ABSTRACT
Eriocaulaceae is a pantropical family whose main center of biodiversity is in Brazil. In general, the family has about 1200 species, in which phytochemical and biological studies have shown a variety of structures and activities. The aim of this research is to compile the compounds isolated in the Eriocaulaceae family and carry out a computational study on their biological targets. The bibliographic research was carried out on six databases. Tables were built and organized according to the chemical class. In addition, a summary of the methods of isolating the compounds was also made. In the computational study were used ChEMBL platform, DRAGON 7.0, and the KNIME 4.4.0 software. Two hundred and twenty-two different compounds have been isolated in sixty-eight species, divided mainly into flavonoids and naphthopyranones, and minor compounds. The ligand-based virtual screening found promising molecules and molecules with multitarget potential, such as xanthones 194, 196, 200 and saponin 202, with xanthone 194 as the most promising. Several compounds with biological activities were isolated in the family, but the chemical profiles of many species are still unknown. The selected structures are a starting point for further studies to develop new antiparasitic and antiviral compounds based on natural products.
Subject(s)
Eriocaulaceae , Eriocaulaceae/chemistry , Flavonoids/chemistry , Phytochemicals/pharmacology , Plant Extracts/pharmacology , Plant Extracts/chemistry , Machine LearningABSTRACT
The naphthopyranones paepalantine and 5-methoxy-3,4-dehydroxanthomegnin isolated from Paepalanthus sp, showed in previous studies antioxidant, anti-inflammatory, antitumour and antimicrobial potential, such as anti-Helicobacter pylori activity. H. pylori infection is one of the main causes of gastric cancer, causing an excessive inflammatory response through the neutrophils and macrophages infiltration, increasing the release of reactive species and thus inducing the production of pro-inflammatory mediators. In the present study, immunomodulatory activity of naphthopyranones in LPS-stimulated macrophages and cytotoxic action in gastric adenocarcinoma cell lines was evaluated. The potential of interaction of these substances in the iNOS binding site was investigated by molecular docking. Cytotoxic activity in gastric adenocarcinoma cells (AGS) was evaluated by the MTT assay. The results evidenced immunomodulatory potential by inhibiting the pro-inflammatory cytokines and nitric oxide produced by LPS-stimulated macrophages. Cytotoxic activity in AGS cell line was also reported. The results indicated that the studied naphthopyranones are viable alternatives in the treatment and prevention of H. pylori infection as well as the diseases related to this infection, especially gastric cancer.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Immunologic Factors/pharmacology , Isocoumarins/pharmacology , Naphthoquinones/pharmacology , Adenocarcinoma/drug therapy , Adenocarcinoma/pathology , Animals , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , Computer Simulation , Cytokines/metabolism , Eriocaulaceae/chemistry , Helicobacter Infections/drug therapy , Helicobacter pylori/drug effects , Humans , Immunologic Factors/isolation & purification , Isocoumarins/isolation & purification , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Macrophages/metabolism , Mice , Molecular Docking Simulation , Naphthoquinones/isolation & purification , Nitric Oxide/metabolism , Nitric Oxide Synthase Type II/metabolism , RAW 264.7 Cells , Stomach Neoplasms/drug therapy , Stomach Neoplasms/pathologyABSTRACT
RATIONALE: Actinocephalus divaricatus (Eriocaulaceae) is an important source of income for rural communities as it is sold as an ornamental plant. To date, no investigation has been conducted concerning the chemical composition and biological studies of the aerial parts of A. divaricatus. METHODS: The methanolic extract of the aerial parts of this species was chemically characterized. We applied an analytical dereplication approach based on Liquid Chromatography coupled to High-Resolution Orbitrap Mass Spectrometry in order to develop, identify and define rapidly the metabolite fingerprint of the aerial parts of A. divaricatus. Biological in vitro antitumor tests were undertaken using breast and lung cell lines of mice and humans. RESULTS: High-Resolution Mass Spectrometry (HRMS) allowed the fast determination of 30 compounds, which comprised three different classes of compounds: naphthopyranones, flavonoids and saponins. Chromatographic fractionation of the crude methanolic extract validated these results, since it led to the isolation of compounds belonging to the aforementioned classes of compounds, including new acyl glycosylated flavonoids (6-hydroxy-7-methoxyquercetin-3-O-(2"-O-acetyl)-ß-D-glucopyranoside and 6-hydroxy-7-methoxyquercetin-3-O-(6"-O-acetyl)-ß-D-glucopyranoside), which were fully characterized by Nuclear Magnetic Resonance and Mass Spectrometry experiments, and a known triterpenic saponin (3-O-ß-D-glucuronopyranosyl-30-norolean-12,20(29)-dien-28-O-ß-D-glucopyranosyl ester). Biological assays indicated that the methanolic extract of the capitula exhibited the best in vitro cytotoxicity against MCF7 cells (human breast cancer). CONCLUSIONS: The HRMS technique enabled us to identify several classes of compounds. In addition, saponins were identified for the first time in plants belonging to the Eriocaulaceae family. Thus, the essential contribution of this work lies in the new elements it brings to the taxonomic discussion which the Actinocephalus genus as a distinct genus of the Paepalanthus. The results obtained show that the methanolic extract of the capitula could be a promising source of bioactive fractions and/or compounds that may contribute towards breast cancer treatment.