RESUMEN
The Aedes aegypti (Diptera: Culicidae) mosquito is the vector of several arboviruses in tropical and subtropical areas of the globe, and synthetic pesticides remain the most widely used combat strategy. This study describes the investigation of secondary metabolites with larvicidal activity from the Malpighiaceae taxon using a metabolomic and bioactivity-based approach. The workflow initially consisted of a larvicidal screening of 394 extracts from the leaves of 197 Malpighiaceae samples, which were extracted using solvents of different polarity, leading to the selection of Heteropterys umbellata for the identification of active compounds. By employing untargeted mass spectrometry-based metabolomics and multivariate analyses (PCA and PLS-DA), it was possible to determine that the metabolic profiles of different plant organs and collection sites differed significantly. A bioguided approach led to the isolation of isochlorogenic acid A (1) and the nitropropanoyl glucosides karakin (2) and 1,2,3,6-tetrakis-O-[3-nitropropanoyl]-beta-glucopyranose (3). These nitro compounds exhibited larvicidal activity, possibly potentialized by synergistic effects of their isomers in chromatographic fractions. Additionally, targeted quantification of the isolated compounds in different extracts corroborated the untargeted results from the statistical analyses. These results support a metabolomic-guided approach in combination with classical phytochemical techniques to search for natural larvicidal compounds for arboviral vector control.
Asunto(s)
Aedes , Insecticidas , Animales , Extractos Vegetales/química , Insecticidas/química , Glicósidos/farmacología , Glicósidos/análisis , Larva , Mosquitos Vectores , Hojas de la Planta/química , Espectrometría de Masas , MetabolómicaRESUMEN
The Aedes aegypti mosquito is a vector of severe diseases with high morbidity and mortality rates. The most commonly used industrial larvicides have considerable toxicity for non-target organisms. This study aimed to develop and evaluate liquid and solid carrier systems to use pentyl cinnamate (PC), derived from natural sources, to control Ae. aegypti larvae. The liquid systems consisting of nanoemulsions with different lecithins systems were obtained and evaluated for stability over 30 days. Microparticles (MPs) were obtained by the spray drying of the nanoemulsions using maltodextrin as an adjuvant. Thermal, NMR and FTIR analysis indicated the presence of PC in microparticles. Indeed, the best nanoemulsion system was also the most stable and generated the highest MP yield. The PC larvicidal activity was increased in the PC nanoemulsion system. Therefore, it was possible to develop, characterize and obtain PC carrier systems active against Ae. aegypti larvae.
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Aedes , Insecticidas , Animales , Insecticidas/química , Mosquitos Vectores , Cinamatos/farmacología , LarvaRESUMEN
Dengue is a neglected disease, present mainly in tropical countries, with more than 5.2 million cases reported in 2019. Vector control remains the most effective protective measure against dengue and other arboviruses. Synthetic insecticides based on organophosphates, pyrethroids, carbamates, neonicotinoids and oxadiazines are unattractive due to their high degree of toxicity to humans, animals and the environment. Conversely, natural-product-based larvicides/insecticides, such as essential oils, present high efficiency, low environmental toxicity and can be easily scaled up for industrial processes. However, essential oils are highly complex and require modern analytical and computational approaches to streamline the identification of bioactive substances. This study combined the GC-MS spectral similarity network approach with larvicidal assays as a new strategy for the discovery of potential bioactive substances in complex biological samples, enabling the systematic and simultaneous annotation of substances in 20 essential oils through LC50 larvicidal assays. This strategy allowed rapid intuitive discovery of distribution patterns between families and metabolic classes in clusters, and the prediction of larvicidal properties of acyclic monoterpene derivatives, including citral, neral, citronellal and citronellol, and their acetate forms (LC50 < 50 µg/mL).
