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1.
Nat Prod Res ; 38(4): 679-684, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-36905171

RESUMEN

Neglected tropical diseases are significant causes of death and temporary or permanent disability for millions living in developing countries. Unfortunately, there is no effective treatment for these diseases. Thus, this work aimed to conduct a chemical analysis using HPLC/UV and GC/MS to identify the major constituents of the hydroalcoholic extracts of Capsicum frutescens and Capsicum baccatum fruits, evaluating these extracts and their constituents' schistosomicidal, leishmanicidal and trypanocidal activities. The results obtained for the extracts of C. frutescens are better when compared to those obtained for C. baccatum, which can be related to the different concentrations of capsaicin (1) present in the extracts. The lysis of trypomastigote forms results for capsaicin (1) led to a significant value of IC50 = 6.23 µM. Thus, the results point to capsaicin (1) as a possible active constituent in these extracts.


Asunto(s)
Capsicum , Capsaicina/farmacología , Cromatografía Líquida de Alta Presión , Extractos Vegetales/farmacología , Extractos Vegetales/análisis , Alcanfor/análisis , Mentol/análisis , Frutas/química
2.
Front Plant Sci ; 14: 1324680, 2023.
Artículo en Inglés | MEDLINE | ID: mdl-38143582

RESUMEN

We report the chemical composition of the crude leaf extracts obtained from Stizophyllum perforatum (Cham.) Miers (Bignoniaceae), a simple high-performance liquid chromatography-diode array detection (HPLC-DAD) method based on mangiferin as an internal standard to quantify verbascoside, and the verbascoside acute oral toxicity and antileishmanial activity. HPLC-high-resolution mass spectrometry-DAD (HPLC-HRMS-DAD) analyses of the crude ethanol S. perforatum leaf extracts (CE-1 and CE-2) revealed that verbascoside was the major constituent in both extracts. CE-1 was purified, and verbascoside and casticin, among other compounds, were isolated. The developed HPLC-DAD method was validated and met the required standards. Investigation of the CE-2 acute toxicity indicated a lethal dose (LD50) greater than 2,000 mg/kg of body weight. Both CE-1 and CE-2 exhibited antileishmanial activity. The isolated compounds, verbascoside and casticin, also displayed antileishmanial activity with effective concentrations (IC50) of 6.23 and 24.20 µM against promastigote forms and 3.71 and 18.97 µM against amastigote forms of Leishmania amazonensis, respectively, but they were not cytotoxic to J774A.1 macrophages. Scanning electron microscopy of the L. amazonensis promastigotes showed that the parasites became more rounded and that their plasma membrane was altered in the presence of verbascoside. Additionally, transmission electron microscopy demonstrated that vacuoles emerged, lipids accumulated, kinetoplast size increased, and interstitial extravasation occurred in L. amazonensis promastigotes exposed to verbascoside. These findings suggest that S. perforatum is a promising candidate for further in vivo investigations against L. amazonensis.

3.
Nat Prod Res ; : 1-7, 2023 Jun 16.
Artículo en Inglés | MEDLINE | ID: mdl-37323030

RESUMEN

Applying elicitors in plants growing under natural conditions change the metabolic content of volatile compounds extracted from their tissues. Here, we have investigated how abiotic elicitors influence the volatile composition of the ethyl acetate extract of Anacardium othonianum seedlings propagated in vitro and ex-vitro cultures. Abiotic factors such as salicylic acid, silver nitrate, light quality, and cultivation mode affected the composition of volatile compounds in ethyl acetate extract of A. othonianum leaves seedlings. GC/MS analysis demonstrated that α-tocopherol was the main metabolite in cultures added with chemical elicitors, reaching 22.48 ± 4.06% in the case of 30 µM salicylic acid. Higher concentrations of salicylic acid decreased the amount of α-tocopherol. The addition of AgNO3 had a linear effect on α-tocopherol. Thus, the production of this metabolite indicates that salicylic acid and AgNO3 elicitors positively affect α-tocopherol production at specific concentrations helping to understand how plant culture can be better manipulated.

