Resumo Este trabalho teve como objetivo caracterizar a lignina na parede celular de Euterpe oleracea Mart. Foram adquiridas amostras de duas regiões da base da palmeira: região externa e região interna (OR e IR, respectivamente). A extração com solventes orgânicos e o tratamento com NaOH 1% foram realizados. O conteúdo de holocelulose, α-celulose e lignina foi quantificado, esta última também isolada pelo método de Björkman para a caracterização estrutural utilizando RMN de 1H e 13C no estado líquido, assim como análises espectroscópicas (FTIR) e cromatográficas. O caule extraído apresentou 10,33% (OR) e 15,66% (IR) de lignina. Após tratamento com NaOH 1%, observou-se uma redução desses valores, e foi possível confirmar esse resultado também através da diminuição nas intensidades dos sinais referentes aos grupos funcionais ligados à lignina e hemicelulose. As análises espectroscópicas e cromatográficas revelaram lignina do tipo GS incorporada com ácido p-hidroxibenzoico e protocatecuico em ambas as amostras. Também foram observadas as principais unidades estruturais presentes na lignina como ligação β-O-4, β-O-4’ ϒ-acetiladas, spiro-dienona, unidade guaiacila, unidade siringila e p-hidroxibenzoato.

Abstract This paper aimed to characterize the lignin in the cell wall of Euterpe oleracea Mart. Samples from two regions of the base of the palm were acquired: outer and inner regions (OR and IR, respectively). The extraction with organic solvents and the treatment with 1% NaOH were carried out. Holocellulose, α-cellulose and lignin content were quantified, the latter also isolated by the Björkman method for the structural characterization using 1H and 13C NMR in the liquid state, as well as spectroscopic (FTIR) and chromatographic analysis. The extracted stem had 10.33% (OR) and 15.66% (IR) of the lignin. After the treatment with 1% NaOH, a reduction in these values was observed, and it was also possible to confirm this result through the decrease in the intensities of the signals referring to the functional groups linked to lignin and hemicellulose. The spectroscopic and chromatographic analyzes revealed GS-type lignin incorporated with p-hydroxybenzoic and protocatechuic acid in both samples. The main structural units present in the lignin were also observed, such as β-O-4 bond, β-O-4’ ϒ-acetyl bond, guaiacyl unit, syringyl unit and p-hydroxybenzoate.

Resumo Este estudo teve como objetivo caracterizar quimicamente os óleos essenciais (OE) de Cinnamomum zeylanicum (canela) e Eremanthus erythropappus (candeia) e avaliar sua atividade acaricida, juntamente com a de seus principais compostos e do derivado de acetato de cinamila, sobre Rhipicephalus microplus. Os compostos do óleo essencial foram identificados por cromatografia gasosa. Foram realizados o Teste de Pacote de Larvas (TPL), em concentrações variando de 0,31 a 10,0 mg/mL, e o Teste de Imersão de Adultos (TIA), em concentrações entre 2,5 e 60,0 mg/mL. (E)-cinnamaldeído e α-bisabolol foram os principais compostos nos OE da canela (86,93%) e da candeia (78,41%), respectivamente. No TPL, os OEs de canela e candeia, e os compostos (E)-cinnamaldeído, α-bisabolol e acetato de cinamila resultaram em 100% de mortalidade nas concentrações de 2,5, 2,5, 5,0, 10,0 e 10,0 mg/mL, respectivamente. No TIA, valores percentuais de controle >95% foram observados para OE de canela e candeia, (E)-cinnamaldeído e α-bisabolol nas concentrações de 5,0, 60,0, 20,0 e 20,0 mg/mL, respectivamente, enquanto o acetato de cinamila apresentou baixa atividade. Conclui-se que os OEs e seus compostos apresentaram alta atividade acaricida, enquanto o derivado acetilado do (E)-cinnamaldeído apresentou menor atividade acaricida em fêmeas ingurgitadas de R. microplus.

Abstract This study aimed to chemically characterize the essential oils (EOs) of Cinnamomum zeylanicum (cinnamon) and Eremanthus erythropappus (candeia) and evaluate their acaricidal activity, together with that of their major compounds and cinnamyl acetate derivative, against Rhipicephalus microplus. Essential oil compounds were identified through gas chromatography. The larval packet test (LPT) at concentrations ranging from 0.31 to 10.0 mg/mL and the adult immersion test (AIT) at concentrations between 2.5 and 60.0 mg/mL were performed. (E)-cinnamaldehyde and α-bisabolol were the major compounds in cinnamon (86.93%) and candeia (78.41%) EOs, respectively. In the LPT, the EOs of cinnamon and candeia and the compounds (E)-cinnamaldehyde, α-bisabolol and cinnamyl acetate resulted in 100% mortality at concentrations of 2.5, 2.5, 5.0, 10.0 and 10.0 mg/mL respectively. In the AIT, percentage control values > 95% were observed for cinnamon and candeia EOs, (E)-cinnamaldehyde and α-bisabolol at the concentrations of 5.0, 60.0, 20.0, and 20.0 mg/mL, respectively, whereas cinnamyl acetate showed low activity. We conclude that EOs and their compounds showed high acaricidal activity, whereas the acetylated derivative of (E)-cinnamaldehyde presented less acaricidal activity on R. microplus engorged females.

