LC-ESI-MS/MS profiling of alkaloids and antiproliferative activity of Pachypoduim lamerei drake leaves

Abstract

In the present study, evaluation of the antiproliferative activity of Pachypodium lamerei Drake leaves (family Apocyaceae) against human breast cancer cell lines MDA-MB-231 was done for the total methanolic extract, crude alkaloidal mixture and ursolic acid using the MTT colorimetric assay. The methanolic extract showed the strongest antiproliferative activity followed by ursolic acid and crude alkaloidal fraction with an IC₅₀ equal to 6.2, 14.55 and 56.3?µg/ml respectively compared to oleocanthal. It is the first record for the LC/ESI-MS/MS alkaloidal profiling of the leaves of P. lamerei. Seven alkaloids were tentatively identified according to their fragmentation patterns. Four alkaloids were related to the parent indole class and two alkaloids belong to the quinoline class in addition to one steroidal alkaloid with a pregnan nucleus. Phytochemical investigation of the methanolic extract led to the isolation of three triterpenoidal compounds including ursolic acid, 11,12-didehydroursolic acid lactone and ursolic acid lactone.     

Multicomponent reaction of amine,carbon disulfide,and fluoronitrobenzene via nucleophilic attack on the fluorinated carbon for the synthesis of nitrophenyl methylcarbamodithioates

In this paper, multicomponent reaction of amine, carbon disulfide and fluoronitrobenzene is reported for the synthesis of nitrophenyl methylcarbamodithioate derivatives. The method is based on the nucleophilic attack of the activated methylcarbamodithioate salt to fluoronitrobenzene. Several starting materials are tested and successfully produced the corresponding nitrophenyl methylcarbamodithioate. A possible mechanism for the reaction is suggested.     

Synthesis and design of polyurethane and its nanocomposites derived from canola-castor oil: Mechanical,thermal and shape memory properties

The recent global pandemic and its tremendous effect on the price fluctuations of crude oil illustrates the side effects of petroleum dependency more evident than ever. Over the past decades, both academic and industrial communities spared endless efforts in order to replace petroleum-based materials with bio-derived resources. In the current study, a series of shape memory polymer composites (SMPC's) was synthesized from epoxidized vegetable oils, namely canola oil and castor oil fatty acids (COFA's) as a 100% bio-based polyol and isophorone diisocyanate (IPDI) as an isocyanate using a solvent/catalyst-free method in order to eventuate polyurethanes (PU's). Thereafter, graphene oxide (GO) nanoplatelets were synthesized and embedded in the neat PU in order to overcome the thermomechanical drawbacks of the neat matrix. The chemical structure of the synthesized components, as well as the dispersion and distribution levels of the nanoparticles, was characterized. In the following, thermal and mechanical properties as well as shape memory behavior of the specimens were comprehensively investigated. Likewise, the thermal conductivity was determined. This study proves that synthesized PU's based on vegetable oil polyols, including graphene nanoparticles, exhibit proper thermal and mechanical properties, which make them stand as a potential candidate to compete with traditional petroleum-based SMPC's.     

Donor ligand, basal ligand and solvent effects on the equilibrium constants of triphenylphosphinecobalt(III) Schiff base complexes with phosphite ligands

The equilibrium constants and the thermodynamic parameters were spectrophotometrically measured for the 1:1 adduct formation of [Co(Salen)(PPh₃)]ClO₄.H₂O, and [Co(7,7′-Me₂Salen)(PPh₃)]ClO₄.H₂O as acceptors, with P(OR)₃ (R = methyl, ethyl, and i-propyl) as donors, in acetonitrile (CH₃CN) and dimethylformamide (DMF) as solvents at constant ionic strength (I = 0.1 M NaClO₄), and various temperatures (t = 10–50 °C). Our results revealed the following trends: stability of the cobalt(III) Schiff base complexes toward a given phosphite donor, [Co(7,7′-Me₂Salen)(PPh₃)]⁺ < [Co(Salen)(PPh₃)]⁺; binding of the donors (phosphites) toward a given cobalt(III) Schiff base complex, P(OEt)₃ > P(OMe)₃ > P(O-ⁱPr)₃; influence of solvent on the stability of a given cobalt(III) Schiff base complex toward a given phosphite donor, CH₃CN < DMF.     

