectra of N-(2,2-diphenylacetyl)-N'-(naphthalen-1yl)-thiourea by Hartree-Fock and density functional methods.

N-(2,2-Diphenylacetyl)-N'-(naphthalen-1yl)-thiourea (PANT) has been synthesized and characterized by elemental analysis, IR spectroscopy and (1)H NMR spectroscopy. The crystal and molecular structure of the title compound has been determined from single crystal X-ray diffraction data. It crystallizes in the triclinic space group P-1, Z=2 with a=10.284(2)A, b=10.790(2)A, c=11.305(2)A, alpha=64.92(3) degrees , beta=89.88(3) degrees , gamma=62.99(3) degrees , V=983.7(3)A(3) and D(calc)=1.339Mg/m(3). The molecular structure, vibrational frequencies and infrared intensities of PANT were calculated by the Hartree-Fock and density functional theory methods (BLYP and B3LYP) using the 6-31G* basis set. The calculated geometric parameters were compared to the corresponding X-ray structure of the title compound. We obtained 22 stable conformers for the title compound; however Conformer 1 is approximately 9.53kcal/mol more stable than Conformer 22. The comparison of the theoretical and experimental geometry of the title compound shows that the X-ray parameters fairly well reproduce the geometry of Conformer 17. The harmonic vibrations computed for this compound by the B3LYP/6-31G* method are in good agreement with the observed IR spectral data. Theoretical vibrational spectra of the title compound were interpreted by means of PEDs using the VEDA 4 program. A general better performance of the investigated methods was calculated by PAVF 1.0 program.

4-Chloro-N-[N-(6-methyl-2-pyrid-yl)car-bamo-thio-yl]benzamide.

In the title compound, C(14)H(12)ClN(3)OS, the short exocyclic N-C bond lengths indicate resonance in the thiourea part of the mol-ecule. The title compound is stabilized by an intra-molecular N-H⋯N hydrogen bond, which results in the formation of a six-membered ring. In addition, it shows a synperiplanar conformation between the thio-carbonyl group and the pyridine group. Inter-molecular N-H⋯S and C-H⋯O inter-actions are also present.

The molecular structure and vibrational spectra of 2-chloro-N-(diethylcarbamothioyl)benzamide by Hartree-Fock and density functional methods.

2-Chloro-N-(diethylcarbamothioyl)benzamide (C(12)H(15)ClN(2)OS) has been synthesized and characterized by elemental analysis and IR spectroscopy. The crystal and molecular structure of the title compound has been determined from single crystal X-ray diffraction data. It crystallizes in the orthorhombic space group Pbca, Z=8 with a=9.581(3)A, b=9.992(3)A, c=26.640(8)A, V=2550.5(13)A(3) and D(calc)=1.410 Mg/m(3). The molecular geometry and vibrational frequencies of 2-chloro-N-(diethylcarbamothioyl)benzamide in the ground state have been calculated using the Hartree-Fock and density functional using Becke's three-parameter hybrid method with the Lee, Yang and Parr correlation functional (B3LYP) methods with 3-21G and 6-31G(d) basis sets. The calculated geometric parameters were compared to the corresponding X-ray structure of the title compound. The raw B3LYP frequencies approximate the experimental data much better than the results of Hartree-Fock. The scaled B3LYP/6-31G(d) results were more reliable than those obtained using the B3LYP/3-21G method with the mean absolute deviation about 13.7 cm(-1). On the basis of the comparison between calculated and experimental results, assignments of fundamental vibrational modes were examined.