ABSTRACT
The sustainability of agroecosystems are maintained with agro-chemicals. However, after more than 80 years of intensive use, many pests and pathogens have developed resistance to the currently used chemistries. Thus, we explored the isolation and bioactivity of a chemical compound, Precocene I, isolated from the perennial grass, Desmosstachya bipinnata (L.) Stapf. Fractions produced from chloroform extractions showed suppressive activity on larvae of Spodoptera litura (Lepidoptera: Noctuidae), the Oriental armyworm. Column chromatography analyses identified Precocene I confirmed using FTIR, HPLC and NMR techniques. The bioactivity of the plant-extracted Dp-Precocene I was compared to a commercially produced Precocene I standard. The percentage of mortality observed in insects fed on plant tissue treated with 60 ppm Db-Precocene I was 97, 87 and 81, respectively, for the second, third and fourth instar larvae. The LC50 value of third instars was 23.2 ppm. The percentages of survival, pupation, fecundity and egg hatch were altered at sub-lethal concentrations of Db-Precocene I (2, 4, 6 and 8 ppm, sprays on castor leaves). The observed effects were negatively correlated with concentration, with a decrease in effects as concentrations increased. Distinct changes in feeding activity and damage to gut tissues were observed upon histological examination of S. litura larvae after the ingestion of Db-Precocene I treatments. Comparative analyses of mortality on a non-target organism, the earthworm, Eisenia fetida, at equal concentrations of Precocene I and two chemical pesticides (cypermethrin and monocrotophos) produced mortality only with the chemical pesticide treatments. These results of Db-Precocene I as a highly active bioactive compound support further research to develop production from the grass D. bipinnata as an affordable resource for Precocene-I-based insecticides.
Subject(s)
Annelida/drug effects , Benzopyrans/pharmacology , Insecticides/pharmacology , Plant Extracts/pharmacology , Poaceae/chemistry , Spodoptera/drug effects , Animals , Benzopyrans/chemistry , Benzopyrans/isolation & purification , Insecticides/chemistry , Insecticides/isolation & purification , Parasitic Sensitivity Tests , Phytochemicals/chemistry , Phytochemicals/pharmacology , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Spectrum AnalysisABSTRACT
CONTEXT: Ginkgo biloba L. (Ginkgoaceae) leaf extract is one of the most frequently sold herbal extracts. There have been reports on poor quality and adulteration of ginkgo leaf extracts or the powdered plant material with extracts or powder of Styphnolobium japonicum (L.) Schott (Fabaceae) (syn. Sophora japonica L.) fruits, which is rich in flavone glycosides. OBJECTIVE: The study investigates whether ginkgo leaves genuinely contain genistein and sophoricoside and whether these two substances could be used as markers to detect adulterations with sophora fruits. MATERIALS AND METHODS: A total of 33 samples of dried ginkgo leaves were sourced from controlled plantations in China, the USA, and France. After extraction, the samples were analyzed using two high-performance liquid chromatography (HPLC) coupled with UV/HRMS methods for the detection of genistein and sophoricoside, respectively. Chromatograms were compared to standard reference materials. RESULTS: In none of the tested ginkgo samples, neither genistein nor sophoricoside could be detected. The applied method was designed to separate genistein from apigenin. The latter is a genuine compound of ginkgo leaves, and its peak may have been previously misidentified as genistein because of the same molecular mass. The method for the detection of sophoricoside allows identification of the adulteration with sophora fruit without prior hydrolysis. By both HPLC methods, it was possible to detect adulterations of ≥2% sophora fruits in the investigated ginkgo extract. CONCLUSION: The methods allow unambiguous detection of adulterations of ginkgo leaves with sophora fruits, using genistein and sophoricoside as marker compounds.
Subject(s)
Ginkgo biloba/chemistry , Plant Extracts/chemistry , Sophora/chemistry , Benzopyrans/analysis , Benzopyrans/isolation & purification , Chromatography, High Pressure Liquid , Drug Contamination , Fruit , Genistein/analysis , Genistein/isolation & purification , Mass Spectrometry , Plant Extracts/analysis , Plant LeavesABSTRACT
Secundiflorol G (SG) is an isoflavan isolated from the root bark of Aeschynomene fascicularis, a Mayan medicinal plant used to treat cancer-like symptoms. SG has been shown to have cytotoxic effects on cervical cancer cells (HeLa). Assays were done to identify the mechanisms of SG's cytotoxic effect.HeLa cells treated with SG exhibited early and late apoptosis, and caspase-9, -8 and -3 activities. It also induces generation of reactive oxygen species and disrupted mitochondrial membrane potential.SG isolated from A. fascicularis induces apoptosis through extrinsic and intrinsic pathways on HeLa cells. SG could be a candidate for in vivo studies and a promising natural compound in cervical cancer treatment.
