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Molecules (Basel, Switzerland) Aug 2022The present study aimed to isolate volatile organic compounds (VOCs) from fresh (FrHSc) and air-dried (DrHSc) (from the Adriatic Sea) by headspace solid-phase...
The present study aimed to isolate volatile organic compounds (VOCs) from fresh (FrHSc) and air-dried (DrHSc) (from the Adriatic Sea) by headspace solid-phase microextraction (HS-SPME) and hydrodistillation (HD) and to analyse them by gas chromatography and mass spectrometry (GC-MS). The impact of the season of growth (May-September) and air-drying on VOC composition was studied for the first time, and the obtained data were elaborated by principal component analysis (PCA). The most abundant headspace compounds were benzaldehyde, pentadecane (a chemical marker of brown macroalgae), and pentadec-1-ene. Benzaldehyde abundance decreased after air-drying while an increment of benzyl alcohol after drying was noticed. The percentage of pentadecane and heptadecane increased after drying, while pentadec-1-ene abundance decreased. Octan-1-ol decreased from May to September. In HD-FrHSc, terpenes were the most abundant in June, July, and August, while, in May and September, unsaturated aliphatic compounds were dominant. In HD-DrHSc terpenes, unsaturated and saturated aliphatic compounds dominated. ()-Phytol was the most abundant compound in HD-FrHSc through all months except September. Its abundance increased from May to August. Two more diterpene alcohols (isopachydictyol A and cembra-4,7,11,15-tetraen-3-ol) and sesquiterpene alcohol gleenol were also detected in high abundance. Among aliphatic compounds, the dominant was pentadec-1-ene with its peak in September, while pentadecane was present with lower abundance. PCA (based on the dominant compound analyses) showed distinct separation of the fresh and dried samples. No correlation was found between compound abundance and temperature change. The results indicate great seasonal variability of isolated VOCs, as well among fresh and dried samples, which is important for further chemical biodiversity studies.
Topics: Alcohols; Benzaldehydes; Phaeophyceae; Scoparia; Seaweed; Solid Phase Microextraction; Terpenes; Volatile Organic Compounds
PubMed: 35956941
DOI: 10.3390/molecules27154997 -
Antimicrobial Agents and Chemotherapy 2015Acanthamoeba is a protist pathogen that can cause serious human infections, including blinding keratitis and a granulomatous amoebic encephalitis that almost always...
Acanthamoeba is a protist pathogen that can cause serious human infections, including blinding keratitis and a granulomatous amoebic encephalitis that almost always results in death. The current treatment for these infections includes a mixture of drugs, and even then, a recurrence can occur. Photochemotherapy has shown promise in the treatment of Acanthamoeba infections; however, the selective targeting of pathogenic Acanthamoeba has remained a major concern. The mannose-binding protein is an important adhesin expressed on the surface membranes of pathogenic Acanthamoeba organisms. To specifically target Acanthamoeba, the overall aim of this study was to synthesize a photosensitizing compound (porphyrin) conjugated with mannose and test its efficacy in vitro. The synthesis of mannose-conjugated porphyrin was achieved by mixing benzaldehyde and pyrrole, yielding tetraphenylporphyrin. Tetraphenylporphyrin was then converted into mono-nitrophenylporphyrin by selectively nitrating the para position of the phenyl rings, as confirmed by nuclear magnetic resonance (NMR) spectroscopy. The mono-nitrophenylporphyrin was reduced to mono-aminophenylporphyrin in the presence of tin dichloride and confirmed by a peak at m/z 629. Finally, mono-aminoporphyrin was conjugated with mannose, resulting in the formation of an imine bond. Mannose-conjugated porphyrin was confirmed through spectroscopic analysis and showed that it absorbed light of wavelengths ranging from 425 to 475 nm. To determine the antiacanthamoebic effects of the derived product, amoebae were incubated with mannose-conjugated porphyrin for 1 h and washed 3 times to remove extracellular compound. Next, the amoebae were exposed to light of the appropriate wavelength for 1 h. The results revealed that mannose-conjugated porphyrin produced potent trophicidal effects and blocked excystation. In contrast, Acanthamoeba castellanii incubated with mannose alone and porphyrin alone did not exhibit an antiamoebic effect. Consistently, pretreatment with mannose-conjugated porphyrin reduced the A. castellanii-mediated host cell cytotoxicity from 97% to 4.9%. In contrast, treatment with porphyrin, mannose, or solvent alone had no protective effects on the host cells. These data suggest that mannose-conjugated porphyrin has application for the targeted photodynamic therapy of Acanthamoeba infections and may serve as a model in the development of therapeutic interventions against other eukaryotic infections.
