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1.
Molecules ; 27(14)2022 Jul 09.
Article in English | MEDLINE | ID: mdl-35889279

ABSTRACT

Guatteria olivacea R. E. Fries (synonym Guatteria punctata (Aubl.) R.A. Howard) is a tree of 10-27 m tall popularly known as "envira-bobó", "envira-fofa", "envireira", "embira", "embira-branca", "embira-preta", envira-branca", and "envira-preta", which can be found in the Brazilian Amazon biome. In this study, we evaluated the cytotoxic and antitumor effects of the essential oil (EO) obtained from the leaves of G. olivacea against liver cancer using HepG2 cells as a model. EO was obtained using a hydrodistillation Clevenger-type apparatus and was qualitatively and quantitatively characterized using GC-MS and GC-FID, respectively. The alamar blue assay was used to assess the cytotoxic potential of EO in a panel of human cancer cell lines and human non-cancerous cells. In HepG2 cells treated with EO, YO-PRO-1/propidium iodide staining, cell cycle distribution, and reactive oxygen species (ROS) were examined. In C.B-17 SCID mice with HepG2 cell xenografts, the efficacy of the EO (20 and 40 mg/kg) was tested in vivo. GC-MS and GC-FID analyses showed germacrene D (17.65%), 1-epi-cubenol (13.21%), caryophyllene oxide (12.03%), spathulenol (11.26%), (E)-caryophyllene (7.26%), bicyclogermacrene (5.87%), and δ-elemene (4.95%) as the major constituents of G. olivacea leaf EO. In vitro cytotoxicity of EO was observed, including anti-liver cancer action with an IC50 value of 30.82 µg/mL for HepG2 cells. In HepG2 cells, EO treatment increased apoptotic cells and DNA fragmentation, without changes in ROS levels. Furthermore, the EO inhibited tumor mass in vivo by 32.8-57.9%. These findings suggest that G. olivacea leaf EO has anti-liver cancer potential.


Subject(s)
Annonaceae , Guatteria , Neoplasms , Oils, Volatile , Animals , Humans , Mice , Mice, SCID , Oils, Volatile/pharmacology , Plant Leaves , Reactive Oxygen Species
2.
Foods ; 10(11)2021 Nov 03.
Article in English | MEDLINE | ID: mdl-34828960

ABSTRACT

Stryphnodendron rotundifolium Mart., popularly known as "barbatimão", is a plant species traditionally used by topical and oral routes for the treatment of infectious and inflammatory diseases. Considering the well-described antioxidant properties of this species, this study investigated the protective effects of its keto-aqueous extract using an in vitro model of iron overload. Phenolic compounds were quantified and identified by Ultra-Performance Liquid Chromatography coupled with quadrupole Time-Of-Flight Electrospray Ionization Mass Spectrometry (UPLC-ESI-qTOF-MS/MS) in positive and negative ions mode analysis. Antioxidant activity was analyzed following the iron-chelating-reducing capacity and deoxyribose degradation (2-DR) protection methods. The analysis identified condensed tannins (54.8 mg catechin/g dry fraction (DF), polyphenols (25 mg gallic acid/g DF), and hydrolyzable tannins (28.8 mg tannic acid/g DF). Among the constituents, prodelphinidin, procyanidin, and prorobinetinidine were isolated and identified. The extract significantly protected 2-DR degradation induced by Fe2+ (72% protection) or •OH (43% protection). The ortho-phenanthroline test revealed Fe2+-chelating and Fe3+-reducing activities of 93% and 84%, respectively. A preliminary toxicological analysis using Artemia salina revealed mortality below 10%, at a concentration of 0.25 mg/mL, indicating low toxicity under the present experimental conditions. In conclusion, the findings of the present study indicate that Stryphnodendron rotundifolium is a source of antioxidant compounds with the potential to be used in drug development in the context of iron overload disorders, which remains to be further investigated in vivo.

