Biological Activity Of Compounds Research Articles

Tanacetum vulgare L. (Tansy) as an effective bioresource with promising pharmacological effects from natural arsenal

The Tanacetum genus is a big treasure with the presence of biologically-active compounds and members of this genus are widely used for the treatment of several diseases in traditional medicine system. Considering this fact, we aimed to analyze the extracts from Tanacetum vulgare L. in case of chemical profiles and biological effects. Chemical characterization was performed by using UHPLC-HRMS technique and showed the presence of several phytochemical groups (107 compounds were identified, including phenolic acids, flavonoids, terpenoids and fatty acids. Biological abilities were examined by using antioxidant (DPPH, ABTS, FRAP, CUPRAC, metal chelating and phosphomolybdenum assays) and enzyme inhibition (tyrosinase, amylase, glucosidase and cholinesterase) properties. Pharmaco-toxicological investigations were also performed with the aim to identify limits of biocompatibility, anti-oxidant and neuromodulatory effects, in hypothalamic HypoE22 cells. A bioinformatic analysis was also carried to unravel the putative protein-targets for the observed biological effects. Generally, the tested hexane and hydroalcoholic extracts displayed stronger activities in antioxidant and enzyme inhibitory assays, when compared with water. In addition, multivariate analysis was performed to understand the differences in both solvents and plant parts and we clearly observed the separation of these parameters. The extracts (10 μg/mL) also stimulated DAT and inhibited TNFα and BDNF gene expression, in HypoE22 cells. In parallel, the extracts were also able to stimulate norepinephrine release from this cell line. By contrast, in the concentration range 50–100 μg/mL, the extracts reduced the HypoE22 viability, thus demonstrating cytotoxicity at concentrations 5–10 fold higher compared to those effective as neuromodulatory. Our observations manifested that T. vulgare has several beneficial effects and it can be used as a potential natural raw material for designing further health-promoting applications in nutraceutical, cosmeceutical, and pharmaceutical areas.

Syrup Hedera helix Extract Poisoning in Dog: a Clinical Report

This clinical report describes a 1-year-old Golden Retriever dog weighing 24 kg that developed gastroenteritis as a result of the unprescribed and random use of a syrup Hedera helix extract, which is for human use only. Diagnosis was made after ruling out other factors that could cause gastroenteritis. An improvement in clinical findings was observed as a result of supportive treatment. It is already widely recognized that triterpene saponins, biological active compounds of Hedera helix, cause gastroenteritis in dogs and it is considered that unprescribed and random use of syrup Hedera helix at high doses, may cause severe gastroenteritis symptoms that will endanger life. It is concluded that successful management of Hedera helix extract poisoning depends on a good anamnesis, physical exams, and laboratory tests, rapidly ruling out other causes of gastroenteritis, quitting the use of syrup immediately and a supportive treatment

Synthesis, characterization, anti-proliferative activity and DFT study of 1H-benzo[f]chromene-2-carbothioamide derivatives

Reaction of 7‑methoxy-2-naphthol with appropriate aromatic aldehydes and 2-cyano-ethanethioamide provided the corresponding 3-amino-1-aryl-9‑methoxy-1H-benzo[f]chromene-2-carbothioamide. The structures of these compounds were established on the basis of IR, 1H NMR, 13C NMR, MS data and elemental analysis. Furthermore, the anti-proliferative properties were evaluated against the human cancer cell lines MCF-7, HepG-2 and PC-3 in comparison to the positive controls Vinblastine and Doxorubicin, employing the viability assay. The obtained results confirmed that some of the tested molecules revealed strong and selective cytotoxic activities against the three cancer cell lines. Moreover, various molecular descriptors, frontier molecular orbitals (FMO), Mulliken analysis and electronic properties were studied to probe the biological activity behavior of the synthesized 1H-benzo[f]chromene-2-carbothioamide derivatives. The effect of electron withdrawing groups (EWGs) and electron donating groups (EDGs) was also explored on the structural parameters and electronic nature of compounds. The energy gaps, reactivity descriptors values and molecular docking studies exhibited that some 1H-benzo[f]chromene-2-carbothioamide derivatives would be active biological compounds.

