ABSTRACT
The aerial parts of Nepeta teucriifolia Willd. were extracted with the solvents of different polarities. The antiproliferative activities of the extracts were evaluated against rat brain tumor (C6) and human cervix carcinoma (HeLa) cell lines. The phytochemical screening of the extracts was performed with TOF-LC/MS. The CH2Cl2 and EtOAc extracts showed considerable antiproliferative activities against HeLa cells at higher concentration (250 µg mL-1). The CH2Cl2 extract was found more active than the others on both cells. The phytochemical studies of the active extract led to the isolation of three new iridoids, teucriifolian A-C (1-3). The structure elucidations of the new compounds were performed using HPLC-TOF/MS, 1D and 2D NMR techniques. The compounds 1-3 were evaluated in terms of their antiproliferative activities against HeLa and C6 cells, respectively. The results indicated that only 2 had moderate antiproliferative activity against HeLa cells at 250 µg mL-1.
Subject(s)
Nepeta , Plant Extracts , Female , Rats , Humans , Animals , HeLa Cells , Plant Extracts/pharmacology , Plant Extracts/chemistry , Iridoids/pharmacology , Iridoids/chemistry , Phytochemicals/chemistry , Plant Components, AerialABSTRACT
Rheum ribes L. (Rhubarb) is one of the most important edible medicinal plants in the Eastern Anatolia region and is called "Iskin" by local people. Resveratrol and 6-O-methylalaternin were isolated from the Rhubarb for the first time in addition to well-known secondary metabolites including emodin, aloe-emodin, ß-sitosterol and rutin. The new semi-synthetic anthraquinone derivatives with the NαFmoc-l-Lys and ethynyl group were synthesized from the isolated anthraquinones emodin and aloe-emodin of Rhubarb to increase the bioactivities. Aloe-emodin derivative with NαFmoc-l-Lys shows the highest inhibition values by 94.11 ± 0.12 and 82.38 ± 0.00% against HT-29 and HeLa cell lines, respectively, at 25 µg/mL. Further, modification of the aloe-emodin with both the ethynyl and the NαFmoc-l-Lys groups showed an antioxidant activity-enhancing effect. From molecular docking studies, the relative binding energies of the emodin and aloe-emodin derivatives to human serum albumin ranged from -7.30 and -10.62 kcal/mol.
Subject(s)
Anthraquinones/chemistry , Antineoplastic Agents/chemical synthesis , Resveratrol/chemistry , Rheum/chemistry , Anthraquinones/chemical synthesis , Anthraquinones/isolation & purification , Anthraquinones/metabolism , Anthraquinones/pharmacology , Antineoplastic Agents/pharmacology , Binding Sites , Cell Line, Tumor , Cell Proliferation/drug effects , Emodin/chemistry , Emodin/isolation & purification , Emodin/metabolism , Emodin/pharmacology , Humans , Molecular Docking Simulation , Plant Components, Aerial/chemistry , Plant Components, Aerial/metabolism , Resveratrol/isolation & purification , Resveratrol/pharmacology , Rheum/metabolism , Serum Albumin/chemistry , Serum Albumin/metabolismABSTRACT
BACKGROUND: Luffa cylindrica is a plant that is widely distributed in Africa and Asia and can be grown in regions with tropical or subtropical climates. Few patents dealt with Loofah biological properties, including some functional foods formulated from its leaves. OBJECTIVE: This study aimed to structurally and functionally characterize the bioactive compounds of L. cylindrica leaves grown in two different environments. METHODS: The extracts of L. cylindrica leaves collected from two Tunisian locations: Essouasi (LE), a semi-arid region and Medenine (LM), an arid region, were investigated for their phenolic compounds and fatty acids using HPLC/TOF-MS and GC-MS techniques, respectively. Furthermore, the antioxidant capacity was evaluated with DPPH, Chelating effect, Hydroxyl radical and Superoxide anion scavenging activities while the anticancer activity against HeLa cell lines was assessed using xCELLigence real time cell analyzer and lactate dehydrogenase cytotoxicity assay. RESULTS: The antiproliferative capacity of both extracts was time and dose-dependent, with LE presenting the lowest HeLa cell index (CI = 0.035 ± 0.018, 250 µg/ml). LE also showed the best cytotoxic capacity (56.49 ± 0.8%) and antioxidant potential (IC50 = 54.41 ± 1.12 µg/ml for DPPH and 12.12 ± 0.07 µg/ml for chelating effect). 14 phenolic compounds were detected in LE, with ferulic acid being the major compound (5128.5 ± 4.09 µg Phenols/g), while LM had only 6 phenolics. GCMS analysis showed the presence of omega-3 fatty acids in LE. CONCLUSIONS: Our findings suggest that L. cylindrica leaves, especially when collected from semiarid regions, are promising for formulating nutraceuticals of interest.