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Eriocaulaceae/chemistry , Mass Spectrometry/methods , Animals , Cell Line, Tumor , Drug Screening Assays, Antitumor/methods , Flavonoids/analysis , Humans , MCF-7 Cells , Magnetic Resonance Spectroscopy , Metabolome , Mice , Naphthalenes/analysis , Plant Components, Aerial/chemistry , Plant Extracts/analysis , Plant Extracts/chemistry , Pyrans/analysis , Saponins/analysis , Spectrometry, Mass, Electrospray IonizationABSTRACT
Eriocauli Flos (Gujingcao; EF), the dried capitulum with the peduncle of Eriocaulon buergerianum Koern. (Eriocaulaceae), is a Chinese herbal medicine for treating eye diseases and inflammation. However, several species of the Eriocaulon genus are used as substitutes in different areas. To examine the species of EF used in Taiwan and to establish the quality control platform, morphological and chemical analyses have been performed. Ten major compounds, including apigenin (7) and its 7-O-ß-D-glucopyranoside (1) and 7-O-(6-O-E-coumaroyl)-ß-D-glucopyranoside (6), hispidulin (8) and its 7-O-ß-D-glucopyranoside (2) and 7-O-(6-O-E-coumaroyl)-ß-D-glucopyranoside (5), jaceosidin (9) and its 7-O-ß-D-glucopyranoside (3), and toralactone (10) and its 9-O-ß-D-glucopyranosyl(1â6)-ß-D-glucopyranoside (4), were isolated and identified from commercially available EF. Morphological investigation showed that two kinds of EFs and most of the EFs sold in Taiwan herbal markets are capitulum without the peduncle. A simultaneous high performance liquid chromatography and ultra performance liquid chromatography analyses of multiple components (1-10) in commercially available EFs, collected from different areas of Taiwan, was conducted. Results showed wide variations in morphology and chemical profiles between capitulum with and without the peduncle. In comparison with an authentic E. buergerianum, we found not only the morphology but also the chemical profile was different from both collected samples. In terms of the morphological examination, the samples without peduncle are closer to the authentic one. To ensure the correct EF materia medica is used in Taiwan so as to guarantee their therapeutic efficacy in clinical practice, further monitoring is necessary.
Subject(s)
Drugs, Chinese Herbal/chemistry , Eriocaulaceae/chemistry , Flowers/growth & development , Chromatography, High Pressure Liquid , Drugs, Chinese Herbal/isolation & purification , Eriocaulaceae/growth & development , Flowers/chemistry , Humans , Magnetic Resonance Spectroscopy , Molecular Structure , Plants, Medicinal/chemistry , Plants, Medicinal/growth & development , TaiwanABSTRACT
Herbal-loaded drug delivery nanotechnological systems have been extensively studied recently. The antimicrobial activity of medicinal plants has shown better pharmacological action when such plants are loaded into a drug delivery system than when they are not loaded. Syngonanthus nitens Bong. (Rhul.) belongs to the Eriocaulaceae family and presents antiulcerogenic, antioxidant, antibacterial, and antifungal activity. The aim of this study was to evaluate the antifungal activity of Syngonanthus nitens (S. nitens) extract that was not loaded (E) or loaded (SE) into a liquid crystal precursor system (S) for the treatment of vulvovaginal candidiasis (VVC) with Candida albicans. The minimal inhibitory concentration (MIC) was determined by the microdilution technique. Additionally, we performed hyphae inhibition and biofilm tests. Finally, experimental candidiasis was evaluated in in vivo models with Wistar female rats. The results showed effective antifungal activity after incorporation into S for all strains tested, with MICs ranging from 31.2 to 62.5 µg/mL. Microscopic observation of SE revealed an absence of filamentous cells 24 h of exposure to a concentration of 31.2 µg/mL. E demonstrated no effective action against biofilms, though SE showed inhibition against biofilms of all strains. In the in vivo experiment, SE was effective in the treatment of infection after only two days of treatment and was more effective than E and amphotericin B. The S. nitens is active against Candida albicans (C. albicans) and the antifungal potential is being enhanced after incorporation into liquid crystal precursor systems (LCPS). These findings represent a promising application of SE in the treatment of VVC.