Mediterranean Fruits and Berries with Bioactive and Toxic Components. A Review

Undoubtedly, natural products with bioactive components such as fruits and berries from the Mediterranean areas are largely appreciated and highly consumed around the world due to their significance as possible novel therapeutical agents, with immense medicinal properties and a possible profound effect on health. According to epidemiological information, there were positive correlations of high consumption of fruits and berries with a low risk of various chronic diseases as these foods are rich sources of nutrients, and energy with a high content of vitamins, minerals, fiber, antioxidants, polyphenols, and numerous other classes of biological active compounds. Apart from the functional role of fruits and berries on health, they may contain components which in turn lead to toxicity on some occasions, inducing mild or severe symptoms (diarrhea, vomiting, paralysis, coma, or even death) that vary based on various factors such as dose, sensitivity of the individual and the way of exposure. Considering the above data, this paper aims to review the recent literature about the biological activities and therapeutic potentials, toxicity, and toxic components of selected Mediterranean fruits and berries, evaluating on the one hand the potential beneficial role of these foods, and on the other hand their possible toxic health effects.

Design and Synthesis of Three Tetracyclic-Dione Derivatives and their Biological Activity on Perfusion Pressure Using an Isolated Rat Heart Model

Several tetracyclic derivatives have been prepared with different biological activity; however, there are few reports on the effects exerted by the tetracyclic derivatives on the cardiovascular system. The objective of this investigation was to prepare three tetracyclic-dione derivatives (compounds 3 to 5) to evaluate their biological activity on perfusion pressure and coronary resistance. The first stage was achieved by the synthesis of three tetracyclic‐dione analogs using some chemical strategies. The second stage involves evaluating biological activity from tetracyclic‐derivatives on perfusion pressure and coronary resistance using an isolated rat heart model. The results showed that only compound 5 increases perfusion pressure and coronary resistance compared with the control conditions. In conclusion, the biological activity of compound 5 exerted against perfusion pressure and coronary resistance depends on the functional groups involved in their chemical structure.

Effects of variety and maturity stage of coconut on physicochemical and sensory characteristics of powdered coconut drink

Introduction. Coconut water is rich in nutrients and biologically-active compounds. However, it has a short shelf life that can be prolonged by freeze drying. The purpose of this study was to analyze the physicochemical and sensory characteristics of fresh and powdered coconut drinks.
 Study objects and methods. The experiments included eight samples, namely fresh and powdered coconut drinks obtained from coconuts of different varieties (tall and hybrid) and maturity stages (4 and 6 m.o.). The samples were analyzed for nutrient content (ash, protein, fat, total carbohydrate, and fibre), physicochemical properties (titratable acidity, pH, viscosity, total soluble solids, turbidity, water activity, and browning index), and sensory characteristics (color, aroma, taste, texture, and overall acceptance).
 Results and discussion. The results obtained showed that there were significant differences among the coconut drinks of different varieties and maturity stages. They differed in nutrient content, pH value, titratable acidity, viscosity, and water activity. Meanwhile, the aroma, taste, and overall acceptance scores of all the samples were not significantly different. The powdered drink from 6 m.o. hybrid coconut was selected as the optimal sample due to its good sensory and physicochemical attributes. These attributes were similar to those of the fresh coconut drink.
 Conclusion. The powdered drink from 6 m.o. hybrid coconut obtained by freeze drying could be considered as an alternative healthy drink with good quality characteristics.

Wastes after distillation of Helichrysum italicum – biological active compounds and free radical scavenging activity

Distillation wastewater, by-products from steam and water distillation as well as raw material used as control of flower heads of Helichrysum italicum were comparative analyzed for content of the biologically active compounds by GC/MS. Acetone exudates, methanol extracts and ethyl acetate fractions obtained after alkaline hydrolyze of the studied materials were received. The three types of extraction products as well as the distillation wastewater were examined for free radical scavenging activity by DPPH assay. Phenol, fatty- and organic acids, sterols, triterpenes, sugars and sugar alcohols were identified. Succinic acid and myo-inositol were identified as main components of distillation wastewater. Hydroxycinnamic acid, caffeic acid and 4(p)-hydroxybenzoic acid were dominant compounds of the ethyl acetate fractions. Triterpenes and fatty acids, sterols and flavonoids are among the main biologically active substances in the methanolic extracts and acetone exudates. The ethyl acetate fractions were found to possess the highest free radical scavenging activity (IC50 < 50 µg/mL). Significant differences in the activity between wastes and raw materials were not found. The results showed that the waste products after distillation of H. italicum contain important biologically active substances and the extracts with high antioxidant activity can be obtained from them.

