Estudo fitoquímico de espécimens cultivados de cumaru (Amburana cearensis A. C. Smith)

Due to the threat of extinction of Amburana cearensis, a tree of medicinal importance for the Northeastern Brazil, a phytochemical analysis was performed with specimens obtained by seed germination. Ten compounds were isolated and identified by spectroscopic methods and comparison with literature data. p-Hydroxybenzoic acid, ayapin, (E/Z)-melilotosides are being reported for the first time for the genus, besides coumarin, isokaempferide, vanillic acid, protocatechuic acid, amburosides A and B which have already been found in the trunk bark. Based on physical and NMR spectroscopy evidences the structures of several melilotosides already described in the literature have been suggested to be revised

Composição química volátil, em diferentes estádios de maturação, de manga 'Tommy Atkins' produzida no Vale do São Francisco

The effect of the maturation stages on the volatile chemical composition of mango fruit cv. Tommy Atkins, cultivated in São Francisco Valley, was investigated using SPME. GC/MS and GC-FID analysis allowed the identification of 32 compounds, consisting mainly of monoterpenes. δ-3-Carene was the major component in all the stages, while α-terpinolene, trans-β-caryophyllene e α-pinene succeded each other as the second most abundant constituent, during the ripening. The aroma of the ripe fruit was characterized by presence of short-chain ethyl esters (C2-C6), whereas the green mango contained the highest concentration of δ-3-carene. Furthermore, some terpenes were detected exclusively at one of the stages

Estudo preliminar sobre a época de colheita na produção de macela-da-terra (Egletes viscosa, Less.)

Atualmente existe uma demanda pelas plantas medicinais nativas, e devido as pesquisas que confirmam a eficácia de muitas espécies silvestres, que já são usadas popularmente, a tendência é o crescimento dessa demanda. Entre as plantas nativas de uso medicinal do Brasil, encontra-se a Egletes viscosa, Less., família Asteraceae (Compositae) e é comum no nordeste brasileiro. Conhecida popularmente por macela da terra cresce às margens de lagoas, açudes, riachos, no início de verão, após a baixa das águas. Seu uso medicinal ocorre principalmente pela forma de infusão dos capítulos, utilizados no tratamento de enfermidades gastrointestinais, inflamatórias, virais, dentre outras. Considerando a importância da macela da terra sua forma de exploração exclusivamente extrativista, e a carência de informações, o presente estudo teve como objetivo iniciar estudos da produção de macela da terra em três épocas de colheita em casa de vegetação. Os tratamentos constituíram de três épocas de colheita (110, 125 e 140 após o transplantio), dispostos em blocos ao acaso, com quatro repetições em vasos de 10L adubados com solo e esterco de curral. A época de colheita influenciou os componentes de produção sendo a que mais se destacou aos 140 dias. Registrou-se ataque de pragas principalmente Bemisia tabaci, prejudicando a produção de macela aos 125 dias

