RESUMO
In recent years, there has been a need for environmentally friendly compounds for weed management in agriculture. This study is aimed to assess the phytotoxic constituents of oils obtained from oleoresins of seven Copaifera species (known as copaiba oils). Copaiba oils were separated from the resins by hydro-distillation, and the distillates were analyzed using gas chromatography-mass spectrometry (GC-MS) to characterize their chemical compositions. Multivariate analyses and molecular networking of GC-MS data were conducted to discern patterns in the chemical composition and phytotoxic activity of the oils, with the aim of identifying key compounds associated with phytotoxic activity. Seed germination bioassay revealed strong or complete germination inhibition against the monocot, Agrostis stolonifera but not the dicot Lactuca sativa. GC-MS analysis showed variations in composition among Copaifera species with some common compounds identified across multiple species. Caryophyllene oxide and junenol were associated with the observed phytotoxic effects. Automated flash chromatography was used to isolate the major compounds of the oils. Isolated compounds exhibited differing levels of phytotoxicity compared to the oils, suggesting the importance of interactions or synergism among oil components. These findings highlight the potential of copaiba oils as natural herbicidal agents and underscore the importance of considering species-specific responses in weed management strategies.
Assuntos
Fabaceae , Cromatografia Gasosa-Espectrometria de Massas , Germinação , Óleos Voláteis , Sementes , Fabaceae/química , Óleos Voláteis/química , Óleos Voláteis/toxicidade , Óleos Voláteis/farmacologia , Sementes/química , Sementes/efeitos dos fármacos , Sementes/crescimento & desenvolvimento , Germinação/efeitos dos fármacos , Óleos de Plantas/química , Óleos de Plantas/toxicidade , Óleos de Plantas/farmacologia , Lactuca/efeitos dos fármacos , Lactuca/crescimento & desenvolvimento , Herbicidas/farmacologia , Herbicidas/química , Herbicidas/toxicidadeRESUMO
The identification of natural and environmentally friendly pesticides is a key area of interest for the agrochemical industry, with many potentially active compounds being sourced from numerous plant species. In this study, we report the bioassay-guided isolation and identification of phytotoxic and antifungal compounds from the ethyl acetate extract of Helietta parvifolia stems. We identified eight compounds, consisting of two coumarins and six alkaloids. Among these, a new alkaloid, 2-hydroxy-3,6,7-trimethoxyquinoline-4-carbaldehyde (6), was elucidated, along with seven known compounds. The phytotoxicity of purified compounds was evaluated, and chalepin (4) was active against Agrostis stolonifera at 1 mM with 50% inhibition of seed germination and it reduced Lemna pausicotata (duckweed) growth by 50% (IC50) at 168 µM. Additionally, we evaluated the antifungal activity against the fungal plant pathogen Colletotrichum fragariae using a thin-layer chromatography bioautography assay, which revealed that three isolated furoquinoline alkaloids (flindersiamine (3), kokusagenine (7), and maculine (8)) among the isolated compounds had the strongest inhibitory effects on the growth of C. fragariae at all tested concentrations. Our results indicate that these active natural compounds, i.e., (3), (4), (7), and (8), could be scaffolds for the production of more active pesticides with better physicochemical properties.
Assuntos
Alcaloides , Praguicidas , Antifúngicos/farmacologia , Extratos Vegetais/química , Alcaloides/farmacologia , PlantasRESUMO
Brazil is one of the largest propolis producers in the world. Propolis is produced by bees from plant exudates and tissues, leading to many variations in the types of propolis. Generally, Brazilian propolis types are green, brown, and red. Despite not being the main research focus as the green and red propolis, brown propolis is the second most produced propolis type in Brazil and has tremendous economic and medicinal importance. Propolis has drawn attention with the rise in the search for healthier lifestyles, functional foods, biocosmetics, and natural products as therapeutic sources. This review covers the main chemical constituents identified in different types of Brazilian brown propolis, and their botanical sources, chemistry, and biological activities. The economic aspect of brown propolis is also presented. There are many gaps to be filled for brown propolis regarding the development of analytical methods, and quality control to allow its standardization, limiting its applicability in the food and pharmaceutical industries. Future perspectives regarding brown propolis research were discussed, especially biological activities, to support the medicinal uses of different types of brown propolis. Supplementary Information: The online version contains supplementary material available at 10.1007/s43450-023-00374-x.