Subject(s)
Dietary Supplements/analysis , Luffa/chemistry , Plant Extracts/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Antioxidants/pharmacology , Cell Line , Cell Proliferation/drug effects , Chromatography, High Pressure Liquid , Gas Chromatography-Mass Spectrometry , Humans , Luffa/growth & development , Mass Spectrometry , Phenols/chemistry , Phenols/isolation & purification , Phenols/pharmacology , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Leaves/chemistry , Plant Leaves/growth & developmentABSTRACT
BACKGROUND: Pistacia atlantica Desf. (Anacardiaceae) has various applications for dietetic and medicinal purposes. OBJECTIVE: The aim of the present study was to evaluate antioxidant, antiproliferative and anticholinesterase activities of different extracts from leaf and stem of Pistacia atlantica Desf. METHODS: The antioxidant activity was performed by four methods: DPPH, ABTS, CUPRAC and reducing power assays. Anti-cholinesterase activity was performed against acetylcholinesterase (AChE) and Butyrylcholinesterase (BuChE) enzymes. Antiproliferative assays were investigated against HeLa cell lines using xCELLigence RTCA instrument. The secondary metabolites composition was established by HPLC-TOF/MS analysis. RESULTS: In DPPH, reducing power and in ABTS .+ scavenging activity, all the extracts showed strong inhibitory activity compared to synthetic antioxidants such as butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA), in which the activities were almost equal to the two standards. The results were less significant in CUPRAC assay. The ethyl acetate (EtOAc) extracts exhibited the best antioxidant activity in all tests. Moreover, P. atlantica extracts inhibited AChE and BChE activities in a dose-dependent manner. The strongest AChE and BuChE inhibition activities were obtained for EtOAc extract of the stem (IC50 values 15.14±0.74 and 24.01±0.21 µg/mL, respectively) compared to galantamine (IC50 values 6.27±1.15 and 34.75±1.99 µg/mL, respectively). P. atlantica extracts also showed significant antiproleferative activity against HeLa cell lines, the best antiproleferative activity was obtained for the methanol and EtOAc extracts. The observed biological activities can be attributed to the presence of phenolic compounds and flavonoids in the extracts. The HPLC-TOF/MS analysis identified the presence of 22 phytochemicals. Gallic acid and rutin were the main compounds detected. Cichoric, gentisic, vanillic, protocatechuic and rosmarinic acids as well as catechin and quercetin were also present. CONCLUSION: This study demonstrated good antioxidant, anticholinesterase and antiproliferative activities of P. atlantica extracts, which opens up new possibilities for pharmaceutical and food industries.