Subject(s)
Antifungal Agents/therapeutic use , Candidiasis, Vulvovaginal/drug therapy , Eriocaulaceae/chemistry , Nanostructures/chemistry , Plant Extracts/therapeutic use , Animals , Antifungal Agents/chemistry , Candida albicans/drug effects , Candida albicans/pathogenicity , Candidiasis, Vulvovaginal/microbiology , Drug Delivery Systems/methods , Female , Plant Extracts/chemistry , Rats , Rats, WistarABSTRACT
BACKGROUND: Production of reactive oxygen species is a common cause in alcohol induced liver diseases. Decoction prepared from the whole plant of Eriocaulon quinquingulare is prescribed to treat liver disorders. The aim of this study was to investigate the hepatoprotective activity and antioxidant capacity of the water extract of E. quinquangulare in vitro. METHOD: The aqueous extract of the whole plant of E. quinquangulare (AEQ) was investigated for its phytochemical constituents, antioxidant and membrane stabilization properties in-vitro. The antioxidant activities of AEQ were investigated using 1,1-Diphenyl-2-picrylhydrazyl (DPPH), hydroxyl radical, nitric oxide scavenging and ferric reducing antioxidant power (FRAP) assays. Membrane stabilizing effect of the extract was determined by hypotonic solution induced human erythrocyte hemolytic assay (HEHA). Further, hepatoprotective activity against ethanol induced hepatotoxicity was carried out using porcine liver slices. RESULTS: The total phenolics and flavonoids were 10.3 ± 1.6 w/w % gallic acid equivalents and 45.6 ± 3.8 w/w % (-)-epigallocatechin gallate equivalents respectively. The values of EC50 for DPPH, hydroxyl radical and nitric oxide scavenging assays were 37.2 ± 1.7 µg/ml, 170.5 ± 6.6 µg/ml and 31.8 ± 2.2 µg/ml respectively. The reducing capability of AEQ was 6.9 ± 0.2 w/w % L-ascorbic acid equivalents in the FRAP assay. For hypotonic solution induced HEHA, the IC50 was 1.79 ± 0.04 mg/ml. A significant decrease (p < 0.05) was observed in ALT, AST and LDH release from the liver slices treated with AEQ compared to the ethanol treated liver slices. A significant reduction in lipid peroxidation (p < 0.05) was also observed in liver slices treated with the plant extract compared to that of the ethanol treated liver slices. CONCLUSIONS: The results suggest AEQ possess hepatoprotective activity against ethanol induced liver toxicity of porcine liver slices which can be attributed to antioxidant properties and membrane stabilizing effects caused by the plant material.
Subject(s)
Antioxidants/pharmacology , Chemical and Drug Induced Liver Injury , Eriocaulaceae/chemistry , Flavonoids/pharmacology , Liver/drug effects , Phenols/pharmacology , Plant Extracts/pharmacology , Animals , Antioxidants/therapeutic use , Biphenyl Compounds/metabolism , Chemical and Drug Induced Liver Injury/drug therapy , Chemical and Drug Induced Liver Injury/metabolism , Erythrocyte Membrane/drug effects , Ethanol/adverse effects , Flavonoids/analysis , Flavonoids/therapeutic use , Free Radicals/metabolism , Humans , In Vitro Techniques , Lipid Peroxidation/drug effects , Liver/metabolism , Nitric Oxide/metabolism , Oxidative Stress , Phenols/analysis , Phenols/therapeutic use , Phytotherapy , Picrates/metabolism , Plant Extracts/therapeutic use , Swine , Transaminases/bloodABSTRACT
BACKGROUND: Syngonanthus arthrotrichus and Syngonanthus bisulcatus, currently known for Comanthera aciphylla (Bong.) L.R.Parra & Giul. and Comanthera bisulcata (Koern.) L.R. Parra & Giul, popularly known in Brazil as "sempre-vivas," are plants from the family Eriocaulaceae. They are found in the states of Minas Gerais and Bahia. The species are known to be rich in flavonoids to which their gastroprotective activity has been attributed. In this research, experimental protocols were performed to elucidate the associated mechanisms of action. METHODS: The activity was evaluated using induced gastric ulcer models (acetic acid and ethanol-induced gastric lesions in NEM or L-NAME pre-treated mice, and by ischemia/reperfusion). Antioxidant enzymes, serum somatostatin, and gastrin were also evaluated. RESULTS: In chronic gastric ulcers, a single daily oral dose of Sa-FRF or Sb-FRF (100 mg/kg body wt.) for 14 consecutive days accelerated ulcer healing to an extent similar to that seen with an equal dose of cimetidine. The pre-treatment of mice with NEM (N-ethylmaleimide) or L-NAME (N-nitro-L-arginine) abolished the protective activity of Sa-FRF, Sa-FDF, Sb-FDF and Sb-FRF or Sa-FRF and Sb-FRF, respectively, which indicates that antioxidant compounds and nitric oxide synthase activity are involved in the gastroprotective. Sa-FRF and Sb-FRF (100 mg/kg p.o) protected the gastric mucosa against ulceration that was induced by ischemia/reperfusion (72 and 76 %, respectively). It also decreased lipid peroxidation and restored total thiols in the gastric wall of mice that had been treated with ethanol. When administered to rats submitted to ethanol-induced gastric lesions, Sa-FRF and Sb-FRF (100 mg/kg, p.o.) increased the somatostatin serum levels, while the gastrin serum levels were proportionally decreased. CONCLUSIONS: The results indicate significant healing effects and gastroprotective activity for the Sa-FRF and Sb-FRF, which probably involves the participation of SH groups, nitric oxide (NO), the antioxidant system, somatostatin, and gastrin. All are integral parts of the gastrointestinal mucosa's cytoprotective mechanisms against aggressive factors.
