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We investigated the total phenolic and flavonoid contents and the anthocyanin profiles in aqueous, ethanol and acetone extracts of Prunus spinosa (Rosaceae) fruit, and their antioxidant, antibacterial, antifungal, antidiabetic and antitumor properties. The contribution of polyphenol contents to the bioactivity of the extracts was calculated and observed through Pearson’s coefficient of correlation. The acetone extract was the richest in phenols and anthocyanins and the ethanol extract in flavonoids. Cyanidin was the most abundant anthocyanin compound in all examined extracts. The ethanol extract showed the most promising antioxidant activity in DPPH, ABTS and FRAP assays. Tested bacteria were more affected by the ethanol than by the aqueous extract. Both the ethanol and aqueous extracts exhibited potential antidiabetic effects, observed as inhibition of α-amylase and α-glucosidase, enzymes linked with diabetes mellitus type II. The ethanol extract was a potent α-glucosidase-inhibitor with a significantly lower IC50 value than the positive control, glucobay, used to treat diabetes mellitus type II. Neither the ethanol nor the aqueous extracts had any effects on tested human malignant cell lines. Our results indicate that the ethanol extract showed the most pronounced in vitro antioxidant and antimicrobial effects, and a potential antidiabetic activity, which can be ascribed to its high flavonoid content. Our results indicate that research of compounds, particularly of flavonoids present in the ethanol extract and their anti-diabetic properties should be examined further. [Projects of the Serbian Ministry of Education, Science and Technological Development, Grant no. 173029, Grant no. 173032 and Grant no. 175011]

Two new complexes with the general formula [Cu2(L)tpmc] (ClO4)3·nH2O (tpmc = N,N′,N′′,N′′′-tetrakis(2-pyridylmethyl)- -1,4,8,11-tetraazacyclotetradecane, L = N-methylglycine, n = 3; L = N,N- -dimethylglycine, n = 2) were isolated and their composition, some physical and chemical properties and geometries were proposed based on elemental analysis (C, H, N), conductometric and magnetic measurements and spectroscopic data (UV–Vis, FTIR). It is evident that the complexes are binuclear and an exo coordination mode of the macrocyclic ligand in the boat conformation was proposed. The co-ligands are coordinated as a bridge using both oxygen atoms of the OCO- group. The cytotoxic activity of Cu(II) complexes as well as their Co(II) analogs, the starting ligands and the free salts were tested against human cervix adenocarcinoma cell line (HeLa), human chronic myelogenous leukemia cells (K562), human breast cancer cell line (MDA-MB-453), and a non-cancerous cell line, human embryonic lung fibroblast (MRC-5). The IC50 values for the Cu(II) complexes were from 21.6±0.04 to 66.1±0.8, and for the Co(II) analogs were within the range from 8.8±0.74 to 15.40±1.52. All four complexes were tested for their antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and the yeast Candida albicans. [Project of the Serbian Ministry of Education, Science and Technological Development, Grant no. 172014]

Growing mushrooms means meeting challenges while aiming for sustainability and circularity. Wherever the producer is located, commercial strains are the same originating from several producers. Customized strains adapted to local conditions are urgently needed. Before introducing new species to the strain development pipeline, the chemical characterization and biological activity of wild ones need to be assessed. Accordingly, the mycoceutical potential of five polypore mushroom species from Serbia was evaluated including: secondary metabolite composition, oxidative damage prevention, anti-tyrosinase, and anti-angiotensin converting enzyme (ACE). The phenolic pattern was comparable in all samples, but the amounts of specific chemicals varied. Hydroxybenzoic acids were the primary components. All samples had varying quantities of ascorbic acid, carotene, and lycopene, and showed a pronounced inhibition of lipid peroxidation (LPx) and ability to scavenge HO•. Extracts were more potent tyrosinase inhibitors but unsuccessful when faced with ACE. Fomitopsis pinicola had the strongest anti-tumor efficacy while Ganoderma lucidum demonstrated strong selectivity in anti-tumor effect in comparison to normal cells. The evaluated species provided a solid foundation for commercial development while keeping local ecology in mind. [ABSTRACT FROM AUTHOR]

