Plantas Oleaginosas Amazônicas: Química e Atividade Antioxidante de Patauá (Oenocarpus bataua Mart.)

The Amazon oilseeds, especially from native palm trees are significant species belonging to the Amazon landscape and culture. The Amazon species produce oil with great potential to generate valuable medicines, cosmetics, nutraceuticals and energy. The Oenocarpus bataua (patawa) is an edible species and from its fruits is produced the "vinho de patauá", a well-known beverage, considered very nutritive and energetic. Fresh fruits collected nearby Manaus-AM, were separated into peel, pulp and seeds. The methanolic extracts from pulp and seeds were evaluated in different antioxidant assays and both extracts were considered active. The seed extract showed antioxidant activity compared to the positive control (quercetin) in the radical scavenging-DPPH assay. The pulp extract were fractionated guided by TLC-antioxidant analysis that led to the isolation of the stilbene, piceatannol. This is the first report of an isolated compound from patawa. Piceatannol is considered a bioactive compound and in some cases was considered more active than resveratrol, a well-known bioactive compound. These results showed the great potential of patawa to produce nutraceutical products

Revues reçues

Endopleura uchi (Huber) Cuatrec. is an Amazon species traditionally used as treatment for inflammations and female disorders. Bergenin was isolated from ethyl acetate fraction of bark of E. uchi by using column chromatography over sephadex LH-20 and then silica gel 60 flash. Its structure was identified on the basis of its NMR spectra. The antimicrobial activity of bergenin and fractions of methanol extract of E. uchi were evaluated against ATCC microorganisms (Escherichia coli, Salmonella enteritidis, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Candida albicans, C. guilliermondii, Aspergillus flavus, A. nidulans). Clinically isolated strains of all of these microorganisms, along with C. tropicalis, A. niger, Shigella sonnei, Serratia marcenses and Klebsiella pneumoniae were also evaluated. The growth inhibition caused by bergenin, extracts and fractions of E. uchi against ATCC microorganisms were similar to the inhibition to microorganisms clinically isolated. The ethyl acetate fraction and the isolate bergenin inhibit the growth of the yeasts C. albicans, C. tropicalis, and C. guilliermondii, but present lower activity against filamentous fungi Aspergillus flavus, A. nidulans, A. niger, and did not inhibit the Gram positive and Gram negative bacteria. The activity of the ethyl acetate fraction and bergenin are in agreement wit its high concentration found in bark extract of E. uchi. Moreover, the selective activity against three Candida species helps to understand its traditional use against infections that affect women.Endopleura uchi (Huber) Cuatrec. é uma espécie amazônica utilizada tradicionalmente para o tratamento de inflamações uterinas e outras afecções femininas. Das cascas de E. uchi foi isolada a substância bergenina, por meio de cromatografia em coluna usando como fases estacionárias sephadex LH-20 e posteriormente, sílica gel 60 flash. A identificação estrutural de bergenina foi realizada por meio de espectros de RMN. A avaliação da atividade antimicrobiana da bergenina, dos extratos e frações de E. uchi foi realizada contra microorganismos ATCC e clinicamente isolados (Escherichia coli, Salmonella enteritidis, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Candida albicans, C. guilliermondii, Aspergillus flavus, A. nidulans). Além desses, foram testados os microorganismos isolados clinicamente (C. tropicalis, A. nidulans, A. niger, Shigella sonnei, Serratia marcenses, Klebsiella pneumoniae e Enterococcus faecalis). A inibição de crescimento dos microorganismos pela bergenina e extratos e frações de E. uchi contra os microorganismos ATCC foram similares à inibição obtida contra microorganimos isolados clinicamente. Os resultados revelaram a bergenina como um inibidor seletivo de Candida albicans, C. tropicalis e C. guilliermondii. Porém, a bergenina apresentou uma atividade inferior contra os fungos Aspergillus flavus, A. nidulans, A. niger, e não inibiu o crescimento de bactérias Gram positivas e Gram negativas. As atividades da fração de acetato de etila e da bergenina pura estão em concordância com a concentração da bergenina nas cascas. A atividade seletiva de bergenina contra três espécies de Candida auxilia na compreensão do seu uso tradicional contra que infecções que afetam o aparelho reprodutor feminino

