Abstract Samanea tubulosa Benth. it has been widely used in traditional medicine to treat inflammatory processes. The present study aimed to investigate the antinociceptive effect and mechanism of action of the fractions obtained from the Samanea tubulosa pods in mice. The antinociceptive activity was evaluated in formalin, capsaicin and glutamate tests and the. The possible mechanisms of action involved in the antinociceptive effect of the hexane and ethyl acetate fraction in the opioid system, also the the K + ATP channels and the L-arigine pathways of nitric oxide were evaluated. The chemical characterization analysis revealed in the hexane fraction the presence of triterpenes such as lupenone and lupeol. In the glutamate test, the hexane and ethyl acetate fractions showed antinociceptive activity at the dose of 12.5 and 25 mg kg-1. The antinociception produced by the hexane and ethyl acetate fractions was significantly reversed by naloxone, indicating that the fractions act through the opioid pathway. Antinociceptive response of the ethyl acetate fraction was blocked by glibenclamide, indicating that this fraction acts via the K + ATP channels activation. It is concluded that the fractions under study exert antinociceptive activity possibly related to the opioid route and through K+ ATP channels activation.

Rhinella jimi toads (Stevaux, 2002) belong to the Bufonidae family, are endemic in the Brazilian Northeast and are commonly found during rainy periods. In general, amphibians of this family have in their poisons different metabolites that show a diversity of pharmacological activities. The isolation and identification of these compounds are of great importance, and techniques such as high-performance liquid chromatography coupled to mass spectrometry are widely used for the discovery of novel and known compounds in these poisons. For R. jimi poison, the ethyl acetate and methanolic extracts were obtained and thirty compounds were identified by combining ultra-performance liquid chromatography coupled to mass spectrometry (UPLC-MS) with direct infusion atmospheric pressure chemical ionization mass spectrometry (DI-APCI-MS/MS) and direct infusion electrospray mass spectrometry (DI-ESI-MS/MS) for each extract, respectively. Marinobufagin (2) and marinobufotoxin (19) were the majorities of each extract, respectively. In addition, other bufadienolides mainly present in the ethyl acetate extract, such other bufotoxins, alkaloids and arginine diacid derivatives were identified in the methanol extract. In a cytotoxic assay by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), the extracts and compound 2 demonstrated half-maximal inhibitory concentration (IC50) values better than the positive control doxorubicin, evidencing excellent cytotoxic. This is the most complete study of the chemical composition of R. jimi toad poison and its respective cytotoxic activity, promoting the enrichment of knowledge about this family and species.

In the present work five acetylene derivatives (1-5), including three unknowns (1, 3 and 4), were isolated from seeds of Porcelia macrocarpa (Annonaceae). The structures of isolated compounds were determined as docos-13-yn-21-enoic acid (1), 3-hydroxy-4-methylene-2-(eicos-11’-yn-19’-enyl)but-2-enolide (2), 3-hydroxy-4-methylene-2-(octadec-9’-yn-17’-enyl)but-2-enolide (3), 3-hydroxy-4-methylene-2-(hexadec-7’-yn-15’-enyl)but-2-enolide (4), and (2S,3R,4R)-3-hydroxy-4-methyl-2-(eicos-11’-yn-19’-enyl)butanolide (5) by analysis of nuclear magnetic resonance (NMR) and electrospray ionization high-resolution mass spectrometry (ESI-HRMS) data. Moreover, all isolated compounds demonstrated selectivity towards intracellular amastigotes of Leishmania (L.) infantum, especially 2-4 with 50% inhibitory concentration (IC50) values of 9.2, 10.4 and 11.0 µM, respectively, indicating superior activity of that determined to positive control miltefosine (IC50 of 17.8 µM). Furthermore, these compounds showed higher selectivity index (SI) in comparison with miltefosine. Since related acetylene fatty acid 1 displayed reduced antiparasitic potential (IC50 of 48.5 µM), the obtained results suggested that the γ-lactone plays an important role in the antileishmanial activity. However, 2-4 exhibited cytotoxicity to mammalian NCTC cells (CC50 ca. 80 µM), which could be a result of the presence of a conjugated carbonyl system in the lactone ring, since 5, the only acetogenin that presents the saturated ring, lacked mammalian cytotoxicity (CC50 > 200 µM).

