-
Frontiers in Chemistry 2024A series of 16 novel prenylated chalcones () was synthesized by microwave-assisted green synthesis using 5-prenyloxy-2-hydroxyacetophenone and different benzaldehydes....
A series of 16 novel prenylated chalcones () was synthesized by microwave-assisted green synthesis using 5-prenyloxy-2-hydroxyacetophenone and different benzaldehydes. Comparisons were also performed between the microwave and conventional methods in terms of the reaction times and yields of all compounds, where the reaction times in the microwave and conventional methods were 1-4 min and 12-48 h, respectively. The synthesized compounds were characterized using different spectroscopic techniques, including IR, H-NMR, C-NMR, and LC-HRMS. The antifungal activities of all compounds were evaluated against and under conditions and were additionally supported by structure-activity relationship (SAR) and molecular docking studies. Out of the 16 compounds screened, 2'-hydroxy-4-benzyloxy-5'--prenylchalcone () showed the highest activity against both and , with ED of 25.02 and 31.87 mg/L, respectively. The molecular docking studies of the prenylated chalcones within the active sites of the EF1 and RPB2 gene sequences and FoCut5a sequence as the respective receptors for and revealed the importance of the compounds, where the binding energies of the docked molecules ranged from -38.3538 to -26.6837 kcal/mol for and -43.400 to -23.839 kcal/mol for . Additional docking parameters showed that these compounds formed stable complexes with the protein molecules.
PubMed: 38746019
DOI: 10.3389/fchem.2024.1389848 -
International Journal of Molecular... May 2024Boronate esters are a class of compounds containing a boron atom bonded to two oxygen atoms in an ester group, often being used as precursors in the synthesis of other...
Boronate esters are a class of compounds containing a boron atom bonded to two oxygen atoms in an ester group, often being used as precursors in the synthesis of other materials. The characterization of the structure and properties of esters is usually carried out by UV-visible, infrared, and nuclear magnetic resonance (NMR) spectroscopic techniques. With the aim to better understand our experimental data, in this article, the density functional theory (DFT) is used to analyze the UV-visible and infrared spectra, as well as the isotropic shielding and chemical shifts of the hydrogen atoms H, carbon C and boron B in the compound 4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)benzaldehyde. Furthermore, this study considers the change in its electronic and spectroscopic properties of this particular ester, when its boron atom is coordinated with a fluoride anion. The calculations were carried out using the LSDA and B3LYP functionals in Gaussian-16, and PBE in CASTEP. The results show that the B3LYP functional gives the best approximation to the experimental data. The formation of a coordinated covalent B-F bond highlights the remarkable sensitivity of the NMR chemical shifts of carbon, oxygen, and boron atoms and their surroundings. Furthermore, this bond also highlights the changes in the electron transitions bands → * and → * during the absorption and emission of a photon in the UV-vis, and in the stretching bands of the C=C bonds, and bending of BO in the infrared spectrum. This study not only contributes to the understanding of the properties of boronate esters but also provides important information on the interactions and responses optoelectronic of the compound when is bonded to a fluorine atom.
Topics: Benzaldehydes; Magnetic Resonance Spectroscopy; Density Functional Theory; Fluorine; Boron; Models, Molecular; Esters; Spectrophotometry, Infrared; Molecular Structure; Ions
PubMed: 38732218
DOI: 10.3390/ijms25095000 -
International Journal of Molecular... Apr 2024This study aimed to synthesize molybdenum complexes coordinated with an aroyl hydrazone-type ligand (HL), which was generated through the condensation of...