3.
Molecules ; 26(19)2021 Sep 23.
Article in English | MEDLINE | ID: mdl-34641314

ABSTRACT

The recent emergence of Zika virus (ZIKV) in Brazil and the increasing resistance developed by pathogenic bacteria to nearly all existing antibiotics should be taken as a wakeup call for the international authority as this represents a risk for global public health. The lack of antiviral drugs and effective antibiotics on the market triggers the need to search for safe therapeutics from medicinal plants to fight viral and microbial infections. In the present study, we investigated whether a mangrove plant, Bruguiera gymnorhiza (L.) Lam. (B. gymnorhiza) collected in Mauritius, possesses antimicrobial and antibiotic potentiating abilities and exerts anti-ZIKV activity at non-cytotoxic doses. Microorganisms Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Klebsiella pneumoniae ATCC 70603, methicillin-resistant Staphylococcus aureus ATCC 43300 (MRSA), Salmonella enteritidis ATCC 13076, Sarcina lutea ATCC 9341, Proteus mirabilis ATCC 25933, Bacillus cereus ATCC 11778 and Candida albicans ATCC 26555 were used to evaluate the antimicrobial properties. Ciprofloxacin, chloramphenicol and streptomycin antibiotics were used for assessing antibiotic potentiating activity. ZIKVMC-MR766NIID (ZIKVGFP) was used for assessing anti-ZIKV activity. In silico docking (Autodock 4) and ADME (SwissADME) analyses were performed on collected data. Antimicrobial results revealed that Bruguiera twig ethyl acetate (BTE) was the most potent extract inhibiting the growth of all nine microbes tested, with minimum inhibitory concentrations ranging from 0.19-0.39 mg/mL. BTE showed partial synergy effects against MRSA and Pseudomonas aeruginosa when applied in combination with streptomycin and ciprofloxacin, respectively. By using a recombinant ZIKV-expressing reporter GFP protein, we identified both Bruguiera root aqueous and Bruguiera fruit aqueous extracts as potent inhibitors of ZIKV infection in human epithelial A549 cells. The mechanisms by which such extracts prevented ZIKV infection are linked to the inability of the virus to bind to the host cell surface. In silico docking showed that ZIKV E protein, which is involved in cell receptor binding, could be a target for cryptochlorogenic acid, a chemical compound identified in B. gymnorhiza. From ADME results, cryptochlorogenic acid is predicted to be not orally bioavailable because it is too polar. Scientific data collected in this present work can open a new avenue for the development of potential inhibitors from B. gymnorhiza to fight ZIKV and microbial infections in the future.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Antiviral Agents/pharmacology , Plant Extracts/pharmacology , Rhizophoraceae/chemistry , Zika Virus/growth & development , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemistry , Antiviral Agents/chemistry , Brazil , Candida albicans/drug effects , Candida albicans/growth & development , Computer Simulation , Drug Synergism , Escherichia coli/drug effects , Escherichia coli/growth & development , Klebsiella pneumoniae/drug effects , Klebsiella pneumoniae/growth & development , Mauritius , Microbial Sensitivity Tests , Microbial Viability/drug effects , Plant Extracts/chemistry , Proteus mirabilis/drug effects , Proteus mirabilis/growth & development , Pseudomonas aeruginosa/drug effects , Pseudomonas aeruginosa/growth & development , Staphylococcus aureus/drug effects , Staphylococcus aureus/growth & development , Zika Virus/drug effects
4.
Molecules ; 26(12)2021 Jun 18.
Article in English | MEDLINE | ID: mdl-34207059

ABSTRACT

Diclinanona calycina R. E. Fries popularly known as "envira", is a species of the Annonaceae family endemic to Brazil. In our ongoing search for bioactive compounds from Annonaceae Amazon plants, the bark of D. calycina was investigated by classical chromatography techniques that yielded thirteen compounds (alkaloids and flavonoids) described for the first time in D. calycina as well as in the genus Diclinanona. The structure of these isolated compounds were established by extensive analysis using 1D/2D-NMR spectroscopy in combination with MS. The isolated alkaloids were identified as belonging to the subclasses: simple isoquinoline, thalifoline (1); aporphine, anonaine (2); oxoaporphine, liriodenine (3); benzyltetrahydroisoquinolines, (S)-(+)-reticuline (4); dehydro-oxonorreticuline (3,4-dihydro-7-hydroxy-6-methoxy-1-isoquinolinyl)(3-hydroxy-4-methoxyphenyl)-methanone) (5); (+)-1S,2R-reticuline Nß-oxide (6); and (+)-1S,2S-reticuline Nα-oxide (7); tetrahydroprotoberberine, coreximine (8); and pavine, bisnorargemonine (9). While the flavonoids belong to the benzylated dihydroflavones, isochamanetin (10), dichamanetin (11), and a mixture of uvarinol (12) and isouvarinol (13). Compound 5 is described for the first time in the literature as a natural product. The cytotoxic activity of the main isolated compounds was evaluated against cancer and non-cancerous cell lines. Among the tested compounds, the most promising results were found for the benzylated dihydroflavones dichamanetin (10), and the mixture of uvarinol (12) and isouvarinol (13), which presented moderate cytotoxic activity against the tested cancer cell lines (<20.0 µg·mL-1) and low cytotoxicity against the non-cancerous cell line MRC-5 (>25.0 µg·mL-1). Dichamanetin (11) showed cytotoxic activity against HL-60 and HCT116 with IC50 values of 15.78 µg·mL-1 (33.70 µmol·L-1) and 18.99 µg·mL-1 (40.56 µmol·L-1), respectively while the mixture of uvarinol (12) and isouvarinol (13) demonstrated cytotoxic activity against HL-60, with an IC50 value of 9.74 µg·mL-1, and HCT116, with an IC50 value of 17.31 µg·mL-1. These cytotoxic activities can be attributed to the presence of one or more hydroxybenzyl groups present in these molecules as well as the position in which these groups are linked. The cytotoxic activities of reticuline, anonaine and liriodenine have been previously established, with liriodenine being the most potent compound.


