Abstract In a previous study, we reported the antispasmodic and gastroprotective effects of the Serjania caracasana (Jacq.) Willd., Sapindaceae, extract. In the present study, we evaluated the LD50, hemolytic and antispasmodic activities of its fractions and characterized its major constituents by isolation and GC–MS. The animals showed non-toxic symptoms with oral doses up to 2000 mg/kg, suggesting a safe oral administration. Furthermore, a low hemolytic activity was detected for the saponin fraction. Antispasmodic activity of the fractions was evaluated through carbachol-induced contractions in rat ileum. The hexane fraction was the most potent (IC50 68.4 ± 5.9 µg/ml) followed by the dichloromethane fraction (IC50 161.3.4 ± 40.7 µg/ml). Butanol fraction was the less effective (IC50 219.8 ± 60.3 µg/ml). The phytochemical study of the S. caracasana fractions afforded the isolation of friedelin, β-amyrin, allantoin and quercitrin. This is the first time that the presence of allantoin and quercitrin in the Serjania genus has been reported. Among the isolated compounds and those characterized by GC–MS, β-amyrin and β-sitosterol were present in the most active fractions, hexane and dichloromethane, and they may be related to its antispasmodic activity. In addition, spathulenol was only found in the hexane fraction and its presence might justify the highest antispasmodic activity observed for this fraction.

AbstractPassiflora alata Curtis, Passifloraceae, is a liana popularly known in Brazil as ‘maracujá-doce’ that has been used for treating different illnesses. Its leaves are described in the Brazilian Pharmacopoeia, but the gastroprotective activity has never been investigated. In the present study a freeze-dried crude 60% ethanol–water extract of P. alata aerial parts was prepared. Total flavonoid content, expressed as vitexin, was 0.67% ± 0.01. The hemolytic activity was 32 units for P. alata, using Saponin (Merck®) as reference. P. alata presented EC50 of 1061.2 ± 8.5 µg/ml in the 2,2-diphenyl-1-picryhydrazyl assay and 1076 ± 85 µmol Trolox/g in the Oxygen Radical Absorbance Capacity assay. P. alata, its solvent fractions and a P. alatananopreparation were investigated for gastroprotective activity. The test samples exhibited gastroprotective activity on HCl/ethanol induced gastric mucosal lesions in rats. P. alata at doses of 100, 200 and 400 mg/kg, using the necrotizing agent at 150 mmol/l, inhibited 100% of ulcer formation (compared to the negative control), while lansoprazole (30 mg/kg) 77%. When tested against a more concentrated necrotizing agent (300 mmol/l), fractions of P. alata at 100 mg/kg reduced 57% (n-hexane), 34% (ethyl acetate) and 72% (aqueous fraction) the ulcer formation. In this assay, lansoprazole (30 mg/kg) inhibited 47%. When encapsulated, P. alata inhibited ulcer formation at 55%, 94% and 90% for dosages of 25, 50 and 100 mg/kg. These results suggest the potential use of P. alata as a gastroprotective herbal medicine.

The neolignans are defined as dimers of allylphenol and propenylphenol between itself or crossed, whose bond does not occur by the 8-8' carbons like lignans. This review centered on stereochemical aspects of the hydrobenzofuran type, a widespread skeleton among neolignans. The chemical structures established based on spectrometric data are registered in the literature. The absolute configurations reported previously were determined by chiroptical techniques. Some chemical transformations with neolignans, performed in previous studies, afforded products which are accumulated in other vegetal species and contributed to assign the unknown stereochemistry of these natural compounds. Possible biosynthetic pathways are also proposed.

This paper describes the incidence of fatty acids in different tissues of nine species of Araceae: Anthurium sellowianum, Caladium bicolor, Dracontium spruceanum, Monstera adamsonii, Philodendron appendiculatum, P. cordatum, P. loefgrenii, Philodendron sp and Xanthosoma maximilianii; the hexane extracts were initially transesterified and subsequently analyzed by the system gas chromatograph-mass spectrometer, yielded palmitic, linoleic, oleic and stearic acids as major constituents in the different tissues of the species studied. Also is reported comparison among leaves, roots and tubers of different species and the occurrence of these acids in each tissues of the nine Araceae species.