This study aimed to synthesize molybdenum complexes coordinated with an aroyl hydrazone-type ligand (HL), which was generated through the condensation of 2-hydroxy-5-nitrobenzaldehyde with benzhydrazide. The synthesis yielded two types of mononuclear complexes, specifically [MoO(L)(MeOH)] and [MoO(L)(HO)], as well as a bipyridine-bridged dinuclear complex, [(MoO(L))(4,4'-bpy)]. Those entities were thoroughly characterized using a suite of analytical techniques, including attenuated total reflectance infrared spectroscopy (IR-ATR), elemental analysis (EA), thermogravimetric analysis (TGA), and single-crystal X-ray diffraction (SCXRD). Additionally, solid-state impedance spectroscopy (SS-IS) was employed to investigate the electrical properties of these complexes. The mononuclear complexes were tested as catalysts in the epoxidation of cyclooctene and the oxidation of linalool. Among these, the water-coordinated mononuclear complex, [MoO(L)(HO)], demonstrated superior electrical and catalytic properties. A novel contribution of this research lies in establishing a correlation between the electrical properties, structural features, and the catalytic efficiency of the complexes, marking this work as one of the pioneering studies in this area for molybdenum coordination complexes, to the best of our knowledge.
Topics: Molybdenum; Catalysis; Oxidation-Reduction; Coordination Complexes; Benzaldehydes; Semiconductors
PubMed: 38732078
DOI: 10.3390/ijms25094859 -
ACS Omega Apr 2024A regioselective enzyme-catalyzed system is selected for the synthesis of 1,3,5-trisubstituted pyrazole derivatives by adding phenyl hydrazines, nitroolefins, and...
A regioselective enzyme-catalyzed system is selected for the synthesis of 1,3,5-trisubstituted pyrazole derivatives by adding phenyl hydrazines, nitroolefins, and benzaldehydes. The reaction is performed in a one-pot vessel with a yield ranging from 49 to 90%. TLL@MMI, immobilized lipase (TLL) on a multivariate of MOF-5/IRMOF-3 (MMI), showed good performance for the catalysis of this reaction. The prepared biocatalyst was characterized by FTIR, XRD, SEM, and EDX. The thermal and solvent stability of TLL@MMI was investigated in MeOH and EtOH after 24 h incubation. In the presence of 100% concentrations of EtOH, TLL@MMI has 80% activity.
PubMed: 38708258
DOI: 10.1021/acsomega.3c09875 -
PloS One 2024The incorporation of phytoactive compounds in the management of malarial vectors holds promise for the development of innovative and efficient alternatives....
Phytomediated stress modulates antioxidant status, induces overexpression of CYP6M2, Hsp70, α-esterase, and suppresses the ABC transporter in Anopheles gambiae (sensu stricto) exposed to Ocimum tenuiflorum extracts.
The incorporation of phytoactive compounds in the management of malarial vectors holds promise for the development of innovative and efficient alternatives. Nevertheless, the molecular and physiological responses that these bioactive substances induce remain underexplored. This present study investigated the toxicity of different concentrations of aqueous and methanol extracts of Ocimum tenuiflorum against larvae of Anopheles gambiae (sensu stricto) and unraveled the possible underlying molecular pathways responsible for the observed physiological effects. FTIR and GCMS analyses of phytoactive compounds in aqueous and methanol crude extracts of O. tenuiflorum showed the presence of OH stretching vibration, C = C stretching modes of aromatics and methylene rocking vibration; ring deformation mode with high levels of trans-β-ocimene, 3,7-dimethyl-1,3,6-octatriene in aqueous extract and 4-methoxy-benzaldehyde, 1,3,5-trimethyl-cyclohexane and o-cymene in methanol extract. The percentage mortality upon exposure to methanol and aqueous extracts of O. tenuiflorum were 21.1% and 26.1% at 24 h, 27.8% and 36.1% at 48 h and 36.1% and 45% at 72 h respectively. Using reverse transcription quantitative polymerase chain reaction (RT-qPCR), down-regulation of ABC transporter, overexpression of CYP6M2, Hsp70, and α-esterase, coupled with significantly increased levels of SOD, CAT, and GSH, were observed in An. gambiae (s.s.) exposed to aqueous and methanol extracts of O. tenuiflorum as compared to the control. Findings from this study have significant implications for our understanding of how An. gambiae (s.s.) larvae detoxify phytoactive compounds.