Subject(s)
Antioxidants/pharmacology , Cholinesterase Inhibitors/pharmacology , Phytochemicals/analysis , Phytochemicals/pharmacology , Pistacia/chemistry , Plant Extracts/analysis , Plant Extracts/pharmacology , Algeria , Cell Proliferation/drug effects , Flavonoids/analysis , Flavonoids/pharmacology , HeLa Cells , Humans , Phenols/analysis , Phenols/pharmacology , Plant Leaves/chemistry , Plant Stems/chemistryABSTRACT
ETHNOPHARMACOLOGY RELEVANCE: Cymbopogon schoenanthus (C. schoenanthus) and Helianthemum lippii (H. lippii) are Saharan species found in the South West of Algeria, in the region of Bechar. Both plants are used in traditional medicine to treat gastrointestinal disorders. OBJECTIVE: The aim of our study was to characterize the composition of the ethyl acetate (EtOAc) and n-Butanol (n-BuOH) extracts of C. schoenanthus and H. lippii, and to elucidate and compare their effect on the reactivity of the rat distal colon. MAIN METHODS: The plants were macerated in a hydroalcoholic solution. After concentration, the aqueous solutions of the residues were submitted to liquid-liquid extractions to obtain EtOAc and n-BuOH extracts. The phenolic and flavonoid content of the extracts was determined by high performance liquid chromatography coupled with mass spectrometry with a time of flight analyzer (HPLC-TOF/MS). The effect of the extracts was tested on the rat distal colon, namely on the basal tone and on KCl- and Ach-induced precontracted preparations. RESULTS: HPLC-TOF/MS identified 32 phenols and flavonoids in the extracts. The four extracts relaxed the rat distal colon, the effect being noticed on the basal tone and on the KCl- and Ach-induced precontractions. The EtOAc and the n-BuOH extracts of H. lippii decreased the basal tone of the rat distal colon more markedly than the correspondent extracts of C. schoenanthus. Moreover, the n-BuOH extract of C. schoenanthus decreased the basal tone more markedly than the EtOAc extract of this plant but there was no difference between extracts of H. lippii. The EtOAc extracts of both C. schoenanthus and H. lippii totally reverted both the KCl- and the Ach-induced precontraction of the rat distal colon. However, the n-BuOH extracts of the two plants reverted the Ach-precontracted colon but not the colon that has been precontracted with KCl. CONCLUSION: Extracts of H. lippii contain a higher level of phenols compared to the extracts of C. schoenanthus. All extracts of C. schoenanthus and H. lippii caused marked relaxation of the isolated rat distal colon, either when applied directly or when tested over KCl- and Ach-induced precontraction. These results give support to the use of C. shoenanthus and H. lippii in traditional medicine, namely for gastrointestinal diseases.
Subject(s)
Cistaceae , Colon/drug effects , Cymbopogon , Gastrointestinal Agents/pharmacology , Muscle, Smooth/drug effects , Plant Extracts/pharmacology , 1-Butanol/chemistry , Acetates/chemistry , Animals , Colon/physiology , Female , Flavonoids/analysis , Flavonoids/pharmacology , Gastrointestinal Agents/chemistry , Muscle Contraction/drug effects , Muscle, Smooth/physiology , Phenols/analysis , Phenols/pharmacology , Plant Extracts/chemistry , Rats , Solvents/chemistryABSTRACT
This study aimed to evaluate the in vitro antiproliferative and inhibition of oxidative DNA-damage activities of n-butanol (n-BuOH) extract of Centaurea sphaerocephala. The in vitro antioxidant activity of the ethyl acetate (EtOAc) and the n-BuOH extracts of this plant were also assayed. To investigate the antioxidant potential, extracts were tested for their capacity to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH·) and to inhibit lipid peroxidation using the TBARs method. The contents of total phenolics and flavonoids were measured. Additionally, antiproliferative activity and DNA-damage inhibition of the n-BuOH extract was determined using XCELLigence RTCA instrument and photolyzing 46966 plasmid, respectively. The results exhibited that the scavenging abilities of the EtOAc extract were better than the n-BuOH extract with an IC50= 11.59 µg/mL and 16.67 µg/mL for both extracts, respectively. The phenolic and flavonoid contents were found higher in the n-BuOH and EtOAc extracts. Furthermore, our results showed that n-BuOH extract exhibited a remarkable inhibition of lipid peroxidation with an IC50 of 340.94±7.49 µg/mL and had an antiproliferative effect against Hela cells. Extracts of C. sphaerocephala showed antioxidant activity on scavenging DPPH·. In addition, the n-BuOH extract inhibited the lipid peroxidation and exhibited an antiproliferative effect against HeLa cells line (human cervix carcinoma).