Este trabajo describe la incidencia de ácidos grasos en los diferentes órganos de nueve especies de Araceae: Anthurium sellowianum, Caladium bicolor, Dracontium spruceanum, Monstera adamsonii, Philodendron appendiculatum, P. cordatum, P. loefgrenii, Philodendron sp. y Xanthosoma maximilianii; a partir del extracto hexánico que inicialmente fue transesterificado y posteriormente fue analizado por cromatografía gaseosa acoplada a un espectrómetro de masas, se encontró que los ácidos palmítico, linoleico, oleico y esteárico son los mayoritarios en los diferentes órganos de las especies en estudio; se realizó también una comparación entre hojas, órganos subterráneos de las diferentes especies y la ocurrencia de éstos ácidos en cada órgano de las nueve especies de Araceae.

This work describes phytochemical analysis of an Araceae species Dracontium spruceanum (Schott) G.Zhu, which occurs in Amazon region and is popularly used against snakebite and treatment of some diseases. The solvent partitions and chromatographic fractionations of extract afforded sitosterol (I), stigmasterol (II), 3-ß-hydroxycolest-5-en-7-one (III), p- hydroxybenzaldehyde (IV), p-hydroxybenzoic acid (V), acyl-glycosyl sitosterol (VI), acyl- glycosyl-7-oxo-sitosterol (VII), sitosteryl-glycoside (VIII), sucrose (IX). The polar fractions were acetylated before the purification and the isolation through chromatographic techniques yielded a mixture of peracetylated carbohydrates: 2,3,4,6-tetra-O-acetyl-1-ethylglucose (X), which was identified by spectroscopic analysis [GC-MS, 13CNMR and ¹HNMR].

Este trabajo describe el análisis fitoquímico de los túberos de Dracontium spruceanum (Schott) G.Zhu, nativo de la región amazónica, el cual es usado popularmente contra picada de la serpiente Bothrops atrox y también para algunas enfermedades. A partir de la extracción con solventes orgánicos y la separación por cromatografía del extracto etanólico, se obtuvo sitosterol (I), estigmasterol (II), 3-ß-hidroxi-5-eno-7-cetona (III), p-hidroxibenzaldehído (IV), ácido p-hidroxybenzoico (V), sitosterol acilglicosilado (VI), 7-oxositosterol acilglicosilado (VII), sitosterolglicosilado (VIII), sacarosa (IX); las fracciones polares fueron acetiladas y sometidas a purificación por cromatografía, que condujeron a una mezcla de carbohidratos peracetilados, 2,3,4,6-tetra-O-acetil-1-etil-glucosa (X); los diez compuestos fueron identificados y elucidados por análisis espectroscópico CG-EM, RMN¹H y RMN13C.

Phytochemical investigations on three Brazilian Lauraceae species from the Cerrado region of São Paulo State, Ocotea corymbosa (Meins) Mez., O. elegans Mez. and Persea pyrifolia Nees & Mart. ex Nees resulted in the isolation of flavonoids, an ester of the 4-O-E-caffeoylquinic acid, an aromatic sesquiterpene besides furofuran lignans. This is the first chemical study on the leaves of Ocotea elegans and O. corymbosa as well as the first report of non-volatile compounds from Persea pyrifolia.

Os índices de refração (IR) de oito amostras de óleo resina de copaíba coletadas para este estudo na RDS Tupé variaram de 1,50284 a 1,50786. As placas de cromatografia de camada delgada (CCD) dos óleo-resinas, reveladas com o reagente anisaldeído-ácido sulfúrico, apresentaram um perfil cromatográfico característico, com manchas em lilás escura com várias manchas menores na parte do Rf baixo e uma grande mancha arredondada, no Rf alto. Por outro lado, as doze amostras de óleo de copaíba adquiridas no mercado local apresentaram IR entre 1,48176 a 1,50886, e, as placas de CCD apresentaram como perfil característico geral manchas de cor azul, com manchas superpostas menores no Rf baixo, manchas superpostas maiores com aparência alongada no Rf alto e uma mancha arredondada incolor no Rf intermediário. Dentre os doze óleos adquiridos do mercado, a) três óleo-resinas apresentaram IR e perfil CCD semelhantes aos de amostras de óleo de copaíbas coletadas; b) seis óleos apresentaram o mesmo IR e perfil em CCD do óleo de soja; e, c) três amostras apresentaram IR semelhantes aos da amostra do Tupé, porém com o perfil cromatográfico semelhante à uma mistura de óleo de soja: óleo de copaíba, sendo duas na proporção de 3:1 e uma na proporção de 1:3. Portanto, a determinação do IR e a análise do perfil em CCD podem ser considerados ensaios rápidos e eficientes para a detecção de óleos vegetais em óleo-resina de copaíba.