Asunto(s)
Aedes , Insecticidas , Aceites Volátiles , Animales , Cromatografía de Gases y Espectrometría de Masas , Humanos , Insecticidas/farmacología , Larva , Mosquitos Vectores , Aceites Volátiles/farmacologíaRESUMEN
BACKGROUND: Eugenia calycina is an endemic species in the Brazilian savannah (the Cerrado) and it is threatened with extinction. Several species of Eugenia are used as insecticides or insect repellents. No data are available on the larvicidal activity of E. calycina. The chemical composition of the essential oil (EO) from leaves of Eugenia calycina was analyzed by gas chromatography coupled to mass spectrometry (GC-MS) and the larvicidal activity against Aedes aegypti larvae in the third stage of development was studied. RESULTS: Oxygenated and non-oxygenated sesquiterpenes were identified, and the main compounds were bicyclogermacrene, spathulenol, and ß-caryophyllene. The EO was fractionated in a chromatographic column and three compounds were isolated and identified: spathulenol, aromadendrane-4ß,10α-diol, and 1ß-11-dihydroxy-5-eudesmene. It is the first time that the last two compounds have been identified in E. calycina. The exposure times in the larvicidal test were 24 h and 48 h and the LC50 values obtained were 199.3 and 166.4 µg mL-1 . The cytotoxicity of the EO in mammalian cells (HeLa and Vero) was evaluated for 24 and 48 h of incubation. The cytotoxic concentrations of the EO for HeLa and Vero cells (266.8 ± 46.5 and 312.1 ± 42.5 µg mL-1 , respectively) in 48 h of exposure were higher than the LC50 , showing low cytotoxicity at the concentration exhibiting larvicidal activity, resulting in a positive selectivity index. CONCLUSION: These results indicate that the EO of E. calycina showed high activity against the A. aegypti larvae but lower cytotoxicity to mammalian cells. The leaves of E. calycina are therefore a very promising source of natural larvicidal products. © 2020 Society of Chemical Industry.
Asunto(s)
Aedes/efectos de los fármacos , Eugenia/química , Insecticidas/farmacología , Aceites Volátiles/farmacología , Extractos Vegetales/farmacología , Aedes/crecimiento & desarrollo , Animales , Brasil , Chlorocebus aethiops , Cromatografía de Gases y Espectrometría de Masas , Insecticidas/química , Larva/efectos de los fármacos , Larva/crecimiento & desarrollo , Aceites Volátiles/química , Extractos Vegetales/química , Hojas de la Planta/química , Células VeroRESUMEN
The number of documented dengue cases has increased dramatically in recent years due to transmission through the Aedes aegypti mosquito bite. Vector control remains the most effective measure to protect against this and other arboviral diseases including Zika, chikungunya and (urban) yellow fever, with an established vaccine only available for yellow fever. Although the quinone class shows potential as leading compounds for larvicide development, limited information restricts the development of optimized structures and/or formulations. Thus, in this contribution we investigated the larvicidal and pupicidal activity of three quinone compounds isolated from a Connarus suberosus root wood ethyl acetate extract together with 28 quinones from other sources. Eight quinones demonstrated larvicidal activity, of which tectoquinone (4) proved to be the most active (LC50 1.1 µg/mL). The essential residual effect parameter of four of these quinones was evaluated in laboratory trials, with tectoquinone (4) and 2-ethylanthraquinone (7) presenting the most prolonged activity. In small-scale field residual tests, tectoquinone (4) caused 100% larvae mortality over 5 days, supporting its selection for formulation trials to develop a prototype larvicide to control Ae. aegypti.
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Aedes/efectos de los fármacos , Insecticidas/química , Insecticidas/farmacología , Larva/efectos de los fármacos , Quinonas/química , Quinonas/farmacología , Animales , Relación Dosis-Respuesta a Droga , Insecticidas/aislamiento & purificación , Estructura Molecular , Quinonas/aislamiento & purificaciónRESUMEN
The new pentacyclic triterpene 11ß-hydroxypristimerin (1), along with the known metabolites pristimerin (2), 6-oxopristimerol (3) and vitideasin (4), were isolated from a Salacia crassifolia root wood extract, following a bioassay-guided fractionation approach. Both the extract and the purified triterpenes displayed pronounced cytotoxic activity against human cancer cell lines. The NCI-60 cell line screen revealed that compound 2 was the most active, with a mean GI50 of 0.17 µM, while compound 1 had a mean GI50 of 8.7 µM. A COMPARE analysis of the screening results showed that pristimerin is likely to be the main compound responsible for the cytotoxic activity of the extract (mean GI50 of 0.3 µg·mL−1). A targeted search for pristimerin and related derivatives using LC-MS/MS revealed the presence of pristimerin (2) and 6-oxopristimerol (3) in all Celastraceae species examined and in all plant parts tested, while vitideasin (4) was only detected in the genus Salacia.