In vitro efficacy of essential oils against Haematobia irritans

The horn fly (Haematobia irritans) infestation in the cattle in Brazil leads to significant economic damage for livestock. The efficacy of many essential oils has been demonstrated in the control of veterinary ectoparasites. This study aimed to evaluate the in vitro efficacy of four essential oils to adult horn fly control. The essential oil from Mesosphaerum suaveolens (L.) Kuntze (Lamiaceae) was extracted by hydro-distillation, while that the water steam distillation method was used to extract the essential oils from Varronia curassavica (Jacq.) Roem. & Schult. (Boraginaceae), Alpinia zerumbet (Pers.) B.L. Burtt & R.M. Sm. (Zingiberaceae) and Psidium guajava L. (Myrtaceae). Afterwards, all the essential oils were analyzed by Gas Chromatography Mass Spectrometry (GC?MS) and Flame Ionization Detector (GC-FID) for determination of their chemical composition. The bioassays in vitro were performed according to the impregnated filter paper methodology. All the essential oils evaluated in this study exhibited efficacy in vitro against H. irritans. The highest mortality of H. irritans was determined by essential oils from A. zerumbet (100%) and M. suaveolens (96.2%) at 50 mg mL-1.  In concentration of 100 mg mL-1 V. curassavica and P. guajava essential oils caused the mortality of 99.2% and 82.8%, respectively. The A. zerumbet, M. suaveolens, V. curassavica and P. guajava essential oils showed in vitro efficacy against H. irritans. Further studies with associations and nanoemultions are necessary to increase the efficacy and stability of these essential oils on field conditions.The horn fly (Haematobia irritans) infestation in the cattle in Brazil leads to significant economic damage for livestock. The efficacy of many essential oils has been demonstrated in the control of veterinary ectoparasites. This study aimed to evaluate the in vitro efficacy of four essential oils to adult horn fly control. The essential oil from Mesosphaerum suaveolens (L.) Kuntze (Lamiaceae) was extracted by hydro-distillation, while that the water steam distillation method was used to extract the essential oils from Varronia curassavica (Jacq.) Roem. & Schult. (Boraginaceae), Alpinia zerumbet (Pers.) B.L. Burtt & R.M. Sm. (Zingiberaceae) and Psidium guajava L. (Myrtaceae). Afterwards, all the essential oils were analyzed by Gas Chromatography Mass Spectrometry (GC?MS) and Flame Ionization Detector (GC-FID) for determination of their chemical composition. The bioassays in vitro were performed according to the impregnated filter paper methodology. All the essential oils evaluated in this study exhibited efficacy in vitro against H. irritans. The highest mortality of H. irritans was determined by essential oils from A. zerumbet (100%) and M. suaveolens (96.2%) at 50 mg mL-1. In concentration of 100 mg mL-1 V. curassavica and P. guajava essential oils caused the mortality of 99.2% and 82.8%, respectively. The A. zerumbet, M. suaveolens, V. curassavica and P. guajava essential oils showed in vitro efficacy against H. irritans. Further studies with associations and nanoemulsions are necessary to increase the efficacy and stability of these essential oils on field conditions

Tutuilamides A–C: vinyl-chloride-containing cyclodepsipeptides from marine cyanobacteria with potent elastase inhibitory properties

Marine cyanobacteria (blue-green algae) have been shown to possess an enormous capacity to produce structurally diverse natural products that exhibit a broad spectrum of potent biological activities, including cytotoxic, antifungal, antiparasitic, antiviral, and antibacterial activities. Using mass-spectrometry-guided fractionation together with molecular networking, cyanobacterial field collections from American Samoa and Palmyra Atoll yielded three new cyclic peptides, tutuilamides A–C. Their structures were established by spectroscopic techniques including 1D and 2D NMR, HR-MS, and chemical derivatization. Structure elucidation was facilitated by employing advanced NMR techniques including nonuniform sampling in combination with the 1,1-ADEQUATE experiment. These cyclic peptides are characterized by the presence of several unusual residues including 3-amino-6-hydroxy-2-piperidone and 2-amino-2-butenoic acid, together with a novel vinyl chloride-containing residue. Tutuilamides A–C show potent elastase inhibitory activity together with moderate potency in H-460 lung cancer cell cytotoxicity assays. The binding mode to elastase was analyzed by X-ray crystallography revealing a reversible binding mode similar to the natural product lyngbyastatin 7. The presence of an additional hydrogen bond with the amino acid backbone of the flexible side chain of tutuilamide A, compared to lyngbyastatin 7, facilitates its stabilization in the elastase binding pocket and possibly explains its enhanced inhibitory potency

Tutuilamides A–C: vinyl-chloride-containing cyclodepsipeptides from marine cyanobacteria with potent elastase inhibitory properties

Marine cyanobacteria (blue-green algae) have been shown to possess an enormous capacity to produce structurally diverse natural products that exhibit a broad spectrum of potent biological activities, including cytotoxic, antifungal, antiparasitic, antiviral, and antibacterial activities. Using mass-spectrometry-guided fractionation together with molecular networking, cyanobacterial field collections from American Samoa and Palmyra Atoll yielded three new cyclic peptides, tutuilamides A–C. Their structures were established by spectroscopic techniques including 1D and 2D NMR, HR-MS, and chemical derivatization. Structure elucidation was facilitated by employing advanced NMR techniques including nonuniform sampling in combination with the 1,1-ADEQUATE experiment. These cyclic peptides are characterized by the presence of several unusual residues including 3-amino-6-hydroxy-2-piperidone and 2-amino-2-butenoic acid, together with a novel vinyl chloride-containing residue. Tutuilamides A–C show potent elastase inhibitory activity together with moderate potency in H-460 lung cancer cell cytotoxicity assays. The binding mode to elastase was analyzed by X-ray crystallography revealing a reversible binding mode similar to the natural product lyngbyastatin 7. The presence of an additional hydrogen bond with the amino acid backbone of the flexible side chain of tutuilamide A, compared to lyngbyastatin 7, facilitates its stabilization in the elastase binding pocket and possibly explains its enhanced inhibitory potency