Topics: Acanthamoeba castellanii; Antiprotozoal Agents; Benzaldehydes; Cell Line; Cells, Cultured; Humans; Magnetic Resonance Spectroscopy; Mannose; Porphyrins; Pyrroles
PubMed: 25753633
DOI: 10.1128/AAC.05126-14 -
Food and Chemical Toxicology : An... Jan 2021This work evaluated the cytotoxic effect of different EOCs-functionalised silica particle types. The in vitro toxicity of eugenol and vanillin-immobilised SAS, MCM-41...
This work evaluated the cytotoxic effect of different EOCs-functionalised silica particle types. The in vitro toxicity of eugenol and vanillin-immobilised SAS, MCM-41 microparticles and MCM-41 nanoparticles was evaluated on HepG2 cells, and compared to free EOCs and pristine materials. The results revealed that free essential oil components and bare silica had a mild cytotoxic effect on HepG2 cells. However, the comparative study showed that free eugenol and vanillin had a milder cytotoxic effect than the equivalent concentrations of immobilised components on the different silica particles, while differences in cell viability between the bare and functionalised particles relied on the type of analysed material. The most cytotoxic materials were eugenol and vanillin-functionalised MCM-41 micro with IC values of 0.19 and 0.17 mg/mL, respectively, at 48 h exposure. Differences in cytotoxicity between functionalised particles may be attributed to the density of the functional components on their surface as a result of the functionalisation reaction performance for different materials. The study of the physico-chemical properties of particles demonstrated that cationic nature and increased hydrophobicity could be responsible for promoting cell-particle interactions for the eugenol and vanillin functionalised silica particles, enhancing their cytotoxic behaviour.
Topics: Benzaldehydes; Cell Survival; Dose-Response Relationship, Drug; Eugenol; Hep G2 Cells; Humans; Inhibitory Concentration 50; Microscopy, Electron, Transmission; Nanoparticles; Oils, Volatile; Silicon Dioxide
PubMed: 33212212
DOI: 10.1016/j.fct.2020.111858 -
Organic Letters May 2020For decades, oxidative dearomatization has been employed as a key step in the synthesis of complex molecules. Challenges in controlling the chemo- and site-selectivity...
For decades, oxidative dearomatization has been employed as a key step in the synthesis of complex molecules. Challenges in controlling the chemo- and site-selectivity of this transformation have sparked the development of a variety of specialized oxidants; however, these result in stoichiometric amounts of organic byproducts. Herein, we describe a photocatalytic method for oxidative dearomatization using molecular oxygen as the stoichiometric oxidant. This provides environmentally benign entry to highly substituted -quinols, reactive intermediates which can be elaborated to a number of natural product families.
Topics: Benzaldehydes; Catalysis; Hydroquinones; Oxidants, Photochemical; Oxidation-Reduction; Photochemical Processes
PubMed: 32293185
DOI: 10.1021/acs.orglett.0c01207 -
Disease Models & Mechanisms Oct 2022Manipulating firing-rate neuronal homeostasis, which enables neurons to regulate their intrinsic excitability, offers an attractive opportunity to prevent seizures....