Asunto(s)
Celastraceae/metabolismo , Metabolómica/métodos , Extractos Vegetales/química , Salacia/química , Triterpenos/química , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Antineoplásicos/metabolismo , Antineoplásicos/uso terapéutico , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Triterpenos Pentacíclicos , Raíces de Plantas/química , Relación Estructura-Actividad , Triterpenos/aislamiento & purificación , Triterpenos/metabolismo , Triterpenos/uso terapéuticoRESUMEN
We describe a Sabicea cinerea endophytic fungus closely related to Diaporthe pseudomangiferae that produces two known metabolites, mycoepoxydiene (1) and altiloxin A (2), as well as enamidin (3) and eremofortin F (4), two compounds not previously described in the literature. The structure of these four metabolites was elucidated using spectroscopic analysis, and their cytotoxic activities were measured against the human cell lines KB, MRC-5, and MDA-MB-435.
Asunto(s)
Antineoplásicos/aislamiento & purificación , Ascomicetos/química , Hidrocarburos Aromáticos con Puentes/aislamiento & purificación , Endófitos/química , Pironas/aislamiento & purificación , Sesquiterpenos/aislamiento & purificación , Antineoplásicos/química , Antineoplásicos/farmacología , Hidrocarburos Aromáticos con Puentes/química , Hidrocarburos Aromáticos con Puentes/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Células KB , Estructura Molecular , Pironas/química , Pironas/farmacología , Sesquiterpenos/química , Sesquiterpenos/farmacologíaRESUMEN
Since the 1960s, fungal infections have become a major worldwide public health problem. Antifungal treatments have many limitations, such as toxicity and resistance. Matayba guianensis Aublet (Sapindaceae) was chemically investigated as part of our ongoing search for lead molecules against fungi in the Brazilian Cerrado biome. The ethanolic extract of M. guianensis root bark revealed the presence of two previously unreported ether diglycosides: matayoside E (1) and F (2) with anti Candida activity, along with two known compounds: cupanioside (3) and stigmasterol (4).
Asunto(s)
Antifúngicos/química , Glicósidos/química , Sapindaceae/química , Antifúngicos/aislamiento & purificación , Antifúngicos/farmacología , Candida/efectos de los fármacos , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Humanos , Leucocitos Mononucleares/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Conformación Molecular , Corteza de la Planta/química , Corteza de la Planta/metabolismo , Raíces de Plantas/química , Raíces de Plantas/metabolismo , Sapindaceae/metabolismoRESUMEN
In this study, extracts of plant species from the Cerrado biome were assessed in order to find potential inhibitors of human salivary alpha-amylase. The plants were collected and extracts were obtained from leaves, bark, and roots. We performed a preliminary phytochemical analysis and a screening for salivar alpha-amylase inhibitory activity. Only three botanical families (Sapotaceae, Sapindaceae and Flacourtiaceae) and 16 extracts showed a substantial inhibition (>75%) of alpha-amylase. The ethanolic extracts of Pouteria ramiflora obtained from stem barks and root barks decreased amylolytic activity above 95% at a final concentration of 20 µg/mL. Thus, adult male Swiss mice were treated orally with P. ramiflora in acute toxicity and glycemic control studies. Daily administration with 25, 50 and 100 mg/kg of aqueous extract of P. ramiflora for eight days can reduce significantly body weight and blood glucose level in mice. These data suggest that the crude polar extract of P. ramiflora decreases salivary amylolytic activity while lowering the blood levels of glucose.