Partial cation substitution can significantly change the physical properties of parent compounds. By controlling the chemical composition and knowing the mutual relationship between composition and physical properties, it is possible to tailor the properties of materials to those that are superior for desired technological application. Using the polyol synthesis procedure, a series of yttrium-substituted iron oxide nanoconstructs, γ-Fe2−xYxO3 (YIONs), was prepared. It was found that Y3+ could substitute Fe3+ in the crystal structures of maghemite (γ-Fe2O3) up to a limited concentration of ~1.5% (γ-Fe1.969Y0.031O3). Analysis of TEM micrographs showed that crystallites or particles were aggregated in flower-like structures with diameters from 53.7 ± 6.2 nm to 97.3 ± 37.0 nm, depending on yttrium concentration. To be investigated for potential applications as magnetic hyperthermia agents, YIONs were tested twice: their heating efficiency was tested and their toxicity was investigated. The Specific Absorption Rate (SAR) values were in the range of 32.6 W/g to 513 W/g and significantly decreased with increased yttrium concentration in the samples. Intrinsic loss power (ILP) for γ-Fe2O3 and γ-Fe1.995Y0.005O3 were ~8–9 nH·m2/Kg, which pointed to their excellent heating efficiency. IC50 values of investigated samples against cancer (HeLa) and normal (MRC-5) cells decreased with increased yttrium concentration and were higher than ~300 μg/mL. The samples of γ-Fe2−xYxO3 did not show a genotoxic effect. The results of toxicity studies show that YIONs are suitable for further in vitro/in vivo studies toward to their potential medical applications, while results of heat generation point to their potential use in magnetic hyperthermia cancer treatment or use as self-heating systems for other technological applications such as catalysis. [ABSTRACT FROM AUTHOR]

Two new p-cymene ruthenium(II) complexes containing as additional ligands N-methylpiperazine ([(η6-p-cymene)RuCl2(CH3NH(CH2)4NH)]PF6, complex 1) or vitamin K3-thiosemicarbazone ([(η6-p-cymene)RuCl2(K3tsc)], complex 2) were synthesized starting from [(η6-p-cymene)2RuCl2]2 and the corresponding ligand. The complexes were characterized by elemental analysis, IR, electronic absorption and NMR spectroscopy. The X-ray crystal structure determination of complex 1 revealed “piano-stool” geometry. The differences in the cytotoxic activity of the two complexes are discussed in terms of the ligand present.

Abstract Background The aim of this research was to determine the intensity and mechanisms of the cytotoxic actions of five extracts isolated from the endemic plant species Helichrysum zivojinii Černjavski & Soška (family Asteraceae) against specific cancer cell lines. In order to evaluate the sensitivity of normal immunocompetent cells implicated in the antitumor immune response, the cytotoxicity of extracts was also tested against healthy peripheral blood mononuclear cells (PBMC). Methods The aerial parts of the plants were air-dried, powdered, and successively extracted with solvents of increasing polarity to obtain hexane, dichloromethane, ethyl-acetate, n-butanol and methanol extracts. The cytotoxic activities of the extracts against human cervix adenocarcinoma HeLa, human melanoma Fem-x, human myelogenous leukemia K562, human breast adenocarcinoma MDA-MB-361 cells and PBMC were evaluated by the MTT test. The mode of HeLa cell death was investigated by morphological analysis. Changes in the cell cycle of HeLa cells treated with the extracts were analyzed by flow cytometry. The apoptotic mechanisms induced by the tested extracts were determined using specific caspase inhibitors. Results The investigated Helichrysum zivojinii extracts exerted selective dose-dependent cytotoxic actions against selected cancer cell lines and healthy immunocompetent PBMC stimulated to proliferate, while the cytotoxic actions exerted on unstimulated PBMC were less pronounced. The tested extracts exhibited considerably stronger cytotoxic activities towards HeLa, Fem-x and K562 cells in comparison to resting and stimulated PBMC. It is worth noting that the cytotoxicity of the extracts was weaker against unstimulated PBMC in comparison to stimulated PBMC. Furthermore, each of the five extracts induced apoptosis in HeLa cells, through the activation of both intrinsic and extrinsic signaling pathways. Conclusion Extracts obtained from the endemic plant Helichrysum zivojinii may represent an important source of novel potential antitumor agents due to their pronounced and selective cytotoxic actions towards malignant cells.