Subject(s)
Apoptosis/drug effects , Benzopyrans/isolation & purification , Benzopyrans/pharmacology , Fabaceae/chemistry , Isoflavones/isolation & purification , Isoflavones/pharmacology , Plants, Medicinal/chemistry , Uterine Cervical Neoplasms/pathology , Antineoplastic Agents/pharmacology , Benzopyrans/chemistry , Caspases/metabolism , Cyclin-Dependent Kinase Inhibitor p21/metabolism , Enzyme Activation/drug effects , Female , HeLa Cells , Humans , Isoflavones/chemistry , Membrane Potential, Mitochondrial/drug effects , Plant Extracts/pharmacology , Reactive Oxygen Species/metabolism , Uterine Cervical Neoplasms/drug therapy , Uterine Cervical Neoplasms/enzymology , bcl-2-Associated X Protein/metabolismABSTRACT
Asthma is a chronic inflammatory lung disorder with continuously increasing prevalence worldwide. Novel strategies are needed to prevent or improve asthma. The aim of this study was to investigate the effects of sophoricoside from Sophora japonica on allergic asthma. The mature seeds of S. japonica contain a large amount of sophoricoside. Sophoricoside reduced allergic and asthmatic symptoms by suppressing airway inflammation and antibody-antigen reaction in mouse models. In particular, sophoricoside suppressed immune cell recruitment into the airway lumens of the lungs and production of pro-inflammatory cytokines in the bronchoalveolar lavage fluid (BALF) of ovalbumin (OVA)-induced mice. It also decreased the amounts of histamine and arachidonic acid metabolites released in OVA-induced mice and antibody-antigen stimulated mast cells. In addition, sophoricoside decreased differentiation of naïve CD4+ T cells into T helper type 1 (Th1), Th2, and Th17 cells. Overall, we demonstrated that sophoricoside improved allergic asthma by suppressing mast cell activation and CD4+ T cell differentiation.
Subject(s)
Anti-Allergic Agents/pharmacology , Anti-Asthmatic Agents/pharmacology , Benzopyrans/pharmacology , CD4-Positive T-Lymphocytes/drug effects , Cell Differentiation/drug effects , Lung/drug effects , Mast Cells/drug effects , Plant Extracts/pharmacology , Sophora , Animals , Anti-Allergic Agents/isolation & purification , Anti-Asthmatic Agents/isolation & purification , Asthma/drug therapy , Asthma/immunology , Asthma/metabolism , Benzopyrans/isolation & purification , CD4-Positive T-Lymphocytes/immunology , CD4-Positive T-Lymphocytes/metabolism , Cell Degranulation/drug effects , Cells, Cultured , Cytokines/metabolism , Disease Models, Animal , Histamine Release/drug effects , Immunoglobulins/metabolism , Inflammation Mediators/metabolism , Lung/immunology , Lung/metabolism , Mast Cells/immunology , Mast Cells/metabolism , Mice, Inbred BALB C , Ovalbumin , Plant Extracts/isolation & purification , Sophora/chemistryABSTRACT
Mallotusapelta(Lour.) Müll.Arg has been used in traditional medicine for the treatment of chronic hepatitis. Six new chromene derivatives, malloapeltas C-H (1-6) and one known compound, malloapelta B (7) were isolated and structured from the leaves of M.apelta. Two pairs of enantiomers (1a/1b and 2a/2b) were successfully separated by chiral high-pressure liquid chromatography (HPLC). The structures and absolute configurations of compounds were determined using spectroscopic methods, including 1D, 2D NMR, and MS and quantum chemical calculation methods. All compounds were evaluated for cytotoxic activity using cell counting kit-8 (CCK-8) assay against ovariancancer cell line (TOV-21G). Compounds 1-5 and 7 exhibited significant growth and viability inhibitory effects with GI50 values ranging from 0.06 to 10.39 µM and IC50 values ranging from 1.62 to 10.42 µM on ovarian cancer cell line, TOV-21G. The most cytotoxic compounds 2, 3, and 7 were chosen for studying in apoptosis mechanism. Compounds 2, 3, and 7-induced apoptosis as evidenced by activated caspase 8, caspase 9, and PARP, increased Bak and Bax, and decreased Bcl-xL and survivin. Moreover, compounds 2, 3, and 7 significantly inhibited the NF-κB signaling pathway. Taken together, our findings propose the potential application of compounds 2, 3, and 7 for treating cancer via modulating NF-κB activity.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Benzopyrans/pharmacology , Mallotus Plant/chemistry , Plant Extracts/pharmacology , Animals , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Apoptosis/drug effects , Benzopyrans/chemistry , Benzopyrans/isolation & purification , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Humans , Mice , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Leaves/chemistry , RAW 264.7 Cells , Stereoisomerism , Structure-Activity RelationshipABSTRACT