Subject(s)
Alkaloids/chemistry , Annonaceae/chemistry , Flavones/chemistry , Isoquinolines/chemistry , Plant Bark/chemistry , Alkaloids/pharmacology , Aporphines/chemistry , Aporphines/pharmacology , Brazil , Cell Line, Tumor , Dioxoles/chemistry , Dioxoles/pharmacology , Flavanones/pharmacology , Flavones/pharmacology , HCT116 Cells , HL-60 Cells , Hep G2 Cells , Humans , Isoquinolines/pharmacology , MCF-7 Cells , Plant Extracts , Plant Leaves/chemistry
5.
J Ethnopharmacol ; 265: 113338, 2021 Jan 30.
Article in English | MEDLINE | ID: mdl-32920137

ABSTRACT

Medicinal plants remain an invaluable source for therapeutics of diseases that affect humanity. Sideritis bilgeriana (Lamiaceae) is medicinal plant used in Turkey folk medicine to reduce inflammation and pain, but few studies scientific corroborates its medicinal use so creating a gap between popular use and scientific evidence. Thus, we aimed to evaluate the pharmacological effects of the methanolic extract of S. bilgeriana (MESB) in rodents nociception models and also performed its phytochemical analysis. Firstly, a screening was carried out that enabled the identification of the presence of phenolic compounds and flavonoids. In view of this, a chromatographic method by HPLC-DAD-UV was developed that made it possible to identify chlorogenic acid and its quantification in MESB. MESB-treated mice (MESB 50, 100 and 200 mg/kg, p.o.) reduced mechanical hyperalgesia and myeloperoxidase activity (p < 0.01), and also showed a reduced pain behavior in capsaicin test. In the carrageenan-induced pleurisy test, MESB (100 mg/kg p.o.) significantly reduced the leukocyte (polymorphonuclear) count in the pleural cavity and equally decreased the TNF-α and IL-1ß levels (p < 0.001). In the PSNL model, mechanical hyperalgesia was reduced on the first evaluation day and during the 7 days of evaluation compared to the vehicle group (p < 0.001). Thermal hyperalgesia was also reduced 1 h after treatment compared to the vehicle group (p < 0.001) and reversed the loss of force initially displayed by the animals, thus inferring an analgesic effect in the muscle strength test. Analysis of the marrow of these animals showed a decrease in the level of pro-inflammatory cytokine IL-6 (p < 0.001) and factor NF-κB, in relation to the control group (p < 0.05). Moreover, the MESB treatment produced no noticeable side effects, no disturb in motor performance and no signs of gastric or hepatic injury. Together, the results suggests that MESB could be useful to management of inflammation and neuropathic pain mainly by the management of pro-inflammatory mediators (NF-κB, TNF-α, IL-1ß and IL-6), so reinforcing its use in popular medicine and corroborating the need for further chemical and pharmacological studies for the species.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Plant Extracts/pharmacology , Sideritis/chemistry , Analgesics/isolation & purification , Analgesics/pharmacology , Animals , Anti-Inflammatory Agents/isolation & purification , Chromatography, High Pressure Liquid , Dose-Response Relationship, Drug , Humans , Inflammation/drug therapy , Inflammation/pathology , Inflammation Mediators/metabolism , Mice , Neuralgia/drug therapy , Plant Extracts/analysis
6.
Chem Biodivers ; 16(12): e1900313, 2019 Dec.
Article in English | MEDLINE | ID: mdl-31545879