Characterization of bergenin in endopleura uchi bark and its anti-inflammatory activity

Endopleura uchi (Huber) Cuatrec. is an Amazon species traditionally used for the treatment of inflammations and female disorders. Pure bergenin was isolated from the methanolic extract of bark of E. uchi, firstly by using liquid-liquid partition chromatography followed by column chromatography over Sephadex LH-20 and then silica gel 60 flash chromatography. The structure of bergenin was identified on the basis of its NMR spectra. The in vitro anti-inflammatory activity was determined by the measurement of the inhibitory concentration (IC) of bergenin against three key enzymes: COX-1, COX-2 (cyclooxygenases) and phospholipase A2 (PLA2). These enzymes were selected because they are important targets for the discovery of new anti-inflammatory drugs associated with the biosynthesis of prostaglandins. The IC50 of bergenin for phopholipase A2 was determined as 156.6 μmol L-1 and bergenin was not considered active as compared to the positive control, tioetheramide PC. Bergenin did not inhibit COX-1 as well (IC50 = 107.2 μmol L-1). However, bergenin selectively inhibited COX-2 (IC50 = 1.2 μmol L-1). Because of the use of E. uchi in traditional medicine, bergenin was quantified in teas prepared as prescribed in traditional medicine by RP-HPLC as being 3% in the bark of E. uchi. The inhibitory activity towards COX-2 is important, since selective inhibitors of COX-2 have been clinically validated as anti-inflammatory therapeutics due to their enhanced gastrointestinal safety. ©2009 Sociedade Brasileira de Química

Atividade antimicrobiana de bergenina isolada de Endopleura uchi (Huber) Cuatrec

Endopleura uchi (Huber) Cuatrec. is an Amazon species traditionally used as treatment for inflammations and female disorders. Bergenin was isolated from ethyl acetate fraction of bark of E. uchi by using column chromatography over sephadex LH-20 and then silica gel 60 flash. Its structure was identified on the basis of its NMR spectra. The antimicrobial activity of bergenin and fractions of methanol extract of E. uchi were evaluated against ATCC microorganisms (Escherichia coli, Salmonella enteritidis, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Candida albicans, C. guilliermondii, Aspergillus flavus, A. nidulans). Clinically isolated strains of all of these microorganisms, along with C. tropicalis, A. niger, Shigella sonnei, Serratia marcenses and Klebsiella pneumoniae were also evaluated. The growth inhibition caused by bergenin, extracts and fractions of E. uchi against ATCC microorganisms were similar to the inhibition to microorganisms clinically isolated. The ethyl acetate fraction and the isolate bergenin inhibit the growth of the yeasts C. albicans, C. tropicalis, and C. guilliermondii, but present lower activity against filamentous fungi Aspergillus flavus, A. nidulans, A. niger, and did not inhibit the Gram positive and Gram negative bacteria. The activity of the ethyl acetate fraction and bergenin are in agreement wit its high concentration found in bark extract of E. uchi. Moreover, the selective activity against three Candida species helps to understand its traditional use against infections that affect women.Endopleura uchi (Huber) Cuatrec. é uma espécie amazônica utilizada tradicionalmente para o tratamento de inflamações uterinas e outras afecções femininas. Das cascas de E. uchi foi isolada a substância bergenina, por meio de cromatografia em coluna usando como fases estacionárias sephadex LH-20 e posteriormente, sílica gel 60 flash. A identificação estrutural de bergenina foi realizada por meio de espectros de RMN. A avaliação da atividade antimicrobiana da bergenina, dos extratos e frações de E. uchi foi realizada contra microorganismos ATCC e clinicamente isolados (Escherichia coli, Salmonella enteritidis, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Candida albicans, C. guilliermondii, Aspergillus flavus, A. nidulans). Além desses, foram testados os microorganismos isolados clinicamente (C. tropicalis, A. nidulans, A. niger, Shigella sonnei, Serratia marcenses, Klebsiella pneumoniae e Enterococcus faecalis). A inibição de crescimento dos microorganismos pela bergenina e extratos e frações de E. uchi contra os microorganismos ATCC foram similares à inibição obtida contra microorganimos isolados clinicamente. Os resultados revelaram a bergenina como um inibidor seletivo de Candida albicans, C. tropicalis e C. guilliermondii. Porém, a bergenina apresentou uma atividade inferior contra os fungos Aspergillus flavus, A. nidulans, A. niger, e não inibiu o crescimento de bactérias Gram positivas e Gram negativas. As atividades da fração de acetato de etila e da bergenina pura estão em concordância com a concentração da bergenina nas cascas. A atividade seletiva de bergenina contra três espécies de Candida auxilia na compreensão do seu uso tradicional contra que infecções que afetam o aparelho reprodutor feminino.18719