The refractive indices (RI) of the eight samples of copaiba oils, collected for this study at RDS Tupé ranged from 1.50284 to 1.50786. The thin layer chromatography (TLC) plates of these oils revealed with anisaldehyde-sulphuric acid reagent showed dark lilac stains with several small stains at low Rf and a large rounded stain at high Rf. On the other hand, the twelve copaiba oils purchased at local markets presented RI between 1.48176 and 1.50886, and the TLC plates, showed as general profile blue stains, with smaller superimposed stains at low Rf, bigger superimposed stains like elongated stain at high Rf and a colorless rounded stain at middle Rf. Among 12 purchased oils at local markets, a) three oil-resins presented similar RI and TLC profile to those observed for collected copaiba oils; b) six oils showed same RI and TLC profiles to those observed for soybean oil; c) three samples presented RI near to those showed by copaiba oil-resin, however the TLC profile was near to profile observed for a prepared mixture soybean oil: copaiba oil, two samples with 3:1 proportion and one sample with 1:3 proportion. Therefore, the RI determination and the TLC profiles could be considered rapid and efficient procedures for detection of vegetal oil in the copaiba oil-resins.

O trabalho consiste na re-investigação dos frutos de Iryanthera juruensis e Virola pavonis e das folhas de V. michelii, bem como no estudo dos frutos de V. mollissima. A partir de I. juruensis foram isoladas uma neolignana ariltetralínica (1) e uma neolignana tetraidrofurânica (2), enquanto que de Virola pavonis foram isoladas neolignanas benzofurânicas (6-9), tetraidrofurânicas (2, 11-13, 17), bifenílica (10), diastereoisômeros de uma hidróxi-neolignana 8.O.4'(14-15) e outras. V. mollissima acumula a neolignana ariltetralônica 4 ou o seu derivado seco (5). As folhas de V. michelii apresentaram a ocorrência de lignanas furofurânicas (18-19). Os lignóides 1 e 2 obtidos dos arilos de I. juruensis apresentaram atividade leishmanicida contra a forma promastigota de Leishmania amazonensis.

This work revisits the fruits of Iryanthera juruensis and Virola pavonis and the leaves from V. michelii, as well as describing a study of the fruits of V. mollissima. In I. juruensis aryltetraline neolignan (1) and tetrahydrofuran neolignan (2), were found while from V. pavonis neolignans of benzofuran type (6-9), the tetrahydrofuran type (2, 11-13, 17) and the biphenyl type (10), in addition to diastereoisomers of the 8.O.4'-oxyneolignan type (14 and 15) and others were isolated. The V. mollissima accumulates the aryltetralone neolignan 4 and its seco derivative (5). The lignoids 1 and 2 obtained from I. juruensis arils possess antileishmanial activity against the promastigote form of Leishmania amazonensis.

Foram isoladas de extratos de folhas de Ocotea catharinensis Mez (Lauraceae) quatorze neolignanas sendo nove benzofurânicas (incluindo três novas substâncias 1e, 2f e 4b), uma secobenzofurânica inédita (3b), duas biciclo[3.2.1]octânicas (incluindo a nova 5c), dois novos dímeros biciclo[3.2.1]octânicos (7a e 7b) e ainda dois sesquiterpenos (incluindo o novo humulanol 9). Nos embriões somáticos de O. catharinensis foram identificadas sete neolignanas incluindo uma nova neolignana biciclo[3.2.1]octânica (4a).

The extracts from leaves of Ocotea catharinensis Mez (Lauraceae) were found to contain fourteen neolignans and two sesquiterpenes: nine benzofuran types (including three new compounds 1e, 2f and 4b), one new seco-benzofuran type (3b), two bicyclo[3.2.1]octane types (including the new compound 5c), two new dimers of bicyclo[3.2.1]octane type (7a and 7b) and two sesquiterpenes (including a new humulanol 9). In addition, seven neolignans were also showed to occur in somatic embryos of O. catharinensis including one new bicyclo[3.2.1]octane type (4a).