ABSTRACT

Cissampelos sympodialis Eichler is well studied and investigated for its antiasthmatic properties, but there are no data in the literature describing antibacterial properties of alkaloids isolated from this botanical species. This work reports the isolation and characterization of phanostenine obtained from roots of C. sympodialis and describes for the first time its antimicrobial and antibiotic modulatory properties. Phanostenine was first isolated from Cissampelos sympodialis and its antibacterial activities were determined. Chemical structures of the alkaloid isolate were determined using spectroscopic and chemical analyses. Phanostenine was also tested for its antibacterial activity against standard strains and clinical isolates of Escherichia coli and Staphylococcus aureus. Minimal inhibitory concentration (MIC) was determined in a microdilution assay and for the evaluation of antibiotic resistance-modifying activity. MIC of the antibiotics was determined in the presence or absence of phanostenine at sub-inhibitory concentrations. The evaluation of antibacterial activity by microdilution assay showed activity for all strains with better values against S. aureus ATCC 12692 and E. coli 27 (787.69 mm). The evaluation of aminoglycoside antibiotic resistance-modifying activity showed reduction in the MIC of the aminoglycosides (amikacin, gentamicin and neomycin) when associated with phanostenine, MIC reduction of antibiotics ranging from 21 % to 80 %. The data demonstrated that phanostenine possesses a relevant ability to modify the antibiotic activity in vitro. We can suggest that phanostenine presents itself as a promising tool as an adjuvant for novel antibiotics formulations against bacterial resistance.


Subject(s)
Alkaloids/chemistry , Anti-Bacterial Agents/chemistry , Benzene Derivatives/chemistry , Cissampelos/chemistry , Heterocyclic Compounds, 4 or More Rings/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Benzene Derivatives/isolation & purification , Benzene Derivatives/pharmacology , Cissampelos/metabolism , Drug Resistance, Bacterial/drug effects , Fused-Ring Compounds , Heterocyclic Compounds, 4 or More Rings/isolation & purification , Heterocyclic Compounds, 4 or More Rings/pharmacology , Microbial Sensitivity Tests , Plant Extracts/chemistry , Plant Roots/chemistry , Plant Roots/metabolism , Staphylococcus aureus/drug effects
7.
Rev. bras. farmacogn ; 29(1): 125-135, Jan.-Feb. 2019. tab
Article in English | LILACS | ID: biblio-990761

ABSTRACT

Abstract Many people use medicinal plants to relieve disorders related to the central nervous system, such as depression, epilepsy, anxiety and pain, even though the effectiveness of most of them has not yet been proven through scientific studies. Plants of the Lippia genus, Verbenaceae, are widely used in ethnobotany as a food, for seasoning and in antiseptic remedies. They are also marketed and used for the treatment of different types of pain, including stomach ache, abdominal pain and headache, as well as being used as sedatives, anxiolytics and anticonvulsants. Despite their widespread use, there are no reviews on the central nervous system profile of plants of this genus. Therefore, the databases Medline-PubMed, Embase, Scopus and Web of Science were searched using the terms Lippia and biologic activity. Thirty-five papers were found. Eleven species of Lippia showed central nervous system activity, with leaves and the aerial parts of plants being the most commonly used, especially in aqueous and ethanol extracts or volatile oil. The species are composed mainly of terpenoids and phenylpropanoids, including polyketides, flavonoids and in less quantity some alkaloids. Although several species of Lippia present analgesic activity, most studies have not explored the mechanisms responsible for this effect, however, there is some evidence that volatile oils and constituents of the extracts may be responsible for the relief of some CNS disorders, but the effects on pain modulation seem to be the most exploited so far.

8.
Chem Biol Interact ; 286: 1-10, 2018 Apr 25.
Article in English | MEDLINE | ID: mdl-29499192

ABSTRACT

BACKGROUND: Indole-3-guanylhydrazone hydrochloride (LQM01) is a new derivative of aminoguanidine hydrochloride, an aromatic aminoguanidine. METHODS: Mice were treated with LQM01 (5, 10, 25 or 50 mg/kg, i.p.), vehicle (0.9% saline i.p.) or a standard drug. The mice were subjected to carrageenan-induced pleurisy, abdominal writhing induced by acetic acid, the formalin test and the hot-plate test. The model of non-inflammatory chronic muscle pain induced by saline acid was also used. Mice from the chronic protocol were assessed for withdrawal threshold, muscle strength and motor coordination. LQM01 or vehicle treated mice were evaluated for Fos protein. RESULTS: LQM01 inhibits TNF-α and IL-1ß production, as well as leukocyte recruitment during inflammation process. The level of IL-10 in LQM01-treated mice increased in pleural fluid. In addition, LQM01 decreased the nociceptive behavior in the acetic acid induced writhing test, the formalin test (both phases) and increased latency time on the hot-plate. LQM01 treatment also decreased mechanical hyperalgesia in mice with chronic muscle pain, with no changes in muscle strength and motor coordination. LQM01 reduced the number of Fos positive cells in the superficial dorsal horn. This compound exhibited antioxidant properties in in vitro assays. CONCLUSIONS: LQM01 has an outstanding anti-inflammatory and analgesic profile, probably mediated through a reduction in proinflammatory cytokines release, increase in IL-10 production and reduction in neuron activity in the dorsal horn of the spinal cord in mice. GENERAL SIGNIFICANCE: Beneficial effects of LQM01 suggest that it has some important clinical features and can play a role in the management of 'dysfunctional pain' and inflammatory diseases.


