Terretonin O: a new meroterpenoid from Aspergillus terreus

Abstract

Terretonin O (1), a new meroterpenoid, was isolated individually from both methanolic extracts of thermophilic Aspergillus terreus TM8 and marine Aspergillus terreus LGO13. The recently reported terretonins M (2) and N (3) were further isolated from the fungus LGO13 along with nine known compounds, terrelumamide A (4), terrein (5), methyl-3,4,5-trimethoxyl-2-[2-(nicotinamide)benzamido] benzoate (6), butyrolactones I-III (7–9), aspulvinone O (10), ergosterol, ergost-4-ene-3-one and methyl linoleate. Structure of terretonin O (1) was established on the bases of HRESIMS, 1D and 2D NMR spectra and comparison with its analogues in literatures. The relative stereochemistry of 1 was assigned on the basis of NOESY spectra and comparison with reported configuration of its congener compounds 2 and 3. The antimicrobial and cytotoxic activities of the fungal extracts and obtained compounds were assayed using a set of microorganisms, and cervix carcinoma cell line (KB-3-1), respectively. Isolation and taxonomical characterization of the producing strains are reported.     

Destabilizing the structural integrity of COVID-19 by caulerpin and its derivatives along with some antiviral drugs: An in silico approaches for a combination therapy

Structural Chemistry - Presently, the SARS-CoV-2 (COVID-19) pandemic has been spreading throughout the world. Some drugs such as lopinavir, simeprevir, hydroxychloroquine, chloroquine, and...     

Inverse gas chromatographic characterization of Porapak Q as an extractant of pollutants from aqueous media

The surface of Porapak Q was characterized by inverse gas chromatography (IGC) carried out by the determination of dispersive and specific adsorption components of Porapak Q surface, calculating γ_s^d and -ΔH _a^s parameters, respectively. An interpretation was given based on the chemical structure of Porapak Q. The obtained results were confirmed through the surface Lewis acidity and basicity constants, K _a and K _b, respectively, correlating well with the determined thermodynamic parameters.     

Synthesis,Characterization, and DFT Calculations of Quinoline and Quinazoline Derivatives

Russian Journal of Organic Chemistry - Treatment of 3-methylcyclohexanone with ethyl formate in the presence of sodium methoxide afforded sodium (2-methyl-6-oxocyclohexylidene)methanolate which...     

Synthesis of new heterocycles festooned with thiophene and evaluating their antioxidant activity

The chemical performance of 5-bromo-2-(bromoacetyl)-thiophene ( 1 ) was tested toward the reaction with numerous bi-nucleophilic reagents (namely; 2-aminobenzothiazoles, 2-aminothiazole, 2-aminotetrazole, 2-aminotriazole, 2-aminopyridines, 2-aminobenzimidazole and o-phenylenediamine). Therefore, a series of bridged nitrogen heterocycles bearing thiophene moiety 3 , 5 , 7 , 9 , 11 , 13 and 15 , respectively was synthesized. In addition, the reaction of 5-bromo-2-(bromoacetyl)-thiophene with the thiocarbamoyl compounds 17 , 19 and/or 24 afforded the corresponding thienyl-thiazoles 18 or dithien-2-yl ketones 20 and 25 , based on the reaction conditions. Treatment of 1 with 2-mercapto-4,6-dimethylnicotinonitrile was achieved to obtain the target dithien-2-yl ketone 28 . The new synthesized scaffolds were examined for their antioxidant activity by means of ABTS antioxidant assay. The thienyl-thiazole scaffold 18c and 2-((2-[thiophen-2-yl]-2-oxoethyl)thio)nicotinonitrile derivative 27 displayed a reasonable radical scavenging activity.     