Phytochemical investigation of Eugenia copacabanensis allowed for the isolation and identification of following compounds: β-sitosterol, β-sitosterol-glucoside, eight triterpenes, (mixture of α- and β-amyrins, ursolic acid, 30-hydroxy-ursolic acid, betulin, friedelin, friedelan-3,4-lactone, and taraxerol), a mixture of three sesquiterpenes, (clovandiol, globulol, and viridiflorol), three flavonoids (kaempferol-3-O-β-D-rhamnoside, quercetin-3-O-α-L-arabinoside, and quercetin), and a mixture of four coumaroyl esters (octacosanyl, heptacosanyl, hexacosanyl, and tetracosanyl coumarates). The structures of these compounds were assigned based on comparison with literature data and spectroscopic analysis, including analysis by two-dimensional NMR techniques. Total phenolic content and total flavonoids were evaluated. Antioxidant activities of methanol extracts and fractions were measured by the 1,2-diphenyl-2-picryl-hidrazyl free radical scavenging assay.

The objective of this study was to identify secondary metabolite classes of tropical kudzu, perennial soybean and archer legumes through identification by phytochemical screening and confirmation by infrared (IR), ¹H and carbon-13 NMR spectroscopy of fractions obtained by organic solvents partition of crude extracts. These analyses allowed for proposing the presence of the following metabolite classes: reducing sugars, saccharides, saponins, cardiac glucosides, terpenes, coumarins, tannins, alkaloids and flavonoids. The tannins, saponins, alkaloids, organic acids and flavonoids had special consideration because they are toxic compounds and can affect the animal metabolism.

This work describes the biflavonoids found in species of Clusiaceae, particularly the genera Garcinia and Calophyllum, emphasizing the importance of these metabolites as chemical markers of this family, their contribution to the pharmacological potential of these species, besides the promising potential of these compounds in the search for new drugs.

This the first phytochemical investigation of Mimosa artemisiana (Leguminosae-Mimosoideae) describing the isolation and identification of quercitrin, myricitrin, 3,5,4´-trihydroxi-6,7-dimethoxyflavone (6,7-dimethylkaepferol), flavolignans, 3-O-β-D-glucopyranosil sitosterol, lupeol, sitostenone, stigmastenone, campestenone, sitosterol, stigmasterol, campesterol, methyl indole-3-carboxilate and indole-3-carboxaldehyde in the extracts from the leaves and wood of this plant. This is the first registry of 6,7-dimethoxy,4'-hydroxy-flavona and the flavonolignans in this genera. The isolation of all metabolites was made by chromatographic methods and the structures were established on the basis of IR, MS, ¹H and 13C NMR spectra analysis, comparison with literature data and GC-MS of mixtures analysis.

Four flavonoids, 3,7,4'-trihydroxyflavanone (garbanzol), 7,4'-dihydroxyflavone, 7,4'-dihydroxy-3'-methoxyflavone (geraldone) and 3,4,7,4'-tetrahydroxyflavane (Rel-2R,3S,4S-leucoguibourtinidine, guibourtacacidine) were isolated from the wood of Schizolobium parahyba (Leg., Caesalpinoideae) together with lignan balonofonine, sitosterol, and stigmasterol. The structures were established by IR, NMR and mass spectral data analysis and comparison with literature values.

Sitosterol, stigmasterol, betulinic acid, lupeol, 3-O-beta-D-glucopiranosylsitosterol, 3-O-alpha-L-rhamnopiranosylchromone, 5,7-dihydroxy-4'-methoxyisoflavone, 3',5,7-trihydroxy-4'-methoxyisoflavone and a mixture of two rel-2R,3S-3-O-alpha-L-rhamnopiranosilflavanonols were isolated from the roots of Andira fraxinifolia. Their structures were established by spectral data analysis.

Abstract The synthesis and structural determination of cinnamates esters derivative let us to obtain some similar products to natural esters isolated from Lafoensia glyptocarpa Koehne, and to evaluate their allelopathic potencial by bioassays of lettuce and tomato seed germination. The substances which promoted more inhibition to seed germination were 3,4-metilenedioxiphenyl hexadecyl acrylate; 3,4-metilenedioxiphenyl hexadecyl propionate; 3,4-metilenedioxi-6-nitrophenyl hexadecyl propionate, and sitosteryl ferulate. The structures were determined by infrared, mass and 1H and 13C NMR spectroscopy.

Resumo A síntese e determinação estrutural de ésteres derivados do ácido cinâmico permitiu obter análogos dos ésteres naturais isolados de Lafoensia glyptocarpa Koehne e avaliar o potencial alelopático dos mesmos através de bioensaios de germinação de sementes de alface e tomate. As substâncias que promoveram maior inibição da germinação das sementes analisadas foram: 3,4-metilenodioxifenil acrilato de hexadecila; 3,4-metilenodioxifenil propionato de hexadecila; 3,4-metilenodioxi-6-nitrofenil propionato de hexadecila; e ferrulato de sitosterila. As estruturas foram determinadas através da análise de dados fornecidos por espectrometria de infravermelho, de massas e de RMN de 1H e 13C.