Three undescribed azaphilones, phomopsones A-C (1-3) and two known azaphilones (4-5) were isolated from the culture of endophytic fungus Phomopsis sp. CGMCC No.5416 from the stems of Achyranthes bidentata. Their structures were determined by spectroscopic analysis (HRESIMS, 1D and 2D NMR), and the absolute configurations were determined by CD spectroscopy. Compounds 2 and 3 showed significant inhibitory activities against HIV-1 with against HIV-1 with IC50 values of 7.6 and 0.5 µmol/L, respectively. Compounds 2 and 3 also displayed moderate cytotoxicity with CC50 values of 3.2-303 µmol/L against A549, MDA-MB-231 and PANC-1 cell lines. Moreover, compound 3 can induce the early apoptosis of PANC-1 cancer cells with the apoptosis rate of 28.54%.
Subject(s)
Anti-HIV Agents/pharmacology , Antineoplastic Agents/pharmacology , Benzopyrans/pharmacology , Biological Products/pharmacology , Phomopsis/chemistry , Pigments, Biological/pharmacology , Achyranthes/microbiology , Anti-HIV Agents/isolation & purification , Antineoplastic Agents/isolation & purification , Apoptosis , Benzopyrans/isolation & purification , Biological Products/isolation & purification , Cell Line, Tumor , China , Endophytes/chemistry , HIV-1/drug effects , Humans , Molecular Structure , Pigments, Biological/isolation & purification , Plant Stems/microbiologyABSTRACT
Twenty new chebulic acid and brevifolincarboxylic acid derivatives, including eight optically pure or achiral compounds (1-7 and 14) and six pairs of enantiomers (8a/8b-13a/13b), along with nine known analogues (15-23), were isolated from an EtOH extract of the aerial parts of Euphorbia hirta. The absolute configurations of the new compounds were assigned based on single-crystal X-ray diffraction analysis and comparison of the experimental and calculated ECD data. Racemic or scalemic mixtures of 8-13 were isolated, and their enantiomers were analyzed by chiral-phase HPLC-ECD measurements. Compound 12 possesses an unprecedented 2H-cyclopenta[de]chromene-2,5(4H)-dione scaffold. Compounds 12, 20, and 23 displayed moderate inhibitory effects against lipopolysaccharide-induced nitric oxide production in BV-2 microglial cells, while all the isolates exhibited significant DPPH radical scavenging activities with EC50 values of 2.2-15.8 µM.
Subject(s)
Benzopyrans/chemistry , Benzopyrans/pharmacology , Euphorbia/chemistry , Benzopyrans/isolation & purification , Carboxylic Acids/chemistry , Carboxylic Acids/isolation & purification , Carboxylic Acids/pharmacology , Cell Line , Cell Survival/drug effects , Chromatography, High Pressure Liquid , Circular Dichroism , Free Radical Scavengers/pharmacology , Humans , Lipopolysaccharides , Molecular Structure , Nitric Oxide/antagonists & inhibitors , Plant Components, Aerial/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Stereoisomerism , X-Ray DiffractionABSTRACT
The phytochemical investigation of Fraxinus hupehensis led to the isolation and characterization of ten compounds which were identified as fraxin (1), fraxetin (2), esculetin (3), cichoriin (4), euphorbetin (5), kaempferol-3-O-ß-rutinoside (6), oleuropein (7), linoleic acid (8), methyl linoleate (9), and ß-sitosterol (10). Structures of the isolated constituents were characterized by 1H NMR, 13C NMR and HRMS. All the compounds, except compounds 3 and 4, were isolated for the first time from this plant. Further, this was the first report for the occurrence of compound 5 in the Fraxinus species. Antifungal activity evaluation showed that compound 2 exhibited significant inhibitory effects against Bipolaris maydis, Sclerotium rolfsii, and Alternaria solani with EC50 values of 0.31 ± 0.01 mmol/L, 10.50 ± 0.02 mmol/L, and 0.40 ± 0.02 mmol/L respectively, compared to the positive control, Carbendazim, with its EC50 values of 0.74 ± 0.01 mmol/L, 1.78 ± 0.01 mmol/L and 1.41 ± 0.00 mmol/L. Herbicidal activity tests showed that compounds 8-10 had strong inhibitory effects against the roots of Echinochloa crus-galli with EC50 values of 1.16 ± 0.23 mmol/L, 1.28 ± 0.58 mmol/L and 1.33 ± 0.35 mmol/L respectively, more potently active than that of the positive control, Cyanazine, with its EC50 values of 1.56 ± 0.44 mmol/L. However, none of the compounds proved to be active against the tested bacteria (Erwinia carotovora, Pseudomonas syringae, and Ralstonia solanacearum).