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In this work we investigated the direct or indirect (through ADCC) cytotoxic action of Herceptin, to two breast carcinoma cell lines: to MDA-MB 361, for HER-2, IHC score (3+) and to MDA-MB 453, IHC score (

Prunus spinosa leaf extracts in solvents of different polarity (water, ethanol and acetone), their phenol, flavonoid and anthocyanin contents and biological properties were the object of this study. The richest in phenols as well as in flavonoids was acetone extract with 181.19 mg GAE and 80.10 mg QE per gram of dry extract, respectively. Moreover, the quantity of anthocyanins obtained by HPLC analysis was also the highest in acetone sample. Examined samples possessed antioxidant properties evaluated through four in vitro assays (DPPH, ABTS, FRAP and TRC). The acetone extract was proved to be the best antioxidant among tested samples, which could be ascribed to polyphenols, especially anthocyanins. The aqueous and the ethanol extract exhibited antibacterial effects, being particularly active against B. cereus and E. cloacae. T. viride, P. funiculosum, P. ochrochloron, P. verrucosum var. cyclopium were the most susceptible among fungal microorganisms examined. Both, the aqueous and the ethanol extract expressed inhibitory activity towards enzymes linked to diabetes mellitus type II. Additionally, the ethanol extract showed significantly higher potential in inhibiting α-glucosidase than the drug used as the positive control. Furthermore, the aqueous sample revealed antitumor effects on following malignant cell lines: HeLa, K562 and MDA-MB-453. The results presented herein suggest that P. spinosa leaves should be considered as a natural source of bioactive compounds with potential application in phytopharmacy and food industry. [ABSTRACT FROM AUTHOR]

Antiproliferative and antibacterial activities of nine glutarimide derivatives (1–9) were reported. Cytotoxicity of compounds was tested toward three human cancer cell lines, HeLa, K562 and MDA-MB-453 by MTT assay. Compound7(2-benzyl-2-azaspiro[5.11]heptadecane-1,3,7-trione), containing 12-membered ketone ring, was found to be the most potent toward all tested cell lines (IC50 = 9–27 μM). Preliminary screening of antibacterial activity by a disk diffusion method showed that Gram-positive bacteria were more susceptible to the tested compounds than Gram-negative bacteria. Minimum inhibitory concentration (MIC) determined by a broth microdilution method confirmed that compounds1,2,4,6–8and9inhibited the growth of all tested Gram-positive and some of the Gram-negative bacteria. The best antibacterial potential was achieved with compound9(ethyl 4-(1-benzyl-2,6-dioxopiperidin-3-yl)butanoate) againstBacillus cereus(MIC 0.625 mg/mL; 1.97 × 10−3 mol/L). Distinction between more and less active/inactive compounds was assessed from the pharmacophoric patterns obtained by molecular interaction fields. [ABSTRACT FROM PUBLISHER]