Subject(s)
Anti-Ulcer Agents/administration & dosage , Eriocaulaceae/chemistry , Plant Extracts/administration & dosage , Protective Agents/administration & dosage , Stomach Ulcer/drug therapy , Animals , Gastric Mucosa/drug effects , Gastric Mucosa/metabolism , Humans , Male , Mice , Nitric Oxide/metabolism , Rats , Rats, Wistar , Stomach Ulcer/metabolism , Stomach Ulcer/physiopathology , Wound Healing/drug effectsABSTRACT
Eriocaulon sieboldianum (Sieb. & Zucc. ex Steud.) is an edible and medicinal plant used in traditional Chinese medicine. Often in combination with other herbs, it is processed into healthcare beverages for expelling wind-heat, protecting eyes, and reducing blood lipids. Besides, its water decoction together with other herbs has been utilized to treat cancer in China. However, the active ingredients and the precise cellular mechanisms of E. sieboldianum remain to be elucidated. The Aurora kinase family plays critical roles in the regulation of cell division and has attracted great attention to the identification of small-molecule Aurora kinase inhibitors for potential treatment of cancer. A molecular docking study was employed for docking of the most bioactive compounds. Hispidulin (HPDL) and quercetin-3-O-(6''-O-galloyl)-ß-D-galactopyranoside (QGGP) were singled out as potent inhibitors of Aurora kinase. Their inhibitory activity towards Aurora kinase was further confirmed by the obvious decrease in autophosphorylation of Aurora-A (Thr288) and Aurora-B (Thr232). Moreover, the induction of cell cycle arrest in HepG2 cells and the suppressed phosphorylation of histone H3 were also consistent with the inhibition of Aurora kinase. The data indicate that the E. sieboldianum extract and its two active compounds, HPDL and QGGP, could effectively induce apoptosis via p53, MAPKs and the mitochondrial apoptotic pathways. These findings could improve the understanding and enhance the development of drugs based on E. sieboldianum and raise its application value in anticancer therapy or prevention. In addition, our results indicated that Aurora kinase might be a novel target of HPDL and QGGP.
Subject(s)
Apoptosis/drug effects , Cell Proliferation/drug effects , Eriocaulaceae/chemistry , Plant Extracts/pharmacology , Protein Kinase Inhibitors/pharmacology , Aurora Kinase A/antagonists & inhibitors , Aurora Kinase A/metabolism , Aurora Kinase B/antagonists & inhibitors , Aurora Kinase B/metabolism , Cell Cycle Checkpoints/drug effects , Cell Line, Tumor , China , Flavones/pharmacology , Galactosides/pharmacology , Gallic Acid/analogs & derivatives , Gallic Acid/pharmacology , Hep G2 Cells , Humans , Phosphorylation , Plant Extracts/chemistry , Quercetin/analogs & derivatives , Quercetin/pharmacologyABSTRACT
Although several plant-derived flavones inhibit aurora B kinase (aurB), quantitative relationships between the structural properties of plant-derived flavones and their inhibitory effects on aurB remain unclear. In this report, these quantitative structure-activity relationships were obtained. For quercetagetin, found in the Eriocaulon species, showing the best IC50 value among the flavone derivatives tested in this report, further biological tests were performed using cell-based assays, including Western blot analysis, flow cytometry, and immunofluorescence microscopy. In vitro cellular experiments demonstrated that quercetagetin inhibits aurB. The molecular-binding mode between quercetagetin and aurB was elucidated using in silico docking. Quercetagetin binds to aurB, aurA, and aurC and prevents the active phosphorylation of all three aurora kinases. In addition, quercetagetin triggers mitotic arrest and caspase-mediated apoptosis. These observations suggest that quercetagetin is an aurora kinase inhibitor. Induction of mitosis-associated tumor cell death by quercetagetin is a promising strategy for developing novel chemotherapeutic anticancer agents.