RESUMO
Propolis is a natural product of great economic and pharmacological importance. The flora surrounding the bee communities is a determining factor in the composition of propolis and therefore in its biological and medicinal properties. Brown propolis is one of the most important types of propolis in Brazil, produced in the southeastern region. The ethanolic extract of a brown propolis sample from Minas Gerais state was chemically characterized for the subsequent development of a RP-HPLC method, validated according to the standards of regulatory agencies. The leishmanicidal activity of this extract was assessed. The brown propolis was characterized by the presence of chemical markers reported on green propolis such as ferulic acid, coumaric acid, caffeic acid, cinnamic acid, baccharin, artepillin and drupanin, indicating a probable origin on Baccharis dracunculifolia. The developed method agreed with the parameters established by the validation guidelines, then proved to be reliable for the analysis of this type of propolis. The brown propolis displayed significant activity against Leishmania amazonensis with IC50 values of 1.8 and 2.4 µg/ml against the promastigote and amastigote forms, respectively. The studied propolis exhibited promising evidence for use as a natural source against L. amazonensis.
Assuntos
Própole , Própole/farmacologia , Própole/química , Brasil , Cromatografia Líquida de Alta Pressão , Extratos Vegetais/química , Padrões de ReferênciaRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: Brazilian red propolis is a natural product known due to its medicinal properties. The efficacy of this natural resin has been proved; however, few studies report the safety of its oral use. Some toxic effects of natural products may not be expressed in traditional use, and preclinical studies are necessary to guarantee their safety. Health regulatory agency currently requires these non-clinical studies to develop drugs and herbal medicines, including genotoxic and oral toxicity tests. AIM OF THE STUDY: Accomplish the preclinical toxicity studies of Brazilian red propolis extract (BRP) in rodents, including genotoxicity, acute and sub-chronic toxicities. MATERIAL AND METHODS: Genotoxicity assays followed the erythrocyte micronucleus test protocol in a range of 500-2000 mg/kg BRP oral treatment on male Swiss mice. After an up-and-down procedure, acute oral toxicity (single dose) was performed on female Wistar Hannover rats, reaching a 2000 mg/kg BRP oral gavage concentration. Animals were monitored periodically until 14 days and euthanized for a macroscopic necropsy analysis. The sub-chronic oral toxicity test (90 days) was achieved with 1000 mg/kg of BRP on Wistar Hannover rats (males/females). Animals were monitored to evaluated behavioral and biometrical changes, then were euthanized to perfomed hematological, biochemical, and histopathological analyses. RESULTS: No genotoxic effect of the BRP was detected. The acute toxicity indicated no toxicity of a single oral dose of 2000 mg/kg of BRP. The long-term oral toxicity performed with 1000 mg/kg of BRP altered water and food intake and the biometrics, hematological and biochemical parameters. Biochemical alterations in hepatic and renal parameters were detected only in the males. Despite the detection of biochemical alterations, no histopathological changes were detected in the organs of any group. CONCLUSIONS: BRP, at a higher dose, showed no signs of immediate toxicity. However, the obtained results suggest that the chemical composition and the intake of higher doses deserve special attention regarding possible toxicity.
Assuntos
Própole , Ratos , Masculino , Camundongos , Feminino , Animais , Própole/toxicidade , Ratos Wistar , Roedores , Brasil , Extratos Vegetais , Ingestão de Alimentos , Testes de Toxicidade Aguda , Testes de Toxicidade SubcrônicaRESUMO
Fungal resistance to different therapeutic drugs has become a growing challenge. This crucial health problem requires new effective drug alternatives. Herein, we report the study of Eucalyptus botryoides' resin used in folk medicine as antimicrobial. Thus, E. botryoides' resin was extracted with aqueous-ethanol and fractionated using Sephadex chromatography, furnishing its major compounds. The crude extracts and the isolated compounds were evaluated for their in vitro antimicrobial activity against bacteria and yeasts. The crude extract displayed MIC of 25 µg/mL against S. salivarius, and for C. albicans, C. glabrata, and C. tropicalis the MIC were between 2.9 and 5.9 µg/mL. The 7-O-Methyl-aromadendrin was the most effective against C. glabrata and C. krusei (MIC = 1.6 µg/mL). 2-O-Galloyl-1,6-O-di-trans-p-coumaroyl-ß-D-glycopyranoside, first time reported, showed MIC of 3.1 µg/mL against C. glabrata and C. krusei. Overall, this work gave promising results, indicating that Eucalyptus botryoides' resin and its compounds have the potential for developing anti-yeast products.