Subject(s)
Analgesics/chemistry , Anti-Inflammatory Agents/chemistry , Guanidines/chemistry , Interleukin-10/analysis , Interleukin-1beta/analysis , Tumor Necrosis Factor-alpha/analysis , Analgesics/pharmacology , Analgesics/therapeutic use , Animals , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/therapeutic use , Antioxidants/metabolism , Behavior, Animal/drug effects , Carrageenan/toxicity , Guanidine/analogs & derivatives , Indoles , Leukocytes/cytology , Leukocytes/drug effects , Leukocytes/metabolism , Male , Mice , Microscopy, Fluorescence , Motor Activity/drug effects , Muscle Strength/drug effects , Pain/chemically induced , Pain/drug therapy , Pleurisy/chemically induced , Pleurisy/drug therapy , Proto-Oncogene Proteins c-fos/metabolism , Spinal Cord/metabolism , Spinal Cord/pathology
9.
Biomed Pharmacother ; 91: 739-747, 2017 Jul.
Article in English | MEDLINE | ID: mdl-28499245

ABSTRACT

BACKGROUND: Due to its unclear pathophysiology, the pharmacological treatment of fibromyalgia is a challenge for researchers. Studies using medicinal plants, such as those from the genus Lippia, complexed with cyclodextrins (CDs) have shown innovative results. OBJECTIVE: The present research intended to evaluate the effect of an inclusion complex containing ß-cyclodextrin (ßCD) inclusion complex with Lippia grata (LG) essential oil in a chronic musculoskeletal pain model, its central activity and its possible interaction with neurotransmitters involved in pain. METHODS: After acid saline-induced chronic muscle pain, male mice were evaluated for primary and secondary hyperalgesia and muscle strength. Moreover, an antagonist assay was performed to assess the possible involvement of the opioidergic, serotonergic and noradrenergic pathways. In addition, Fos protein in the spinal cord was assessed, and a docking study and antioxidant assays were performed. RESULTS: The treatment with LG-ßCD, especially in the dose of 24mg/kg, was able to significantly decrease (p<0.05) the paw withdrawal and muscle threshold. Furthermore, LG-ßCD was shown to affect the opioidergic and serotonergic pathways. There were no significant changes in muscle strength. Fos protein immunofluorescence showed a significant decrease in expression in the dorsal horn of the spinal cord. The main compounds of LG showed through the docking study interaction energies with the alpha-adrenergic and µOpioid receptors. In all antioxidant assays, LG exhibited stronger antioxidant activities than LG-ßCD. CONCLUSION: This study suggested that LG-ßCD could be considered as a valuable source for designing new drugs in the treatment of chronic pain, especially musculoskeletal pain.


Subject(s)
Antioxidants/analysis , Chronic Pain/drug therapy , Hyperalgesia/drug therapy , Lippia/chemistry , Molecular Docking Simulation , Musculoskeletal Pain/drug therapy , Oils, Volatile/therapeutic use , beta-Cyclodextrins/chemistry , Analgesics/therapeutic use , Animals , Chronic Pain/complications , Disease Models, Animal , Hyperalgesia/complications , Male , Methysergide/therapeutic use , Mice , Musculoskeletal Pain/complications , Naloxone/therapeutic use , Plant Leaves/chemistry , Proto-Oncogene Proteins c-fos/metabolism , Spinal Cord Dorsal Horn/drug effects , Spinal Cord Dorsal Horn/metabolism , Spinal Cord Dorsal Horn/pathology , Yohimbine/therapeutic use
10.
Z Naturforsch C J Biosci ; 72(3-4): 93-97, 2017 Mar 01.
Article in English | MEDLINE | ID: mdl-28107177