Asunto(s)
Glucemia/efectos de los fármacos , Inhibidores Enzimáticos/farmacología , Extractos Vegetales/farmacología , Pouteria/química , alfa-Amilasas Salivales/antagonistas & inhibidores , Animales , Masculino , RatonesRESUMEN
Worldwide pesticide usage was estimated in up to 3.5 million tons in 2020. The number of approved products varies among different countries, however, in Brazil, there are nearly 5000 of such products available. Among them, insecticides correspond to a group of mounting importance for controlling crop pests and disease-associated vectors in public health. Unfortunately, resistance to commercially approved insecticides is commonly observed, limiting the use of these products. Thus, the search for more effective and environmentally friendly products is both a challenge and a necessity since several insecticides are no longer allowed in many countries. In this review, we discuss the historical strategies used in the development of modern insecticides, including chemical structure alterations, mechanism of action and their impact on insecticidal activity. The environmental impact of each pesticide class is also discussed, with persistence data and activity on non-target organisms, along with the human toxicological effect. By tracing the historical route of discovery and development of blockbuster pesticides like DDT, pyrethroids and organophosphates, we also aim to categorize and relate the successful chemical alterations and novel pesticide development strategies that resulted in safer alternatives. A brief discussion on the Brazilian registration procedure and a perspective of insecticides currently approved in the country was also included.
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Insecticidas , Plaguicidas , Piretrinas , Ambiente , Humanos , Resistencia a los Insecticidas , Insecticidas/toxicidad , Organofosfatos , Plaguicidas/farmacologíaRESUMEN
As part of an arbovirus vector control strategy, chemical control continues to be a mainstay in mitigating the burden of disease. The current arsenal of chemicals used for this purpose, however, are becoming challenged rapidly because of issues of insecticide resistance and environmental pressure. Newer, environmentally friendly actives are of interest to supplement aging chemistries; therefore efforts to screen compounds for insecticidal activity are warranted. This study evaluated the efficacy of the high-throughput screening system (HITSS) for measuring the behavior-modifying actions of Brazilian Cerrado plant extracts, oils, and other compounds against Aedes aegypti. Different concentrations were evaluated, with 8 of 34 samples tested demonstrating either contact irritancy, spatial repellency, or attractiveness. We concluded several natural products screened in this study showed promise for use against mosquito vectors like Ae. aegypti, and that the compact modular HITSS assay constitutes a robust tool for measuring the behavioral responses of mosquitoes in the search for novel insecticides derived from natural products.
Asunto(s)
Aedes , Productos Biológicos , Repelentes de Insectos , Insecticidas , Aedes/fisiología , Animales , Femenino , Ensayos Analíticos de Alto Rendimiento , Control de Mosquitos , Mosquitos VectoresRESUMEN
In patients with severe forms of COVID-19, thromboelastometry has been reported to display a hypercoagulant pattern. However, an algorithm to differentiate severe COVID-19 patients from nonsevere patients and healthy controls based on thromboelastometry parameters has not been developed. Forty-one patients over 18 years of age with positive qRT-PCR for SARS-CoV-2 were classified according to the severity of the disease: nonsevere (NS, n = 20) or severe (S, n = 21). A healthy control (HC, n = 9) group was also examined. Blood samples from all participants were tested by extrinsic (EXTEM), intrinsic (INTEM), non-activated (NATEM) and functional assessment of fibrinogen (FIBTEM) assays of thromboelastometry. The thrombodynamic potential index (TPI) was also calculated. Severe COVID-19 patients exhibited a thromboelastometry profile with clear hypercoagulability, which was significantly different from the NS and HC groups. Nonsevere COVID-19 cases showed a trend to thrombotic pole. The NATEM test suggested that nonsevere and severe COVID-19 patients presented endogenous coagulation activation (reduced clotting time and clot formation time). TPI data were significantly different between the NS and S groups. The maximum clot firmness profile obtained by FIBTEM showed moderate/elevated accuracy to differentiate severe patients from NS and HC. A decision tree algorithm based on the FIBTEM-MCF profile was proposed to differentiate S from HC and NS. Thromboelastometric parameters are a useful tool to differentiate the coagulation profile of nonsevere and severe COVID-19 patients for therapeutic intervention purposes.
