Echinophora tenuifolia L. branches phytochemical profile and antiproliferative activity on human cancer cell lines

Abstract

The methanolic extract of Echinophora tenuifolia L. branches and its fractions were evaluated for their in vitro cell growth inhibitory activity on different human cancer cell lines (C32, LoVo and SKBr3) and the normal BJ fibroblasts. All tested samples were effective against the melanoma cell line C32, with IC₅₀ values ranging from 22.8?±?0.8 to 78.7?±?1.2?μg/mL, the antiproliferative activity of the dichloromethane fraction being significantly higher. This fraction was also effective against the LoVo adenocarcinoma cell line, with an IC₅₀ value of 53.0?±?2.1?μg/mL. The ethyl acetate and dichloromethane fractions showed the highest lipid peroxidation inhibitory activity, verified by means of the β-carotene bleaching test. The phytochemical profiles of E. tenuifolia branches extract were established by means of GC-MS and HPTLC. Overall, branches of E. tenuifolia L. could represent a rich source of bioactive compounds, potentially useful in the pharmaceutical field.     

Comparison of the Phenolic Compound Profile and Antioxidant Potential of Achillea atrata L. and Achillea millefolium L.

In the present study, Achillea atrata L. and A. millefolium L. were compared for the first time with regard to their phenolic compound profile and antioxidant activity by applying the 2,2-diphenyl-picryl hydrazyl radical assay. For this purpose, aerial plant parts were consecutively extracted with solvents of increasing polarity (dichloromethane, n-butanol, ethyl acetate), revealing that the A. atrata ethyl acetate fraction showed the highest antioxidant activity with an IC₅₀ value of 12.2 ± 0.29 µg/mL compared to 17.0 ± 0.26 µg/mL for A. millefolium. Both species revealed the presence of luteolin, apigenin, centaureidin, and nevadensin exclusively in this most polar fraction, which are known as effective 2,2-diphenyl-picryl hydrazyl radical scavengers. The antioxidant capacity of the aforementioned fractions strikingly correlated with their total phenolic contents, which was highest in the ethyl acetate fraction of A. atrata. Characterization of the metabolite profiles of both Achillea species showed only marginal differences in the presence of key compounds, whereas the concentrations of individual compounds appeared to be species-specific. Our results suggest that A. atrata, based on its compound pattern and bioactivity characteristics, has similar qualities for phytotherapy as A. millefolium.     

Antioxidant and toxicological evaluation of a Tamarindus indica L. leaf fluid extract

In the scientific community, there is a growing interest in Tamarindus indica L. leaves, both as a valuable nutrient and as a functional food. This paper focuses on exploring its safety and antioxidant properties. A tamarind leaf fluid extract (TFE) wholly characterised was evaluated for its anti-DPPH activity (IC₅₀ = 44.36 μg/mL) and its reducing power activity (IC₅₀ = 60.87 μg/mL). TFE also exhibited a high ferrous ion-chelating capacity, with an estimated binding constant of 1.085 mol L^? 1 while its influence over nitric oxide production in human leucocytes was irregular. At low concentrations, TFE stimulated NO output, but it significantly inhibited it when there was an increase in concentration. TFE was also classified as a non-toxic substance in two toxicity tests: the acute oral toxicity test and the oral mucous irritability test. Further toxicological assays are needed, although results so far suggest that TFE might become a functional dietary supplement.     

Ferula L. Plant Extracts and Dose-Dependent Activity of Natural Sesquiterpene Ferutinin: From Antioxidant Potential to Cytotoxic Effects