Plants from Fabaceae family have several secondary metabolites and high biological potential. The subfamily Papilionoideae (Fabaceae) has 28 tribes, of which Dalbergieae comprises 49 genera and 1325 species. Isoflavonoids are chemotaxonomic markers of Papilionoideae and have important biological properties. This review describes the isoflavonoids and biological activities from the tribe Dalbergieae (Fabaceae-Papilionoideae) species, in the period of 1945 to 2019. A total of 240 isoflavonoids were found in 69 species and in 15 genera. Formononetin, biochanin A and medicarpin were the most frequent isoflavonoids in this tribe. Dalbergia, Machaerium, Andira and Pterocarpus genera had a high number of species with occurrence of isoflavonoids. A total of 81 isoflavanoids and 46 species showed biological activities. This suggests that more works are necessary to evaluate the potential of this tribe. The present study contributes to the taxonomic classification of genus or species in the family, subfamily or tribe, once the correlation between secondary metabolites and morphological data is an important tool for the classification, phylogeny and evolution of species. This compilation also contributes to extend and update the researched period on the occurrence of isoflavonoids in species of the tribe Dalbergieae, described in the literature in other bibliographic reviews.

Phytochemical investigation of the CHCl3 fraction from EtOH extract of Tocoyena hispidula (Rubiaceae) stem resulted in the isolation and identification of D-(+)-mannitol, lupenone, 3-O-acetyloleanolic acid, lapachol, dimethyl chelidonate, morindolide and four mixtures (M1-M4): M1 (palmitate, margarate, linoleate, oleate e stearate of the multiflorenyl, lupeyl, sitosteryl and stigmasteryl), M2 (lupeol, taraxerol, germanicol, β-amyrin and E-fitol), M3 (campesterol, campestanol, stigmasterol, Δ22-stigmastenol, sitosterol and sitostanol) and M4 (7-ketositosterol and 7-ketostigmasterol). Structural identification of the compounds was performed by analysis 1H and 13C NMR spectra and by GC-MS. Extract, fractions, dimethyl chelidonate and morindolide inhibited the growth of Leishmania major promastigotes, being the CHCl3 (IC50 = 26.25 µg mL-1) and EtOAc (IC50 = 29.77 µg mL-1) fractions the more active.

ABSTRACT Chemical investigation of the leaves of Casearia gossypiosperma Briq., Salicaceae, led to the isolation of two known flavonoids, (+)-taxifolin and quercetin, the leaves of Casearia decandra Jacq. have afforded hydroquinone, the leaves of Casearia rupestris Eichler and Casearia lasiophylla Eichler have afforded a diterpene, (E)-phytol, and the leaves of C. rupestris and Casearia obliqua Spreng. have afforded sitosterol. The twigs of Casearia lasiophylla Eichler led to the isolation of two compounds (+)-pinoresinol, and N-trans-feruloyltyramine, and the twigs of C. obliqua have afforded N-trans-feruloyltyramine, N-trans-cumaroyltyramine, and cinamic acid. This is the first report of the compounds (+)-taxifolin, quercetin, hydroquinone, (+)-pinoresinol and N-trans-cumaroyltyramine from the Casearia genus.

Phytochemical investigation from carnauba (Copernicia prunifera) wax led to the identification of sixteen dammarane-type triterpenes, including thirteen new characterized as: (24R*)-methyldammara-20,25-dien-3α-ol and a mixture of alkyl (24R*)-methyldammar-25-en-20-ol-3β-carboxylates, together with three previously described triterpenes: carnaubadiol, (24R*)-methyldammara-20,25-dien-3β-ol and (24R*)-24-methyldammara-20,25-dien-3-one. Moreover, four fatty alcohols (eicosanol, docosanol, tetracosanol and hexacosanol) as well as four sterols (cholesterol, campesterol, stigmasterol, and sitosterol) were also obtained. These compounds were isolated using classical chromatographic methods and their structures were determined by spectroscopic and chemical methods.

Hybrid magnetite materials are interesting for both biomedical and catalytic applications due to their well-known biocompatibility, as well as their magnetic and electric properties. In this work we prepared Fe3O4 nanoparticles (NPs) coated with tannic acid (TA), a natural polyphenol, through two different synthetic routes, aiming to understand the influence of TA in the synthesis step and contribute to the development of water-dispersible magnetic materials. The coating process was verified by information obtained from transmission electron microscopy (TEM), zeta-potential and Fourier transform infrared (FTIR) spectroscopy. The incorporation of TA after Fe3O4 NPs production generated spherical NPs smaller than 10 nm, suggesting that TA plays a fundamental role in the nucleation and organization of Fe3O4 NPs. Data from both density functional theory (DFT) and FTIR allowed us to infer that Fe3O4 interacts mainly with the carbonyl groups of TA. Hybrid materials having improved water-dispersibility are very attractive for biomedical applications.