Assuntos
Anti-Infecciosos , Eucalyptus , Extratos Vegetais/química , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Bactérias , Leveduras , Testes de Sensibilidade Microbiana , Antifúngicos/químicaRESUMO
The skin is a critical organ for the maintenance of the integrity and protection of the organism. When a wound occurs, a sequence of healing mechanisms is triggered to reconstruct the wounded area. ß-caryophyllene is a sesquiterpene in Copaifera langsdorffii oleoresin with antioxidant and anti-inflammatory potential. On the basis of previous studies with C. langsdorffii, ß-caryophyllene was selected to evaluate its wound healing potential and pharmacological mechanisms. The excision wound model was used with male Wistar rats and macroscopic, histological, immunohistochemical and biochemical analyses were performed with skin samples, comparing the ß-caryophyllene-treated group with reference drugs. The results showed macroscopic retraction of the wounds treated with ß-caryophyllene. Biochemical assays revealed the antioxidant and anti-inflammatory mechanisms of the ß-caryophyllene-treated group with increasing levels of IL-10 and GPx and decreasing levels of pro-inflammatory molecules, including TNF-α, IFN-γ, IL-1ß and IL-6. After ß-caryophyllene treatment, immunohistochemical assays showed enhanced re-epithelialization, through the increase in laminin-γ2 and desmoglein-3 immunolabeling. ß-caryophyllene also act in the remodeling mechanism, increasing the collagen content in the Masson's trichrome staining. These findings indicated the wound-healing potential of ß-caryophyllene topical formulation in rat skin wounds, mediated by antioxidant, anti-inflammatory and re-epithelialization mechanisms.
Assuntos
Anti-Inflamatórios não Esteroides/administração & dosagem , Antioxidantes/administração & dosagem , Fabaceae/química , Compostos Fitoquímicos/administração & dosagem , Fitoterapia/métodos , Extratos Vegetais/administração & dosagem , Sesquiterpenos Policíclicos/administração & dosagem , Reepitelização/efeitos dos fármacos , Pele/lesões , Cicatrização/efeitos dos fármacos , Ferimentos Penetrantes/tratamento farmacológico , Administração Tópica , Animais , Citocinas/metabolismo , Masculino , Modelos Animais , Ratos , Ratos Wistar , Transdução de Sinais/efeitos dos fármacos , Resultado do Tratamento , Ferimentos Penetrantes/metabolismoRESUMO
BACKGROUND: This study aimed to analyze cultures of mononuclear (MN) cells with Giardia lamblia to determine the levels of the cytokines IFN-γ and TGF-ß and the functional activity of MN cells after incubation with cytokines. METHODS: This study was conducted in 2018 in Barra do Garças, Mato Grosso State, Brazil. Blood samples were collected from 60 healthy volunteer donors to obtain leukocytes. The levels of IFN-γ and TGF-ß were quantified in trophozoite cell culture supernatants. Superoxide release, phagocytosis, microbicidal activity, apoptosis and intracellular calcium release were analyzed. RESULTS: The cytokines evaluated were detected in the culture supernatant of MN cells and G. lamblia. Regardless of the type of cytokine, MN cells increased superoxide release in the presence of G. lamblia. Phagocytosis, microbicidal activity and apoptosis were higher when MN phagocytes were treated with cytokines. The highest microbicidal activity and apoptosis rates were observed in MN cells cultured with TGF-ß. IFN-γ increased the release of intracellular calcium by MN phagocytes. CONCLUSION: Cytokines play a beneficial role in the host by activating MN cells against G. lamblia. In addition, phagocytosis causes G. lamblia death and that the modulation of the functional activity of blood MN phagocytes by cytokines is an alternative mechanism for eliminating G. lamblia.