Synthesis of some novel pyrazoline‐thiazole hybrids and their antimicrobial activities

A series of novel thiazolyl pyrazolines 7a‐h , 9a‐f , and 11a‐f have been synthesized by the reaction of thioamide derivatives 5a , b with 1‐aryl‐2‐bromoethanones 6a‐d , chloroacetones 8a‐c , and hydrazonoyl chlorides 10a‐c . Additionally, pyrazoles 15a‐c and 20 were prepared starting from enaminone 13 . These newly synthesized compounds were screened for their in vitro antibacterial activity against four bacterial species. Compound 11b showed a moderate activity against Klebsiella pneumoniae. Compounds 7c and 11c revealed a moderate activity against Pseudomonas aeruginosa. In addition, the antifungal activity of the newly synthesized compounds was determined against five fungal strains. Compounds 7e , 7g , and 11e showed a good activity against Aspergillus flavus and Penicillium expansum.     

Spectrophotometric determination of some amino heterocyclic donors through charge transfer complex formation with chloranilic acid in acetonitrile

The present study is directed toward a development of simple, rapid and accurate spectrophotometric method for determination of some amino heterocyclic donors. The Charge transfer (CT) interactions between 3-aminopyrazole (AP), 3,5-dimethyl-pyrazole (DMP), 3-amino-5-methyl-pyrazole (AMP), 2-amino-4-methyl-thiazole (AMT), 2-amino-5-methyl-1,3,4-thiadiazole (AMTD) and 2-amino-5,6-dimethyl-1,2,4-triazine (ADMT) with chloranilic acid (CLA) as π-acceptor have been investigated spectrophotometrically in acetonitrile. Factors controlling the CT-reactions were also studied and optimized. Under the optimum conditions, linear relationships with good correlation coefficients were identified with high accuracy and precision. Job's method of continuous variation, spectrophotometric and conductometric titrations were used to identify the composition of the formed CT-complexes. Benesi-Hildebrand (BH) equation has been used to calculate the formation constants of the charge transfer reactions K_CT and the molar extinction coefficients ε. Free energy change (ΔG^o), oscillator strength (f), transition dipole moment (µ), ionization potential (I_P) and charge transfer energy of the formed CT-complexes (E_CT) were also determined and evaluated.     

Aqueous polymerization of methyl methacrylate catalyzed by corundum and characterization of the obtained polymers

The aqueous polymerization of methyl methacrylate (MMA) was studied using sodium bi-sulfite as initiator in the absence and presence of corundum (Al₂O₃). It was found that corundum has a catalytic effect on the polymerization reaction. The polymers obtained in the presence of corundum were found to have a wider molecular weight distribution than in its absence; this was deduced by thin-layer chromatographic analysis in a binary mixture (benzene: methanol 1:1.5 by volume) at 25°C. The apparent energy of activation was calculated between 40 and 50°C, and was found to be 4.50 × 10⁴ and 1.70 × 10⁴ J/mol in the absence and presence of 0.5 g corundum (type 600 grit)/105 mL of the reaction mixture, respectively.     

Combination and tricombination therapy to destabilize the structural integrity of COVID-19 by some bioactive compounds with antiviral drugs: insights from molecular docking study

Structural Chemistry - Recently, the SARS-CoV-2 (COVID-19) pandemic virus has been spreading throughout the world. Until now, no certified drugs have been discovered to efficiently inhibit the...     

Steam pretreatment of douglas-fir wood chips

Douglas-fir sapwood and heartwood were impregnated with SO₂ and steam exploded at three severity levels, and the cellulose-rich, water-insoluble component was enzymatically hydrolyzed. The high-severity conditions resulted in near complete solubilization and some degradation of hemicelluloses and a significant improvement in the efficiency of enzymatic digestibility of the cell ulose component. At lower severity, some of the hemicellulose remained un hydrolyzed, and the cellulose present in the pretreated solids was not readily hydrolyzed. The medium-severity pretreatment conditions proved to be a good compromise because they improved the enzymatic hydrolyzability of the solids and resulted in the recovery of the majority of hemicellulose in a monomeric form within the water-soluble stream. Sapwood-derived wood chips exhibited a higher susceptibility to both pretreatment and hydrolysis and, on steam explosion, formed smaller particles as compared to heartwood-derived wood chips.