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Coagulación Sanguínea , COVID-19/sangre , Tromboelastografía , Trombofilia/sangre , Adulto , Anciano , Algoritmos , COVID-19/complicaciones , COVID-19/diagnóstico , Femenino , Humanos , Estudios Longitudinales , Masculino , Persona de Mediana Edad , SARS-CoV-2/aislamiento & purificación , Índice de Severidad de la Enfermedad , Trombofilia/diagnóstico , Trombofilia/etiología , Adulto JovenRESUMEN
Natural products constitute an important source of molecules for product development. However, despite numerous reports of compounds and active extracts from biodiversity, poor and developing countries continue to suffer with endemic diseases caused by arboviral vectors, including dengue, Zika, chikungunya and urban yellow fever. Vector control remains the most efficient disease prevention strategy. Wide and prolonged use of insecticides has resulted in vector resistance, making the search for new chemical prototypes imperative. Considering the potential of natural products chemistry for developing natural products-based products, including insecticides, this contribution discusses the general aspects and specific characteristics involved in the development of drug leads for vector control. Throughout this work, we highlight the obstacles that need to be overcome in order for natural products compounds to be considered promising prototypes. Moreover, we analyze the bottlenecks that should be addressed, together with potential strategies, to rationalize and improve the efficiency of the drug discovery process.
RESUMEN
Plants have historically been a rich source of successful anticancer drugs and chemotherapeutic agents, with research indicating that this trend will continue. In this contribution, we performed high-throughput cytotoxicity screening of 702 extracts from 95 plant species, representing 40 families of the Brazilian Cerrado biome. Activity was investigated against the following cancer cell lines: colon (Colo205 and Km12), renal (A498 and U031), liver (HEP3B and SKHEP), and osteosarcoma (MG63 and MG63.3). Dose-response tests were conducted with 44 of the most active extracts, with 22 demonstrating IC50 values ranging from <1.3 to 20 µg/mL. A molecular networking strategy was formulated using the Global Natural Product Social Molecular Networking (GNPS) platform to visualize, analyze, and annotate the compounds present in 17 extracts active against NCI-60 cell lines. Significant cytotoxic activity was found for Salacia crassifolia, Salacia elliptica, Simarouba versicolor, Diospyros hispida, Schinus terebinthifolia, Casearia sylvestris var. lingua, Magonia pubescens, and Rapanea guianensis. Molecular networking resulted in the annotation of 27 compounds. This strategy provided an initial overview of a complex and diverse natural product data set, yielded a large amount of chemical information, identified patterns and known compounds, and assisted in defining priorities for further studies.
Asunto(s)
Ecosistema , Ensayos Analíticos de Alto Rendimiento , Extractos Vegetales/análisis , Extractos Vegetales/farmacología , Brasil , Línea Celular Tumoral , Geografía , Humanos , Concentración 50 Inhibidora , SolventesRESUMEN
BACKGROUND: Plant extracts and isolated compounds are known for their insecticidal activity. The Aedes aegypti mosquito has a significant medical impact as it transmits a number of arboviruses and is able to develop resistance to the commercially available insecticides. This study investigates larvicidal compounds isolated from Machaerium acutifolium, designated by the Brazilian Forest Service as a sustainable species. RESULTS: A M. acutifolium trunk ethyl acetate extract was fractionated using chromatographic methods with full structural elucidation by mass spectrometry (MS), nuclear magnetic resonance and specific rotation analyses revealing: one new 3-arylcoumarin derivative 1; two flavonoids 2 and 3; a trans-stilbene 4, and an unprecedented natural indene 5. The larvicidal activity against Ae. aegypti after 24 h exposure was: crude extract (median lethal dose, LC50 205 mg L-1 ), fraction C (LC50 27 mg L-1 ) and 5 (LC50 24 mg L-1 ). CONCLUSION: A M. acutifolium extract showed larvicidal activity, which increased with prolonged exposure, demonstrating LC50 75 mg L-1 after 72 h. Although the flavonoids 2 and 3 and trans-stilbene 4 were deemed inactive according to the adopted mortality limit, additional tests revealed their ability to cause 65% Ae. aegypti larvae mortality, suggesting they could contribute to the larvicidal activity. Compound 5, identified by liquid chromatography-MS, was over eight-fold more toxic to larvae than the crude extract after 24 h. Therefore, 5 constitutes a structural model for new prototypes to control Ae. aegypti. These data reinforce the potential of natural products as a source of commercial alternatives for vector control strategies, respecting both sustainability and eco-friendly principles. © 2020 Society of Chemical Industry.