The reactivity, cytotoxic studies and hydrolytic behaviour of diamine bis(phenolate) titanium complexes are reported. The reactions of [Ti(tBu2O2NN')Cl]2(μ-O) (1) with LiOiPr or HOiPr in the presence of NEt3, aiming at the synthesis of the alkoxido derivative of 1 led to no reaction or to the synthesis of the monomeric complex [Ti(tBu2O2NN')(OiPr)2] (3), respectively. A small amount of the alkoxidotitanium dimer [Ti-(tBu2O2NN')(OiPr)]2(μ-O) (2) crystallized out of a solution of 3 and DFT calculations showed that the transformation of 1 into 3 is a thermodynamically favorable process in the presence of a base (NEt3) (∆G = -14.7 kcal mol-1). 2 was quantitatively obtained through the direct reaction of the ligand precursor H2(tBu2O2NN') with titanium tetra(isopropoxido). Further reaction of 2 with an excess of TMSCl was revealed to be the most suitable method for the preparation of [Ti(tBu2O2NN')Cl2] (4). 1 and 3 disclosed cytotoxic activity towards HeLa, Fem-x, MDA-MB-361 and K562 cells and 1 exhibited moderate binding affinity to FS-DNA. ¹H NMR hydrolysis studies attested the fast decomposition of 4 in the presence of D2O. The hydrolysis of 3 is slower and proceeds through the formation of [Ti(tBu2O2NN')(OH)]2(μ-O) (5) that was crystallographically characterized. Upon D2O addition 1 immediately forms complex new species, stable in solution for long periods (weeks). [ABSTRACT FROM AUTHOR]

Correction for ‘Synthesis, cytotoxic and hydrolytic studies of titanium complexes anchored by a tripodal diamine bis(phenolate) ligand’ by Sónia Barroso et al., Dalton Trans., 2014, 43, 17422–17433. [ABSTRACT FROM AUTHOR]

In this study, lipid extracts obtained by supercritical fluid extraction and essential oils of Satureja montana L., Coriandrum sativum L. and Ocimum basilicum L., as well as the mixture of these aromatic herbs were investigated. Obtained extracts and essential oils were analyzed by GC–MS and GC-FID. The chemical profile of obtained EOs and extracts showed that carvacrol was the major compound in S. montana , while in C. sativum and O. basilicum linalool was the most abundant compound. In the EO obtained from herbal mixture of three aromatic plants, the predominant compounds were linalool and carvacrol, followed by geraniol, γ-terpinene and eugenol, similar with extract obtained by SFE (100 bar, 40 °C). The antioxidant activity was determined by DPPH assay, while antiproliferative activity of the obtained CO 2 extracts and the essential oils were evaluated in vitro against three different human cancer cell lines (HeLa, MDA-MB-453, K562) and normal MRC-5 human fibroblasts. [ABSTRACT FROM AUTHOR]

Abstract: New R2eddip-type esters (R=cyclopentyl, L3·2HCl 1.5H2O; cyclohexyl, L4·2HCl·H2O) and corresponding palladium(II) complexes, [PdCl2 L3] (3) and [PdCl2 L4]·H2O (4), as well as [PdCl2 L2] (2; L2 diisobutyl ester of eddip) were synthesized and characterized by IR, 1H and 13C NMR spectroscopies and elemental analysis. The crystal structure of L3·2HCl·2CHCl3 was resolved and is given herein. The NMR spectroscopy confirmed the presence of two isomers (from three possible) for each palladium(II) complex. DFT calculations support the formation of two diastereoisomers. In addition, antitumoral investigations were performed and these investigations also included the diisopropyl ester of eddip (L1) and corresponding palladium(II) complex, [PdCl2 L1] (1). In vitro antiproliferative activity was determined against several tumor cell lines HeLa, Fem-x, K562 and rested and stimulated normal immunocompetent cells (human peripheral blood mononuclear cells -PBMCs) using MTT test. [Copyright &y& Elsevier]

The cytotoxic activity on tumour cell lines, human adenocarcinoma HeLa, human myelogenous leukemia K562, human malignant melanoma Fem-x and normal immunocompetent cells, was tested for four different ansa-titanocene dichloride derivatives with potentially reactive substituents [Ti{Me(CH2=CH)Si(η5-5Me4) (η5-C5H4)}Cl2] (1), [Ti{Me(H)Si(η5-C5Me4)2}Cl2] (2), [Ti{Me{(CH2=CH)Me2SiCH2CH2}Si(η5-C5Me4)(η5-C5H4)}Cl2] (3) and [Ti{Me2Si(η5-C5Me4)(η5-C5H3(CMe2(CH2CH2CH=CH2)))}Cl2] (4), showing a very promising activity and opening up the possibility of extensive investigation in this field. [Copyright &y& Elsevier]