The employment studies of natural extracts in the prevention and treatment of several diseases highlighted the role of different species of genus Ferula L., belonging to the Apiaceae family, dicotyledonous plants present in many temperate zones of our planet. Ferula communis L. is the main source of sesquiterpene ferutinin, a bioactive compound studied both in vitro and in vivo, because of different effects, such as phytoestrogenic, antioxidant, anti-inflammatory, but also antiproliferative and cytotoxic activity, performed in a dose-dependent and cell-dependent way. The present review will focus on the molecular mechanisms involved in the different activities of Ferutinin, starting from its antioxidant potential at low doses until its ionophoric property and the subsequent mitochondrial dysfunction induced through administration of high doses, which represent the key point of its anticancer action. Furthermore, we will summarize the data acquired from some experimental studies on different cell types and on several diseases. The results obtained showed an important antioxidant and phytoestrogenic regulation with lack of typical side effects related to estrogenic therapy. The preferential cell death induction for tumor cell lines suggests that ferutinin may have anti-neoplastic properties, and may be used as an antiproliferative and cytotoxic agent in an estrogen dependent and independent manner. Nevertheless, more data are needed to clearly understand the effect of ferutinin in animals before using it as a phytoestrogen or anticancer drug.     

Seasonal Variability of Juniperus communis L. Berry Ethanol Extracts: 2. In Vitro Ferric Reducing Ability of Plasma (FRAP) Assay

In the present study, the seasonal variability of the in vitro ferric reducing ability of plasma (FRAP), total phenols, and terpene hydrocarbon content in 70% ethanol extracts were evaluated. The samples of crushed (CBs) and non-crushed ripe juniper berries (NCBs) collected at five localities in North-East Slovakia during the years 2012–2014 were compared. The method of preparation of the extract influenced the amount of dry matter (DM) in the extracts. In the CB extracts were statistically higher contents of DM (from 13.91 ± 0.11 g·L⁻¹ to 23.84 ± 0.14 g·L⁻¹) compared to NCB extracts (from 1.39 ± 0.01 g·L⁻¹ to 16.55 ± 0.09 g·L⁻¹). The differences in antioxidant activity between the investigated localities were statistically significant for both types of extract. For example, in 2013 in the locality of Zbojné, the FRAP in NCBs was 76.62 µmol·L⁻¹·g⁻¹ DM and in CBs was 138.27 µmol·L⁻¹·g⁻¹ DM, while in the Miľpoš locality, in NCBs there was 232.66 µmol·L⁻¹·g⁻¹ DM and in CBs there was 1178.98 µmol·L⁻¹·g⁻¹ DM. The differences in the antioxidant activity between the studied years in the case of NCB extracts were not statistically significant. In the case of CB extracts, significant differences between the evaluated years were found. Statistics by ANOVA confirmed that CB extracts prepared from berries in the year 2013 showed significantly higher activity compared to CB extracts from berries from the years 2012 and 2014. Based on the Pearson we found a negative correlation coefficient between the FRAP assay and the content of total polyphenols in NCB extracts (−0.531 in 2012; −0.349 in 2013; and −0.224 in 2014). In contrast, CB extracts showed a positive correlation coefficient (0.843 in 2012; 0.742 in 2013; 0.617 in 2014).     

Antioxidant and antifungal activity of different extracts obtained from aerial parts of Inula crithmoides L.

The total phenolic content, antioxidant and antifungal activities of three Inula crithmoides extracts (n-hexane, methylene chloride and MeOH) were investigated. The methanolic extract showed the highest total phenolic content. In the DPPH assay, the methanolic and hexane extracts exhibited the highest DPPH-radical scavenging activity; in the 5-lipoxygenase assay, the hexane extract showed greater inhibitory effect with an IC₅₀ similar to that of Trolox and ascorbic acid. The antifungal activity of the methanolic extract revealed a higher activity against Phytophtora cryptogea and Alternaria solani.     

Novel 2-formylpyridine 4-allyl-S-methylisothiosemicarbazone and Zn(II), Cu(II), Ni(II) and Co(III) complexes: Synthesis,characterization, crystal structure,antioxidant, antimicrobial and antiproliferative activity