RESUMO Zanthoxylum rhoifolium Lam. (Rutaceae) tem sido utilizada tradicionalmente no tratamento de infecções microbianas e doenças parasitárias. No presente estudo, o efeito antileishmania induzido pelo extrato etanólico de cascas do caule de Z. rhoifolium (ZR-EEtOH) e sua fração hexânica (ZR-FHEX) sobre a infecção e infectividade de macrófagos por formas promastigotas de Leishmania amazonensis foram investigados. Em diferentes experimentos, macrófagos ou promastigotas foram pré-tratadas com ZR-EEtOH ou ZR-FHEX em concentrações não-letais por 24 horas, e então os macrófagos foram submetidos à infecção pelas promastigotas. Além disso, seus efeitos sobre a ativação de macrófagos, assim como concentração de DNA, tamanho e número de promastigotas por citometria de fluxo também foram avaliados. A taxa de infecção e o número de formas amastigotas internalizadas foram consideravelmente reduzidos após os pré-tratamentos de macrófagos ou de promastigotas quando comparados com células não tratadas. O aumento na capacidade fagocítica e nas concentrações de nitrito também foi observado. Por sua vez, a redução na concentração de DNA, tamanho e número de promastigotas também foram observados. Em conclusão, ZR-EEtOH e ZR-FHEX promoveram um significativo efeito antileishmania e redução na infecção de macrófagos, provavelmente envolvendo ativação de mecanismos de defesa em macrófagos. Estes achados reforçam a potencial aplicação de Z. rhoifolium no tratamento da leishmaniose.

ABSTRACT Zanthoxylum rhoifolium Lam. (Rutaceae) has been traditionally used in the treatment of microbial infections and parasitic diseases. In the present study, the antileishmanial effect induced by the ethanol extract of stem barks from Z. rhoifolium (ZR-EEtOH) and its n-hexane fraction (ZR-FHEX) on infection and infectivity of murine macrophages by promastigote forms of Leishmania amazonensis were investigated. In different set of experiments, macrophages or promastigotes were pretreated with ZR-EEtOH or ZR-FHEX at non-lethal concentrations for 24 hours, and then macrophages were submitted to infection by promastigotes. Moreover, their effects on activation of macrophages, as well as on the DNA content, size and number of promastigotes by flow cytometry were also evaluated. The infection rate and the number of internalized amastigote forms were markedly decreased after pretreatment of macrophages or promastigotes when compared with non-treated cells. The increase in phagocytic capability and nitrite content was also observed. Furthermore, the decrease of DNA content, size and number of promastigotes was also observed. In conclusion, ZR-EEtOH and ZR-FHEX promoted a markedly significant antileishmanial effect and reduction of infection of macrophages, probably underlying defense mechanisms activation in macrophages. These findings reinforce the potential application of Z. rhoifolium in the treatment of leishmaniasis.

A fração em acetato de etila (EtOAc) obtida a partir da partição do extrato de etanol (EtOH) das folhas de O. sessiliflora R. E. Fries (Annonaceae) foi submetida a diversos procedimentos cromatográficos, incluindo cromatografia líquida de alta eficiência (HPLC), o que resultou no isolamento dos flavonóides: quercetina-3-O-α-L-ramnopiranosil-(1→4)-β-D-glucopiranosídeo (1), inédito na literatura, canferol-3-O-α-L-ramnopiranosil-(1→4)-β-D-glucopiranosídeo (2), rutina (3) e canferol-3-O-rutinosídeo (4). As estruturas foram definidas através da análise dos espectros de ressonância magnética nuclear (NMR) de ¹H e de 13C (1D e 2D) e espectrometria de massas.

The ethyl acetate (EtOAc) phase obtained from the partition of the ethanol (EtOH) extract from leaves of O. sessiliflora R. E. Fries (Annonaceae) was subjected to several chromatographic steps, including high efficiency liquid chromatography (HPLC), to afford the flavonoids: quercetin-3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranoside (1), unprecedented in the literature, kaempferol-3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranoside (2), rutin (3), and kaempferol-3-O-rutinoside (4). The structures were elucidated by analysis of their ¹H and 13C nuclear magnetic resonance (NMR) (1D and 2D) spectra and mass spectrometry.

The phytochemical investigation of the ethanol extract from leaves of Lecythis pisonis Cambess., Lecythidaceae, resulted in the isolation of seven triterpenes: α- and β-amyrin, uvaol and erythrodiol, ursolic and oleanolic acids and 3β-friedelinol, as well as a mixture of sitosterol and stigmasterol steroids and a diterpene (E)-phytol. The structures of these compounds were identified by¹H and 13C NMR spectral analysis and compared with literature data. The mixture of triterpenes ursolic and oleanolic acids isolated from the active ethereal fraction showed moderate cytotoxic activity. This paper describes for the first time the phytochemical and cytotoxic study of Lecythis pisonis' leaves.