4.
Braz. J. Pharm. Sci. (Online) ; 58: e20278, 2022. tab, graf
Artículo en Inglés | LILACS | ID: biblio-1403705

RESUMEN

Abstract Adenocalymma axillarum (K.Schum.) L.G. Lohmann is a liana belonging to the family Bignoniaceae. In traditional medicine, the genus Adenocalymma is used to treat fever, skin ailments, and body, joint, and facial muscle pains, and it is also applied as cosmetic. Biological assays conducted with the A. axillarum crude leaf ethanol extract have indicated leishmanicidal activity and absence of cytotoxicity. This study aimed to analyze the A. axillarum leaf ethanol crude extract by high-performance liquid chromatography-high-resolution mass spectrometry- diode array detector (HPLC-HRMS-DAD) and to evaluate the leishmanicidal and cytotoxic activities of this crude extract, its fractions, and isolated compounds. HPLC-HRMS-DAD analysis of this extract revealed that it consisted mainly of flavonoids, with nine major compounds. Extract purification yielded 4-hydroxy-N-methylproline, 6-β-hydroxyipolamiide, quercetin-3-O-robinobioside, hyperin, isorhamnetin-3-O-robinobioside, and 3'-O-methylhyperin, which were identified by Nuclear Magnetic Resonance. The isolated compounds were inactive against Leishmania amazonensis promastigotes and human lung fibroblast cells.


Asunto(s)
Espectrometría de Masas/métodos , Espectroscopía de Resonancia Magnética/métodos , Cromatografía Líquida de Alta Presión/métodos , Hojas de la Planta/clasificación , Mezclas Complejas/química , Leishmania/clasificación , Bignoniaceae/clasificación , Articulaciones/anomalías
5.
Arch Microbiol ; 203(7): 4313-4318, 2021 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-34110481

RESUMEN

The genus Absidia is widely used in the biotransformation of different classes of natural products. This study evaluates the ability of the Absidia coerulea 3A9 marine derived strain isolated from the ascidian Distaplia stilyfera to perform biotransformations by conducting assays with (-)-cubebin, as substrate. The experiment was optimized using the experimental design proposed by Plackett-Burman for seven factors and eight experiments, to establish the biotransformation conditions that would allow maximum production of biotransformed dibenzylbutyrolactone (-)-hinokinin. An analytical method based on Reverse-Phase-High Performance Liquid Chromatography (RP-HPLC) was developed to quantify the fungal biotransformation product. The factor that influenced the (-)-hinokinin peak area the most positively was the percentage of seawater (%seawater) given that its %relative standard deviation (%RSD) showed a 32.92% deviation from the real value.


Asunto(s)
4-Butirolactona/análogos & derivados , Absidia , Benzodioxoles , Lignanos , 4-Butirolactona/síntesis química , Organismos Acuáticos/metabolismo , Benzodioxoles/síntesis química , Biotransformación , Lignanos/síntesis química , Lignanos/química , Lignanos/metabolismo , Agua de Mar/química
6.
J Toxicol Environ Health A ; 84(14): 582-592, 2021 07 18.
Artículo en Inglés | MEDLINE | ID: mdl-33825664

RESUMEN

Styrax camporum Pohl, a typical species from the Brazilian cerrado, commonly known as "benjoeiro", is used to treat gastroduodenal diseases. In previous studies carried out by our research group, hydroalcoholic extract of S. camporum stems (SCHE) exhibited antigenotoxic and antiproliferative effects. For a comparative analysis of the chemopreventive effect of SCHE, the aim of this study was to investigate the influence of SCHE against carcinogen 1,2-dimethylhydrazine (DMH)-induced DNA damage and pre-neoplastic lesions in Wistar rat colon. Animals were treated orally with SCHE at 250, 500 or 1000 mg/kg body weight in conjunction with a subcutaneous injection of DMH. DNA damage was assessed using the comet assay while tpre-neoplastic lesions by aberrant crypt foci (ACF) assay. The following hepatic oxidative stress markers were determined including activities of catalase (CAT) and glutathione S-transferase (GST) as well as levels of reduced glutathione (GSH) and malondialdehyde (MDA). Treatment with SCHE was not genotoxic or carcinogenic at the highest dose tested (1000 mg/kg b.w.). The extract effectively inhibited DNA damage and pre-neoplastic lesions induced by DMH administration at all concentrations tested. Measurement of CAT, and GST activities and levels of GSH showed that SCHE did not reduce oxidative processes. In contrast, treatment with SCHE (1000 mg/kg b.w.) decreased liver MDA levels. Taken together, these findings suggested the chemopreventive effect attributed to SCHE in colon carcinogenesis, may be related to its capacity to inhibit DNA damage as well as an antioxidant action associated with its chemical constituents egonol and homoegonol.