Dynamic stereochemistry of erigeroside by measurement of 1H-1H and 13C-1H coupling constants

Erigeroside was extracted from Satureja khuzistanica Jamzad (Marzeh Khuzistani in Persian, family of lamiaceae), and (1)H, (13)C, (13)C{(1)H}, (1)H-(1)H COSY, HMQC and J-HMBC were obtained to identify this compound and determine a complete set of J-coupling constants ((1)J(C-H), (2)J(C-H), (3)J(C-H) and (3)J(H-H)) values within the exocyclic hydroxymethyl group (CH(2)OH) and anomeric center. In parallel, density functional theory (DFT) using B3LYP functional and split-valance 6-311++G** basis set has been used to optimized the structures and conformers of erigeroside. In all calculations solvent effects were considered using a polarized continuum (overlapping spheres) model (PCM). The dependencies of (1)J, (2)J and (3)J involving (1)H and (13)C on the C(5')-C(6') (omega), C(6')-O(6') (theta) and C(1')-O(1') (phi) torsion angles in erigeroside were computed using DFT method. Complete hyper surfaces for (1)J(C1',H1'), (2)J(C5',H6'R), (2)J(C5',H6'S), (2)J(C6',H5'), (3)J(C4',H6'R), (3)J(C4',H6'S) and (2)J(H6'R-H5'S) as well as (3)J(H5',H6'R) were obtained and used to derive Karplus equations to correlate these couplings to omega, theta and phi. These calculated J-couplings are in agreement with experimental values. These results confirm the reliability of DFT calculated coupling constants in aqueous solution.     

MCM-41 Catalyzed Efficient Regioselective Synthesis of β-Aminoalcohol under Solvent-free Conditions

β‐Aminoalcohols were synthesized in high yields by reaction of epoxides with amines in the presence of MCM‐41 as a green and reusable catalyst under solvent‐free conditions.     

Keggin Heteropolyacid Catalyzed Synthesis of Isoxazolo[5,4-d]pyrimidine-4,6(5H,7H)-diones at Room Temperature

Isoxazolo[5,4‐d]pyrimidine‐4,6(5H,7H)diones 2a – 2f have been synthesized from the reaction of ethyl 5‐amino‐3‐methyl‐4‐isoxazole carboxylate ( 1 ) with aryl isocyanates in the presence of Keggin heteropolyacid H₃[PW₁₂O₄₀] as a green solid acid catalyst at room temperature in a one‐pot process in good yields.     

Metallation of tetradentate N<Subscript>2</Subscript>O<Subscript>2</Subscript> Schiff base with Mn(II), Co(II), Cu(II) and Zn(II): synthesis,characterization and formation constants measurement

Four Schiff base ligands, salabza-H₂ = N,N′-bis(salicylidene)-2-aminobenzylamine, were synthesized by condensation of one mole of 2-aminobenzylamine and two moles of salicylaldehyde and/or two moles of substituted salicylaldehyde (5-OMe, 5-Br, 5-NO₂). All the four Schiff bases and their Mn(II), Co(II), Cu(II) and Zn(II) complexes are characterized by UV-Vis, FT-IR, ¹H NMR spectroscopy, mass spectrometry and elemental analysis. The formation constants and the Gibbs free energies were measured spectrophotometrically for 1:1 complexes in methanol in constant ionic strength (I = 0.1 mol dm⁻³ NaClO₄) and at 25°C. The data refinement was carried out with the SQUAD program. The trend of formation constants of H₂L¹ with M(II) follows the order: Mn(II) (3.97) < Zn(II) (4.30) < Co(II) (4.89) < Cu(II) (5.73)     

Efficient and solvent-free synthesis of 1-amidoalkyl-2-naphthols using <Emphasis Type="Italic">N,N,N’,N’</Emphasis>-tetrabromobenzene-1,3-disulfonamide

N,N,N,’N’-Tetrabromobenzene-1,3-disulfonamide [TBBDA] is found to be a reusable catalyst for efficient synthesis of various amidoalkyl naphthols from β-naphthol, aromatic aldehydes and urea in good to high yields under solvent-free conditions.      

Gold-catalysed synthesis of amino acid-derived 2,5-disubstituted oxazoles

Amino acid-derived propargylic amides are cyclised in a one-pot, Au(III)-catalysed operation to yield 5-bromomethyl oxazoles. These compounds are further elaborated to bis-heterocycles, dipeptide mimics and more.