ABSTRACT

Aristolochia trilobata L. is an aromatic plant, popularly known as "mil-homens", and its essential oil (EO) is generally used to treat colic, diarrhea and dysentery disorders. We evaluated the antinociceptive effect of A. trilobata stem EO and of its major compound, the (R)-(-)-6-methyl-5-hepten-2-yl acetate (sulcatyl acetate: SA), using acetic acid (0.85%)-induced writhing response and formalin-induced (20 µL of 1%) nociceptive behavior in mice. We also evaluated the EO and SA effect on motor coordination, using the rota-rod apparatus. EO (25, 50 and 100 mg/kg) or SA (25 and 50 mg/kg) reduced nociceptive behavior in the writhing test (p<0.001). EO (100 mg/kg) and SA (25 and 50 mg/kg) decreased the nociception on the first phase of the formalin test (p<0.05). On the second phase, EO (25: p<0.01; 50: p<0.05 and 100 mg/kg: p<0.001) and SA (25 and 50 mg/kg; p<0.001) reduced the nociceptive response induced by formalin. EO and SA were not able to cause changes in the motor coordination of animals. Together, our results suggest that EO has an analgesic profile and SA seems to be one of the active compounds in this effect.


Subject(s)
Analgesics/pharmacology , Aristolochia/chemistry , Heptanol/pharmacology , Oils, Volatile/isolation & purification , Plant Stems/chemistry , Acetates/antagonists & inhibitors , Acetates/pharmacology , Analgesics/isolation & purification , Animals , Heptanol/analogs & derivatives , Heptanol/isolation & purification , Male , Mice , Oils, Volatile/chemistry , Pain Measurement , Plant Extracts/chemistry , Psychomotor Performance/drug effects , Rotarod Performance Test
11.
J Ethnopharmacol ; 191: 9-18, 2016 Sep 15.
Article in English | MEDLINE | ID: mdl-27292196

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: Stachys lavandulifolia Vahl (Lamiaceae) is a medicinal plant widely used in Turkey and Iranian folk medicine due to its analgesic and anti-inflammatory properties, but little is known about its essential oil. AIM OF THIS STUDY: We studied the antinociceptive and anti-inflammatory effects of S. lavandulifolia essential oil (EOSl) and (-)-α-bisabolol (BIS), its main compound, in algogen-induced orofacial nociceptive behavior in mice, and assessed the possible involvement of pro-inflammatory cytokines in these profiles. MATERIALS AND METHODS: The GC-FID and GC-MS analysis of EOSl demonstrated the presence of (-)-α-bisabolol (56.4%), bicyclogermacrene (5.3%), δ-cadinene (4.2%) and spathulenol (2.9%) as the main compounds. Male Swiss mice were pretreated with EOSl (25 or 50mg/kg, p.o.), BIS (25 or 50mg/kg, p.o.), morphine (3mg/kg, i.p.) or vehicle (saline 0.9% with two drops of tween 80, 0.2%), before formalin- (20µl, 2%), capsaicin- (20µl, 2.5µg) or glutamate- (20µl, 25Mm) injection into the right upper lip (perinasal area) in mice. The anti-inflammatory profile of EOSl or BIS (50mg/kg) was assessed by the inflammatory response induced by carrageenan (2% in 0.2mL) in mice (pleurisy model). RESULTS: Our results showed that p.o. treatment with EOSl and BIS displayed significant inhibitory (p<0.05 or p<0.01 or p<0.001) effects in different orofacial pain tests on mice, but BIS proved to be more effective, significantly reducing nociceptive behavior in all tests including both phases of the formalin test. The analgesic effect is not related to any abnormality since EOSl- or BIS-treated mice exhibited no performance alteration in grip strength. Moreover, EOS1 and BIS exhibited a significant anti-inflammatory effect (p<0.001) in the pleurisy model of inflammation, which seems to be related to a significant reduction (p<0.05) of the pro-inflammatory cytokine TNF-α in BIS treatment, and of the pro-inflammatory cytokine IL-1ß (p<0.01) in EOS1 treatment. CONCLUSION: Our results corroborate the use of S. lavandulifolia in traditional medicine as an analgesic and anti-inflammatory, which seems to be related to (-)-α-Bisabolol, the main compound of EOSl.