New zinc (II), copper (II), nickel (II) and cobalt (III) complexes, [Zn (HL)₂]I₂ (1) , [Cu (HL)Cl₂] (2) , [Cu (HL)Br₂] (3) , [Cu (HL)(H₂O)₂](ClO₄)₂ (4) , [Ni (HL)₂]I₂·H₂O (5) , [Co(L)₂]Cl (6) , [Co(L)₂]NO₃ (7) , [Co(L)₂]I·[Co(L)₂](I₃) (8) were obtained with 2-formylpyridine 4-allyl-S-methylisothiosemicarbazone ( HL ). The isothiosemicarbazone ligand was characterized by NMR (¹H and ¹³C), IR spectroscopy and X-ray diffraction. All the complexes were characterized by elemental analysis, IR, UV–Vis, ESI-MS spectroscopy, molar conductivity, magnetic susceptibility measurements. X-ray diffraction analysis on the monocrystal and powder elucidated the structure of the complexes 1 , 5 , 7 and 8 . The ligand and the complexes were tested for their antioxidant and antimicrobial activity against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae and Candida albicans. Also, the antiproliferative properties of these compounds on human leukemia HL-60, human cervical epithelial HeLa, human epithelial pancreatic adenocarcinoma BxPC-3, human muscle rhabdomyosarcoma spindle, large multinucleated RD cells and normal MDCK cells have been investigated. The nickel complex 5 and cobalt complexes 6 , 7 showed promising antiproliferative activity and low toxicity.     

Characterisation and antiproliferative activity of irinotecan and sulphonatocalixarene inclusion complex

The interaction between water-soluble sulphonatocalix[4]arene (SC4A) and irinotecan (CPT-11) was investigated by using UV spectrophotometry. Inclusion complex of SC4A with CPT-11 was confirmed by ¹H NMR and DSC analysis. Water solubility study showed that SC4A has remarkable solubilisation on CPT-11 and the complex has good water solubility. The antiproliferative activity of the complex was evaluated. The results showed that the complexation of CPT-11 with SC4A increases the antiproliferative activity of CPT-11.     

Green synthesis of silver nanoparticles using aqueous extract of Stachys lavandulifolia flower,and their cytotoxicity,antioxidant, antibacterial and cutaneous wound‐healing properties

In a biological process where the herbal tea (Stachys lavandulifolia) aqueous extract was applied as a capping and reducing agent, nanoparticles (NPs) of silver (Ag) were synthesized. These AgNPs were characterized using Fourier transform‐infrared spectroscopy, field emission‐scanning electron microscopy, energy‐dispersive X‐ray spectroscopy, transmission electron microscopy and ultraviolet–visible spectroscopy. The synthesized AgNPs had great cell viability dose‐dependently [investigating the effect of the plant on human umbilical vein endothelial cell line] and indicated this method was non‐toxic. In this study, the 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) free radical scavenging test was carried out to examine antioxidant properties, which revealed similar antioxidant properties for AgNPs and butylated hydroxytoluene. Agar diffusion tests were applied to determine the antibacterial characteristics. The macro‐broth tube test was run to determine minimum inhibitory concentration. All data of antibacterial and cutaneous wound‐healing examinations were analyzed by SPSS 21 software (Duncan post hoc test). AgNPs showed higher antibacterial property than all standard antibiotics (p ≤ 0.01). Also, AgNPs prevented the growth of all bacteria at 2–8 mg/ml concentrations and destroyed them at 2–16 mg/ml concentrations (p ≤ 0.01). For the in vivo experiment, after creating the cutaneous wound, the rats were randomly divided into six groups: untreated control; treatment with Eucerin basal ointment; treatment with 3% tetracycline ointment; treatment with 0.2% AgNO₃ ointment; treatment with 0.2% S. lavandulifolia ointment; and treatment with 0.2% AgNPs ointment. These groups were treated for 10 days. For histopathological and biochemical analysis of the healing trend, a 3 × 3‐cm section was prepared from all dermal thicknesses at day 10. Use of AgNPs ointment in the treatment groups substantially reduced (p ≤ 0.01) the wound area, total cells, neutrophil, macrophage and lymphocyte, and remarkably raised (p ≤ 0.01) the wound contracture, hydroxyl proline, hexosamine, hexuronic acid, fibrocyte and fibrocytes/fibroblast rate compared with other groups. Seemingly, AgNPs can be used as a medical supplement owing to their non‐cytotoxic, antioxidant, antibacterial and cutaneous wound‐healing properties.     