Topics: Animals; Anopheles; Plant Extracts; Antioxidants; Ocimum; ATP-Binding Cassette Transporters; HSP70 Heat-Shock Proteins; Cytochrome P-450 Enzyme System; Larva; Insect Proteins; Stress, Physiological
PubMed: 38696463
DOI: 10.1371/journal.pone.0302677 -
Microbial Pathogenesis Apr 2024Quorum sensing (QS) has a central role in biofilm lifestyle and antimicrobial resistance, and disrupting these signaling pathways is a promising strategy to control...
Quorum sensing (QS) has a central role in biofilm lifestyle and antimicrobial resistance, and disrupting these signaling pathways is a promising strategy to control bacterial pathogenicity and virulence. In this study, the efficacy of three structurally related benzaldehydes (4-hydroxybenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde (vanillin) and 4-hydroxy-3,5-dimethoxybenzaldehyde (syringaldehyde)) in disrupting the las and pqs systems of Pseudomonas aeruginosa was investigated using bioreporter strains and computational simulations. Additionally, these benzaldehydes were combined with tobramycin and ciprofloxacin antibiotics to evaluate their ability to increase antibiotic efficacy in preventing and eradicating P. aeruginosa biofilms. To this end, the total biomass, metabolic activity and culturability of the biofilm cells were determined. In vitro assays results indicated that the aromatic aldehydes have potential to inhibit the las and pqs systems by > 80 %. Molecular docking studies supported these findings, revealing the aldehydes binding in the same pocket as the natural ligands or receptor proteins (LasR, PQSA, PQSE, PQSR). Benzaldehydes were shown to act as virulence factor attenuators, with vanillin achieving a 48 % reduction in pyocyanin production. The benzaldehyde-tobramycin combination led not only to a 60 % reduction in biomass production but also to a 90 % reduction in the metabolic activity of established biofilms. A similar result was observed when benzaldehydes were combined with ciprofloxacin. 4-Hydroxybenzaldehyde demonstrated relevant action in increasing biofilm susceptibility to ciprofloxacin, resulting in a 65 % reduction in biomass. This study discloses, for the first time, that the benzaldehydes studied are potent QS inhibitors and also enhancers of antibiotics antibiofilm activity against P. aeruginosa.
PubMed: 38679246
DOI: 10.1016/j.micpath.2024.106663 -
Molecules (Basel, Switzerland) Apr 2024Chalcones are polyphenols that belong to the flavonoids family, known for their broad pharmacological properties. They have thus attracted the attention of chemists for...
Chalcones are polyphenols that belong to the flavonoids family, known for their broad pharmacological properties. They have thus attracted the attention of chemists for their obtention and potential activities. In our study, a library of compounds from 2'-hydroxychalcone's family was first synthesized. A one-step mechanochemical synthesis via Claisen-Schmidt condensation reaction under ball mill conditions was studied, first in a model reaction between a 5'-fluoro-2'-hydroxyacetophenone and 3,4-dimethoxybenzaldehyde. The reaction was optimized in terms of catalysts, ratio of reagents, reaction time, and influence of additives. Among all assays, we retained the best one, which gave the highest yield of 96% when operating in the presence of 1 + 1 eq. of substituted benzaldehyde and 2 eq. of KOH under two grinding cycles of 30 min. Thus, this protocol was adopted for the synthesis of the selected library of 2'-hydroxychalcones derivatives. The biological activities of 17 compounds were then assessed against , parasite development, as well as melanoma cell lines by inhibiting their viability and proliferation. Compounds and are the most potent against exhibiting IC values of 2.33 µM and 2.82 µM, respectively, better than the reference drug Miltefosine (3.66 µM). Compound presented the most interesting antimalarial activity against the 3D7 strain, with IC = 3.21 µM. Finally, chalcone gave the best result against IGR-39 melanoma cell lines, with an IC value of 12 µM better than the reference drug Dacarbazine (IC = 25 µM).
Topics: Chalcones; Humans; Cell Line, Tumor; Plasmodium falciparum; Leishmania donovani; Antimalarials; Antineoplastic Agents; Cell Proliferation; Cell Survival; Molecular Structure
PubMed: 38675640
DOI: 10.3390/molecules29081819 -
International Journal of Molecular... Apr 2024A library of regioisomeric monoterpene-based aminodiols was synthesised and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The synthesis of...