Subject(s)
Fraxinus/chemistry , Fraxinus/metabolism , Plant Extracts/isolation & purification , Antifungal Agents/pharmacology , Benzopyrans/isolation & purification , Coumarins/isolation & purification , Glucosides/isolation & purification , Herbicides/chemistry , Iridoid Glucosides , Iridoids/isolation & purification , Kaempferols/isolation & purification , Linoleic Acid/isolation & purification , Linoleic Acids/isolation & purification , Plant Extracts/metabolism , Plant Roots , Sitosterols/isolation & purification , Umbelliferones/isolation & purificationABSTRACT
A new series of azaphilone pigments named atrorosins have been isolated from the filamentous fungus Talaromyces atroroseus. Atrorosins have a similar azaphilone scaffold as the orange Monascus pigment PP-O, with a carboxylic acid group at C-1, but are unique by their incorporation of amino acids into the isochromene system. Despite that the atrorosin precursor PP-O, during fermentation, was initially produced as two isomers (3:2, cis:trans ratio), the atrorosins were surprisingly almost exclusively (99.5%) produced as the cis-form, possibly due to steric interactions with the incorporated amino acid. When grown on complex media, a whole range of atrorosins is produced, whereas individual atrorosins can be produced selectively during fermentation by supplementing with the desired primary amine-containing compound.
Subject(s)
Benzopyrans/chemistry , Benzopyrans/isolation & purification , Pigments, Biological/chemistry , Pigments, Biological/isolation & purification , Talaromyces/chemistry , Amino Acids/metabolism , Culture Media/chemistry , Talaromyces/growth & development , Talaromyces/metabolismABSTRACT
The rhizomes of Bergenia ciliata (B. ciliata, Family: Saxifragaceae) are widely used for treating gastric ulcers in folk medicine in Asia. It was hypothesized that anti-ulcer activity of B. ciliata is due to its anti-Helicobacter pylori (H. pylori) activity. The anti-H. pylori activity was investigated on six clinical bacterial isolates using agar well-diffusion and broth micro-dilution methods. The anti-H. pylori activity of amoxicillin (standard) was the highest (Zone of inhibition; ZI = 25 mm, minimum inhibitory concentration; MIC=0.125 µg/µL) whereas among all the extracts of the rhizomes, methanol extract showed the highest activity (ZI = 16 mm, MIC = 12.50 µg/µL). Bioassay guided isolation of methanol extract using chromatographic and crystallization techniques isolated bergenin (ZI = 21mm, MIC = 0.391µg/µL) as constituent responsible for anti-H. pylori activity. The present study describes for the first time anti-H. pylori activity and possible mechanism of anti-ulcer properties of rhizomes of B. ciliata.