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Seven phenolic compounds (ferulic acid, caffeic acid, 4-methoxycinnamic acid, 3,4-dimethoxycinnamic acid, 3-hydroxy-4-methoxybenzaldehyde, 3-methoxy-4-hydroxypropiophenone and 1-O,2-O-digalloyl-6-O-trans-p-coumaroyl-ß-D-glucopyranoside), a flavanonol (7-O-methylaromadendrin), two lignans (pinoresinol and matairesinol) and six diterpenic acids/alcohol (19-acetoxy-13-hydroxyabda-8(17),14-diene, totarol, 7-oxodehydroabietic acid, dehydroabietic acid, communic acid and isopimaric acid) were isolated from the hydroalcoholic extract of a Brazilian Brown Propolis and characterized by NMR spectral data analysis. The volatile fraction of brown propolis was characterized by CG-MS, composed mainly of monoterpenes and sesquiterpenes, being the major α-pinene (18.4 %) and ß-pinene (10.3 %). This propolis chemical profile indicates that Pinus spp., Eucalyptus spp. and Araucaria angustifolia might be its primary plants source. The brown propolis displayed significant activity against Plasmodium falciparum D6 and W2 strains with IC50 of 5.3 and 9.7â µg/mL, respectively. The volatile fraction was also active with IC50 of 22.5 and 41.8â µg/mL, respectively. Among the compounds, 1-O,2-O-digalloyl-6-O-trans-p-coumaroyl-ß-D-glucopyranoside showed IC50 of 3.1 and 1.0â µg/mL against D6 and W2 strains, respectively, while communic acid showed an IC50 of 4.0â µg/mL against W2 strain. Cytotoxicity was determined on four tumor cell lines (SK-MEL, KB, BT-549, and SK-OV-3) and two normal renal cell lines (LLC-PK1 and VERO). Matairesinol, 7-O-methylaromadendrin, and isopimaric acid showed an IC50 range of 1.8-0.78â µg/mL, 7.3-100â µg/mL, and 17-18â µg/mL, respectively, against the tumor cell lines but they were not cytotoxic against normal cell lines. The crude extract of brown propolis displayed antimicrobial activity against C.â neoformans, methicillin-resistant Staphylococcus aureus, and P.â aeruginosa at 29.9â µg/mL, 178.9â µg/mL, and 160.7â µg/mL, respectively. The volatile fraction inhibited the growth of C.â neoformans at 53.0â µg/mL. The compounds 3-hydroxy-4-methoxybenzaldehyde, 3-methoxy-4-hydroxypropiophenone and 7-oxodehydroabietic acid were active against C.â neoformans, and caffeic and communic acids were active against methicillin-resistant Staphylococcus aureus.
Assuntos
Antibacterianos/farmacologia , Antimaláricos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Compostos Fitoquímicos/farmacologia , Própole/química , Animais , Antibacterianos/biossíntese , Antibacterianos/química , Antimaláricos/química , Antimaláricos/metabolismo , Antineoplásicos Fitogênicos/biossíntese , Antineoplásicos Fitogênicos/química , Abelhas , Brasil , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cryptococcus neoformans/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Testes de Sensibilidade Parasitária , Compostos Fitoquímicos/biossíntese , Compostos Fitoquímicos/química , Plasmodium falciparum/efeitos dos fármacos , Pseudomonas aeruginosa/efeitos dos fármacos , Staphylococcus aureus/efeitos dos fármacosRESUMO
Propolis comprises a complex resinous product composed of plant's parts or exudates, pollen, bee wax, and enzymes. Brazilian brown propolis from Araucaria sp displays several biological activities. Considering the lack of validated analytical methods for its analysis, we are reporting the development of a validated high-performance liquid chromatography with photodiode array detector method to analyze Araucaria brown propolis. The crude propolis were extracted and chromatographed, furnishing six main diterpenes. The isolated standards were used to draw the analytical curves, allowing the studies of selectivity, precision, accuracy, recovery, robustness, the determination of limits of detection and limits of quantification. The mobile phase consisted of 0.1% acetic acid in water and acetonitrile, using an octadecylsilane column, 1 mL/min flow rate and detection at 200 or 241 nm. Relative standard deviation values obtained for intra-day and inter-day precision were lower than 4% for all diterpenes. From the five parameters for robustness, wavelength detection and flow rate were the critical ones. Limits of detection and quantification ranged from 0.808 to 10.359 µg/mL and from 2.448 to 31.392 µg/mL, respectively. The recoveries were between 105.03 and 108.13%, with relative standard deviation values around 5.0%. The developed method is precise, sensitive, and reliable for analyzing Araucaria brown propolis.
Assuntos
Araucaria/metabolismo , Cromatografia Líquida de Alta Pressão/métodos , Diterpenos/análise , Própole/análise , Abietanos/análise , Brasil , Ácidos Carboxílicos/análise , Técnicas de Química Analítica , Limite de Detecção , Modelos Lineares , Reprodutibilidade dos Testes , Tetra-Hidronaftalenos/análiseRESUMO
Propolis is a natural product produced from the interaction between bees and plants. Brazilian red propolis results from Apis mellifera collection of resins from two plant species, being Dalbergia ecastaphyllum(L.) Taub, Fabaceae, the primary botanical source, containing isoflavonoids and other characteristic phenolic compounds. Several biological activities of Brazilian red propolis and their isolated compounds have been described in the literature. However, to our knowledge, there are no validated analytical methods for the analysis and standardization of products derived from this type of propolis reported in the literature. We developed a reverse-phase high-performance liquid chromatography analytical method for the detection and quantification of nine red propolis chemical markers: liquiritigenin, calycosin, isoliquiritigenin,formononetin, vestitol, neovestitol, medicarpin, biochanin A, and 7-O-methylvestitol, present in Brazilian red propolis extracts and D. ecastaphyllum. The developed method was also applied to the analyses of D. ecastaphyllum samples and seasonal analysis of Brazilian red propolis. Good detection response, linearity, precision, and robustness were obtained by the method, being reliable for the quality control of Brazilian red propolis extracts, raw propolis, plant material, and their derived products. The red propolis chemical markers were present in D. ecastaphyllum stems at lower concentrations. The seasonal analysis of Brazilian red propolis extract showed higher phenolic compound concentration on periods of the rainy season with higher humidity and lower solar radiation.