Anti-inflammatory and antiproliferative activities of Ixora brevifolia Benth. (Rubiaceae)

The crude extract and fractions from the branches of Ixora brevifolia, a tree found in the Brazilian Cerrado, were tested for anti-inflammatory and in vitro antiproliferative effects. The crude extract and n-hexane fraction exhibited significant inhibition of ear oedema in mice, while n-hexane-precipitated and chloroform fractions strongly inhibited the myeloperoxidase activity in ear tissue. The n-hexane and n-hexane-precipitated fractions showed strong growth inhibition for glioma cell line and the hydromethanolic fraction inhibited the growth of leukaemia cell line.     

Anticarcinogenic and Antioxidant Action of an Edible Aquatic Flora Jussiaea repens L. Using In Vitro Bioassays and In Vivo Zebrafish Model

Oxidative stress is the major cause of many health conditions, and regular consumption of antioxidants helped to encounter and prevent such oxidative stress-related diseases. Due to safety concerns over long-term uses of synthetic antioxidants, natural antioxidants are more preferred. The purpose of this study is to investigate the antioxidant and anticancer activities of Jussiaea repens L., a wild edible flora found in Manipur, India. The antioxidant activity was evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), Ferric reducing antioxidant power (FRAP) assay and DNA-nicking assay. The anticancer activity was tested using five cancer lines viz., SKOV3 cells (ovarian), HeLa (cervical), MDA-MB-231 (breast), PANC-1 (pancreatic), and PC3 (prostate). The toxicity, developmental effect, antiproliferative activity was further tested using zebrafish embryos. The methanolic plant extract had higher polyphenol content than flavonoids. The in vitro study demonstrated a promising antioxidant capacity and DNA protection ability of this plant. The extract also showed cytotoxic activity against SKOV3, HeLa, MDA-MB-23, and PANC-1 cancer cell lines. The in vivo studies on zebrafish embryos demonstrated the extract’s ability to suppress the developmental process and elicited more cytotoxicity to cancer cells than developing zebrafish embryos. Moreover, the in vivo studies on zebrafish embryos also indicated the antiproliferative activity of J. repens L. extract.     

Isolation and antiproliferative activity of chemical constituents from Asystasia buettneri Lindau

N-hexane and methanol extracts of Asystasia buettneri Lindau aerial parts exhibited antiproliferative activity on leukaemia blood carcinoma, K-562. Hexadecane (1), 1,3-propan-2-ol (9Z,12′Z,15″Z)-bis(doeicos-9,12,15-trienoate) (2), hydrocarbon, 2,3,3,10,23-pentamethyl tetraeicos-10,13,16-trien-1-ol (3), hexadecanoic acid (4) and taraxerol (5) were isolated from n-hexane extract; stigmasterol (6) and (Z)-9-octadecenoic acid (7) were isolated from ethyl acetate extract; while unsaturated hydrocarbons, octadecene (8), 8-methyl tetradec-6-ene (9) and 19-methyl eicos-1-ene (10), fatty acids, (Z)-5-hexadecenoic acid (11), 11,22-dimethyl ethyltrieicos-11-enoate (12) and taraxasterol (13) were isolated from methanol extract of the plant. Compounds 4, 5, 7, 11, 12 and 13 exhibited antiproliferative activity against K-562, while compounds 5, 6, 7 and 9 revealed antiproliferative activity by inhibiting hepatic liver (WRL68) cell lines.     

Chemical composition and antiproliferative activity of Croton campestris A.St.-Hil. essential oil

Herein, the antiproliferative potential of the essential oil obtained from fresh leaves of Croton campestris against human tumour cell lines was investigated for the first time. Furthermore, the essential oil obtained by hydrodistillation had the composition determined by gas chromatography–mass spectrometry (GC/MS). Ten major components were identified that comprised 91.59% of the total content, with 23.8% consisting of (Z)-caryophyllene and 16.08% consisting of γ-elemene as main components. The cytotoxic activity was observed mainly for breast (MCF-7) and colon (HT-29) human tumour cell lines, with GI₅₀ (50% growth inhibition) concentration of 8.61 and 9.94 μg/mL, respectively. The results of this study showed that the essential oil obtained from Croton campestris A.St.-Hil. represents a potential source for the search of new antitumour agents.     