Asunto(s)
Aedes , Fabaceae , Insecticidas , Animales , Brasil , Insecticidas/análisis , Larva , Mosquitos Vectores , Extractos Vegetales/farmacología , Hojas de la Planta/químicaRESUMEN
Research on antifungal compounds from the durable wood from French Guiana Amazonian forest trees highlights the correlation between the activity of their extracts against wood-rotting fungi and human pathogens. The fractionation of an ethyl acetate extract of Sextonia rubra wood led to the isolation of rubrenolide (1) and rubrynolide (2). The potential of compounds 1 and 2 is described through the evaluation of their activity against 16 pathogenic fungi and their cytotoxicity toward NIH-3T3 mammalian fibroblast cells.
Asunto(s)
Acetales/aislamiento & purificación , Acetales/farmacología , Alquenos/aislamiento & purificación , Alquenos/farmacología , Alquinos/aislamiento & purificación , Alquinos/farmacología , Antifúngicos/aislamiento & purificación , Antifúngicos/farmacología , Basidiomycota/química , Polyporaceae/química , Árboles/microbiología , Acetales/química , Alquenos/química , Alquinos/química , Animales , Antifúngicos/química , Guyana Francesa , Lauraceae/microbiología , Ratones , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Células 3T3 NIH , Tallos de la Planta/química , Madera/microbiologíaRESUMEN
Leishmaniasis is a disease impacting public health worldwide due to its high incidence, morbidity and mortality. Available treatments are costly, lengthy and toxic, not to mention the problem of parasite resistance. The development of alternative treatments is warranted and natural products demonstrate promising activity. This study investigated the activity of Connarus suberosus extracts and compounds against Leishmania species. Several C. suberosus extracts were tested against L. amazonensis promastigotes. Active and inactive extracts were analyzed by UHPLC-MS and data evaluated using a metabolomics platform, revealing an unknown neoflavonoid (connarin, 3), isolated together with the pterocarpans: hemileiocarpin (1) and leiocarpin (2). The aforementioned compounds (1-3), together with the benzoquinones: rapanone (4), embelin (5) and suberonone (6) previously isolated by our group from the same species, were tested against: (i) L. amazonensis and L. infantum promastigotes, and (ii) L. amazonensis intracellular amastigotes, with the most active compound (3) also tested against L. infantum amastigotes. Cytotoxicity against murine peritoneal macrophages was also investigated. Compounds 2 and 3 presented an IC50 33.8 µM and 11.4 µM for L. amazonensis promastigotes; and 44.3 µM and 13.3 µM for L. infantum promastigotes, respectively. For L. amazonensis amastigotes, the IC50 of 2 was 20.4 µM with a selectivity index (SI) of 5.7, while the IC50 of 3 was 2.9 µM with an SI of 6.3. For L. infantum amastigotes, the IC50 of 3 was 7.7 µM. Compounds 2 and 3 presented activity comparable with the miltefosine positive control, with compound 3 found to be 2-4 times more active than the positive control, depending on the Leishmania species and form. The extracts and isolated compounds showed moderate toxicity against macrophages. Compounds 2 and 3 altered the mitochondrial membrane potential (ΔΨm) and neutral lipid body accumulation, while 2 also impacted plasma membrane permeabilization, culminating in cellular disorder and parasite death. Transmission electron microscopy of L. amazonensis promastigotes treated with compound 3 confirmed the presence of lipid bodies. Leiocarpin (2) and connarin (3) demonstrated antileishmanial activity. This study provides knowledge of natural products with antileishmanial activity, paving the way for prototype development to fight this neglected tropical disease.