A library of regioisomeric monoterpene-based aminodiols was synthesised and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The synthesis of the first type of aminodiols was achieved starting from (-)-8,9-dihydroperillaldehyde via reductive amination, followed by Boc protection and dihydroxylation with the OsO/NMO system. Separation of formed stereoisomers resulted in a library of aminodiol diastereoisomers. The library of regioisomeric analogues was obtained starting from (-)-8,9-dihydroperillic alcohol, which was transformed into a mixture of allylic trichloroacetamides via Overman rearrangement. Changing the protecting group to a Boc function, the protected enamines were subjected to dihydroxylation with the OsO/NMO system, leading to a 71:16:13 mixture of diastereoisomers, which were separated, affording the three isomers in isolated form. The obtained primary aminodiols were transformed into secondary derivatives. The regioselectivity of the ring closure of the -benzyl-substituted aminodiols with formaldehyde was also investigated, resulting in 1,3-oxazines in an exclusive manner. To explain the stability difference between diastereoisomeric 1,3-oxazines, a series of comparative theoretical modelling studies was carried out. The obtained potential catalysts were applied in the reaction of aromatic aldehydes and diethylzinc with moderate to good enantioselectivities (up to 94% ), whereas the opposite chiral selectivity was observed between secondary aminodiols and their ring-closed 1,3-oxazine analogues.
Topics: Stereoisomerism; Catalysis; Monoterpenes; Benzaldehydes; Amino Alcohols; Molecular Structure; Aldehydes; Organometallic Compounds
PubMed: 38673908
DOI: 10.3390/ijms25084325 -
Foods (Basel, Switzerland) Apr 2024Strong-flavor Daqu, as a fermentation agent, plays a significant role in shaping the quality of strong-flavor baijius, and fungal species in Daqu are important factors...
Strong-flavor Daqu, as a fermentation agent, plays a significant role in shaping the quality of strong-flavor baijius, and fungal species in Daqu are important factors affecting the quality of Daqu. Therefore, we selected strong-flavor Daqu from seven different origins to study the fungal composition and the effects of the fungal composition on the physicochemical properties and volatile organic compounds (VOCs). It was found that the fungal composition influences the physicochemical properties of Daqu. Specifically, there was a positive link between , , , and liquefying activity and a positive correlation between and fermenting activity. Furthermore, the relationships between esterifying activity and , , , , and were found to be positive. The VOCs in Daqu were affected by , , , and . was significantly positively correlated with benzeneethanol as well as and pentadecanoic acid ethyl ester, ethyl myristate. and were significantly negatively correlated with benzaldehyde and 2-furaldehyde. This study deepens our understanding of the relationship between VOCs, the physicochemical properties with microbial communities, and reference significance for the production of better-quality strong-flavor Daqu.
PubMed: 38672935
DOI: 10.3390/foods13081263 -
Foods (Basel, Switzerland) Apr 2024Lushan Yunwu tea (LSYWT) is a famous green tea in China. However, the effects of intercropping tea with flowering cherry on the overall aroma of tea have not been well...
Lushan Yunwu tea (LSYWT) is a famous green tea in China. However, the effects of intercropping tea with flowering cherry on the overall aroma of tea have not been well understood. In this study, headspace solid-phase microextraction (HS-SPME) coupled with gas chromatography-mass spectrometry (GC-MS) was used for analysis. A total of 54 volatile compounds from eight chemical classes were identified in tea samples from both the intercropping and pure-tea-plantation groups. Principal component analysis (PCA), orthogonal partial least-squares discriminant analysis (OPLS-DA), and odor activity value (OAV) methods combined with sensory evaluation identified cis-jasmone, nonanal, and linalool as the key aroma compounds in the intercropping group. Benzaldehyde, α-farnesene, and methyl benzene were identified as the main volatile compounds in the flowering cherry using headspace solid-phase microextraction/gas chromatography-mass spectrometry (HS-SPME/GC-MS). These findings will enrich the research on tea aroma chemistry and offer new insights into the product development and quality improvement of LSYWT.
PubMed: 38672924
DOI: 10.3390/foods13081252