Assuntos
Dalbergia , Própole , Animais , Abelhas , Brasil , Cromatografia Líquida de Alta Pressão , FenóisRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: Copaifera species folkloric names are "copaíbas, copaibeiras, copaívas or oil stick", which are widely used in Brazilian folk medicine. Among all ethnopharmacological applications described for Copaifera spp oleoresins, their anti-inflammatory effect stands out. However, the knowledge of anti-inflammatory and antinociceptive properties of Copaifera pubiflora Benth is scarce. AIM OF THE STUDY: To investigate the cytotoxic, anti-inflammatory, and antinociceptive activities of C. pubiflora oleoresin (CPO), and its major compound ent-hardwickiic acid (HA). MATERIAL AND METHODS: The phosphatase assay was used to evaluate the cytotoxicity of CPO and HA in three different cell lines. CPO and HA doses of 1, 3, and 10 mg/kg were employed in the biological assays. The assessment of motor activity was performed using open-field and rotarod tests. Anti-inflammatory activity of CPO and HA was assessed through luciferase assay, measurement of INF-γ, IL-1ß, IL-6, IL-10, and TNF-α in a multi-spot system with the immortalized cell line THP-1, zymosan-induced arthritis, and carrageenan-induced paw edema. Acetic acid-induced abdominal writhing and formalin tests were undertaken to evaluate the antinociceptive potential of CPO and HA. In addition, the evaluation using carrageenan was performed to investigate the effect of CPO in pain intensity to a mechanical stimulus (mechanical hyperalgesia), using the von Frey filaments. A tail-flick test was used to evaluate possible central CPO and HA actions. RESULTS: In the cytotoxicity evaluation, CPO and HA were not cytotoxic to the cell lines tested. CPO and HA (10 mg/kg) did not affect animals' locomotor capacity in both open-field and rotarod tests. In the luciferase assay, CPO and HA significantly reduced luciferase activity (p < 0.05). This reduction indicates a decrease in NF-κB activity. HA and CPO decreased INF-γ, IL-1ß, IL-6, IL-10, and TNF-α at 24 and 72 h in the multi-spot system. In zymosan-induced arthritis, CPO and HA decreased the number of neutrophils in the joint of arthritic mice and the number of total leukocytes (p < 0.05). In experimental arthritis HA significantly decreased joint swelling (p < 0.05). CPO and HA also increased the mechanical threshold during experimental arthritis. HA and CPO significantly inhibited the carrageenan-induced paw edema, being the doses of 10 mg/kg the most effective, registering maximum inhibitions of 58 ± 8% and 76 ± 6% respectively, p < 0.05. CPO and HA reduced the nociceptive behavior in both phases of formalin at all tested doses. The highest doses tested displayed inhibitions of 87 ± 1% and 72 ± 4%, respectively, p < 0.001, in the first phase, and 87 ± 1% and 81 ± 2%, respectively, p < 0.001, in the second phase. Oral treatment of CPO and HA (1, 3, 10 mg/kg) significantly reduced the nociceptive response in acetic acid-induced abdominal writhings, and the 10 mg/kg dose was the most effective with maximum inhibitions of 86 ± 2% and 82 ± 1%, respectively, p < 0.001. Both HA and CPO significantly decreased the intensity of mechanical inflammatory hyper-nociception on carrageenan-induced hyperalgesia at all tested doses, and 10 mg/kg was the most effective dose with maximum inhibitions of 73 ± 5% and 74 ± 7%, respectively, p < 0.05.CPO increased the tail-flick latencies in mice, and concomitant administration of naloxone partially reduced its effect. CONCLUSIONS: CPO and HA may inhibit the production of inflammatory cytokines by suppressing the NF-κB signaling pathway, resulting in anti-inflammatory and antinociceptive activities.