Manipulating firing-rate neuronal homeostasis, which enables neurons to regulate their intrinsic excitability, offers an attractive opportunity to prevent seizures. However, to date, no drug-based interventions have been reported that manipulate this type of neuronal homeostatic mechanism. Here, we used a combination of Drosophila and mouse, and, in the latter, both a pentylenetetrazole (PTZ)-induced seizure model and an electrically induced seizure model for refractory seizures to evaluate the anticonvulsant efficacy of a novel class of anticonvulsant compounds, based on 4-tert-butyl-benzaldehyde (4-TBB). The mode of action included increased expression of the firing rate homeostatic regulator Pumilio (PUM). Knockdown of pum expression, in Drosophila, blocked anticonvulsive effects of 4-TBB, while analysis of validated PUM targets in mouse brain revealed significant reductions following exposure to this compound. A structure-activity study identified the active parts of the molecule and, further, showed that the pyrazole analogue demonstrates highest efficacy, being active against both PTZ-induced and electrically induced seizures. This study provides a proof of principle that anticonvulsant effects can be achieved through regulation of firing rate neuronal homeostasis and identifies a possible chemical compound for future development.
Topics: Animals; Anticonvulsants; Benzaldehydes; Drosophila; Homeostasis; Mice; Neurons; Pentylenetetrazole; Pyrazoles; Seizures
PubMed: 36073607
DOI: 10.1242/dmm.049703 -
Frontiers in Cellular and Infection... 2021Biocontrol of root-knot nematode has attracted increasing attention over the past two decades. The inconsistent field performance of biocontrol agents, which is caused...
Methylglyoxal Has Different Impacts on the Fungistatic Roles of Ammonia and Benzaldehyde, and Lactoylglutathione Lyase Is Necessary for the Resistance of to Soil Fungistasis.
Biocontrol of root-knot nematode has attracted increasing attention over the past two decades. The inconsistent field performance of biocontrol agents, which is caused by soil fungistasis, often restricts their commercial application. There is still a lack of research on the genes involved in biocontrol fungi response to soil fungistasis, which is important for optimizing practical applications of biocontrol fungi. In this study, the lactoylglutathione lyase-encoding in the nematophagous fungi was knocked out, and three mutant strains were obtained. The hyphal growth of mutants on the three media was almost the same as that of the wild-type strain, but mutants had slightly higher resistance to NaCl, SDS, and HO. Methylglyoxal (MG) significantly increased the resistance of to ammonia, but decreased the resistance to benzaldehyde. Furthermore, the resistance of the mutants to soil fungistasis was largely weakened and MG could not increase the resistance of to soil fungistasis. Our results revealed that MG has different effects on the fungistatic roles of ammonia and benzaldehyde and that lactoylglutathione lyase is very important for to resist soil fungistasis.
Topics: Ammonia; Animals; Ascomycota; Benzaldehydes; Hydrogen Peroxide; Lactoylglutathione Lyase; Nematoda; Pyruvaldehyde; Soil
PubMed: 33996625
DOI: 10.3389/fcimb.2021.640823 -
Molecules (Basel, Switzerland) Sep 2013The Paternò-Büchi reaction is a photochemical reaction between a carbonyl compound and an alkene to give the corresponding oxetane. In this review the mechanism of the... (Review)
Review
The Paternò-Büchi reaction is a photochemical reaction between a carbonyl compound and an alkene to give the corresponding oxetane. In this review the mechanism of the reaction is discussed. On this basis the described use in the reaction with electron rich alkenes (enolethers, enol esters, enol silyl ethers, enanines, heterocyclic compounds has been reported. The stereochemical behavior of the reaction is particularly stressed. We pointed out the reported applications of this reaction to the synthesis of naturally occuring compounds.
Topics: Benzaldehydes; Cycloaddition Reaction; Ethers, Cyclic; Free Radicals; Furans; Humans; Models, Chemical; Photochemical Processes; Quantum Theory; Stereoisomerism
PubMed: 24043139
DOI: 10.3390/molecules180911384 -
Molecules (Basel, Switzerland) Aug 2022Oxyfunctionalization of toluene to value-added benzaldehyde, benzyl alcohol and benzoic acid is of great significance. In this work, Co-Schiff bases were immobilized on...