Constituintes químicos dos galhos de simaba guianensis subesp. ecaudata (cronquist)

Simaba guianensis subesp. ecaudata (Simaroubaceae) is a tree found in the Brazilian Amazon. This work describes for the first time the fractionation of stems of this species that resulted in the isolation of the cytotoxic triterpene piscidinol A, the alkaloid 9-methoxycanthin-6-one, caryophyllene oxide, also isolated for the first time from this species and a new alkaloid (6-methoxy-(9H-β-carbolin-1-il)-(Z)-2-propenoic acid). Quantification of 9-methoxycanthin-6-one in different extracts and fractions of stems of S. guianensis by high performance liquid chromatography was also performed. The concentration of 9-methoxycanthin-6-one in methanolic and aqueous extracts were inferior to the known cytotoxic concentration of this compound

Triterpenos e alcalóide tipo cantinona dos galhos de Simaba polyphylla (cavalcante) W.W. Thomas (simaroubaceae)

Simaba polyphylla is a small tree found in the Amazon region, known by the common names "marupazinho" or "serve para tudo". It is used in traditional medicine for the treatment of fevers. This work describes the phytochemical study of the hexane extract and chloroform fraction obtained by partitioning the methanol extract of stems, which led to isolation and identification of the triterpenes niloticin, dyhidroniloticin, taraxerone and of the cytotoxic alkaloid 9-methoxy-canthin-6-one. These compounds are described for the first time in S. polyphylla

In Vitro and In Silico Evaluation of Cholinesterase Inhibition by Alkaloids Obtained from Branches of Abuta panurensis Eichler

Alkaloids are natural products known as ethnobotanicals that have attracted increasing attention due to a wide range of their pharmacological properties. In this study, cholinesterase inhibitors were obtained from branches of Abuta panurensis Eichler (Menispermaceae), an endemic species from the Amazonian rainforest. Five alkaloids were isolated, and their structure was elucidated by a combination of 1D and 2D 1H and 13C NMR spectroscopy, HPLC-MS, and high-resolution MS: Lindoldhamine isomer m/z 569.2674 (1), stepharine m/z 298.1461 (2), palmatine m/z 352.1616 (3), 5-N-methylmaytenine m/z 420.2669 (4) and the N-trans-feruloyltyramine m/z 314.1404 (5). The compounds 1, 3, and 5 were isolated from A. panurensis for the first time. Interaction of the above-mentioned alkaloids with acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes was investigated in silico by molecular docking and molecular dynamics. The molecules under investigation were able to bind effectively with the active sites of the AChE and BChE enzymes. The compounds 1–4 demonstrated in vitro an inhibitory effect on acetylcholinesterase with IC50 values in the range of 19.55 µM to 61.24 µM. The data obtained in silico corroborate the results of AChE enzyme inhibition