Abstract: Examination of the aerial parts of Achillea clavennae afforded eight guaianolides (1–8), three bisabolenes (9–11), four flavonols (12–15), sesamin (lignan) and isofraxidin (coumarin). The structures of the new compounds (2, 4, 5, 7 and 10) were determined by spectroscopic methods. The antiproliferative action of 2, 8, 9 and 12 were tested to HeLa, K562 and Fem-X human cancer cell lines. Guaianolides 2 (9α-acetoxyartecanin) and 8 (apressin) showed significant cytotoxic effects to all tested lines and inducumenone (9) exhibited a moderate activity. The most active was flavonol centaureidin (12), already known as cytotoxic compound. [Copyright &y& Elsevier]

Foodborne bacteria biofilms present a major concern for the food industry. Although their numerous biological activities are well established, there is little research to date on the use of polysaccharides of mushroom origin as a possible solution for preventing biofilm formation. Therefore, the aim of this study was to examine the antiadhesion and antibiofilm effects of several types of Pleurotus flabellatus strain Mynuk polysaccharide extracts (PFSMpe), produced by air-lift submerged fermentation, against American Type Culture Collection (ATCC) and clinical strains of foodborne bacteria, as well as the cytotoxicity of these extracts. PFSMpe exhibited antiadhesion activity toward clinical isolates, and the percentage of adhesion inhibition was highest for water (WE) and exopolysaccharide (EXOPE) extracts (>50%) against Enterococcus faecalis. Selected ATCC strains were more resistant than clinical strains, indicating the antiquorum sensing mechanism of PFSMpe action. Antibiofilm activity was similar to antiadhesion activity and WE showed the strongest effect, again on E. faecalis. Differences in antiadhesion and antibiofilm effects of PFSMpe may be explained by differences in chemical composition, with crude extracts showing greater efficiency due to a synergistic effect. PFSMpe did not exhibit cyctotoxic activity against normal human cell lines. Overall, the findings of this study show that PFSMpe represents a promising novel strategy against bacterial biofilms. • Mushroom polysaccharides (MP) negatively affect the adhesion of foodborne bacteria. • MP disturbe the biofilm forming ability of foodborne bacteria. • Crude polysaccharide exhibited the strongest antiadhesion and biofilm activity. • Water extract potency caused by synergistic interaction. • MP exhibits no cytotoxic activity toward two normal human cell lines. [ABSTRACT FROM AUTHOR]

This study focuses on the designing and characterization, and anticancer evaluation of chitosan-based nanoparticles (NPs) loaded (enriched) with a Biginelli hybrid compound (BH). NPs based on chitosan (CH) or chitosan oligosaccharide lactate (CHOL), are carefully designed to encapsulate a tetrahydropyrimidine derivative (BH) with already proven anticancer properties. The formulations were evaluated for their physicochemical properties, including particle size distribution and morphology, using techniques such as infrared spectroscopy, scanning electron microscopy, and X-ray diffraction. The cytotoxicity profiles were assessed on different cancer cell lines, showing a higher selectivity towards HeLa and A549 cells related to BH. BH-CH showed better cytotoxic profile related to BH-CHOL NPs. A cell cycle analysis revealed an accumulation of cells in the G 2 /M phase after a treatment with these NPs, indicating the ability to induce mitotic arrest in cancer cells. In summary, the results underscore the promising application of CH-based natural nanocarriers for the targeted delivery of Biginelli hybrids, showcasing a significant potential for further in vivo testing., Competing Interests: The authors confirm that they do not have any competing financial interests or personal relationships that could have influenced the work reported in this article., (This journal is © The Royal Society of Chemistry.)