Subject(s)
Aurora Kinase B/antagonists & inhibitors , Flavones/chemistry , Protein Kinase Inhibitors/chemistry , Quantitative Structure-Activity Relationship , Apoptosis/drug effects , Aurora Kinase A/antagonists & inhibitors , Aurora Kinase A/metabolism , Aurora Kinase B/metabolism , Aurora Kinase C/antagonists & inhibitors , Aurora Kinase C/metabolism , Binding Sites , Chromones/chemistry , Chromones/isolation & purification , Chromones/toxicity , Eriocaulaceae/chemistry , Eriocaulaceae/metabolism , Flavones/isolation & purification , Flavones/toxicity , G2 Phase Cell Cycle Checkpoints/drug effects , HCT116 Cells , Humans , M Phase Cell Cycle Checkpoints/drug effects , Microscopy, Fluorescence , Molecular Docking Simulation , Phosphorylation/drug effects , Protein Kinase Inhibitors/isolation & purification , Protein Kinase Inhibitors/toxicity , Protein Structure, TertiaryABSTRACT
Vaginal infections caused by Candida krusei are a problem of extreme complexity due to the intrinsic resistance to azole drugs. The species Syngonanthus nitens (Bong.) Ruhland is a plant of the Eriocaulaceae family that has demonstrated promising antifungal activity. In phyto-formulation research, liquid crystal precursor mucoadhesive systems (LCPM) stand out as drug delivery systems for vaginal administration because they increase the activity and overcome the problems associated with plant-based medicines. Therefore, the objective of this study was to evaluate the potential of the methanolic extract of scapes of S. nitens (S. nitens extract [SNE]) and an SNE-loaded LCPM against C. krusei as prophylaxis for vulvovaginal candidiasis. LCPM formulation developed consisted of oleic acid as the oil phase (50% w/w), polyoxypropylene (5) polyoxyethylene (20) cetyl alcohol (40% w/w) as the surfactant and a polymeric dispersion containing 2.5% Carbopol(®) 974P and 2.5% polycarbophil (10% w/w) as the aqueous phase. LCPM formulation developed was characterized using polarized light microscopy, rheological analysis, and in vitro mucoadhesive studies. Different strains of C. krusei, including one standard strain (American Type Culture Collection 6258) and three clinically isolated strains from the vaginal region (CKV1, 2, and 3), were used to determine the minimum inhibitory concentration, inhibition of biofilms, and time kill. The in vivo prophylaxis assay was performed using the standard strain (American Type Culture Collection 6258). The analyses of F by polarized light microscopy and rheology showed isotropy; however, the addition of 100% artificial vaginal mucus (F100) made it more viscous and anisotropic. Moreover, the mucoadhesive strength was modified, which makes F an excellent formulation for vaginal applications. SNE was active against all strains studied, with minimum inhibitory concentration values ranging from 125 to 62.5 µg/mL; after incorporating SNE into F (FE), these values decreased to 62.5 to 31.2 µg/mL, demonstrating that incorporation into the formulation potentiated the action of SNE. Additionally, the time kill assays showed that both forms of SNE were capable of controlling growth, thereby suggesting a possible fungistatic mechanism. Unloaded SNE was not active against C. krusei biofilms, but FE was active against a clinical strain (CKV2). In vivo analysis showed that FE was able to prevent the development of infection following 10 days of administration. We concluded that the formulation developed in this study was an important vehicle for the delivery of SNE based on the improved antifungal activity in all in vitro and in vivo analyses. Furthermore, the extract incorporated into the system may serve as an important prophylactic agent against vaginal infections caused by C. krusei.
Subject(s)
Antifungal Agents/pharmacology , Candida/drug effects , Candidiasis, Vulvovaginal/drug therapy , Drug Delivery Systems , Eriocaulaceae/chemistry , Liquid Crystals , Mucus/chemistry , Plant Extracts/pharmacology , Animals , Antibiotic Prophylaxis , Antifungal Agents/chemistry , Candidiasis, Vulvovaginal/microbiology , Drug Carriers , Female , Microbial Sensitivity Tests , Plant Extracts/isolation & purification , Rats , Rats, WistarABSTRACT
OBJECTIVES: Syngonanthus macrolepis, popularly known in Brazil as 'sempre-vivas', is a plant from the family Eriocaulaceae, it is found in the states of Minas Gerais and Bahia. The species contains a variety of constituents, including flavonoids with gastroprotective effect. In this work, a flavonoid-rich fraction (Sm-FRF) obtained from scapes of S. macrolepis was investigated for preventing gastric ulceration in mice and rats. METHODS: The activity was evaluated in models of induced gastric ulcer (absolute ethanol, stress, non-steroidal anti-inflammatory drugs and pylorus ligation). The cytoprotective mechanisms of the Sm-FRF in relation to sulfhydryl (SH) groups, nitric oxide (NO) and antioxidant enzymes were also evaluated. KEY FINDINGS: The Sm-FRF (100 mg/kg, p.o.) significantly reduced gastric injury in all models, and did not alter gastric juice parameters after pylorus ligation. CONCLUSIONS: The results indicate significant gastroprotective activity for the Sm-FRF, which probably involves the participation of both SH groups and the antioxidant system. Both are integral parts of the gastrointestinal mucosa's cytoprotective mechanisms against aggressive factors.