Assuntos
Analgésicos/uso terapêutico , Anti-Inflamatórios/uso terapêutico , Artrite Experimental/tratamento farmacológico , Diterpenos/uso terapêutico , Edema/tratamento farmacológico , Fabaceae/química , Extratos Vegetais/uso terapêutico , Ácido Acético/toxicidade , Analgésicos/farmacologia , Animais , Anti-Inflamatórios/farmacologia , Artrite Experimental/induzido quimicamente , Comportamento Animal/efeitos dos fármacos , Brasil , Carragenina/toxicidade , Linhagem Celular , Citocinas/metabolismo , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Edema/induzido quimicamente , Formaldeído/toxicidade , Humanos , Hiperalgesia/induzido quimicamente , Hiperalgesia/tratamento farmacológico , Locomoção/efeitos dos fármacos , Medicina Tradicional , Camundongos , Camundongos Endogâmicos BALB C , NF-kappa B/metabolismo , Extratos Vegetais/farmacologia , Zimosan/toxicidadeRESUMO
INTRODUCTION: Propolis is widely used in folk medicine, and many factors can affect its chemical composition, including abiotic factors that can influence plants and bees. Therefore, analytical methods are powerful techniques in the quality control of such products. OBJECTIVE: Develop and validate an analytical method for quantifying volatile compounds in Brazilian brown propolis, and evaluate its biological activities. METHODS: A gas chromatography flame ionisation detector (GC-FID) analytical method was validated, attending the parameters of international validation guidelines as ANVISA 2017 and ICH 2005, for quantification of compounds present in volatile oils from propolis. Evaluation of cytotoxic, antimicrobial, and leishmanicidal activities of the oil. RESULTS: The compounds 1,8-cineole, terpinen-4-ol, α-copaene, ß-caryophyllene, γ-muurolene, nerolidol, spathulenol, and γ-palmitolactone were isolated from the volatile fraction of a Brazilian brown propolis and used in the method validation. All the validation parameters of the method were satisfactory. The volatile fraction displayed a significant leishmanicidal activity, with half maximal inhibition concentration (IC50 ) = 21.3 µg/mL against amastigote forms and IC50 = 25.1 µg/mL against promastigote forms of Leishmania amazonensis. The oil also displayed an antibacterial effect by inhibiting the growth of Streptococcus mutans and Staphylococcus aureus at 25 µg/mL and 50 µg/mL, respectively, but it was not cytotoxic against AGP-01, He-La and CHO-K1cell lines, with IC50 > 100 µg/mL. CONCLUSION: The GC-FID method can be a useful tool in the quality control of propolis material. The southeast brown propolis showed a high chemical complexity in its volatile fraction, which displayed leishmanicidal activity and bactericidal activity.
Assuntos
Anti-Infecciosos , Óleos Voláteis , Própole , Animais , Antibacterianos/farmacologia , Anti-Infecciosos/farmacologia , Abelhas , Brasil , Cromatografia Gasosa , Óleos Voláteis/farmacologia , Própole/farmacologiaRESUMO
Propolis is a viscous resin consisting of plant material (shoots, flowers, and plant exudates), salivary secretions and waxes produced by Apis mellifera bees. Its popular use aroused the interests of scientific research, which proved to be a potential source of various bioactive substances. The chemical composition of propolis depends on several factors, such as the different types of plant sources collected by bees, geographic origin, and the time of year in which they are produced, but it is known that phenolic represent the main bioactive constituents of propolis. Baccharis dracunculifolia DC (Asteraceae) is the most important botanical source of propolis and a native to southeastern Brazil. It is widely known as the green propolis because of its deep green color. One of its major phenolic acids is artepillin C (Art-C), a diprenyl-p-hydroxycinnamic acid derivative. This review aims to provide a comprehensive summary of the pharmacological effects of Art-C. The limited number of publications on this topic over the past two decades have been collected from databases and summarized. Numerous biological activities have been described for the Art-C, such as gastroprotective, anti-inflammatory, antimicrobial, antioxidant, antitumor. This article describes aspects of occurrence, synthesis, biological activities and pharmacokinetic approaches.