Asunto(s)
Anticarcinógenos/farmacología , Daño del ADN/efectos de los fármacos , Estrés Oxidativo/efectos de los fármacos , Extractos Vegetales/farmacología , Sustancias Protectoras/farmacología , Styrax/química , Animales , Carcinógenos/farmacología , Carcinógenos/toxicidad , Neoplasias del Colon/tratamiento farmacológico , Neoplasias del Colon/patología , Ensayo Cometa , Dimetilhidrazinas/farmacología , Dimetilhidrazinas/toxicidad , Masculino , Extractos Vegetales/química , Tallos de la Planta/química , Sustancias Protectoras/química , Ratas , Ratas Wistar
7.
Plants (Basel) ; 8(11)2019 Nov 11.
Artículo en Inglés | MEDLINE | ID: mdl-31718037

RESUMEN

Candidiasis therapy, especially for candidiasis caused by Candida non-albicans species, is limited by the relatively reduced number of antifungal drugs and the emergence of antifungal tolerance. This study evaluates the anticandidal activity of 41 plant-derived products against Candida species, in both planktonic and biofilm cells. This study also evaluates the toxicity and the therapeutic action of the most active compounds by using the Caenorhabditis elegans-Candida model. The planktonic cells were cultured with various concentrations of the tested agents. The Cupressus sempervirens, Citrus limon, and Litsea cubeba essential oils as well as gallic acid were the most active anticandidal compounds. Candida cell re-growth after treatment with these agents for 48 h demonstrated that the L. cubeba essential oil and gallic acid displayed fungistatic activity, whereas the C. limon and C. sempervirens essential oils exhibited fungicidal activity. The C. sempervirens essential oil was not toxic and increased the survival of C. elegans worms infected with C. glabrata or C. orthopsilosis. All the plant-derived products assayed at 250 µg/mL affected C. krusei biofilms. The tested plant-derived products proved to be potential therapeutic agents against Candida, especially Candida non-albicans species, and should be considered when developing new anticandidal agents.

8.
Ciênc. rural (Online) ; 49(2): e20180278, 2019. tab
Artículo en Inglés | LILACS | ID: biblio-1045293

RESUMEN

ABSTRACT: Hyptis marrubioides (Lamiaceae) is a medicinal plant that is native from Brazilian Cerrado. In vitro propagation techniques make use of elicitors to alter metabolic pathways, affecting how molecules are produced both qualitatively and quantitatively. This research aimed to evaluate how abiotic elicitors salicylic acid (SA) and silver nitrate (SN) at concentrations of 30µM or 60µM influence Hyptis marrubioides seedling growth by two different in vitro culture methods. The rutin content was quantified by HPLC-DAD. Compared to an untreated culture, the H. marrubioides methanolic extracts cultured in MS medium for 10 days followed by culture in MS medium containing SN (30µM) for 20 days had 1.28 times higher rutin content. In a second experiment, seedlings were cultured in MS medium for 20 days, and then the desired elicitor was added to the culture and allowed to remain in contact with the medium for three and six days. SA (30µM) gave the best results: rutin production was 16.56-foldhigher than the control after six days. SN (30µM) increased the rutin content by 1.17-fold. At the two concentrations evaluated during the elicitation experiments, neither SA nor SN altered the growth parameters shoot length, leaf number, and fresh and dry weight of H. marrubioides seedlings grown in vitro as compared to the control. Based on these results, the abiotic elicitors SA and SN successfully provide Hyptis marrubioides with increased rutin content in vitro.