Subject(s)
Anti-Ulcer Agents/therapeutic use , Antioxidants/therapeutic use , Eriocaulaceae/chemistry , Flavonoids/therapeutic use , Phytotherapy , Plant Extracts/therapeutic use , Stomach Ulcer/prevention & control , Animals , Anti-Ulcer Agents/pharmacology , Antioxidants/metabolism , Antioxidants/pharmacology , Disease Models, Animal , Flavonoids/pharmacology , Gastric Juice , Gastric Mucosa/drug effects , Ligation , Mice , Mice, Inbred Strains , Nitric Oxide/metabolism , Plant Extracts/pharmacology , Rats , Rats, Wistar , Stomach Ulcer/etiology , Stomach Ulcer/metabolism , Sulfhydryl Compounds/metabolismABSTRACT
The possible benefits of some bioactive flavones and xanthones present in plants of the genus Syngonanthus prompted us to screen them for estrogenic activity. However, scientific research has shown that such substances may have undesirable properties, such as mutagenicity, carcinogenicity and toxicity, which restrict their use as therapeutic agents. Hence, the aim of this study was to assess the estrogenicity and mutagenic and antimutagenic properties. We used recombinant yeast assay (RYA), with the strain BY4741 of Saccharomyces cerevisiae, and Ames test, with strains TA100, TA98, TA97a and TA102 of Salmonella typhimirium, to evaluate estrogenicity, mutagenicity and antimutagenicity of methanolic extracts of Syngonanthus dealbatus (S.d.), Syngonanthus macrolepsis (S.m.), Syngonanthus nitens (S.n.) and Syngonanthus suberosus (S.s.), and of 9 compounds isolated from them (1=luteolin, 2=mix of A-1,3,6-trihydroxy-2-methoxyxanthone and B-1,3,6-trihydroxy-2,5-dimethoxyxanthone, 3=1,5,7-trihydroxy-3,6-dimethoxyxanthone, 4=1,3,6,8-tetrahydroxy-2,5-dimethoxyxanthone, 5=1,3,6,8-tetrahydroxy-5-methoxyxanthone, 6=7-methoxyluteolin-8-C-ß-glucopyranoside, 7=7-methoxyluteolin-6-C-ß-glucopyranoside, 8=7,3'-dimethoxyluteolin-6-C-ß-glucopyranoside and 9=6-hydroxyluteolin). The results indicated the estrogenic potential of the S. nitens methanol extract and four of its isolated xanthones, which exhibited, respectively, 14.74±1.63 nM; 19.54±6.61; 7.20±0.37; 6.71±1.02 e 10.01±4.26 nM of estradiol-equivalents (EEQ). None of the extracts or isolated compounds showed mutagenicity in any of the test strains and all of them showed antimutagenic potential, in particular preventing mutations caused by aflatoxin B1 (AFB1) and benzo[a]pyrene (B[a]P). The results show that the xanthones, only isolated from the methanol extract of S. nitens capitula, probably were the responsible for its estrogenic activity and could be useful as phytoestrogens, providing a new opportunity to develop hormonal agents. In addition, flavones and xanthones could also be used as a new antimutagenic agent. Since, the mutagens are involved in the initiation and promotion of several human diseases, including cancer, the significance of novel bioactive phytocompounds in counteracting these pro-mutagenic and carcinogenic effects is now gaining credence.
Subject(s)
Antimutagenic Agents/pharmacology , Eriocaulaceae/chemistry , Estrogens/pharmacology , Flavones/pharmacology , Xanthones/pharmacology , Antimutagenic Agents/isolation & purification , Antimutagenic Agents/toxicity , Chemoprevention , Estrogens/isolation & purification , Estrogens/toxicity , Flavones/isolation & purification , Flavones/toxicity , Humans , Methanol/chemistry , Mutagens/toxicity , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Extracts/toxicity , Saccharomyces cerevisiae/drug effects , Salmonella/drug effects , Xanthones/isolation & purification , Xanthones/toxicityABSTRACT
The purpose of this study was to evaluate the in vitro anticandidal activity of a methanolic extract of Syngonanthus nitens scapes against different Candida species and clinical isolates from patients with vulvovaginal candidiasis (VVC), and its effect in vivo in the treatment of vaginal infection. Chemical characterization of the extract was performed by HPLC-UV analyses and showed the presence of flavones derivatives. The extract was effective against several Candida strains from our collection and species recovered from VVC patients, and was able to inhibit the yeast-hyphal transition. No cytotoxic activity against human female reproductive tract epithelial cells and no hemolytic activity against human red blood cells were observed. In the in vivo model of VVC, we evaluated the efficacy of the intravaginal treatment with a cream containing the extract at doses of 0.5, 1.0 and 2.0%. The treatment eradicated the vaginal fungal burden in infected rats after 8 days of treatment. S. nitens extract could be considered as an effective and non-toxic natural antifungal agent in the treatment of vulvovaginal candidiasis.