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Copaifera langsdorffii L. is one of the most known medicinal species in Brazil. Its leaves are rich in phenolic compounds with potential biological activities as an antioxidant and chelating agent. This paper reports the isolation of four compounds from the hydroalcoholic extract of the leaves of C. langsdorffii and the investigation of their possible cytoprotective effects against heavy metal poisoning. Quercitrin (1), afzelin (2), 3,5-di-O-(3-O-methyl galloyl) quinic acid (3) and 4,5-di-O-(3-O-methyl galloyl) quinic acid (4), were associated with toxic doses of methylmercury and lead and evaluated by Alamar blue cell viability assays in HepG2 and PC12. The compounds displayed significant cytoprotective effect for the HepG2 cell line against both metals. Compounds 1-4 did not protect PC12 cells against methylmercury induced-cytotoxicity, but at lower concentrations, they protected against lead induced-cytotoxicity. The evaluated compounds showed a promising cytoprotection effect against exposure to heavy metals and should be further investigated as protective agents.
Assuntos
Fabaceae/química , Intoxicação por Metais Pesados/tratamento farmacológico , Compostos de Metilmercúrio/antagonistas & inibidores , Extratos Vegetais/farmacologia , Substâncias Protetoras/isolamento & purificação , Animais , Antioxidantes , Brasil , Linhagem Celular , Intoxicação por Metais Pesados/prevenção & controle , Humanos , Chumbo/toxicidade , Intoxicação por Chumbo/tratamento farmacológico , Intoxicação por Chumbo/prevenção & controle , Manosídeos , Intoxicação por Mercúrio/tratamento farmacológico , Intoxicação por Mercúrio/prevenção & controle , Compostos de Metilmercúrio/toxicidade , Fenóis , Folhas de Planta/química , Proantocianidinas , Substâncias Protetoras/farmacologia , Quercetina/análogos & derivados , Ácido Quínico , RatosRESUMO
Copaifera is a tree that produces an oleoresin that has great historical and economic importance. These oleoresins display several pharmacological properties, such as anti-inflammatory and antimicrobial, among others. The commercialization of Copaifera oleoresin occurs, in many cases, without any quality control, which facilitates its adulteration. Validated analytical methods can provide a safe quality control. In this work, the 800 Automatic Spinning Band Distillation equipment was used to perform the fractionation of the volatile oils obtained by hydrodistillation of Copaifera multijuga, C. paupera, C. Publifora and C. langsdorffii, aiming to isolate and purify the major compounds present in these oils. For purification, classical column chromatography was used, furnishing six isolated sesquiterpenes. The sesquiterpenes were used as standards in the development and validation of the method by GC-FID. The evaluated parameters were selectivity, linearity, precision, accuracy and robustness and they are all in accordance with ANVISA and International Conference on Harmonization guidelines. The developed method is reliable for the quantification of sesquiterpenes in Copaifera oleoresins. Both volatile oils and isolated sesquiterpenes had their minimum inhibitory concentration determined against strains of Gram-negative and Gram-positive bacteria and yeasts. Copaifera langsdorffi oleoresin was the only one active against all of the evaluated microorganisms, displaying good antimicrobial potential.
Assuntos
Anti-Infecciosos/isolamento & purificação , Cromatografia Gasosa/métodos , Destilação/métodos , Fabaceae/química , Óleos Voláteis/isolamento & purificação , Anti-Infecciosos/análise , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Bactérias/efeitos dos fármacos , Candida/efeitos dos fármacos , Limite de Detecção , Modelos Lineares , Óleos Voláteis/análise , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Extratos Vegetais/química , Reprodutibilidade dos TestesRESUMO
Copaifera is a genus of large trees found in Brazil, mainly in Amazon forest, but also in Atlantic forest and cerrado biomes. It has also been found in other countries in South America. In Africa, it is found mainly in Congo, Cameroon, Guinea and Angola. Its oleoresin has been used in folk medicine in the treatment of numerous healthy disorders, such as urinary, respiratory, skin and inflammatory diseases, for which there are several studies corroborating its ethnopharmacological uses. It is also extensively employed in the pharmaceutical and cosmetic industries in the development of ointments, pills, soaps, perfumes, among others. Copaifera oleoresin contains mainly diterpenes, such as: kaurenoic acid, kaurenol, copalic acid, agathic acid, hardwiickic acid, polyalthic acid, and sesquiterpenes, comprising ß-caryophyllene, caryophyllene oxide, α-copaene, α-humulene, γ-muurolene and ß-bisabolol, among other compounds. On the other hand, Copaifera leaves contain mainly phenolic compounds, such as flavonoids and methylated galloylquinic acid derivatives. Therefore, considering the economic importance of Copaifera oleoresin, its ethnopharmacological uses, the need to develop new pharmaceuticals for the treatment of many diseases, as well as the pharmacological potential of the compounds found in Copaifera spp., it was undertaken a review covering mostly the last two decades on the distribution, chemistry, pharmacology, quality control and safety of Copaifera species.