Chemical aspects of the investigations to interdisciplinar (chemistry-agronomy-pharmacology)de Amburana cearensis A. C. Smith

Amburana cearensis A.C. Smith (sin. Torresea cearensis Fr. All) à uma Ãrvore tÃpica da caatinga nordestina, popularmente conhecida como imburana-de-cheiro ou cumaru, caracterizada por sua casca vermelho-pardacenta e odor peculiar agradÃvel, atribuÃdo à cumarina. Apresenta relevante importÃncia econÃmica, sobretudo na carpintaria e perfumaria, e inestimÃvel valor medicinal (propriedades terapÃuticas contra afecÃÃes respiratÃrias cientificamente comprovadas), todavia esta espÃcie sofre ameaÃa de extinÃÃo devido ao extrativismo predatÃrio. Em virtude da necessidade de elaboraÃÃo de um modelo de exploraÃÃo auto-sustentÃvel de A. cearensis, foi proposto um estudo integrado QuÃmica-Agronomia-Farmacologia. Este trabalho relata a abordagem fitoquÃmica da pesquisa interdisciplinar, visando o isolamento, a purificaÃÃo e a caracterizaÃÃo estrutural de novos constituintes quÃmicos da planta adulta (silvestre), bem como a identificaÃÃo e a quantificaÃÃo de compostos quÃmicos jà conhecidos, considerados biomarcadores, em espÃcimens jovens de diferentes meses de desenvolvimento (cultivados). As investigaÃÃes quÃmicas da planta silvestre de A. cearensis foram realizadas com os extratos etanÃlicos da casca do caule, coletadas no municÃpio de Quixeramobim-CE, e das sementes, adquiridas no comÃrcio de Fortaleza-CE. Os extratos etanÃlicos foram submetidos a partiÃÃes lÃquido-lÃquido, cromatografias convencionais (adsorÃÃo-gel de sÃlica e exclusÃo- gel de dextrana) e modernas (HPLC-fase reversa), resultando no isolamento e identificaÃÃo de: A. Cumarinas- 6-hidroxi-cumarina e protocatecuato de 6-cumarila; B. Ãcidos fenÃlicos- Ãcido vanÃlico e Ãcido (E)-o-cumÃrico; C. FlavonÃides- quercetina, formononetina, e os biflavonÃides amburanina A e B; AmburosÃdios- amburosÃdio A, ferulato de 6â-amburosila, protocatecuato de 6â-amburosila, galato de 6â-amburosila, acetato de 6â-amburosila, sinapato de 6â-amburosila e vanilato de 6â-amburosila. Os espÃcimens cultivados de A. cearensis, divididos em parte aÃrea e xilopÃdio, foram extraÃdos com etanol e submetidos a uma metodologia quÃmica semelhante à adotada para a planta silvestre. Da parte aÃrea foram obtidos cumarina, aiapina, amburanina B, isocampferÃdio, Ãcido vanÃlico e Ãcido (E)-o-cumÃrico glicosilado, enquanto que do xilopÃdio foram isolados Ãcido p-hidroxi-benzÃico, Ãcido (Z)-o-cumÃrico glicosilado e amburosÃdio B. As substÃncias quÃmicas isoladas tiveram suas estruturas elucidadas por mÃtodos fÃsicos (ponto de fusÃo e rotaÃÃo Ãptica) e espectromÃtricos (Espectrometria na regiÃo do Infravermelho, Espectrometria de Massa e RessonÃncia MagnÃtica Nuclear de 1H e 13C, incluindo tÃcnicas uni e bidimensionais), alÃm de comparaÃÃo com dados da literatura. Os extratos etanÃlicos da planta silvestre (casca do caule) e de espÃcimens cultivados (parte aÃrea e xilopÃdio) foram quimicamente comparados atravÃs de anÃlises por HPLC, empregando-se mÃtodo cromatogrÃfico validado (linearidade, precisÃo, exatidÃo, fator de recuperaÃÃo aceitÃveis) e utilizando-se padrÃes de Ãcido protocatecuico, Ãcido vanÃlico, cumarina e amburosÃdio A, obtidos em estudos anteriores. AmburosÃdio A foi o constituinte majoritÃrio do extrato da planta silvestre. Nos espÃcimens jovens, Ãcido vanÃlico e cumarina revezaram-se como principais componentes, dependendo da parte e da idade da planta estudada.Amburana cearensis A.C. Smith is a typical tree of the northeastern Brazil flora designated âcaatingaâ. It is popularly known either as âimburana-de-cheiroâ or âcumaruâ and characterized by its red-gray bark of peculiar and pleasant smell due to coumarin. Despite A. cearensis relevant economical (particularly for carpentry and perfumery) and medicinal importance (therapeutic properties against respiratory affections scientifically proved), it is one of the plant species treated of extinction due to predatory extractivism. Taking in account the necessity of elaborating a sustainable plan of exploitation it was suggested an integrated study covering the chemical, agronomical and pharmacological aspects of A. cearensis. This work reports the phytochemical component of the interdisciplinary study pursuing the isolation, purification and structure characterization of new secondary metabolites of the wild adult plant, as well as the identification and quantification of the already known chemicals, considered the plant biomarkers, from young cultivated specimens at different developmental stages. The chemical investigation of adult wild plants was performed with the ethanol extract from barks of A. cearensis collected at Quixeramobim County, Cearà state, and the hexane extract of seeds purchased from herbal stores at Fortaleza. The ethanol extracts were submitted to liquid-liquid partition, conventional (silica gel adsorption and gel exclusion with dextran) and modern (HPLC) chromatography leading to the isolation and characterization of: A. Coumarins 6-hydroxy-coumarin, 6-coumaryl protocatechuate, acid; B. Phenol Acids- vanillic acid, o-coumaric; C. Flavonoids- quercetin, formononetin, amburanin A and B; AmburosÃdes- amburoside A, 6â-amburosyl-ferulate, 6â-amburosyl-protocatechuate, 6â-amburosyl-galate, 6â-amburosyl-acetate, 6â-amburosyl-sinapate and 6â-amburosyl-vanillate. The cultivated specimens, separated in aerial part and xylopode, were extracted with ethanol and submitted to the same methodology employed for the wild plant. From the aerial part were isolated coumarin, ayapin, amburanin B, isokaempferide, vanillic acid, (E)-o-coumaric acid glucoside, while from the xylopode were isolated p-hydroxy-benzoic acid, (Z)-o-coumaric acid glucoside and amburoside B. All chemical substances had their structures elucidated through physical (mp and optical rotation) and spectroscopical methods (IR, MS and NMR, including uni and bidimensional techniques) and comparison to the literature wherever the case. The ethanol extracts from either wild or cultivated (aerial part and xylopode) plants were compared by HPLC through a validated chromatographic method (acceptable linearity, precision, accuracy and recovering factor) using as standard the protocatechuic acid, vanillic acid, coumarin and amburoside A, obtained from the previous studies. Amburoside A was the major component of wild plant, while coumarin and vanilic acid take turns as the principal metabolites of cultivated young plants depending on the plant part and plant age

Avaliação do uso de inibidores de etileno sobre a produção de compostos voláteis e de mangiferina em manga Evaluation of the use of ethylene inhibitors on production of volatile compounds and mangiferin in mango fruit

<abstract language="eng">Effects of two ethylene inhibitors, 1-methylcylopropene (1-MCP) and aminoethoxyvinylglycine (AVG), on production of volatile compounds and mangiferin (a bioactive xanthone) in 'Tommy Atkins' mango fruit were investigated. Volatile composition and mangiferin content, in treated and untreated fruits at three maturity, stages were determined by SPME-GC-MS and HPLC, respectively. These chromatographical analysis revealed that the volatile profiles and mangiferin concentrations were not significantly different, suggesting that the use of ethylene inhibitors does not affect the mango aroma and functional properties relative to this xanthone. Moreover, a simple, precise and accurate HPLC method was developed for quantifying mangiferin in mango pulp