Subject(s)
Benzopyrans/isolation & purification , Helicobacter pylori/drug effects , Rhizome , Saxifragaceae/chemistry , Ulcer/drug therapy , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Asia , Benzopyrans/therapeutic use , Humans , Medicine, Traditional , Microbial Sensitivity Tests , Plant Extracts/chemistry , Plant Extracts/pharmacology , Stomach Ulcer/drug therapyABSTRACT
ETHNOPHARMACOLOGICAL RELEVANCE: Bergenin is a well-known active compound that exhibits antioxidant, antiarrhythmic, hepatoprotective, and anti-inflammatory activities. However, the resource reserve of Rodgersia sambucifolia, one of the main raw materials for extracting bergenin, have sharply declined, and the bergenin content in different germplasms differs vastly, resulting in a serious shortage of the market supply of bergenin. AIM OF THE STUDY: To investigate the influence of genetic diversity and environmental factors on bergenin content in Rodgersia sambucifolia. MATERIALS AND METHODS: Fifty Rodgersia sambucifolia samples with a growth period of 2-3 years were collected from different areas across China and the bergenin content was determined via HPLC. Meanwhile the total genomic DNA was extracted and ISSR was performed. The bergenin content as measured using HPLC and the environmental data gathered from the meteorological stations and field work were combined and analyzed using correlation tests in XLSTAT 2018 to detect the key factors affecting bergenin content. The genetic UPGMA tree constructed based on genetic distances of the 50 samples and the chemical dendrogram constructed according to the distance between the bergenin content were compared to determine the correlation between genetic and chemical differentiation. RESULTS: Among the 50 individuals, bergenin content varied from 2.83 to 12.54%, with the highest content being 4.43-fold that of the lowest content. The survey of the 50 individuals produced a total of 193 amplified bands, 187 of which were polymorphic (96.89%). In the study, bergenin content was positively correlated with annual mean temperature (AMT) (râ¯=â¯0.583, Pâ¯<â¯0.0001) and 1-12 month monthly mean temperature (MMT) (Pâ¯<â¯0.0001). A comparison of the genetic dendrogram with the AHC dendrogram found no corresponding relationship between them. Mantel correlation analyses also showed that there was no significant correlation between them (râ¯=â¯0.144). CONCLUSIONS: There were large differences in bergenin content among different germplasms that were not correlated with the high genetic variation in Rodgersia sambucifolia but were significantly correlated with environmental factors, such as temperature. This study lays the foundation for subsequent superior germplasm selection and artificial breeding of Rodgersia sambucifolia to improve the bergenin content and meet market demands.
Subject(s)
Benzopyrans/metabolism , Biological Products/metabolism , Biosynthetic Pathways/genetics , Genetic Variation , Saxifragaceae/metabolism , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/metabolism , Antioxidants/isolation & purification , Antioxidants/metabolism , Benzopyrans/isolation & purification , Biological Products/isolation & purification , China , DNA, Plant/genetics , DNA, Plant/isolation & purification , Phylogeny , Plant Breeding , Saxifragaceae/genetics , Seeds/genetics , Seeds/metabolism , TemperatureABSTRACT
Brazilein is among the main chemical constituents of Caesalpinia sappan. It has diverse pharmacological activities. Modern pharmacological studies have shown that the compound has antitumor, anti-inflammatory, antibacterial, antioxidant, immunomodulatory, and other pharmacological activities. Brazilein is often used as a stain in various industries. The separation of brazilein by traditional column chromatography will not only result in contamination of the chromatographic column materials, but also lead to loss of the active ingredient. Countercurrent chromatography is an advanced liquid-liquid chromatographic separation technique. It has been widely used for natural product separation and isolation as it offers several advantages, such as low solvent consumption, a highly selective solvent system, and high recoveries. Typical countercurrent chromatography techniques include centrifugal partition chromatography (CPC), high-speed countercurrent chromatography (HSCCC), and high performance countercurrent chromatography (HPCCC). It is well known that choosing a suitable solvent system is vital in countercurrent separation. Therefore, two methods were introduced for choosing a suitable solvent system. One is the generally useful estimation of solvent systems (GUESS) method, which employs thin-layer chromatography (TLC) to identify a suitable solvent system with minimal labor for the rapid purification of target compounds, and another is the Shake-Flash method. The solvent system could be determined by observing the distribution of the sample in the upper and lower phases. Two kinds of solvent systems were screened using the TLC-GUESS and Shake-Flash methods, and tested through the analysis mode of the HPCCC instrument. The results showed that chloroform-methanol-water (4:3:2, v/v/v) was the optimal solvent system for HPCCC separation. A total of 15.2 mg of brazilein and 5.7 mg of caesappanin C were obtained from an ethyl acetate extract with high purities (95.6% and 89.0%, analyzed by HPLC) in one step using the preparation mode of HPCCC, the reversed-phase liquid chromatography mode with the apparatus rotated at 1600 r/min, a flow rate of 10 mL/min, separation temperature of 25â, and detection wavelength of 285 nm. Their structures were determined by spectroscopic and spectrometric analyses. Brazilein stained the solid packing material in the column and was difficult to elute. The results showed that the use of HPCCC for the separation of brazilein can not only prevent the loss of target active ingredients in Caesalpinia sappan, but also shorten the separation and purification times and improve the operating efficiency. Therefore, HPCCC can be used for the separation and preparation of other pigment compounds in Caesalpinia sappan and other dye plants.