RESUMO: Hyptis marrubioides (Lamiaceae) é uma planta medicinal nativa do Cerrado brasileiro. Técnicas de propagação in vitro fazem uso de elicitores para alterar as vias metabólicas, afetando a produção de moléculas qualitativa e quantitativamente. Este trabalho teve como objetivo avaliar como os elicitores abióticos ácido salicílico (SA) e nitrato de prata (SN) nas concentrações de 30µM ou 60µM influenciam no crescimento de plântulas de Hyptis marrubioides por dois diferentes métodos de cultivo in vitro. O teor de rutina foi quantificado por CLAE-DAD. Em comparação com uma cultura não tratada, os extratos metanólicos de H. marrubioides cultivados em meio MS por 10 dias, seguidos de cultura em meio MS contendo SN (30µM) por 20 dias, apresentaram 1,28 vezes maior teor de rutina. Em um segundo experimento, as plântulas foram cultivadas em meio MS por 20 dias, e então o elicitor desejado foi adicionado à cultura e deixado em contato com o meio por três e seis dias. SA (30µM) forneceu os melhores resultados na produção de rutina, sendo 16,56 vezes maior do que o controle após seis dias. SN (30µM) aumentou o teor de rutina em 1,17 vezes. Nas duas concentrações avaliadas durante os experimentos de elicitação, nem SA nem SN alteraram os parâmetros de crescimento, como comprimento da parte aérea, número de folhas ou peso fresco e seco das plântulas de H. marrubioides cultivadas in vitro em relação ao controle. Com base nestes resultados, os elicitores abióticos SA e SN forneceram com sucesso Hyptis marrubioides in vitro com maior conteúdo de rutina.

9.
Biol Pharm Bull ; 39(11): 1839-1845, 2016.
Artículo en Inglés | MEDLINE | ID: mdl-27803455

RESUMEN

This study evaluated the influence of Styrax camporum stems hydroalcoholic extract (SCHE) and of chemical markers of the genus, egonol (EG) and homoegonol (HE), on DNA damage induced in V79 cells by mutagens with different mechanisms of action. These natural products were combined with different mutagens [methyl methanesulfonate (MMS), hydrogen peroxide (H2O2), (S)-(+)-camptothecin (CPT), and etoposide (VP-16)] to evaluate the modulatory effect on DNA damage. The results showed that SCHE was genotoxic at the highest concentration tested (60 µg/mL). Treatment with EG or HE alone induced no genotoxic effect, while genotoxic activity was observed when the two compounds were combined. The SCHE extract was able to reduce the frequency of micronuclei induced by H2O2 and VP-16. Similar results were observed when the cell cultures were treated with EG and/or HE plus VP-16. In contrast, the highest concentration (40 µg/mL) SCHE potentiated DNA damage induced by VP-16. Neolignan EG alone or combined with HE also potentiated H2O2-induced genotoxicity. However, these natural products did not influence the frequency of DNA damage induced by MMS or CPT. Therefore, the influence of SCHE and of chemical markers (EG and HE) of the genus on the induction of DNA damage depends on the concentration tested and on the mutagen used.


Asunto(s)
Anisoles/farmacología , Benzofuranos/farmacología , Daño del ADN/efectos de los fármacos , Mutágenos/toxicidad , Extractos Vegetales/farmacología , Styrax , Animales , Anisoles/toxicidad , Benzofuranos/toxicidad , Camptotecina/toxicidad , Línea Celular , Ensayo Cometa , Cricetulus , Etopósido/toxicidad , Peróxido de Hidrógeno/toxicidad , Metilmetanosulfonato/toxicidad , Pruebas de Micronúcleos , Extractos Vegetales/toxicidad
10.
Cytotechnology ; 68(4): 1597-602, 2016 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-25795470