Assuntos
Fabaceae/química , Medicina Tradicional/métodos , Preparações de Plantas/farmacologia , África , Animais , Etnofarmacologia , Humanos , Preparações de Plantas/efeitos adversos , Preparações de Plantas/química , América do SulRESUMO
CONTEXT: Inflammatory disorders are common in modern life, and medicinal plants provide an interesting source for new compounds bearing anti-inflammatory properties. In this regard, Brazilian medicinal plants are considered to be a promising supply of such compounds due to their great biodiversity. OBJECTIVES: To undertake a review on Brazilian medicinal plants with corroborated anti-inflammatory activities by selecting data from the literature reporting the efficacy of plants used in folk medicine as anti-inflammatory, including the mechanisms of action of their extracts and isolated compounds. METHODS: A search in the literature was undertaken by using the following Web tools: Web of Science, SciFinder, Pub-Med and Science Direct. The terms 'anti-inflammatory' and 'Brazilian medicinal plants' were used as keywords in search engine. Tropicos and Reflora websites were used to verify the origin of the plants, and only the native plants of Brazil were included in this review. The publications reporting the use of well-accepted scientific protocols to corroborate the anti-inflammatory activities of Brazilian medicinal plants with anti-inflammatory potential were considered. RESULTS: We selected 70 Brazilian medicinal plants with anti-inflammatory activity. The plants were grouped according to their anti-inflammatory mechanisms of action. The main mechanisms involved inflammatory mediators, such as interleukins (ILs), nuclear factor kappa B (NF-κB), prostaglandin E2 (PGE2), cyclooxygenase (COX) and reactive oxygen species (ROS). CONCLUSIONS: The collected data on Brazilian medicinal plants, in the form of crude extract and/or isolated compounds, showed significant anti-inflammatory activities involving different mechanisms of action, indicating Brazilian plants as an important source of anti-inflammatory compounds.
Assuntos
Anti-Inflamatórios/uso terapêutico , Inflamação/prevenção & controle , Medicina Tradicional , Extratos Vegetais/uso terapêutico , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Antioxidantes/isolamento & purificação , Antioxidantes/uso terapêutico , Brasil , Inibidores de Ciclo-Oxigenase/isolamento & purificação , Inibidores de Ciclo-Oxigenase/uso terapêutico , Dinoprostona/metabolismo , Humanos , Inflamação/imunologia , Inflamação/metabolismo , Mediadores da Inflamação/metabolismo , Interleucinas/metabolismo , Estrutura Molecular , NF-kappa B/metabolismo , Óxido Nítrico/metabolismo , Óxido Nítrico Sintase/antagonistas & inibidores , Óxido Nítrico Sintase/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Fitoterapia , Extratos Vegetais/isolamento & purificação , Plantas Medicinais , Prostaglandina-Endoperóxido Sintases/metabolismo , Relação Quantitativa Estrutura-Atividade , Espécies Reativas de Oxigênio/metabolismoRESUMO
BACKGROUND: Entamoeba histolytica (E. histolytica) causes amoebiasis, which is a disease with significant morbidity and mortality. Phagocytic cells and cytokines appear to be important in amoebiasis, but very little is known about the influence of these cells and cytokines in protozoan infections. The aim of this study was to analyse the supernatant of cultures of mononuclear (MN) cells with E. histolytica to determine: 1) the levels of the cytokines IFN-γ and TGF-ß, and 2) the amoebicidal activity of MN cells after incubation with cytokines. METHODS: Blood samples were collected from 30 volunteer donors. The cytokine concentrations in MN cells culture supernatants, superoxide release, leukophagocytosis, amoebicide activity, intracellular calcium release and apoptosis were analysed. RESULTS: The IFN-γ concentrations were 6.22 ± 0.36 and TGF-ß concentrations were 17.01 ± 2.21 in cells-trophozoite culture supernatants. MN cells, independently of cytokines, in the presence of amoeba increase the superoxide release. In the absence of cytokines, the ingestion of MN cells by amoebae was higher. In the presence of IFN- γ or TGF- ß, a lower ingestion of MN cells was observed by amoebae. MN cells treated with cytokines exhibited higher amoebicide and apoptosis indexes. The incubation of cytokines increased the intracellular calcium release by MN cells. CONCLUSIONS: These results suggest that cytokines play a beneficial role for the host by activating MN cells against E. histolytica. The increased death of amoebae during the leukophagocytosis suggests that both cytokines (IFN-γ and TGF-ß) can modulate the functional activity of MN cells and that these cytokines probably are important in the control of amoebic infections.