Natural Products Targeting Cancer Stem Cells: A Revisit.

The proposed central role of cancer stem cells (CSCs) in tumor development has been extended to explain the diverse oncologic phenomena such as multidrug resistance, metastasis and tumor recurrence in clinics. Due to the enhanced expression of ATP-binding cassette transporters and anti-apoptotic factors, stagnation on G0 phase and the strong ability of self-renewal, the CSCs were highly resistant to clinical anticancer drugs. Therefore, the discovery of new drug candidates that could effectively eradicate cancer stem cells afforded promising outcomes in cancer therapy. Natural products and their synthetic analogues are a rich source of biologically active compounds and several of them have already been recognized as potent CSCs killers. We aim to provide a collection of recently identified natural products that suppressed the survival of the small invasive CSC populations and combated the drug resistance of these cells in chemotherapy. These anti-CSCs natural products included flavonoids, stilbenes, quinones, terpenoids, polyketide antibiotics, steroids and alkaloids. In the present review, we highlighted the therapeutic potential of natural products and their derivatives against the proliferation and drug resistance of CSCs, their working mechanisms and related structure- activity relationships. Meanwhile, in this survey, several natural products with diverse cellular targets such as the naphthoquinone shikonin and the stilbene resveratrol were characterized as promising lead compounds for future development.

Biginelli Reaction and β-Secretase Inhibition: A Multicomponent Reaction as a Friendly Educational Approach to Bioactive Compounds

Multicomponent reactions (MCRs) represent very interesting tools to reach eco-friendly and sustainable transformations in organic chemistry. In particular, the Biginelli reaction furnishes a very easy approach to the synthesis of a library of biological active compounds in an academic course. Here we describe the realization of several experiments involving the synthesis of potential inhibitors of β-secretase by the Biginelli reaction. All of the obtained compounds were tested with a FRET fluorimetric assay. The experiments were proposed to students either at entry level or during advanced laboratory courses of organic and bioorganic chemistry. The learning objectives at the advanced level were to introduce the students to the practice of combinatorial synthesis and to the evaluation of biological activity of combinatorial libraries by enzyme inhibition assays. The meeting of the learning objectives was probed first by analyzing their daily performance in the laboratory and their increasing proactive attitude, and the contents of their final presentations. The resulting marks obtained by the students were compared with the average evaluation of their career. Second, the students were asked to evaluate the course and their own experience, and the outcome of their evaluation was compared with that of the teachers.

The antibacterial effect of β-pinene derived from Citrus aurantifolia against oral Streptococcus mutans

Introduction: Streptococcus mutans has been known to play a major role in dental caries development. This tooth decay is the most common oral disease affecting people in the world. Hence, discovering the new herbal antibacterial agent seems to become promising yet challenging. One of herbal antibacterial source is Jeruk Nipis or namely Citrus aurantifolia, as it is believed to contain biological active compounds that may act as antibacterial to kill pathogenic oral microbes. This study was aimed evaluated antibacterial effect of β-pinene derived from Citrus aurantifolia against oral Streptococcus mutans. Methods: Type of research is quasi experimental research. The essential of C. aurantifolia essential oil was prepared and isolated using the hydro-distillation technique and further isolation of antibacterial compounds was conducted by combination column chromatography using organic solvent, and the structure was determined by infrared (IR), 1D NMR of 1H-, 13C-NMR and DEPT 135° in CDCl3, and UV-Vis spectrometer methods. The antibacterial activity was tested against Streptococcus mutans using the Kirby-Bauer method. Results: 0.75% yield was extracted from the essential oil of Citrus aurantifolia and after purification, an antibacterial compound was identified as β-pinene with the molecular formula C10H16. Furthermore, the Citrus aurantifolia exerted inhibition growth of Streptococcus mutans at concentration of 2000, 1000, and 500 ppm showed reduction in paper disk as much as 13.0, 11.9, and 11.6 mm respectively. Conclusion: Antibacterial effect of β-pinene derived from Citrus aurantifolia against oral Streptococcus mutans. This is proven that β-pinene derived from Citrus aurantifolia prospective as antibacterial compound that potentially can be used as another herbal antibacterial of choice to manage dental disease associated with Streptococcus mutans infection.