RESUMEN

The benzofuran lignans egonol and homoegonol are found in all species of the genus Styrax. Since natural products are important sources of new anticancer drugs, this study evaluated the cytotoxic activity of a hydroalcoholic extract of the stems of S. camporum (SCHE) and their chemical markers, egonol (EG) and homoegonol (HE), against different tumor cell lines (B16F10, MCF-7, HeLa, HepG2, and MO59J). A normal human cell line (GM07492A) was included. Cytotoxic activity was evaluated at different treatment times (24, 48 and 72 h) using the XTT assay. More effective results were observed after 72 h of treatment. The lowest IC50 values were found for the HepG2 cell line, ranging from 11.2 to 55.0 µg/mL. The combination of EG and HE exerted higher cytotoxic activity than SCHE or treatment with either lignan alone, with the lowest IC50 (13.31 µg/mL) being observed for the MCF-7 line. Furthermore, treatment with these lignans was significantly more cytotoxic for some tumor cell lines compared to the normal cell line, GM07492A, indicating selectivity. These results suggest that these lignans may be used to treat cancer without affecting normal cells.

11.
Mar Drugs ; 12(6): 3608-33, 2014 Jun 12.
Artículo en Inglés | MEDLINE | ID: mdl-24927227

RESUMEN

Ascidians of the genus Aplidium are recognized as an important source of chemical diversity and bioactive natural products. Among the compounds produced by this genus are non-nitrogenous metabolites, mainly prenylated quinones and hydroquinones. This review discusses the isolation, structural elucidation, and biological activities of quinones, hydroquinones, rossinones, longithorones, longithorols, floresolides, scabellones, conicaquinones, aplidinones, thiaplidiaquinones, and conithiaquinones. A compilation of the 13C-NMR spectral data of these compounds is also presented.


Asunto(s)
Hidroquinonas/aislamiento & purificación , Quinonas/aislamiento & purificación , Urocordados/metabolismo , Animales , Productos Biológicos/química , Productos Biológicos/aislamiento & purificación , Productos Biológicos/farmacología , Espectroscopía de Resonancia Magnética con Carbono-13 , Humanos , Hidroquinonas/química , Hidroquinonas/farmacología , Quinonas/química , Quinonas/farmacología
12.
Planta Med ; 79(17): 1653-5, 2013 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-24288276

RESUMEN

Protozoans of the trypanosomatid family cause the neglected tropical diseases leishmaniasis and trypanosomiasis, for which few drugs are available. In this context our group has recently reported that the essential oil obtained by steam distillation of the fruits of Piper cubeba is active against Schistosoma mansoni. Therefore, we have investigated the in vitro effects of the essential oil against the trypomastigote and amastigote forms of Trypanosoma cruzi isolated from an LLCMK2 cell line culture and the promastigote forms of Leishmania amazonensis. The in vitro activity of the essential oil against trypomastigotes of T. cruzi increased upon rising concentrations, giving IC50 values of 45.5 and 87.9 µg ·â€ŠmL⁻¹ against trypomastigotes and amastigotes, respectively. The essential oil was not active against L. amazonensis, since it displayed lyses of only 24 % at 400 µg ·â€ŠmL⁻¹, and an IC50 of 326.5 µg ·â€ŠmL⁻¹. Therefore, the essential oil should be further investigated to determine the compounds responsible for the observed activities, as well as its mechanism of action.


Asunto(s)
Antiparasitarios/farmacología , Leishmania/efectos de los fármacos , Aceites Volátiles/farmacología , Piper/química , Extractos Vegetales/farmacología , Trypanosoma cruzi/efectos de los fármacos , Línea Celular , Frutas/química , Concentración 50 Inhibidora , Leishmaniasis/microbiología , Estadios del Ciclo de Vida , Macrófagos , Pruebas de Sensibilidad Parasitaria
13.
Braz. j. pharm. sci ; 49(4): 653-658, Oct.-Dec. 2013. ilus, tab
Artículo en Inglés | LILACS | ID: lil-704096