Subject(s)
Antifungal Agents/therapeutic use , Candida/drug effects , Candidiasis, Vulvovaginal/drug therapy , Eriocaulaceae/chemistry , Plant Extracts/therapeutic use , Administration, Topical , Animals , Antifungal Agents/isolation & purification , Antifungal Agents/pharmacology , Antifungal Agents/toxicity , Candida/isolation & purification , Candidiasis, Vulvovaginal/microbiology , Cell Survival/drug effects , Chromatography, High Pressure Liquid , Colony Count, Microbial , Disease Models, Animal , Epithelial Cells/drug effects , Erythrocytes/drug effects , Female , Flavones/isolation & purification , Flavones/pharmacology , Flavones/therapeutic use , Flavones/toxicity , Humans , Microbial Sensitivity Tests , Ointments/therapeutic use , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Extracts/toxicity , Rats , Rats, Wistar , Spectrophotometry, Ultraviolet , Treatment OutcomeABSTRACT
A flavan, eriocaulin A (1), and three flavone acyl glucosides, eriocaulosides A-C (2-4) were isolated from the capitula of Eriocaulon australe R. Br. (Eriocaulaceae), a Chinese medicine and an herb for health care beverages, together with seven known flavones and three isoflavones (5-14). The new flavonoids were elucidated as (2S)-3',4'-methylenedioxy-5-methoxy-7-hydroxyflavan (1), hispidulin 7-O-ß-D-(6-O-cinnamoyl)glucopyranoside (2), jaceosidin 7-O-ß-D-(6-O-p-coumaroyl)glucopyranoside (3), jaceosidin 7-O-ß-D-(6-O-p-hydroxybenzoyl)glucopyranoside (4) based on their spectroscopic data. All the 14 flavonoids were obtained from this species for the first time. The in vitro cytotoxicity of compounds 1-14 against human lung adenocarcinoma A549, human breast adenocarcinoma MCF-7, and human cervical carcinoma HeLa cell lines was evaluated using the MTT colourimetric assay. Compounds 1, 7, and 9 were cytotoxic to A549, compounds 1, 2, 7, 9, 12, and 14 to MCF-7, and compounds 7, 9, and 14 to HeLa cells, with IC50 values ranging from 7.17 to 29.57 µg/ml, while the others were inactive (IC50>50 µg/ml).
Subject(s)
Eriocaulaceae/chemistry , Flavonoids/chemistry , Flowers/chemistry , Plant Extracts/chemistry , Cell Line , Cell Proliferation/drug effects , Flavonoids/isolation & purification , Flavonoids/toxicity , Humans , Molecular Structure , Plant Extracts/isolation & purification , Plant Extracts/toxicityABSTRACT
A HPLC-ESI-IT-MSn method, based on high-performance liquid chromatography coupled to electrospray negative ionization multistage ion trap mass spectrometry, was developed for rapid identification of 24 flavonoid and naphthopyranone compounds. The methanol extracts of the capitulae and scapes of P. chiquitensis exhibited mutagenic activity in the Salmonella/microsome assay, against strain TA97a.
Subject(s)
Eriocaulaceae/chemistry , Flavonoids/chemistry , Plant Extracts/chemistry , Chromatography, High Pressure Liquid , Mutagens/toxicity , Plant Extracts/pharmacology , Salmonella/drug effects , Salmonella/growth & development , Spectrometry, Mass, Electrospray Ionization , Tandem Mass SpectrometryABSTRACT
The biological activities of a plant extract depend on a complex sum of individual properties including the antioxidant activity. Several biological activities protect against the harmful action of reactive oxygen species (ROS), and here we focused our attention on the relationship between the biological activities tested and the antioxidant properties. In this study, the total flavonoid content as well as the antioxidant, antimicrobial, hemolytic and cytotoxicity activities of the methanolic extract of Leitothrix spiralis leaves were evaluated. The extract showed a total flavonoid content of 19.26% and the chemical characterization by HPLC-PAD confirmed the presence of flavonoids as the major secondary metabolite compounds. Significant antioxidant activity (IC(50) = 1.743 µg/mL ± 0.063) was demonstrated and was effective against Gram-negative organisms and all Candida strains tested, and showed an ability to inhibit hyphal formation. Non-hemolytic and antiproliferative activity could be demonstrated.
Subject(s)
Antioxidants/pharmacology , Candida albicans/growth & development , Eriocaulaceae/chemistry , Gram-Negative Bacteria/growth & development , Hemolysis/drug effects , Plant Extracts/pharmacology , Plant Leaves/chemistry , Antioxidants/chemistry , Erythrocytes/cytology , Erythrocytes/metabolism , HeLa Cells , Humans , Plant Extracts/chemistryABSTRACT
The methanol extract of the flowers of Paepalanthus geniculatus Kunth. showed radical-scavenging activity in the TEAC assay. An analytical approach based on HPLC-ESIMS(n) was applied to obtain the metabolite profile of this extract and led to the rapid identification of 19 polyphenolic compounds comprising flavonoids and naphthopyranones. The new naphthopyranone (10, 16), quercetagetin (1, 5, 7, 13), and galetine derivatives (9, 11, 17, 19), and a flavonol glucoside cyclodimer in the truxillate form (12), were identified. Compounds 2, 6, and 7 showed the highest antioxidant capacity and ability to affect the levels of intracellular ROS in human prostate cancer cells (PC3).