Biological contour,molecular docking and antiproliferative studies of DNA targeted histidine based transition metal(II) complexes: Invention and its depiction

A novel series of histidine derived transition metal complexes were synthesized and characterized by multispectral techniques such as UV‐Vis., FT IR, EPR, NMR, ESI‐mass analysis and other physico‐chemical methods like elemental analysis, molar conductivity, magnetic susceptibility. The synthesized compounds were attempted for their biological prospective. The biological studies involved are DNA interaction (binding and damage), antimicrobial, antioxidant, antiproliferative and molecular docking. DNA interaction studies were carried out with the help of UV‐Vis absorption titration, viscosity measurement and cyclic voltammetric techniques which revealed that the synthesized compounds could interact with CT‐DNA through intercalative binding mode. A gel electrophoresis assay demonstrated the ability of complexes to cleave the supercoiled pUC18 DNA. The antioxidant property shows that the metal complexes have preferable ability to scavenge hydroxyl radical than the ligand. Moreover, the antimicrobial assay indicates that these complexes are good antimicrobial agents against various pathogens. Furthermore, the in vitro antiproliferative activities of the complexes were examined on HeLa, Hep G2 and NIH 3 T3 cell lines using an MTT assay. The morphological changes were investigated using Hoechst 33258 staining apoptosis assay. In addition, molecular docking studies were executed to considerate the nature of binding of the synthesized complexes with protein and DNA.     

New naphthopyrones from marine-derived fungus Aspergillus niger 2HL-M-8 and their in vitro antiproliferative activity

A new cytotoxic dimeric naphthopyrone, aurasperone H (1), together with eight related known polyketides (2–9) was isolated from a marine-derived fungus Aspergillus niger 2HL-M-8. The structure of new compound 1 was elucidated on the basis of its spectroscopic data (1D, 2D NMR and CD). Compound 1 exhibited moderate inhibitory activity against the human lung adenocarcinoma A549 and the human leukaemia HL-60 cell lines. Compound 5 displayed significant in vitro antiproliferative activity against HL-60 cell line with an IC₅₀ value of 0.8 μM.     

Cholinesterases Inhibition,Anticancer and Antioxidant Activity of Novel Benzoxazole and Naphthoxazole Analogs

Benzoxazole and naphthoxazole fused systems are found in many biologically active molecules. Novel benzoxazole and naphthoxazole analogs functionalized by the 2,4-dihydroxyphenyl moiety were designed, obtained and evaluated as a broad spectrum of biological potency compounds. Sulfinylbis[(2,4-dihydroxyphenyl)methanethione] or its analogs and 2-aminophenols or 1-amino-2-naphthol were used as starting reagents. 4-(Naphtho[1,2-d][1,3]oxazol-2-yl)benzene-1,3-diol was identified as the most promising compound of the nanomolar activity against AChE (IC₅₀ = 58 nM) of the mixed-type inhibition and of the moderate activity against BChE (IC₅₀ = 981 nM). The higher antiproliferative potency against a panel of human cancer cell lines for naphtho[1,2-d][1,3]oxazoles than for benzoxazoles was found. The activity of the analog with chlorine atom was in the range of 2.18–2.89 µM (IC₅₀) against all studied cells and it is similar to that of cisplatin studied comparatively. Moreover, this compound was not toxic at this concentration to human normal breast cells and keratinocytes. For some compounds it also has proved antioxidant properties at the level of IC₅₀ = 0.214 µM, for the most active compound. The lipophilicity of all compounds, expressed as log p values, is within the range recommended for potential drugs. The biological activity profile of the considered analogs and their lipophilic level justify the search for agents used in AD or in anticancer therapy in this group of compounds.     

番石榴叶提取物的鉴定及其抗菌作用

采用纸片扩散法对番石榴叶提取物进行体外抗菌试验研究,以了解其抗菌谱.结果表明番石榴叶提取物中存在有效抗菌成分,其中以乙醇提取物中白念珠菌、甲醇提取物中大肠埃希菌高度敏感.     