Plinia edulis (Myrtaceae), popularmente conhecida como "cambucá", é uma planta medicinal nativa do Brasil e empregada no tratamento de problemas estomacais e afecções de garganta por populações caiçaras. Buscando contribuir para o conhecimento da espécie, as folhas de P. edulis foram caracterizadas macro e microscopicamente e a composição química do óleo volátil foi determinada usando uma combinação de CG/EM e índices de retenção. O extrato hidroetanólico das folhas foi avaliado quanto ao perfil fitoquímico e à atividade antimicrobiana procurando-se a correlação dos metabólitos secundários e o uso tradicional. As folhas apresentam características morfológicas comuns a outras mirtáceas e algumas particularidades, como a presença de 2 a 4 idioblastos, contendo drusas e cristais prismáticos, dispostos perpendicularmente à face adaxial. No óleo volátil foram identificados 15 componentes, dentre os quais o epi-α-cadinol (21.7%), o α-cadinol (20.2%) e o trans-cariofileno (14.2%) foram os majoritários. A triagem fitoquímica do extrato hidroetanólico evidenciou a presença de substâncias de interesse farmacológico, tais como flavonóides, taninos, saponinas e terpenóides. No entanto, apesar da presença destas classes, o extrato não inibiu o crescimento de Aspergillus niger, Candida albicans, Escherichia coli e Staphylococcus aureus na concentração de até 1.000 mg/mL.

Plinia edulis (Myrtaceae), popularly known as "cambucá", is a Brazilian medicinal plant employed in the treatment of stomach problems and throat affections by the "caiçaras", fishermen of coastal localities. Aiming to contribute with the species knowledge the leaves of P. edulis were analyzed macro and microscopically and the chemical composition of the volatile oil was determined using a combination of GC/MS and retention indices. The antimicrobial assay and the phytochemical screening of the aqueous ethanol extract of the leaves have been performed to correlate the secondary metabolites and the traditional use. Leaves present morphological characteristics of others Myrtaceae species and some particularities, such as the circular idioblasts in number of 2 to 4, scattered perpendicularly at the adaxial surface, with druses or prismatic crystals. In the volatile oil fifteen components have been identified, of which epi-α-cadinol (21.7%), α-cadinol (20.2%) and trans-caryophyllene (14.2%) were major. The phytochemical screening of the aqueous ethanol extract showed the presence of substances with pharmacological interest, such as flavonoids, tannins, saponins and terpenoids but, despite of the presence of these classes, the extract did not inhibit the growth of Aspergillus niger, Candida albicans, Escherichia coli and Staphylococcus aureus in a concentration of 1,000 mg/mL.

O extrato etanólico das folhas de Nectandra grandiflora coletadas na Mata Atlântica, Brasil, mostrou atividade antioxidante frente ao b-caroteno em teste usando cromatografia em camada delgada. O fracionamento biomonitorado levou ao isolamento do ácido protocatecuico e de dois flavonóides glicosilados: afzelina e quercetrina, os quais exibiram atividade sequestradora de radicais livres frente ao DPPH (DA 32, 16 e 73% a 50 µmol L-1) e foram comparados aos antioxidantes comerciais rutina (81% a 50 µmol L-1) e BHT (9% a 50 µmol L-1), usados como substâncias de referência. Além disso, três neolignanas inativas, incluindo a nova neolignana biciclo[3.2.1]octânica 2'-oxo-piperol B, foram obtidas e caracterizadas por métodos espectrométricos.

The EtOH crude extract from the leaves of Nectandra grandiflora collected in the Atlantic Forest, Brazil, showed antioxidant activity towards b-carotene in a TLC assay. The bioassay-guided fractionation led to the isolation of protocatechuic acid and two flavonol glycosides: afzelin and quercetrin, which showed free radical scavenging activity towards DPPH (DA 32, 16 and 73% at 50 µmol L-1) and were compared to commercial antioxidants rutin (81% at 50 µmol L-1) and BHT (9% at 50 µmol L-1), used as standard compounds. Additionally, three inactive neolignans, including the new bicycle[3.2.1]octane neolignan 2'-oxo-piperol B were obtained and characterized by spectrometric methods.

Através de experimentos de administração in vivo em plântulas de Virola surinamensis, observaram-se as incorporações de fenilalanina e do fenilpropanóide E-isoeugenol no 4-O-metil-5-metoxi-E-isoeugenol (E-isoelemicina) e na lignana tetraidrofurânica verrucosina.