RESUMEN

The antibacterial activity of the compounds egonol (1) and homoegonol (2), of the crude ethanolic extract of Styrax pohlii (Styracaceae) aerial parts (EE), and of its n-hexane (HF), EtOAc (EF), n-BuOH (BF), and hydromethanolic (HMF) fractions was evaluated against the following microorganisms: Streptococcus pneumoniae (ATCC 6305), S. pyogenes (ATCC 19615), Haemophilus influenzae (ATCC 10211), Pseudomonas aeruginosa (ATCC 27853), and Klebsiella pneumoniae (ATCC 10031). The broth microdilution method was used for determination of the minimum inhibitory concentration (MIC) during preliminary evaluation of antibacterial activity. The EE yielded MIC values of 400 µg/mL for S. pneumoniae and P. aeruginosa and 300 µg/mL for H. influenzae. The HF and EF fractions exhibited enhanced antibacterial activity, with MIC values of 200 µg/mL against S. pneumoniae, but only EF displayed activity against H. influenzae (MIC 200 µg/mL). The best MIC value with compounds 1 and 2 (400 µg/mL) was obtained for (1) against S. pneumoniae and P. aeruginosa. Therefore, 1 exhibited weak antibacterial activity against these standard strains.


As atividades antimicrobianas das substâncias egonol (1) e homoegonol (2), do extrato etanólico das partes aéreas de Styrax pohlii (Styracaceae) (EE), bem como das frações n-hexano (HF), AcOEt (EF), n-BuOH (BF) e hidrometanólica (HMF) foram avaliadas frente aos seguintes microorganismos: Streptococcus pneumoniae (ATCC 6305), S. pyogenes (ATCC 19615), Haemophilus influenzae (ATCC 10211), Pseudomonas aeruginosa (ATCC 27853) e Klebsiella pneumoniae (ATCC 10031). O método de microdiluição em caldo foi utilizado para a determinação da concentração inibitória mínima (CIM) na avaliação preliminar da atividade antimicrobiana. EE mostrou valores de CIM de 400 µg/mL para S. pneumoniae e P. aeruginosa, e 300 µg/mL para H. influenzae. As frações HF e EF apresentaram melhora na atividade antimicrobiana, com valores de CIM de 200 µg/mL frente S. pneumoniae, mas apenas EF apresentou ação contra H. influenzae (200 µg/mL). Em relação às substâncias 1 e 2, o melhor valor de CIM (400 µg/mL) foi obtido por 1 frente a S. pneumoniae e P. aeruginosa, que exibiu fraca atividade antimicrobiana contra estas cepas padrões.


Asunto(s)
Styracaceae/clasificación , Styrax/clasificación , Bioensayo/métodos , Productos Biológicos/análisis
14.
Planta Med ; 78(18): 1899-905, 2012 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-23254694

RESUMEN

Styrax camporum Pohl is a tall shrub or a tree with small white flowers, which grows in the states of São Paulo and Minas Gerais and is popularly used for the treatment of gastroduodenal diseases. Considering this last fact, the aim of this study was to evaluate the genotoxic potential of S. camporum hydroalcoholic extract and its influence on genotoxicity induced by doxorubicin and methyl methanesulfonate in Swiss mice using the micronucleus and comet assays, respectively. The animals were treated by gavage with different doses of the extract (250, 500, and 1000 mg/kg body weight). For antigenotoxicity assessment, different doses of the S. camporum extract were administered simultaneously with doxorubicin (micronucleus test; 15 mg/kg) and methanesulfonate (comet assay; 40 mg/kg). The results showed that the S. camporum extract itself was not genotoxic in the mouse micronucleus or comet assay. The number of micronucleated polychromatic erythrocytes was significantly lower in animals treated with the S. camporum extract and doxorubicin when compared to animals treated only with doxorubicin. In the comet assay, the S. camporum extract, at the doses tested, significantly reduced the extent of DNA damage in liver cells induced by methanesulfonate. The putative activity of the active compounds of S. camporum extract may explain the effect of this plant on genotoxicity induced by doxorubicin and methanesulfonate.