The leishmaniases are severe parasitic diseases that occur worldwide, caused by protozoa of the genus Leishmania. Studies with medicinal plants can lead to a range of possibilities for treating and improving the patients' quality of life. Research on Azadirachta indica fractions and extracts has shown that they have excellent anti-leishmanial activity based on bioactivity-guided fractionation of ethanolic extracts of leaves and seeds and in vitro activity against promastigotes. In this research the most efficient extracts and fractions were selected for tests on intracellular amastigotes of Leishmania amazonensis. The ethanolic extract of the leaves and dichloromethane and chloroform fractions had IC50 values of 38, 3.9 and 1.2 μg/mL for promastigotes and 9.8, 1.1 and 0.6 μg/mL for amastigotes, respectively, at 72 hours. For the ethanolic extract and dichloromethane fraction from nut tegument, the IC50 was 2.7 and 2.1 μg/mL for promastigotes and 0.4 and 0.6 μg/mL for amastigotes. The cytotoxicity of the fractions presented selectivity that was between 8 to 32 times more toxic to promastigotes and 15 to 72 times to amastigotes than to macrophages. The extracts and fractions from leaves and fruits were more effective against amastigotes, and the fractionation increased activity against both promastigotes and amastigotes, enabling us to obtain potentially active fractions with low toxicity.

This work describes the phytochemical analysis of Croton adenocalyx Baill (Euphorbiaceae), a plant that is representative of the species from Ceará State (Brazil). The GC-MS analysis of the essential oil, obtained by hydrodistillation of the leaves from C. adenocalyx, allowed the identification of eleven volatile constituents; the main components were identified as α-pinene (32.63%); bicyclogermacrene (13.96%); trans-caryophyllene (10.23%); germacrene D (10.14%); β-pinene (10.11%) and β-elemene (8.31%). The chromatographic purification of the ethanolic extract from the trunk bark, allowed the isolation and identification of the 6-methoxy-7-hydroxycoumarin (1) and 3,5-dihydroxy-3,4,7-trimethoxyflavone (2).

Este trabajo describe el análisis fitoquímico de Croton adenocalyx Baill (Euphorbiaceae), una planta representativa de las especies del Estado de Ceará- Brasil. El análisis por CG-EM del aceite esencial, obtenido por hidrodestilación de las hojas de C. adenocalyx Baill, permitió la identificación de diez constituyentes volátiles. Los componentes mayoritarios fueron identificados como α-pineno (32.63%), biciclogermacreno (13.96%), trans-cariofileno (10.23%), germacreno D (10.14%), β-pineno (10.11%) y β-elemeno (8.31%). La purificación cromatográfica del extracto etanólico de la corteza del tronco, permitió aislar e identificar la coumarina 6-metoxi-7-hidroxicumarina (1) y el 3,5-dihidroxi-3,4,7-trimetoxiflavona (2).

O presente artigo relata o isolamento e identificação do palmitato, oleato e linoleato de sitosterila, sitosterol, estigmasterol, 3-O-β-D-galactopiranosídeo do sitosterol, 3-O-β-Dgalactopiranosídeo do estigmasterol, 3-O-β-D-glicopiranosídeo do sitosterol e uma mistura de ácidos anacárdicos (monoeno e dieno) do extrato etanólico de cascas do caule de Anacardium occidentale L., Anacardiaceae, bem como do sitosterol, estigmasterol, lupeol, β-amirina, catequina e epicatequina do extrato etanólico do tegumento da castanha de caju in natura. Os extratos EtOH da casca e do tegumento foram avaliados quanto ao conteúdo de fenóis totais e atividade antioxidante. O extrato etanólico das cascas do caule apresentou maior conteúdo de compostos fenólicos e percentual de atividade antioxidante.

This paper describes the isolation and identification of a mixture of sitosteryl ester derivatives of fatty acids (palmitic, oleic and linoleic), sitosterol, stigmasterol, sitosterol-3-O-β-galactopyranoside, stigmasterol-3-O-β-galactopyranoside, sitosterol-3-O-β-glucopyranoside and a mixture of anacardic acids (monoene and diene) from stem bark of Anacardium occidentale L., Anacardiaceae, as well as sitosterol, stigmasterol, lupeol, β-amyrin, catechin and epicatechin from in natura cashew nut testa. Ethanol extracts from stem bark and testa were analyzed for antioxidant activity and total phenol content. The ethanol extract from stem bark exhibited the maximum of antioxidant activity and phenol content.

The objective of this work was to study the potentialities of Dipteryx lacunifera Ducke seeds oil for biodiesel production. The yield in oil was of 46.11 ± 0.37%. Methyl biodiesel was prepared by base catalyzed transesterification yielding 88.13% and percentage conversion of triglycerides to corresponding methyl ester of 89.1%. The addition of the tertiary butylhydroquinone (TBHQ, 50 ppm), butylated hydroxytoluene (BHT, 50 ppm) and cashew nut shell liquid (CNSL, 2000 ppm) antioxidants in the biodiesel contributed to the increase of the induction period of 2.97 h for 8.08; 6.06 and 6.02 h, respectively.