Subject(s)
Benzopyrans , Caesalpinia , Indenes , Plant Extracts/chemistry , Benzopyrans/isolation & purification , Caesalpinia/chemistry , Chromatography, High Pressure Liquid , Countercurrent Distribution , Indenes/isolation & purificationABSTRACT
Ionic liquids (ILs) have gained much attention as alternative solvents to volatile organic solvents due to their attractive properties. This study aimed to develop an efficient method for the selective separation of decursin (D) and decursinol angelate (DA) from Angelica gigas Nakai (A. gigas) using ILs and crystallization. The IL 1-butyl-3-methylimidazolium tetrafluoroborate ((BMIm)BF4) was the most efficient at extracting D and DA. Parameters including solid-to-liquid ratio, time, and temperature were optimized by response surface methodology (RSM). Under optimal extraction conditions (1 g/6.5 mL solid-to-liquid ratio, 60 °C temperature, and 120 min time), the extraction yields of D and DA were 43.32 mg/g (97.06%) and 17.87 mg/g (97.12%), respectively. Moreover, drowning out crystallization using deionized water (DW) as an anti-solvent offered an excellent ability to recover D and DA from the A. gigas-(BMIm)BF4 extraction solution. The rates of recovery and the total purity of D and DA were found to be greater than 97%. Therefore, a rapid and efficient method of combining ILs with crystallization was effectively achieved for the selective separation of D and DA. This approach is assumed to be beneficial in the pharmaceutical industry for the effective obtention of D- and DA-enriched products.
Subject(s)
Angelica/chemistry , Benzopyrans/isolation & purification , Imidazoles/chemistry , Benzopyrans/chemistry , Butyrates , Crystallization , Ionic Liquids/chemistry , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/isolation & purificationABSTRACT
Two azaphilone pigments (1 and 2), two dihydrobenzofurans (3 and 4), two macrodiolides (5 and 6), and a dimeric alkyl aromatic constituent (7) were isolated from the goose dung-derived fungus Coniella fragariae. Compounds 1-3 proved to be new natural products. Coniellins H and I (1 and 2) feature a tetracyclic core and an aldehyde group at C-5, which is unusual for azaphilone derivatives. The X-ray structure of pyrenophorin (5) is reported for the first time. Pyrenophorin (5) showed strong cytotoxicity against several cancer cell lines with IC50 values ranging from 0.07 to 7.8⯵M.
Subject(s)
Ascomycota/chemistry , Benzopyrans/pharmacology , Pigments, Biological/pharmacology , Animals , Benzofurans/isolation & purification , Benzopyrans/isolation & purification , Cell Line, Tumor , Drug Screening Assays, Antitumor , Feces/microbiology , Geese/microbiology , Germany , Humans , Molecular Structure , North Sea , Pigments, Biological/isolation & purificationABSTRACT
OBJECTIVE: The objective of the work was to optimize the extraction conditions of Caesalpinia sappan L. heartwood in order to maximize the brazilin content and antibacterial activity of the extract. METHODS: Two independent factors were studied: extraction temperature (45-95⯰C) and extraction time (30-60â¯min). In addition, five dependent factors were monitored, including extraction yield, brazilin content, and clear zones against Staphylococcus aureus TISTR 1466, Staphylococcus epidermidis TISTR 518 and Propionibacterium acnes DMST 14961. The brazilin content was quantified by high-performance liquid chromatography and antibacterial activity was determined by disk diffusion assay. RESULTS: The high temperature provided high total extract yield as well as brazilin content, while extraction time had little effect on yield or brazilin content. Extraction time had a positive effect, while extraction temperature had little effect on clear zone against S. aureus. The largest clear zone against S. epidermidis was achieved at low extraction temperature and long extraction time. Conversely, short extraction time and high extraction temperature provided the largest clear zone against P. acnes. The optimal conditions providing the highest brazilin content was an extraction temperature and extraction time of 95⯰C and 30â¯min, respectively. The same optimal conditions also provided the simultaneous greatest antibacterial activity against the three bacteria. Modeled optimal conditions were validated be conducting extraction using these values. Yield and antibacterial activity of the resulting extract demonstrated that the model had a low percentage error. CONCLUSION: The optimal condition will be used as a standard condition for extraction of C. sappan heartwood to maximize brazilin content and antibacterial activity.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Benzopyrans/isolation & purification , Caesalpinia/chemistry , Plant Extracts/isolation & purification , Anti-Bacterial Agents/pharmacology , Benzopyrans/pharmacology , Chromatography, High Pressure Liquid , Plant Extracts/pharmacology , Propionibacterium acnes/drug effects , Staphylococcus aureus/drug effects , Staphylococcus epidermidis/drug effects , ThailandABSTRACT