Asunto(s)
Antimutagênicos/farmacología , Daño del ADN/efectos de los fármacos , Doxorrubicina/antagonistas & inhibidores , Metilmetanosulfonato/antagonistas & inhibidores , Micronúcleos con Defecto Cromosómico/efectos de los fármacos , Extractos Vegetales/farmacología , Styrax/química , Animales , Ensayo Cometa , Relación Dosis-Respuesta a Droga , Doxorrubicina/toxicidad , Liposomas , Masculino , Metilmetanosulfonato/toxicidad , Ratones , Pruebas de Micronúcleos , Tallos de la Planta/química
15.
Artículo en Inglés | MEDLINE | ID: mdl-22924053

RESUMEN

Miconia langsdorffii Cogn. (Melastomataceae), Roupala montana Aubl. (Proteaceae), Struthanthus syringifolius (Mart.) (Loranthaceae), and Schefflera vinosa (Cham. & Schltdl.) Frodin (Araliaceae) are plant species from the Brazilian Cerrado whose schistosomicidal potential has not yet been described. The crude extracts, fractions, the triterpenes betulin, oleanolic acid, ursolic acid and the flavonoids quercetin 3-O-ß-D-rhamnoside, quercetin 3-O-ß-D-glucoside, quercetin 3-O-ß-D-glucopyranosyl-(1-2)-α-L-rhamnopyranoside and isorhamnetin 3-O-ß-D-glucopyranosyl-(1-2)-α-L-rhamnopyranoside were evaluated in vitro against Schistosoma mansoni adult worms and the bioactive n-hexane fractions of the mentioned species were also analyzed by GC-MS. Betulin was able to cause worm death percentage values of 25% after 120 h (at 100 µM), and 25% and 50% after 24 and 120 h (at 200 µM), respectively; besides the flavonoid quercetin 3-O-ß-D-rhamnoside promoted 25% of death of the parasites at 100 µM. Farther the flavonoids quercetin 3-O-ß-D-glucoside and quercetin 3-O-ß-D-rhamnoside at 100 µM exhibited significantly reduction in motor activity, 75% and 87.5%, respectively. Biological results indicated that crude extracts of R. montana, S. vinosa, and M. langsdorffii and some n-hexane and EtOAc fractions of this species were able to induce worm death to some extent. The results suggest that lupane-type triterpenes and flavonoid monoglycosides should be considered for further antiparasites studies.

16.
Pharm Biol ; 50(7): 925-9, 2012 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-22480261

RESUMEN

CONTEXT: Schistosomiasis is a major health problem worldwide. Thus, the search for new schistosomicidal agents from natural sources can provide prototypes for drug discovery. OBJECTIVE: The present study investigated the chemical composition of the EtOAc fractions of Styrax pohlii Pohl (Styracaceae) (EF-SP) aerial parts and S. camporum A. DC. leaves (EF-SC), as well as schistosomicidal activities against Schistosoma mansoni adult worms, which have not yet been studied. MATERIALS AND METHODS: The crude ethanol extracts of S. camporum leaves and S. pohlii aerial parts (EE-SC and EE-SP) were partitioned with n-hexane, EtOAc, and n-BuOH. The EtOAc fractions were purified by preparative HPLC. The crude extracts, EtOAc fractions and pure compounds were tested against S. mansoni adult worms in vitro. RESULTS: The purification procedure resulted in the isolation of kaempferol-3-O-(2'',4''-di-O-(E)-p-coumaroyl)-ß-d-glucopyranoside (1), kaempferol-3-O-(2'',6''-di-O-(E)-p-coumaroyl)-ß-d-glucopyranoside (2), quercetin (3), and kaempferol (4). The bioassay results indicated that EE-SC, EF-SC, EF-SP, and compounds 2 and 4 are able to separate coupled S. mansoni adult worms. Additionally, EE-SC, EF-SP, and compound 4 killed the adult schistosomes in vitro at 100 µg/mL and 100 µM. DISCUSSION AND CONCLUSION: This is the first time that the presence of compounds 1-2 in S. pohlii and 3-4 in S. camporum has been reported. Additionally, biological results indicated that S. pohlii and S. camporum have great potential as a source of active compounds.