Subject(s)
Analgesics/pharmacology , Anti-Infective Agents/pharmacology , Facial Pain/prevention & control , Interleukin-1beta/metabolism , Nociceptive Pain/prevention & control , Oils, Volatile/pharmacology , Plant Extracts/pharmacology , Plant Oils/pharmacology , Pleurisy/prevention & control , Sesquiterpenes/pharmacology , Stachys/chemistry , Tumor Necrosis Factor-alpha/metabolism , Analgesics/isolation & purification , Animals , Anti-Infective Agents/isolation & purification , Capsaicin , Carrageenan , Disease Models, Animal , Dose-Response Relationship, Drug , Facial Pain/chemically induced , Facial Pain/physiopathology , Flame Ionization , Formaldehyde , Gas Chromatography-Mass Spectrometry , Glutamic Acid , Male , Mice , Monocyclic Sesquiterpenes , Nociception/drug effects , Nociceptive Pain/chemically induced , Nociceptive Pain/physiopathology , Oils, Volatile/isolation & purification , Phytotherapy , Plant Extracts/isolation & purification , Plant Oils/isolation & purification , Plants, Medicinal , Pleurisy/chemically induced , Pleurisy/metabolism , Sesquiterpenes/isolation & purification , Time Factors
12.
Rev Biol Trop ; 62(1): 337-46, 2014 Mar.
Article in English | MEDLINE | ID: mdl-24912363

ABSTRACT

Adenocarpus complicatus is distributed throughout the Anatolian peninsula and is widely used for human and animal nutrition. The purpose of this work was to study the antioxidant properties and fatty acid composition of different parts of this plant (fruits and mixed materials). The species was collected from Golyuzu village of the Seydisehir district near Konya province, Turkey. Fruit and mixed parts obtained from this species were ground and a 15g sample was used to prepare methanolic extracts. Powdered plant samples were extracted with 100mL methanol in a mechanical shaker. The obtained extracts were filtered and concentrated to dryness under reduced pressure and were subsequently stored at -20 degrees C. Antioxidant components, namely total phenolic and flavonoid content, were detected for each extract using spectrophotometric methods. Antioxidant capacity was evaluated by various assays including phosphomolybdenum, DPPH free radical scavenging capacity, metal chelating activity, and ferric and cupric ion reducing power. The fatty acid profiles of plant parts were also determined by using gas chromatography. The total phenolic content of fruit (36.21mgGAE/g) was higher than that of mixed materials (13.79mgGAE/g). The methanolic extract of mixed material had higher amounts of flavonoid than fruit extract. The free radical scavenging activity of extracts was expressed as IC50 value (microg/mL) (amount required to inhibit DPPH radical formation by 50%). The lower IC50 value reflects better free radical scavenging action. The radical scavenging activity of the samples was compared with BHT, it showed the mixed material to be almost two times more potent than the fruit extract. However, BHT is an excellent free radical scavenger with an IC50 of 34.061 microg/mL. The ferric and cupric reducing power potentials of the extracts were expressed as EC50 value (the effective concentration at which the absorbance was 0.5). Fruit extract exhibited strong ferric reducing power with an EC50 of 871.25 microg/mL. The metal chelating activity of the extracts increased with concentration. Chelating effect was 83.60% for fruit extract at 1mg/mL concentration. Oil content of fruit and mixed parts were detected as 6.71 and 6.14%, respectively. A total of 32 fatty acids were found in the oil. Essential fatty acids (linoleic and a-linolenic acid) were identified as the most abundant fatty acids in the oil. These results demonstrated that this plant species can be considered as an alternative to synthetic antioxidants. Likewise, the oil obtained from the plant can be used as a source of essential fatty acids for food and pharmacological applications.


Subject(s)
Antioxidants/analysis , Fabaceae/chemistry , Fatty Acids/analysis , Flavonoids/analysis , Phenols/analysis , Fabaceae/classification , Gas Chromatography-Mass Spectrometry , Turkey
13.
Rev. biol. trop ; Rev. biol. trop;62(1): 349-358, ene.-mar. 2014. graf, tab
Article in English | LILACS | ID: lil-715435