O fracionamento cromatográfico dos extratos das folhas de Ouratea hexasperma (Ochnaceae) forneceu, além do novo biflavonóide 5-hidróxi-7-metoxiflavona-(4'-O-8")-5",4"'-diidróxi-7" -metoxiflavona, a agathisflavona, 7"-metilagathisflavona, epicatequina, 6-C-glicopiranosil-luteolina e a 3-O-glicopiranosil-quercetina já registradas na literatura. As estruturas desses compostos foram estabelecidas através da análise dos dados espectrométricos de IV, EM e RMN.

Chromatographic fractionation of the extracts from the leaves of Ouratea hexasperma (Ochnaceae) afforded a new flavone dimer 5-hydroxy-7-methoxyflavone-(4'-O-8")-5",4"' -dihydroxy-7"-methoxyflavone besides known agathisflavone, 7"-methylagathisflavone, epicatechin, 6-C-glycopyranosyl-luteolin and 3-O-glycopyranosyl-quercetin. The IR, NMR and mass spectra data analyses were used to establish the structures of these compounds.

During the last decades several flavonoids of Solanum species have been isolated. This review describes the flavones, flavonols and their glycosides presently known as constituents of Solanum species.

ABSTRACT The total glycoalkaloids fraction obtained from the unripe fruit of Solanum crinitum was chromatographed on sephadex LH-20 column to yield the solasonine, a glycoalkaloid which structure was identified by IR and NMR spectral data analysis. The allelopathic effect of the extract and solasonine on the seeds germination and lettuce seedlings development was detected. The tests were conduced with four replications of five concentration (0, 100, 200, 400, 800 ppm) using 25 seeds. Although both show high allelopathic activity. The solasonine was more effetive.

RESUMO Afração contendo os alcalóides glicosilados totais dos frutos verdes de Solanum crinitum foi cromatografado em coluna de Sephadex e forneceu a solasonina, um alcalóide glicosilado cuja estrutura foi definida através da análise de dados espectrométricos no IV e de RMN de 1H e 13C. Os testes realizados com quatro repetições de cinco concentrações (0, 100, 200, 400 e 800 ppm) usando 25 sementes de alface (Lactuca sativa) permitiram verificar elevada atividade do extrato dos alcalóides glicosilados totais e da solasonina sobre a germinação e o desenvolvimento dessas plântulas, sendo a solasonina mais ativa.

Chromatographic fractionation of bark extracts from Simira glaziovii (Rubiaceae) afforded the steroids beta-sitostenone, stigmastenone, beta-sitosterol and stigmasterol, methyl trans-4-hidroxy-3-methoxycinamate (1), the alkaloids harmane (2) and the new stereoisomer of ophiorine B (3). The structures were established by ¹H and 13C NMR, including 2D techniques and mass spectral analysis, of the natural products and pentaacetyllyalosidic acid (4a) and beta-carboline monoterpene tetraacetylglucoside (5, 1,22-lactamlyaloside) derivatives obtained by chemical transformations.

ABSTRACT Cromatographic fracionation of leaves extracts from Simira glaziovii (Rubiaceae) afforded methyl hexadecanoate, hexadecanoic, octadecanoic and eicosanoic acids, inositol, sitosterol, two triterpenes acetyl derivatives, butirospermol acetate and eufol acetate beside the saponin, 3b-O-b-D-glucopyranosylsitosterol. From the woods were isolated a carbohydrate mixture beside the harmane alkaloid. The identification of the compounds were stablished by IR, 1H and 13C NMR and GC-MS analysis beside comparison with the literature data.

RESUMO O fracionamento cromatográfico dos extratos obtidos com solventes orgânicos das folhas de Simira glaziovii permitiu o isolamento do sitosterol, dois triterpenos acetilados, acetato de butirospermol e acetato de eufol, hexadecanoato de metila, os ácidos hexadecanóico, octadecanóico e eicosanóico, inositol e a saponina 3b-O-b-D-glicopiranosilsitosterol. Do extrato metanólico da madeira isolaram-se mistura de carboidratos e o alcalóide harmana. As substâncias foram identificadas através de análise dos dados espectrométricos de IV, RMN de 1H e 13C (PND e DEPT) e CG-EM, incluindo comparação com dados da literatura.

Phytochemical investigation of the flowers of Wedelia paludosa afforded two diterpenes, ent-kaur-16-en-19-oic acid and ent-kaur-9(11),16-dien-19-oic acid, three acylated triterpenes, 3beta-O-hexa-decanoylolean-12-en-28-oic acid, 3beta-O-pentadecanoylolean-12-en-28-oic acid and 3beta-O-tetradecanoylolean-12-en-28-oic acid, and three steroids, stigmasterol, 3beta-O-beta-D-glycopyranosyl sitosterol and 3beta-O-beta-D-glycopyrano-sylstigmasterol. The substances were identified by their spectral data.