Antispasmodic activity from Serjania caracasana fractions and their safety

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.

Evaluation of gastroprotective activity of Passiflora alata

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.

Uptake of Seeds Secondary Metabolites by Virola surinamensis Seedlings.

The major secondary metabolites and fatty acids occurring in the seeds of Virola surinamensis were monitored by GC-MS during germination and seedling development. The role as carbon source for seedling development was indicated considering that both classes of compounds were similarly consumed in the seeds and that no selective consumption of compounds could be detected.

Detection of adulterated copaiba (Copaifera multijuga Hayne) oil-resins by refractive index and thin layer chromatography / Detecção de óleo-resinas de copaíba adulterados através do índice de refração e da cromatografia de camada delgada

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.

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.

Evaluation of gastroprotective activity of Plinia edulis (Vell.) Sobral (Myrtaceae) leaves in rats.

Plinia edulis, an arboreous species popularly known as "cambucá", is native to the Brazilian Atlantic Rain Forest. Despite its traditional uses, no reports are available on the safety of this utilization or on the relationship between the antiulcer activity of its extract and its phytochemical compounds. This paper reports on the investigation of the acute toxicity and gastroprotective effect of the aqueous ethanol extract of leaves of Plinia edulis on HCl/ethanol-induced ulcers. In order to correlate the secondary metabolites and the efficacy of the crude drug in traditional medicine, the extract was submitted to chromatographic fractionation after solvent partition. The extract did not show acute toxicity in mice treated with 5 g/kg p.o., but exhibited significant antiulcer activity in rats at doses of 100, 200, and 400mg/kg p.o., more active than the reference drug lansoprazole.The ethyl acetate fraction yielded beta-amyrin, oleanolic acid, ursolic acid, and maslinic acid, which were identified based on spectrometric analyses. Since antiulcerogenic activity is not restricted to one class of compounds in plants, the triterpenoids isolated in the extract can be associated with the observed effect.

New butenolides in plantlets of Virola surinamensis (Myristicaceae).

A phytochemical investigation in plantlets of the Brazilian medicinal tree Virola surinamensis resulted in the isolation and structural determination of four new compounds: 3-hydroxy-4-methyl-2-(11'-piperonyl-n-undecyl)-butenolide; 3-hydroxy-4-methyl-2-(7'-piperonyl-n-heptyl)-butanolide; 9'-(3,4-methylenedioxy-phenyl)-nonanoic acid and 13'-(3,4-methylene-dioxyphenyl)-tridecanoic acid. Thirteen compounds previously isolated from seeds and adult plants were also reported.

Biosynthesis of tetrahydrofuran lignans in Virola surinamensis

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

Chemical transformations of neolignans

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.

Avaliação da atividade antibiótica de extratos de lauraceae

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.

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.

Avaliação da atividade antibiótica de extratos de lauraceae

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.

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.

The chemistry of Brazilian Lauraceae. LXV. 5, 7, 8, 3', 4', 5' - Hexamethoxyflavone from an Aniba species

Abstract Aniba species (Lauraceae) are characterized by the presence of neolignans or of 6-aryl (or 6-styryl-) 2-pyrones. Flavonoids occur either together with pyrones or, in rare cases, as predominant micromolecular type. The branch wood of an Aniba species from Marapi, Parú do Oeste River, near Tiriós (Para State), constitutes such a case. It contains 5,7,8,3'.4',5'-hexam-thoxyflavone, obtained for the first time from a natural source.

Espécies de Aniba (Lauraceae) são caracterizadas pela presença de neolignanas ou de 6-aril-(ou 6-estiril-) 2-pironas. Flavonoides ocorrem seja juntos com pironas, seja, em raros casos, como tipo micromolecular predominante. A madeira dos ramos de uma espécie de Aniba coletada em Marapi, no alto rio Paru do Oeste, nas proximidades de Tiriós (Pará), constitui um caso desta índole. Contém 5,7,8.3',4'.5'-hexametoxiflavona, obtida pela primeira vez de fonte natural.

The chemistry of Brazilian Lauraceae. LXV. 5, 7, 8, 3', 4', 5' - Hexamethoxyflavone from an Aniba species

Abstract Aniba species (Lauraceae) are characterized by the presence of neolignans or of 6-aryl (or 6-styryl-) 2-pyrones. Flavonoids occur either together with pyrones or, in rare cases, as predominant micromolecular type. The branch wood of an Aniba species from Marapi, Parú do Oeste River, near Tiriós (Para State), constitutes such a case. It contains 5,7,8,3'.4',5'-hexam-thoxyflavone, obtained for the first time from a natural source.

Espécies de Aniba (Lauraceae) são caracterizadas pela presença de neolignanas ou de 6-aril-(ou 6-estiril-) 2-pironas. Flavonoides ocorrem seja juntos com pironas, seja, em raros casos, como tipo micromolecular predominante. A madeira dos ramos de uma espécie de Aniba coletada em Marapi, no alto rio Paru do Oeste, nas proximidades de Tiriós (Pará), constitui um caso desta índole. Contém 5,7,8.3',4'.5'-hexametoxiflavona, obtida pela primeira vez de fonte natural.