BACKGROUND: Glycyrrhiza (licorice) species are rich in bioactive secondary metabolites and their roots are used traditionally for the treatment of several diseases. In recent years, secondary metabolites of licorice are gaining popularity, especially due to their significant cytotoxic and antitumor effects. However, Glycyrrhiza iconica, an endemic species to Turkey, was not investigated in terms of its anticancer secondary metabolites previously. PURPOSE: This study aimed to isolate the cytotoxic compounds from G. iconica through bioactivity-guided fractionation and to elucidate mechanisms of action of the most potent compounds. METHODS: Total MeOH extract and CHCl3, EtOAc, n-buOH and rH2O subextracts were prepared from G. iconica roots. Sequential chromatographic techniques were conducted for the isolation studies. The chemical structures of the isolates were established based on NMR and HR-MS analysis. Sulforhodamine B assay was used to evaluate the cytotoxic activity of extracts, main fractions as well as isolates against hepatocellular (Huh7), breast (MCF7) and colorectal (HCT116) cancer cell lines. The mechanisms underlying the cytotoxicity of the most active compounds in Huh7 cells were elucidated by using Hoechst staining, Fluorescence-activated cell sorting and Western blot assays. RESULTS: A new dihydrochalcone, iconichalcone (1) along with 15 known phenolic compounds were isolated from the active CHCl3, EtOAc and n-buOH subextracts. Compounds 2-5, 7-16 were found to be responsible for the in vitro cytotoxic activity of G. iconica against all tested cancer cell lines with IC50 values ranging from 2.4 to 33⯵M. Amongst these compounds, licoricidin (10), dehydroglyasperin C (12), iconisoflaven (13) and 1-methoxyficifolinol (15) were found to be the most active compounds according to SRB and real time bioactivity assays and submitted to further mechanistic investigations in Huh7 cells. Compounds 10, 12, 13 and 15 caused accumulation of cells in different phases of cell cycle. Moreover, 10, 12, 13 and 15 induced apoptosis through caspase activation. Besides, 12 showed activation of p53 expression and thus G2/M arrest as well as a condensed nuclei, established very promising results. CONCLUSION: The results demonstrated that the aforementioned compounds, particularly 12 could be potential lead molecules for anticancer drug development that deserve further in vivo and clinical investigations.
Subject(s)
Antioxidants/pharmacology , Benzopyrans/pharmacology , Glycyrrhiza/chemistry , Liver Neoplasms/drug therapy , Phenols/pharmacology , Plant Extracts/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Apoptosis/drug effects , Benzopyrans/chemistry , Benzopyrans/isolation & purification , Cell Cycle/drug effects , Cell Line, Tumor , Humans , Phenols/chemistry , Phenols/isolation & purification , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Roots/chemistryABSTRACT
Millettia ovalifolia is traditionally used in variety of diseases including inflammation. In our investigation in to the phytochemical constituents of Millettia ovalifolia an effort was made to find out bioactive constituent from medicinal Plant M. ovalifolia to scientifically validate its use in inflammatory disorders. The compound 7-hydroxy-6-methoxy-2H-chromen-2-one was isolated from the bark of M. ovalifolia and was found to exhibited significant lipoxygenase (LOX) inhibitory activity with (IC50 value: 116.83±0.02µM). The Standard compounds Baicalein and Tenidap sodium revealed IC50 value being 22.1±0.03µM and 41.6±0.02µM. Molecular docking study further displayed significant molecular interactions between 7-hydroxy-6-methoxy-2H-chromen-2-one and LOX showed potential for further optimization as a possible anti-inflammatory lead compound.