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Connaraceae/química , Flavonoides/farmacología , Metabolómica/métodos , Extractos Vegetales/farmacología , Animales , Antiprotozoarios/química , Antiprotozoarios/aislamiento & purificación , Antiprotozoarios/farmacología , Supervivencia Celular , Cromatografía Líquida de Alta Presión , Flavonoides/química , Flavonoides/aislamiento & purificación , Leishmania mexicana/efectos de los fármacos , Leishmania mexicana/crecimiento & desarrollo , Macrófagos Peritoneales/citología , Macrófagos Peritoneales/efectos de los fármacos , Macrófagos Peritoneales/parasitología , Espectrometría de Masas , Ratones , Ratones Endogámicos BALB C , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificaciónRESUMEN
Metabolomics is a powerful tool in the analysis and identification of metabolites responsible for biological properties. Regarding natural product chemistry, it constitutes a potential strategy to streamline the classic and laborious process of isolating natural products, which often involves the re-isolation and identification of known compounds. In this contribution, we establish a mass spectrometry-based metabolomics strategy to discover compounds with larvicidal activity against Aedes aegypti. We analyse the Brazilian plant Annona crassiflora using different platforms to annotate the active compounds in different extracts/fractions of various plant parts. The MetaboAnalyst and GNPS platforms, which consider LC-MS and LC-MS/MS data, respectively, were chosen to identify compounds that differentiate active and inactive samples. Bio-guided isolation was subsequently performed to confirm compound activity. Results proved the capacity of metabolomics to predict metabolite differences between active and inactive samples using LC-MS and LC-MS/MS data. Moreover, we discuss the limitations, possibilities, and strategies to have a broad view of vast data.
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Aedes/efectos de los fármacos , Annona/química , Productos Biológicos/farmacología , Insecticidas/farmacología , Metabolómica/métodos , Extractos Vegetales/farmacología , Animales , Productos Biológicos/análisis , Productos Biológicos/aislamiento & purificación , Cromatografía Liquida/métodos , Insecticidas/análisis , Insecticidas/aislamiento & purificación , Larva/efectos de los fármacos , Metabolismo Secundario , Espectrometría de Masas en Tándem/métodosRESUMEN
Phytochemical-analysis of the ethyl acetate extract of stem wood of Salvertia convallariodora A. St.-Hil. (Vochysiaceae), a Brazilian Cerrado species, led to the isolation and full characterization of three new non-aromatic B-ring flavanones (1-3) as well as the terpene mixture of sericic acid (4), 24-hydroxytormentic acid (5); 24-hydroxytormentic acid glucosyl ester (6), and sericoside (7), all identified for the first time from S. convallariodora. The structures of the new flavanones (1-3) were established from IR, LC-PDA-qTOF-MS, and NMR spectral data, including 2D NMR experiments.
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Flavanonas/química , Myrtales/química , Extractos Vegetales/química , Brasil , Flavanonas/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/aislamiento & purificación , Tallos de la Planta/química , Espectrometría de Masas en TándemRESUMEN
BACKGROUND: Qualea parviflora and Qualea grandiflora (Vochysiaceae), commonly known in Brazil as "pau-terra" and "pau-terrinha," respectively, have been widely used in the treatment of ulcer and gastritis. These therapeutic effects are attributed to various compounds present in the plants, including phenolic compounds such as gallic acid, due to their important antioxidant activity. OBJECTIVE: The aim of the present study was to validate a high performance liquid chromatography with diode array detection (HPLC-DAD) method for the quantitative determination of gallic acid in the stem bark of Q. parviflora and Q. grandiflora hydroalcoholic extracts. MATERIALS AND METHODS: The chromatography analysis was successfully achieved on a Dionex column, Acclaim(®) 120 (250 mm × 4.60 mm, 5 µm) with a gradient elution of water and methanol at a flow rate of 0.8 mL/min and ultraviolet detection at 280 nm. RESULTS: The validation data, including linearity, precision, specificity, accuracy and robustness of this method demonstrated good reliability and sensitivity. CONCLUSION: The method is able to quantify gallic acid in the stem bark of both species. What is more, the chromatographic peaks showed good resolution and there are also the advantages of easy sample preparation and a short time between each injection.