The labelled substrates phenylalanine and phenylpropanoid E-isoeugenol were incorporated to 5-methoxy-4-O-methyl-E-isoeugenol (E-isoelemicin) and to the tetrahydrofuran lignan verrucosin in plantlets of Virola surinamensis (Myristicaceae).

Os deslocamentos químicos de RMN 13C de carbonos a , b , g e d de 17 conjuntos de haletos (F, Cl Br e I) alifáticos, inclusive compostos mono, bi e tricíclicos, podem ser reproduzidos por uma equação linear de duas constantes e duas variáveis do tipo : d R-X = A*d R-X1 + B*d R-X2 onde A e B são constantes obtidas por regressão multilinear a partir de deslocamentos químicos de 13C; d R-X, o deslocamento químico de 13C do composto com halogênio (R-X); d R-X1 e d R-X2 deslocamentos químicos de outros haletos. Para brometos (R-X) alifáticos a melhor correlação foi obtida com os dados de fluoretos (R-X1) e iodetos (R-X2) com R2 de 0,9989 e desvio médio absoluto (DM) de 0,39ppm. Para cloretos (R-X) a melhor correlação foi com dados de brometos (R-X1) e iodetos (R-X2) com R2 de 0,9960 e DM de 0,76ppm. Para fluoretos (R-X) a melhor correlação foi com brometos (R-X1) e iodetos (R-X2) com R2 de 0,9977 e DM de 1,10ppm e para iodetos (R-X) foi com fluoretos (R-X1) e brometos (R-X2) com R2 de 0,9972 e desvio médio absoluto de 0,60 ppm.

The 13C NMR chemical shifts of the a , b , g and d carbons of 17 sets of aliphatic halides (F, Cl, Br and I ), including mono, bi and tricyclic componds, can be reproduced by a linear equation composed with two constants and two variables: d R-X = A * d R-X1 + B* d R-X2, where A and B are constants derived from multilinear regression of 13C chemical shifts observed; d R-X, the chemical shifts of aliphatic halide (R-X) and d R-X1, d R-X2 the chemical shifts of other halides. Were observed better correlation for aliphatic bromides (R-X) by using data of aliphatic fluorides (R-X1) and aliphatic iodides (R-X2), resulting R2 of 0.9989 and average absolute deviation (AVG) of 0.39 ppm. For the clorides (R-X), the better correlation were observed by using data of bromides (R-X1) and iodides (R-X2), R2 of 0.9960 and AVG of 0.76ppm. For the fluorides (R-X) were observed better correlation with data of bromides (R-X1) and iodides (R-X2), R2 of 0.9977 and AVG of 1.10 ppm. For the iodides (R-X) were observed better correlation with data of fluorides (R-X1) and bromides (R-X2), R2 of 0.9972 and AVG of 0.60.

Neolignans, generated by oxydative dimerization of propenylphenol and/or allylphenol, undergo further modifying steps. These biosynthetic reactions, confirmed in vitro, include Cope, retro-Claisen and Claisen rearrangements. Additionally acid catalysis effects convertions of bicyclo [3.2.1] octanoid neolignans into hydrobenzofuranoid neolignans, or inversely of hydrobenzofuranoid neolignans into bicyclo [3.2.1] octanoid neolignans, of hydrobenzofuranoid neolignans into futoenone type neolignans, of tetrahydrofuran neolignans into aryltetralin neolignans, as well as modifications by Friedel - Crafts reactions and the transformation of aryltetralin neolignans into arylindanones by pinacoline - pinacolone type rearrangement.

Os extratos hexânicas, clarofórmicos e hidroalcoólicos da cálices e dos frutos de quatro espécies de lauráceaes da Amazônia, Licaria armeniaca, Licaria chrysophylla, Aniba riparia e Aniba sp (No provisório 62), foram avaliados quanto à sua atividade antibiótica. Para os ensaios foram utilizadas bactérias Gram-Positivas, bactérias Gram-negativas e leveduras. Os extratos hexânicos e clorofórmicos das duas espécies de Aniba mostraram atividade contra diversos microorganismos.

Hexane, chloroform and aqueous ethanol extrats of calices and fruits of four especies of Lauraceae ( Licaria armeniaca, L. chrysophylla, Aniba riparia and Aniba sp) were prepared and investigated for their antibiotic activities. The hexane and chloroform extrats of both species of Aniba inhibited the growth of some of the microorganisms tested.