The Perspective of Croatian Old Apple Cultivars in Extensive Farming for the Production of Functional Foods.

The Republic of Croatia has a long tradition of fruit growing due to its geographical location, climatic conditions, and high quality of fruit crops, especially apple fruits. Apples can be used for the formulation of functional foods either in processed form (e.g., juice), or as a by-product (e.g., apple pomace). However, there is a growing demand for functional foods derived from ancient and traditional plant sources as they are recognized as a very valuable source of health-promoting bioactive ingredients. Similarly, old apple cultivars (Malus domestica Borkh.) are characterized by good morphological and pomological properties, less need for chemicals during cultivation and the higher share of biologically active compounds (BACs) with better sensory acceptability compared to commercial cultivars. However, their nutritional and biological potential is underestimated, as is their ability to be processed into functional food. The importance in preserving old apple cultivars can also be seen in their significance for improving the nutritional composition of other apple cultivars through innovative cultivation strategies, and therefore old local apple cultivars could be of great importance in future breeding programs.

Pyrazole Carboxylic Acid and Derivatives: Synthesis and Biological Applications

The heterocyclic compounds are the building blocks for the synthesis of the different biologically active compounds in the organic chemistry. Heterocyclic compounds have versatile synthetic applicability and biological activity. Pyrazole carboxylic acid derivatives are significant scaffold structures in heterocyclic compounds due to biologic activities such as antimicrobial, anticancer, inflammatory, antidepressant, antifungal anti-tubercular and antiviral, etc. The aim of this mini-review is an overview synthesis of pyrazole carboxylic acid derivatives and their biologic applications. The summarized literature survey presents biological activities of pyrazole carboxylic acid derivatives and their various synthetic methods in detail. This mini-review can be a guide to many scientists in medicinal chemistry.

Thermal characterization and stability evaluation of leishmanicidal selenocyanate and diselenide derivatives

In this study, the thermal behavior of a series of leishmanicidal selenocyanate and diselenide biological active compounds has been studied by means of differential scanning calorimetry, X-ray diffraction and thermogravimetry in order to establish thermal stability criteria and investigate their polymorphism. Moreover, stability under acid, alkaline and oxidative media was tested using high-performance liquid chromatography with fluorescence detection. The results of the experiments show that there are five types of polymorphic behaviors for the studied compounds. In addition, relationship is found among stability and a series of structural effects and stress conditions of compounds.

Retracted: A new Co(II)‐coordination polymer: Photocatalytic studies and treatment values on mania by reducing the ErbB4 expression on the noradrenergic neurons

AbstractA novel coordination polymer based on Co(II) has been generated utilizing the 4,4′,4″‐phosphanetriyltribenzoic acid (H3tpp) as the tritopic connector in the existence of a second N‐donor ligand 3,3′‐bipyridine (3,3′‐bpy) under the solvothermal reaction conditions, and its chemical formula is [Co3(tpp)2(3,3′‐bpy)]·7DMF (1). Moreover, under ultraviolet irradiation, complex 1 has high photocatalytic activities for methylene blue degradation, and its photodegradation performance does not show much reduction after three cycles of experiments. Furthermore, the compound's biological activity against the mania was assessed, and the protentional mechanism was discussed. First, the neuroregulin1 content in the hippocampus was detected via enzyme‐linked immunosorbent assay to evaluate the compound's treatment activity on mania. Then, the ErbB4 relative expression levels were detected using real‐time reverse transcription‐polymerase chain reaction. The carboxyl groups have been confirmed to be responsible for all the binding interactions formed by molecular docking simulation.