Subject(s)
Benzopyrans/pharmacokinetics , Drug Discovery/methods , Lipoxygenase Inhibitors/pharmacology , Lipoxygenases/metabolism , Millettia , Molecular Docking Simulation , Plant Extracts/pharmacology , Benzopyrans/chemistry , Benzopyrans/isolation & purification , Flavanones/pharmacology , Lipoxygenase Inhibitors/chemistry , Lipoxygenase Inhibitors/isolation & purification , Lipoxygenases/chemistry , Millettia/chemistry , Oxindoles/pharmacology , Plant Bark , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Protein Conformation , Structure-Activity RelationshipABSTRACT
Three new benzaldehyde derivatives, sporulosaldeins Aâ-âC (1: -3: ), and 3 new benzopyran derivatives, sporulosaldeins Dâ-âF (4: -6: ), were discovered from an endophytic fungus, Paraphaeosphaeria sp. F03, which was isolated from Paepalanthus planifolius leaves. Compounds 1: -6: were elucidated by 1- and 2-dimensional nuclear magnetic resonance experiments and high-resolution mass spectrometry analysis. The absolute configuration of compound 5: was determined through the comparison of experimental and calculated electronic circular dichroism data. Compounds 1: -6: were found to exhibit antifungal activity with minimum inhibitory concentration (MIC) values of 7.8â-â250 µg/mL and racemic mixture of compound 6: exhibited weak cytotoxicity against MCF-7 and LM3 with IC50 values of 34.4 and 39.2 µM, respectively.
Subject(s)
Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Ascomycota/chemistry , Benzaldehydes/pharmacology , Benzopyrans/pharmacology , Cytotoxins/pharmacology , Animals , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemistry , Antifungal Agents/isolation & purification , Benzaldehydes/chemistry , Benzaldehydes/isolation & purification , Benzopyrans/chemistry , Benzopyrans/isolation & purification , Cell Line, Tumor , Cytotoxins/chemistry , Cytotoxins/isolation & purification , Endophytes , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Mice , Microbial Sensitivity Tests , Molecular StructureABSTRACT
Anethum sowa L. has been used as a spice herb in the Asian and European culinary systems to add flavour and taste. The studied plant has diverse folkloric medicinal value. Present study was designed to isolate phytochemicals from the hexane, chloroform and ethyl acetate extracts of the roots by various chromatographic techniques. Based on spectral analysis (IR, LC-MS, NMR) the isolated compounds were identified as physcione (1), ß-sitosterol (2), stigmasterol (3), 2-oxo-3-propyl-2H-chromene-7-carboxylic acid (4), bergapten (5), 3-ethyl-7-hydroxy-2H-chromen-2-one (6) and graveolone (7). The mentioned compounds have been isolated for the first time from the roots part of the plant. Based on extensive literature review, physcione and bergapten were inferred to exhibit crucial bioactivities including inhibitory efficacy against various forms of cancer. Accordingly, in the present research approach molecular docking investigations of the isolated phytochemicals have been robustly executed with different oncogenes that have been reported to be actively involved in various forms of carcinoma. In silico investigations encompassing molecular docking analysis and drug-likeness profiling was executed to estimate the potential therapeutic tendencies of the phytochemicals targeted towards effective cancer therapy. Current investigation offers meaningful know-how pertaining to potential anticancer activities of the phytochemicals extracted from the roots of Anethum sowa L. and might open up new revenues towards effective drug development against cancer.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Apiaceae/chemistry , Molecular Docking Simulation , Plant Extracts/pharmacology , Plant Roots/chemistry , 5-Methoxypsoralen/chemistry , 5-Methoxypsoralen/isolation & purification , 5-Methoxypsoralen/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Benzopyrans/chemistry , Benzopyrans/isolation & purification , Benzopyrans/pharmacology , Carboxylic Acids/chemistry , Carboxylic Acids/isolation & purification , Carboxylic Acids/pharmacology , Cell Proliferation/drug effects , Drug Screening Assays, Antitumor , Humans , Methoxsalen/analogs & derivatives , Methoxsalen/chemistry , Methoxsalen/isolation & purification , Methoxsalen/pharmacology , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Sitosterols/chemistry , Sitosterols/isolation & purification , Sitosterols/pharmacology , Stigmasterol/chemistry , Stigmasterol/isolation & purification , Stigmasterol/pharmacologyABSTRACT
Rhinacanthus nasutus (L.) Kurz (Acanthaceae) is known as traditional medicine for the treatment of fungal and herpes virus infections. A new naphthoquinone racemate, rhinacasutone (1) together with seven known compounds, rhinacanthone (2), rhinacanthins C, D, N, Q, and E (3-7), and heliobuphthalmin (8) were isolated from root of R. nasutus. Their structures were determined on the basis of extensive spectroscopic methods, including 1D-, 2D-NMR and MS data. All the isolated compounds were tested for their antiviral activities against PR8, HRV1B, and CVB3-infected vero cells. Compounds 3-6 exhibited significant antiviral activities with the IC50 value ranging from 0.03 to 23.7 µM in all three infections.