Chemical Composition,Antioxidant and Antiproliferative Activities of Taraxacum officinale Essential Oil

Taraxacum officinale (TO) has been historically used for medicinal purposes due to its biological activity against specific disorders. To investigate the antioxidant and the antiproliferativepotential of TO essential oil in vitro and in vivo, the chemical composition of the essential oil was analyzed by GC-MS. The in vivo antioxidant capacity was assessed on liver and kidney homogenate samples from mice subjected to acetaminophen-induced oxidative stress and treated with TO essential oil (600 and 12,000 mg/kg BW) for 14 days. The in vitro scavenging activity was assayed using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) and the reducing power methods. The cytotoxic effects against the HeLa cancer cell line were analyzed. The GC-MS analysis showed the presence of 34 compounds, 8 of which were identified as major constituents. The TO essential oil protected mice’s liver and kidneys from acetaminophen-induced oxidative stress by enhancing antioxidant enzymes (catalase, superoxide dismutase, and glutathione) and lowering malondialdehyde levels. In vitro, the TO essential oil demonstrated low scavenging activity against DPPH (IC₅₀ = 2.00 ± 0.05 mg/mL) and modest reducing power (EC₅₀ = 0.963 ± 0.006 mg/mL). The growth of the HeLa cells was also reduced by the TO essential oil with an inhibition rate of 83.58% at 95 µg/mL. Current results reveal significant antioxidant and antiproliferative effects in a dose-dependent manner and suggest that Taraxacum officinale essential oil could be useful in formulations for cancer therapy.     

Chemical Composition and In Vitro Antioxidant Activity of Sida rhombifolia L. Volatile Organic Compounds

In the current study, the phytochemical constituents of volatile organic compounds (VOCs) obtained from Sida rhombifolia L. were identified by GC-FID and GC-MS analysis. A total of 73 volatile organic compounds were identified. The major components of S. rhombifolia VOCs were identified as palmitic acid (21.56%), phytol (7.02%), 6,10,14-trimethyl-2-pentadecanone (6.30%), oleic acid (5.48%), 2-pentyl-furan (5.23%), and linoleic acid (3.21%). The VOCs are rich in fatty acids (32.50%), olefine aldehyde (9.59%), ketone (9.41%), enol (9.02%), aldehyde (8.63%), and ketene (6.41%). The antioxidant capacity of S. rhombifolia VOCs was determined by 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH), 2,2-azinobis-(3-ethylbenzothiazolin-6-sulfonic acid) diammonium salt (ABTS), and ferric reducing/antioxidant power (FRAP) methods with butylated hydroxytoluene (BHT) and Trolox as standard. The VOCs showed dose-dependent antioxidant activity with IC50 (50% inhibitory concentration) values of 5.48 ± 0.024 and 1.47 ± 0.012 mg/mL for DPPH and ABTS assays, respectively. FRAP antioxidant capacity was 83.10 ± 1.66 mM/g. The results show that the VOCs distilled from S. rhombifolia have a moderate antioxidant property that can be utilized as a natural botanical supplement or an antioxidant.     

Polyphenolic characterisation and bioactivity of an Oxalis pes-caprae L. leaf extract

The present work is focused on the characterisation of the polyphenolic content of an Oxalis pes-caprae L. leaf extract and on the evaluation of its bioactivity with particular interest on its vascular activity and antioxidant potential. The polyphenolic content was characterised by HPLC-DAD and LC-MS/MS. The vascular activity was evaluated according to the influence on the serotonergic and adrenergic systems of the human internal mammary artery (HIMA). Antioxidant and neuroprotective studies were also conducted. Several luteolin and apigenin derivatives were identified as main constituents of the extract, which did not present any contractile effect nor had any effect on the serotonergic system of HIMA. However, it showed antagonistic effect on the adrenergic system, inhibiting the contraction to noradrenaline (reduction of 58.44% of maximum contraction). The extract showed antioxidant activity and standardised luteolin and apigenin derivatives showed neuroprotective potential, particularly homoorientin.