Chemical characterization of Saudi propolis and its antiparasitic and anticancer properties

Propolis, is a gummy material produced by honey bees from different parts of plants and is enriched with varied biological active compounds like flavonoids, phenolics and phenolic acids with wide applicability in the food, pharmaceutical and cosmetics industries. The current report is focused on the characterisation of propolis collected from Asir region, South-west of Saudi Arabia and its effect on Trypanosoma brucei (the causative organism of African sleeping sickness) and cytotoxic effect against U937 human leukemia cells. The Chemical composition and spectral characteristics of Saudi propolis was studied by Liquid Chromatography Mass Spectrometry (LC–MS) and High-performance liquid chromatography–evaporative light scattering detector (HPLC–ELSD).The two main active compounds isolated from Saudi propolis via column chromatography and size exclusion chromatography were fisetinidol and ferulic acid. High resolution electrospray ionization–mass spectrophotometer (HRESI–MS) and nuclear magnetic resonance (NMR) were used to elucidate the structures of the isolated compounds. All crudes extracts, fractions as well as isolated compounds were subjected for biological testing against Trypanosoma brucei (S427 WT), and their cytotoxicity against U937 human leukemia cells. Amongst the various samples investigated, S-6 fraction demonstrated highest anti-trypanosomal activity at 2.4 µg/ml MIC followed by fisetinidol at 4.7 µg/ml reflecting that the anti-trypanosomal activity is attributable to the presence of fisetinidol in the fraction. Similarly, all the tested samples exhibited cytotoxicity with an IC50 > 60 µg/ml. S-6 fractions exhibited highest cytotoxic activity against U937 cells with an IC50 of 58.7 µg/ml followed by ferulic acid with an IC50 87.7 µg/ml indicating that the cytotoxic effect of propolis might be due to the presence of ferulic acid. In conclusion, the biological activity of propolis could be attributed to the synergistic action of the two active compounds-ferulic acid and fisetinidol. The data obtained in the study is thus indicative of the role of propolis as potential anti-trypanosomal and anticancer agent for effective cancer therapy.

1,3-Diazepine: A privileged scaffold in medicinal chemistry.

Privileged structures have been widely used as effective templates for drug discovery. While benzo-1,4-diazepine constitutes the first historical example of such a structure, the 1,3 analogue is just as rich in terms of applications in medicinal chemistry. The 1,3-diazepine moiety is present in numerous biological active compounds including natural products, and is used to design compounds displaying a large range of biological activities. It is present in the clinically used anticancer compound pentostatin, in several recent FDA approved β-lactamase inhibitors (e.g., avibactam) and also in coformycin, a natural product known as a ring-expanded purine analogue displaying antiviral and anticancer activities. Several other 1,3-diazepine containing compounds have entered into clinical trials. This heterocyclic structure has been and is still widely used in medicinal chemistry to design enzyme inhibitors, GPCR ligands, and so forth. This review endeavours to highlight the main use of the 1,3-diazepine scaffold and its derivatives, and their applications in medicinal chemistry, drug design, and therapy. We will focus more particularly on the development of enzyme inhibitors incorporating this scaffold, with a strong emphasis on the molecular interactions involved in the inhibition mechanism.

CO-CYCLIZATION OF ETNCO AND ME2CO AS THE RESULTS OF THEIR SELECTIVE INSERTION INTO THE NIOBIUM-CHLORINE BOND

Development of the new methods for drug production is impossible without reliance on the novel and unorthodox approaches to the synthesis of heterocyclic complexes and compounds.The method is based on the study of new aspects of the of two types of behavior of the coordinated molecules in reaction - their ability to insert into the same transition metal-halogen bond, and their ability to form the unusual heterocyclic ligands, or even molecules after leaving the complex’s coordination sphere. This will make it possible not only to synthesize the already-known compounds under milder conditions, but to also obtain new ones as products of such mixed condensation reactions. On the one hand, this opens up new possibilities for designing and performing the intraspherical "stitching" of ligands and their synthesis with high efficiency and selectivity. 
 On the other hand, these reactions can be considered a significant contribution to the fundamental coordination chemistry in terms of illustration of the new modalities of the mutual influence of ligands, namely their ability to stimulate each other for a mutual insertion, and sheds light on the mechanisms of the intraspheric condensation. Oxadiazine derivatives, just like the derivatives of triazine we synthesized and reported previously, could become a foundation for the generation of biologically-active compounds, often containing heterocyclic fragments and frequently used for the treatment of malignant tumors. It can be expected that the developed method will find use in the synthesis of the new classes of potential antitumor compounds.
 We have previously found that organic isocyanate not only themselves insert into M-Hal bond, but can also activate the insertion of acetonitrile, the resulting heteromolecular chain of inserted molecules being composed of two MeNCO and one MeCN fragments. Such a structure of this complexes was confirmed be synthesis of striazine derivatives on their base. In this work was to determine optimum condition for the insertion of ethyl isocyanate with acetone into niobium-chlorine bond, as well as their subsequent mixed co-cyclization with obtaining of oxadiazine derivative.