Subject(s)
Antioxidants/isolation & purification , Antioxidants/pharmacology , Eriocaulaceae/chemistry , Flavonoids/isolation & purification , Flavonoids/pharmacology , Free Radical Scavengers/isolation & purification , Free Radical Scavengers/pharmacology , Glucosides/isolation & purification , Glucosides/pharmacology , Phenols/isolation & purification , Phenols/pharmacology , Antioxidants/chemistry , Brazil , Chromatography, High Pressure Liquid , Electron Spin Resonance Spectroscopy , Flavonoids/chemistry , Flowers/chemistry , Free Radical Scavengers/chemistry , Glucosides/chemistry , Humans , Male , Molecular Structure , Phenols/chemistry , Prostatic Neoplasms/drug therapy , Reactive Oxygen Species/analysisABSTRACT
Eriocaulon buergerianum Koern. is the botanical source for the Chinese herbal medicine Gu-Jing-Cao. Other Eriocaulon species are also used as the same herb in local areas and are difficult to be differentiated. In order to improve the quality control of Gu-Jing-Cao, chemical constituents of E. buergerianum and adulterating species were analyzed by high-performance liquid chromatography with diode array detection and electrospray ionization tandem mass spectrometry (HPLC-DAD-ESI-MS(n)). The 70% methanol extracts were separated on a Zorbax SB-C(18) column and eluted with acetonitrile-water (each containing 0.1% formic acid). The compounds were identified by ion-trap mass spectrometry in both positive and negative ion modes. From E. buergerianum, E. faberi, E. sexangulare and E. cinereum, a total of 72 compounds were characterized, including 37 flavonols, 6 flavones, 4 isoflavones, 6 xanthones, 14 naphthopyranones, 3 phenolic acids, and 2 other flavonoids. Chemical variation of these four species were studied at three tiers, HPLC fingerprinting, quantitation of six major flavonoids, and semi-quantitative analysis of all characterized compounds, in combination with principal component analysis. E. buergerianum contained abundant flavonols and naphthopyranones, with minor flavones and xanthones; E. cinereum contained abundant isoflavones and flavones, together with few naphthopyranones; E. sexangulare was rich in flavones; and E. faberi contained abundant xanthones. Based on the above chemical analysis, E. buergerianum could be explicitly differentiated from the adulterating species, and the botanical species of 13 commercial batches of Gu-Jing-Cao were identified correctly. This is the first report on comprehensive chemical analysis of Eriocaulon species.
Subject(s)
Chromatography, High Pressure Liquid/methods , Eriocaulaceae/chemistry , Spectrometry, Mass, Electrospray Ionization/methods , Tandem Mass Spectrometry/methods , Principal Component AnalysisABSTRACT
Quantification of prepared samples by analysis using high performance liquid chromatography with DAD detection was developed to analyze rutin, 6-methoxyapigenin, and 6-methoxyapigenin-7-O-beta-D-glucopyranoside isolated from methanolic extracts of different genus: Syngonanthus, Leiothix and Eriocaulon (Eriocaulaceae). The linearity, accuracy, and the inter-day precision of the procedure were evaluated. The calibration curves were linear. The recoveries of the flavonoids in the samples analyzed were 96.3% to 98.5%. The percentage coefficient of variation for the quantitative analysis of the flavonoids in the analyses of the samples was under 5%. The antimicrobial activity of the five methanol extracts of these Eriocaulaceae species was assayed against the microorganisms Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Salmonella setubal, Saccharomyces cerevisiae and Candida albicans. Measured MIC values ranged from 1.25 to 10.00 mg/mL. The flavonoid contents suggest that Eriocaulaceae species may be a promising source of compounds to produce natural phytomedicines.
Subject(s)
Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Bacteria/drug effects , Eriocaulaceae/chemistry , Flavonoids , Fungi/drug effects , Plant Extracts , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemistry , Candida albicans/drug effects , Chromatography, High Pressure Liquid , Flavonoids/chemistry , Flavonoids/pharmacology , Microbial Sensitivity Tests , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/pharmacology , Pseudomonas aeruginosa/drug effects , Saccharomyces cerevisiae/drug effects , Staphylococcus aureus/drug effectsABSTRACT
Liquid chromatography-electrospray ionization multistage ion trap mass spectrometry (LC-ESI-IT-MS(n)) was used to analyze the secondary metabolites in the methanol extract of the capitulae of Eriocaulon ligulatum. The major components were mono- and diglycosides of flavonoids and naphthopyranones. Eleven compounds, including four new flavonol glycosides, were identified based on their fragmentation patterns in MS experiments and on NMR analysis of the isolated compounds. The described data may contribute to a better understanding of the taxonomic classification of the Eriocaulaceae family.