Subject(s)
1-Butanol/pharmacology , Acetates/pharmacology , Antioxidants/pharmacology , Cell Proliferation/drug effects , Centaurea/chemistry , DNA Damage/drug effects , Plant Extracts/pharmacology , 1-Butanol/isolation & purification , Acetates/isolation & purification , Antioxidants/isolation & purification , Cell Line, Tumor , Humans , Mass SpectrometryABSTRACT
The current study aims to optimize and validate a comprehensive LC-MS/MS method for the quantification of 37 phytochemicals (15 phenolic acids, 17 flavonoids, 3 non-phenolic organic acids, 1 phenolic aldehyde and 1 benzopyrene) in Achillea species. Though Achillea species were chosen as real life samples, the current method is applicable to a wide range of plant species. The developed method was fully validated in terms of linearity, accuracy (recovery), inter-day and intra-day precision (repeatability), limits of detection and quantification (LOD/LOQ) and relative standard uncertainty (U% at 95% confidence level (kâ¯=â¯2)). Reversed-phase ultrahigh performance liquid chromatography was optimized to achive optimum separation for 37 phytochemical compounds and to overcome the suppression effects. MS detection was performed using a triple quadrupole mass spectrometer and negative or positive ionization modes were optimized for each analyte. Multiple reaction monitoring (MRM) was used to quantify the analytes, related molecular ions and transition ions were optimized. Phytochemical screening of ethanol and methanol-chloroform extracts of root and aerial parts of A. coarctata and A. monocephala were performed by using the developed and validated LC-MS/MS method. Root and aerial parts of both species have considerable amounts of certain phenolic-nonphenolic acids (quinic, malic, fumaric, chlorogenic and vanillic acids) and flavonoids (rutin, hesperidin, isoquercitrin, apigetrin, luteolin, apigenin). Additionally, total phenolic and flavonoid amounts, antioxidant (DPPH free radical scavenging assay, ABTS radical cation decolorization assay, ß-carotene lipid peroxidation test system and CUPRAC cupper reduction capacity methods), anticholinesterase, tyrosinase, urease inhibition and cytotoxic activities (on HeLa (Human Cervical Carcinoma Cell Line) of A. coarctata and A. monocephala were also investigated. It has been determined that the studied Achillea species, that are rich in total phenolic-flavonoid and chlorogenic acid contents, have high antioxidant and cytotoxic potential at the same time. According to the results of LC-MS/MS, antioxidant and cytotoxic activity studies, after detailed chemical investigation and toxicity studies on these species, A. coarctata and A. monocephala may be promoted as promising sources of natural agents and used for the development of nutraceuticals or functional food ingredients in future.
Subject(s)
Achillea/chemistry , Phytochemicals/chemistry , Plant Extracts/chemistry , Antioxidants/chemistry , Cell Line, Tumor , Chlorogenic Acid/chemistry , Chlorogenic Acid/pharmacology , Cholinesterase Inhibitors/metabolism , Chromatography, Liquid/methods , Cytotoxins/chemistry , Cytotoxins/pharmacology , Flavonoids/chemistry , Flavonoids/pharmacology , HeLa Cells , Humans , Lipid Peroxidation/drug effects , Monophenol Monooxygenase/metabolism , Phenols/chemistry , Phytochemicals/pharmacology , Plant Extracts/pharmacology , Tandem Mass Spectrometry/methods , beta Carotene/metabolismABSTRACT
AIM AND OBJECTIVE: Due to the common ethnopharmacological used or scientifically examined biochemical properties, Elaeagnaceae family, Elaeagnus umbellate (Thunb.) (EU, Guz yemisi) was worth investigating. MATERIALS AND METHODS: In this investigation, we revealed antioxidant, antiproliferative and enzyme inhibition activities of the water, methanol, ethanol, acetone, ethyl acetate and hexane extracts of EU as well as the contents of their phenolic, flavonoid, anthocyanin, ascorbic acid, lycopene and ß- carotene. The antioxidant activity was screened by total antioxidant (phosphomolybdenum), inhibition of linoleic acid peroxidation, reducing power, 2-deoxyribose degradation assay, H2O2 scavenging and metal chelating activities of the samples were tested in vitro. Additionally, the scavenging activities of the extracts were determined against 1,1-diphenyl-2-picrylhydrazyl (DPPHË), 2,2-azino-bis(3-ethylbenzothiazloine-6-sulfonicacid (ABTSË+), superoxide anion and peroxide radicals. The samples were determined for their inhibitory activities against urease, acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). In vitro, antiproliferative activities of six different extracts were tested using the xCELLigence system against HeLa and HT29 cell lines. RESULTS: The antioxidant activities of the extracts were found higher than standard antioxidants. The water extracts of fruit and leaf showed the best antioxidant activity. In inhibition assays of urease, AChE and BuChE, all extracts exhibited remarkable inhibition potential. Ethyl acetate extracts, especially, showed better inhibition capacity. It was found that the antioxidant activities of the extracts presented consistently with their chemical contents. The antiproliferative activities of leaf extracts were more effective than the fruit extracts. The chromatographic methods were applied to the different solvents to analyses phenolic secondery metabolites. It was found that fumaric acid, 4- hydroxybenzoic acid, rutin and quercetin-3-ß-D-glucoside, neohesperidin, hesperidin determined to have higher contents all the extracts. CONCLUSION: EU can be suggested as a potential natural source of antioxidants appropriate for utilization in nutritional/pharmaceutical fields.