Oxyfunctionalization of toluene to value-added benzaldehyde, benzyl alcohol and benzoic acid is of great significance. In this work, Co-Schiff bases were immobilized on commercial silica gel by covalent anchoring, and resulting catalysts were used to catalyze the oxidation of toluene in the presence of the cocatalyst N-hydroxyphthalimide (NHPI). The catalysts exhibited excellent textural and structural properties, reliable bonding and a predomination of the cobaltous ions. The catalyst synthesized by diethylamino salicylaldehyde (EASA) possessed a grafting density of 0.14 mmol/g and exhibited a toluene conversion of 37.5%, with predominant selectivities to benzaldehyde, benzyl alcohol and benzoic acid under solvent-free conditions. It is concluded that the effect of ligands on their catalytic performance might be related to their electron-donating or -withdrawing properties.
Topics: Benzaldehydes; Benzoic Acid; Benzyl Alcohol; Schiff Bases; Toluene
PubMed: 36014538
DOI: 10.3390/molecules27165302 -
Molecules (Basel, Switzerland) May 2018Reaction between pyrogallol and benzaldehyde results in a conformational mixture of tetra(phenyl)pyrogallol[4]arene (crown and chair). The conformer mixture was...
Reaction between pyrogallol and benzaldehyde results in a conformational mixture of tetra(phenyl)pyrogallol[4]arene (crown and chair). The conformer mixture was separated using crystallization procedures and the structures were determined using FTIR, ¹H-NMR, and C-NMR. -acetylation of tetra(phenyl)pyrogallol[4]arene (chair) with acetic anhydride, in pyridine results in the formation of dodecaacetyl-tetra(phenyl)pyrogallol[4]arene. The structure was determined using ¹H-NMR and C-NMR finding that the product maintains the conformation of the starting conformer. On the other hand, the -acetylation reaction of tetra(phenyl)pirogallol[4]arene (crown) under same conditions proceeded efficiently, and its structure was determined using ¹H-NMR and C-NMR. Dynamic ¹H-NMR of acetylated pyrogallolarene was studied by means of variable temperature in DMSO-₆ solution, and it revealed that two conformers are formed in the solution. Boat conformations for acetylated pyrogallolarene showed a slow interconversion at room temperature.
Topics: Acetic Anhydrides; Acetylation; Benzaldehydes; Crystallography, X-Ray; Magnetic Resonance Spectroscopy; Molecular Conformation; Molecular Structure; Pyrogallol
PubMed: 29783780
DOI: 10.3390/molecules23051225 -
International Journal of Antimicrobial... Nov 2023Angiostrongylus cantonensis, also known as rat lungworm, is an important food-borne zoonotic parasite that causes severe neuropathological damage and symptoms, including...
Angiostrongylus cantonensis, also known as rat lungworm, is an important food-borne zoonotic parasite that causes severe neuropathological damage and symptoms, including eosinophilic meningitis and eosinophilic meningoencephalitis, in humans. At present, the therapeutic strategy for cerebral angiostrongyliasis remains controversial. Benzaldehyde, an important bioactive constituent of Gastrodia elata (Tianma), reduces oxidative stress by inhibiting the production of reactive oxygen species. This study aimed to evaluate the therapeutic effect of benzaldehyde in combination with albendazole on angiostrongyliasis in animal models. First, the data from body weight monitoring and behavioural analyses demonstrated that benzaldehyde improved body weight and cognitive function changes after A. cantonensis infection. Next, blood‒brain barrier breakdown and pathological changes were reduced after benzaldehyde and albendazole treatment in BALB/c mice infected with A. cantonensis. Subsequently, four RNA-seq datasets were established from mouse brains that had undergone different treatments: normal, infection, infection + albendazole, and infection + albendazole + 3-hydroxybenzaldehyde groups. Ultimately, benzaldehyde was found to regulate cell apoptosis, oxidative stress and Sonic Hedgehog signalling in mouse brains infected with A. cantonensis. This study evaluated the therapeutic effect of benzaldehyde on angiostrongyliasis, and provided a potential therapeutic strategy for human angiostrongyliasis in the clinical setting. Moreover, the molecular mechanism of benzaldehyde in mouse brains infected with A. cantonensis was elucidated.
Topics: Mice; Rats; Humans; Animals; Albendazole; Benzaldehydes; Hedgehog Proteins; Angiostrongylus cantonensis; Brain Injuries; Body Weight; Brain
PubMed: 37666435
DOI: 10.1016/j.ijantimicag.2023.106963