Asunto(s)
Flavonoides/farmacología , Extractos Vegetales/farmacología , Schistosoma mansoni/efectos de los fármacos , Esquistosomicidas/farmacología , Styrax , Animales , Evaluación Preclínica de Medicamentos/métodos , Flavonoides/aislamiento & purificación , Ratones , Ratones Endogámicos BALB C , Extractos Vegetales/aislamiento & purificación , Schistosoma mansoni/fisiología , Esquistosomicidas/aislamiento & purificación , Especificidad de la Especie
17.
Mar Drugs ; 8(5): 1526-49, 2010 Apr 28.
Artículo en Inglés | MEDLINE | ID: mdl-20559487

RESUMEN

This review discusses the isolation, structural elucidation, and biological activities of halogenated indole alkaloids obtained from marine invertebrates. Meridianins and related compounds (variolins, psammopemmins, and aplicyanins), as well as aplysinopsins and leptoclinidamines, are focused on. A compilation of the (13)C-NMR spectral data of these selected natural indole alkaloids is also provided.


Asunto(s)
Alcaloides Indólicos/química , Alcaloides Indólicos/aislamiento & purificación , Invertebrados/metabolismo , Animales , Halogenación , Humanos , Alcaloides Indólicos/metabolismo , Alcaloides Indólicos/farmacología , Biología Marina , Agua de Mar
18.
Chem Pharm Bull (Tokyo) ; 56(5): 723-6, 2008 May.
Artículo en Inglés | MEDLINE | ID: mdl-18451567

RESUMEN

Two new flavone glucosides, nitensosides A and B (1, 2), together with four known compounds, sorbifolin (3), sorbifolin 6-O-beta-glucopyranoside (4), pedalitin (5), and pedalitin 6-O-beta-glucopyranoside (6) were isolated from Pterogyne nitens. Their structures were elucidated from 1D and 2D NMR analysis, as well as by high resolution mass spectrometry. All the isolated flavones were evaluated for their myeloperoxidase (MPO) inhibitory activity. The most active compound, pedalitin, exhibited IC50 value of 3.75 nM on MPO. Additionally, the radical-scavenging capacity of flavones 1-6 was evaluated towards ABTS and DPPH radicals and compared to standard compounds quercetin and Trolox.


Asunto(s)
Inhibidores Enzimáticos/farmacología , Fabaceae/química , Flavonas/farmacología , Depuradores de Radicales Libres/farmacología , Glucósidos/farmacología , Peroxidasa/antagonistas & inhibidores , Benzotiazoles/química , Compuestos de Bifenilo , Flavonas/aislamiento & purificación , Glucósidos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Picratos/química , Hojas de la Planta/química , Ácidos Sulfónicos/química
19.
J Nat Prod ; 66(10): 1384-7, 2003 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-14575443

RESUMEN

Three new C-glucosylxanthones, 2-(2'-O-trans-caffeoyl)-C-beta-d-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (1), 2-(2'-O-trans-cinnamoyl)-C-beta-d-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (2), and 2-(2'-O-trans-coumaroyl)-C-beta-d-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (3), were isolated from the stems of Arrabidaea samydoides, in addition to three known C-glucosylxanthones, mangiferin (4), 2-(2'-O-benzoyl)-C-beta-d-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (5), and muraxanthone (6). Their chemical structures were assigned on the basis of MS and 1D and 2D NMR experiments. Xanthones 1-6 showed moderate free radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as antioxidant activity evidenced by redox properties measured on ElCD-HPLC.


Asunto(s)
Antioxidantes/aislamiento & purificación , Ácidos Cafeicos/aislamiento & purificación , Cinamatos/aislamiento & purificación , Cumarinas/aislamiento & purificación , Glucósidos/aislamiento & purificación , Plantas Medicinales/química , Xantonas/aislamiento & purificación , Antioxidantes/química , Antioxidantes/farmacología , Brasil , Ácidos Cafeicos/química , Ácidos Cafeicos/farmacología , Cromatografía Líquida de Alta Presión , Cinamatos/química , Cinamatos/farmacología , Cumarinas/química , Cumarinas/farmacología , Glucósidos/química , Glucósidos/farmacología , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Oxidación-Reducción , Tallos de la Planta/química , Estereoisomerismo , Xantonas/química , Xantonas/farmacología
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