Subject(s)
Acetylcholinesterase/metabolism , Antineoplastic Agents, Phytogenic/pharmacology , Antioxidants/pharmacology , Elaeagnaceae/chemistry , Enzyme Inhibitors/pharmacology , Phytochemicals/pharmacology , Urease/antagonists & inhibitors , Animals , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antioxidants/chemistry , Antioxidants/isolation & purification , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , HT29 Cells , HeLa Cells , High-Throughput Screening Assays , Horses , Humans , Phytochemicals/chemistry , Phytochemicals/isolation & purification , Structure-Activity Relationship , Urease/metabolismABSTRACT
The aim of this study was to examine the anticancer activities and phytochemical profiles of Dicranum scoparium against HeLa cell lines. The bio-guided fractionation studies of dichloromethane extract have high antiproliferative activities. Fractions 7, 9, 19, 20 are rich source of unsaturated fatty acids, and- in the case of Fr-19 may improve the antiproliferative activities as well as increase the unsaturated fatty acid content. The effect of proliferative activities in hexane extract can be attributed to the saturated fatty acid composition of D. scoparium. The Fr-9 exhibited strong antiproliferative activity at concentrations of 100 and 50 µg mL(-1) compared to 5-FU. The fractions of 7, 9, 19 and 20 from dichloromethane extracts exhibited antiproliferative activities at a concentration of 100 µg mL(-1). The HPLC-TOF/MS studies gave nine compounds from the most active fraction of dichloromethane at concentrations of 250 and 100 µg mL(-1). The lower activities were obtained from the fractions including steroid derivatives.
Subject(s)
Bryophyta/chemistry , Volatile Organic Compounds/pharmacology , Cell Proliferation/drug effects , Chromatography, Gas , Chromatography, High Pressure Liquid , Dose-Response Relationship, Drug , HeLa Cells , Humans , Mass Spectrometry , Molecular Structure , Plant Extracts/chemistry , Structure-Activity Relationship , Volatile Organic Compounds/chemistry , Volatile Organic Compounds/isolation & purificationABSTRACT
The composition of fatty acids and insecticidal effects was performed for the Turkish mosses Dicranum scoparium, Hypnum cupressiforme, Polytrichastrum formosum, Homalothecium lutescens and the Turkish liverwort Conocephalum conicum. All structures were determined by means of gas chromatography and gas chromatography-mass spectrometry techniques. The determination of fatty acids was done using a simple and mild method that utilized different solvent extractions ranging from nonpolar to polar solvents (hexane, dichloromethane, chloroform, ethyl acetate and methanol, respectively), and the samples were powdered with and without liquid nitrogen. The correlations between the saturated and unsaturated fatty acid contents depending on the solvent polarity and their crushing process by liquid nitrogen were observed. The insecticidal activity of the bryophytes was analyzed by using the methanol, hexane and esterified methanol extracts. The hexane extracts of Polytrichastrum formosum showed the highest insecticidal activity (70.33%) against Sitophilus granarius. Contact toxicity activities of lauric, myristic and palmitic acids besides single dose studies of the solvent extracts were carried out. The highest mortality rate (53.34%) was obtained from the myristic acid among the tested pure fatty acids. The activities of palmitic and lauric acids were 17.75% and 4.32%, respectively.