Alkaloids of Abuta panurensis Eichler : In silico and in vitro study of acetylcholinesterase inhibition, cytotoxic and immunomodulatory activities

Natural products obtained from species of the genusAbuta(Menispermaceae) are known as ethnobotanicals that are attracting increasing attention due to a wide range of their pharmacological properties. In this study, the alkaloids stepharine and 5-N-methylmaytenine were first isolated from branches ofAbuta panurensisEichler, an endemic species from the Amazonian rainforest. Structure of the compounds was elucidated by a combination of 1D and 2D NMR spectroscopic and MS and HRMS spectrometric techniques. Interaction of the above-mentioned alkaloids with acetylcholinesterase enzyme and interleukins IL-6 and IL-8 was investigatedin silicoby molecular docking. The molecules under investigation were able to bind effectively with the active sites of the AChE enzyme, IL-6, and IL-8 showing affinity towards the proteins. Along with the theoretical study, acetylcholinesterase enzyme inhibition, cytotoxic, and immunomodulatory activity of the compounds were assessed byin vitroassays. The data obtainedin silicocorroborate the results of AChE enzyme inhibition, the IC(50)values of 61.24 mu M for stepharine and 19.55 mu M for 5-N-methylmaytenine were found. The compounds showed cytotoxic activity against two tumor cell lines (K562 and U937) with IC(50)values ranging from 11.77 mu M to 28.48 mu M. Thein vitroassays revealed that both alkaloids were non-toxic to Vero and human PBMC cells. As for the immunomodulatory activity, both compounds inhibited the production of IL-6 at similar levels. Stepharine inhibited considerably the production of IL-8 in comparison to 5-N-methylmaytenine, which showed a dose dependent action (inhibitory at the IC(50)dose, and stimulatory at the twofold IC(50)one). Such a behavior may possibly be explained by different binding modes of the alkaloids to the interleukin structural fragments. Occurrence of the polyamine alkaloid 5-N-methylmaytenine was reported for the first time for the Menispermaceae family, as well as the presence of stepharine inA.panurensis.Peer reviewe

Leaf and stem anatomy of Picrolemma sprucei Hook (Simaroubaceae)

Anatomical studies of the leaves and stems of Picrolemma sprucei revealed that the epidermes of the leaves are glabrous, with undulating cell walls and anomocytic stomata. The mesophyll is dorsiventral with a layer of cells in palisade and a spongy parenchyma. The vascular bundles are bicollateral and have a dark tannin containing idioblast. The stem possesses a developed cortical parenchyma with schlerenchymatous thick walled cells. These are either isolated or gathered in small groups. Internally the vascular region exhibits xylematic vessels some isolated and some in groups submerged in fibrous tissue. The stem possesses a paratracheal, vasicentric parenchyma with central pith. Histochemical tests (sudan III and ferric chloride) made on the central section of the midrib and on the petiole showed the presence, respectively, of tannin or oleoresin in some cells.Os estudos anatômicos das folhas e caules de Picrolemma sprucei revelaram que as epidermes das folhas são glabras, apresentam células de paredes onduladas e estômatos anomocíticos. O mesofilo é dorsiventral com uma camada de células em paliçada e um parênquima lacunoso. Os feixes vasculares são bicolaterais e apresentam idioblastos escuros de conteúdo tânico. No caule evidencia-se um parênquima cortical desenvolvido, com células de natureza esclerenquimática, isoladas ou reunidas em pequenos grupos, de paredes espessas. Internamente observa-se a região vascular com vasos xilemáticos isolados ou em grupos imersos em tecido fibroso, sendo o parênquima do tipo paratraqueal, vasicêntrico. Na região central encontra-se uma medula desenvolvida. Testes histoquímicos (sudam III e cloreto férrico) realizados na nervura mediana do terço médio do limbo foliar e no pecíolo revelaram respectivamente, a presença de um conteúdo tânico e óleo-resinoso em algumas de suas células