Argemone species: Potential source of biofuel and high-value biological active compounds

The Argemone genus includes weed species of great importance in traditional medicine due to biological activities attributed to secondary metabolites, mainly alkaloids, distributed in all tissues of this species. In addition, their seeds contain a large amount of oil (30 to 40%). For this reason, several authors have discussed the potential of this species as a non-edible source to produce multi-purpose raw materials and a low cost-crop for example in the production of biofuels such as biodiesel. Argemone species grows in poor soils with low water and nutrient requirements. This makes the Argemone species an attractive economical and environmentally friendly candidate for biofuels production. Furthermore, the Argemone species can also provide high-value by-products for the agrochemical and pharmaceutical industry. In this work, we compiled the ethnomedical information, biochemical features, and biofuel production efforts that have been published by testing different Argemone species, in order to compare the research efforts and analyze its biotechnological potential. After analyzing the literature, we conclude that the genus has great potential for high-value pharmaceutical products and energy production purposes, and also to control plant pests. We also consider that other species of the genus may have also potential applications in this field.

THE CONTENT OF PHENOLIC COMPOUNDS AND FLAVONOIDS IN Deschampsia antarctica TISSUE CULTURE

Aim. The aim of the study was to determine the quantitative and qualitative content of phenolic compounds and flavonoids in Deschampsia antarctica E. Desv. tissue cultures obtained from plants originating from different islands of the maritime Antarctic. Methods. In vitro tissue culture, Folin-Ciocalteu method, spectrophotometry, HPLC analysis. Results. The quantitative content of phenolic compounds and flavonoids in D. antarctica tissue cultures obtained from plants of six genotypes (DAR12, DAR13, G/D12-2a, Y66, R30 and L57) was determined. The highest content of phenolic compounds (4.46 and 3.75 mg/g) was found in tissue cultures obtained from root and leaf explants of plant genotype L57. The highest amount of flavonoids (7.17 mg/g) was accumulated in G/D12-2a tissue culture of root origin. The content of the studied biologically active compounds (BACs) did not change with increasing number of subculture generations (from passage 10 to 19). HPLC analysis showed that in D. antarctica tissue cultures, a shift in the biosynthesis of BACs occurred towards the synthesis of more polar metabolites compared to explant donor plants. Conclusions. It was found that the transition of cells to undifferentiated growth affected the content of BACs, the amount of which decreased 2–5 times simultaneously with a significant change in their profile. This provided a basis for further biochemical studies, as well as for careful selection of tissue culture of D. antarctica to use it as a potential source of BACs.

Medical Plaster Enhancement by Coating with Cistus L. Extracts within a Chitosan Matrix: From Natural Complexity to Health Care Simplicity

Our investigation was focused on the preparation and characterization of novel plasters based on Carboxymethyl Chitosan derivative (CMC), to be used for the treatment of radiation dermatitis with Biologic Active Compounds (BACs) in a moist wound-healing environment. After performing the extraction and characterization of BACs from Cistus L., we optimized the BACs/CMC solution for subsequent plaster preparation. Then, plasters were prepared by dip-coating with a different number of layers, and we characterized them by Environmental Scanning Electron Microscopy (ESEM), Contact Angle (CA) and release tests in water for 24 h. Taking into account the flexibility of the plasters and the amount of released BACs after 24 h, the sample obtained after two dip-coating steps (2La) appeared promising in regard to comfortable mechanical properties and active principles administration. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) test performed on keratinocytes cultured in standard medium shows that cells treated with released extract from 2La start to proliferate, extend cellular viability and form colonies typical for epidermal cells.