ABSTRACT

Adenocarpus complicatus is distributed throughout the Anatolian peninsula and is widely used for human and animal nutrition. The purpose of this work was to study the antioxidant properties and fatty acid composition of different parts of this plant (fruits and mixed materials). The species was collected from Golyuzu village of the Seydisehir district near Konya province, Turkey. Fruit and mixed parts obtained from this species were ground and a 15g sample was used to prepare methanolic extracts. Powdered plant samples were extracted with 100mL methanol in a mechanical shaker. The obtained extracts were filtered and concentrated to dryness under reduced pressure and were subsequently stored at -20°C. Antioxidant components, namely total phenolic and flavonoid content, were detected for each extract using spectrophotometric methods. Antioxidant capacity was evaluated by various assays including phosphomolybdenum, DPPH free radical scavenging capacity, metal chelating activity, and ferric and cupric ion reducing power. The fatty acid profiles of plant parts were also determined by using gas chromatography. The total phenolic content of fruit (36.21mgGAE/g) was higher than that of mixed materials (13.79mgGAE/g). The methanolic extract of mixed material had higher amounts of flavonoid than fruit extract. The free radical scavenging activity of extracts was expressed as IC50 value (μg/mL) (amount required to inhibit DPPH radical formation by 50%). The lower IC50 value reflects better free radical scavenging action. The radical scavenging activity of the samples was compared with BHT, it showed the mixed material to be almost two times more potent than the fruit extract. However, BHT is an excellent free radical scavenger with an IC50 of 34.061μg/mL. The ferric and cupric reducing power potentials of the extracts were expressed as EC50 value (the effective concentration at which the absorbance was 0.5). Fruit extract exhibited strong ferric reducing power with an EC50 of 871.25μg/mL. The metal chelating activity of the extracts increased with concentration. Chelating effect was 83.60% for fruit extract at 1mg/mL concentration. Oil content of fruit and mixed parts were detected as 6.71 and 6.14%, respectively. A total of 32 fatty acids were found in the oil. Essential fatty acids (linoleic and α-linolenic acid) were identified as the most abundant fatty acids in the oil. These results demonstrated that this plant species can be considered as an alternative to synthetic antioxidants. Likewise, the oil obtained from the plant can be used as a source of essential fatty acids for food and pharmacological applications. Rev. Biol. Trop. 62 (1): 337-346. Epub 2014 March 01.


Adenocarpus complicatus se distribuye por toda la península de Anatolia y es ampliamente utilizado para la nutrición humana y animal. El propósito de este trabajo fue estudiar las propiedades antioxidantes y la composición de ácidos grasos de diferentes partes de la planta (frutos y partes mezcladas). Las especies fueron recolectadas en Golyuzu, Seydisehir, cerca de la provincia Konya en Turquía. Para preparar los extractos metanólicos se tomó una muestra de 15g de frutas y partes mezcladas de esta especie. Muestras de plantas en polvo se extrajeron con 100ml de metanol en un agitador mecánico. Los extractos obtenidos se filtraron y se concentraron a sequedad bajo presión reducida y posteriormente se almacenaron a -20°C. Para cada extracto, mediante métodos espectrofotométricos se detectaron los componentes antioxidantes, llamados contenido total de fenoles y flavonoides. La capacidad antioxidante se evaluó mediante diversos ensayos: fosfomolibdeno, capacidad de captación de radicales libres DPPH, actividad quelante de metales y poder reductor de iones férricos y cúpricos. También se determinaron los perfiles de ácidos grasos de partes de la planta mediante el uso de cromatografía de gases. El contenido fenólico total de la fruta (36.21mgGAE/g) fue mayor que la de los materiales mezclados (13.79mgGAE/g). El extracto metanólico de material mezclado tenía una mayor cantidad de flavonoides que el extracto de la fruta. La actividad captadora de radicales libres de los extractos se expresó como valor de IC50 (mg/ml) (cantidad necesaria para inhibir la formación de radicales DPPH en un 50%). El valor bajo de IC50 refleja mejor acción eliminadora de radicales libres. La actividad captadora de radicales de las muestras se comparó con BHT, se mostró que el material mezclado es casi dos veces más potente que el extracto de la fruta. Sin embargo, BHT es un excelente eliminador de radicales libres con una IC50 de 34.061μg/mL. El potencial de reducción férrico y cúprico de los extractos se expresó como valor de CE50 (la concentración efectiva a la que la absorbancia fue de 0.5). El extracto de la fruta exhibe fuerte poder reductor férrico con una EC50 de 871.25μg/mL. La actividad quelante de metales de los extractos aumentó con la concentración. El efecto quelante de extracto de fruta fue de 83.60% en una concentración de 1mg/ml. El contenido de aceite del fruto y partes mixtas fue 6.71 y 6.14%, respectivamente. Un total de 32 ácidos grasos fueron encontrados en el aceite. Los ácidos grasos esenciales (ácido linoleico y α-linolénico) fueron identificados como los ácidos grasos más abundantes en el aceite. Estos resultados demostraron que esta especie vegetal se puede considerar como una alternativa a los antioxidantes sintéticos. Del mismo modo, el aceite obtenido de la planta se puede utilizar como una fuente de ácidos grasos esenciales para alimentos y aplicaciones farmacológicas.


Subject(s)
Antioxidants/analysis , Fabaceae/chemistry , Fatty Acids/analysis , Flavonoids/analysis , Phenols/analysis , Fabaceae/classification , Gas Chromatography-Mass Spectrometry , Turkey
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