A new oxidant, containing m -chloroperoxybenzoic acid (MCPBA) and an iron salt, was developed and used for oxidation of steroidal phenols to a quinol/epoxyquinol mixture. Reaction was optimized for estrone, by varying initiators (Fe-salts), reaction temperature, time and mode of MCPBA application. A series of five more substrates (17β-estradiol and its hydrophobized derivatives) was subjected to the optimized oxidation, providing corresponding p -quinols and 4β,5β-epoxyquinols in good to moderate yields. The obtained epoxyquinols were additionally transformed by oxidation, as well as the acid-catalyzed oxirane opening. In a preliminary study of the antiproliferative activity against human cancer cell lines, all newly synthesized compounds expressed moderate to high activity., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)

Tetrahydropyrimidines are a class of azaheterocycles, also called Biginelli hybrids (obtained from the Biginelli reaction), that have attracted an enormous interest in the medicinal chemistry community in recent years, due to a broad biological activity, such as anticancer, antiviral, anti-inflammatory, antidiabetic, antituberculosis activities, etc. According to SciFinder®, more than 70 000 different Biginelli-like compounds have been covered in publications. However, although the Biginelli reaction can yield a large number of compounds with a broad range of activities, none of them have been captured in a carrier. In this study, chitosan-based (Ch) nanoparticles (NPs) containing three different molecules (Biginelli hybrids) were developed and tested for the first time as simple and promising vehicles for anticancer Biginelli-based drugs. The key features of NPs, such as size, surface morphology, drug encapsulation efficiency, and in vitro release were systematically investigated. Rather weak cell selectivity of pure Biginelli hybrids (A-C) to selected cancer cell lines has improved and this has been accompanied with two-to-four times stronger cytotoxic effect of A-C loaded Ch NPs, with a triple reduction in toxicity to healthy cells (MRC-5). It has been observed that the examined NPs induce apoptosis. The cell cycle analysis has confirmed the influence of A-loaded Ch (A-Ch), B-loaded Ch (B-Ch), and C-loaded Ch (C-Ch) on the cell cycle distribution, which was homogenously affected. This is the difference with regard to the effect of A, B, and C on the cell cycle. It has been established that the increased selectivity and antitumor activity of NPs are related to the presence of the carrier., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)

In the present study, subcritical water was used for extraction of bioactive compounds of Symphytum officinale root. Temperature (120-200 °C), extraction time (10-30 min) and HCl concentration in extraction solvent (0-1.5%) were investigated as independent variables in order to obtain the optimal conditions for extraction and to maximize the yield of total phenols, flavonoids and antioxidant activity of obtained extracts. The application of optimal conditions (200 °C, 25.6 min and 0.0075%) provided extracts rich in total phenols and flavonoids and high antioxidant activity. Results also demonstrated that subcritical water extraction showed significant advantages for recovery of comfrey root bioactive compounds comparing to maceration and ultrasound-assisted extraction techniques. In addition, subcritical water extracts of S. officinale root are the promising sources of compounds with antioxidant, ACE inhibition, and antiproliferative properties and could potentially be used for production of new pharmacologically-active formulations.

Cinnamic acid derivatives can be found in plant material, and they possess a remarkable variety of biological effects. In the present study, we have investigated the cytotoxic effects of representative cinnamic acid esters and amides. The cytotoxicity was determined by MTT test on human cervix adenocarcinoma (HeLa), myelogenous leukemia (K562), malignant melanoma (Fem-x), and estrogen-receptor-positive breast cancer (MCF-7) cells, versus peripheral blood mononuclear cells (PBMCs) without or with the addition of the plant lectin phytohemaglutinin (PHA). The compounds tested showed significant cytotoxicity (IC50s between 42 and 166 µM) and furthermore selectivity of these cytotoxic effects on the malignant cell lines versus the PBMCs was also seen, especially when electron-withdrawing groups, such as a cyano group (compound 5), were present on the aromatic rings of the alcohol or amine parts of the cinnamic acid derivatives. The additional study on cell cycle phase distribution indicated that novel cinnamic acid derivatives inhibit cell growth by induction of cell death. Thus, cinnamic acids derivatives represent important lead compounds for further development of antineoplastic agents.