ABSTRACT
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.
ABSTRACT
ABSTRACT Annona hypoglauca Mart., Annonaceae, popularly known as “beribá”, was collected in flooded areas of the Amazonian Rain Forest. The crude extract obtained from this species was found to be cytotoxic against human cancer cells. Chemical information on A. hypoglauca is scarce. So, the present work aimed the isolation and identification of its alkaloids and to test their cytotoxic activity. Alkaloids were obtained from stem by acid–base partitioning and the remaining alkaloid-free extract was partitioned with organic solvents. Gas chromatography–mass spectrometry GC/MS analysis of total alkaloids allowed the identification of four aporphine alkaloids: actinodaphnine, anonaine, isoboldine and nornuciferine. Total alkaloids were fractionated by column chromatography and were purified by preparative thin-layer-chromatography, which allowed the isolation of two aporphine alkaloids, actinodaphnine and isoboldine, characterized by NMR and CG–MS analyses. This is the first report for the occurrence of actinodaphnine in Annona species. All the samples were tested in cytotoxic and antibacterial assays. Total alkaloid extract and its fractions showed antimicrobial activity against Staphylococcus aureus and Enterococcus faecalis. In the cytotoxicity assay, the crude extract showed a lethal effect against breast and colon cancer cells. Isoboldine-containing FA5 and actinodaphnine-containing FA6 showed activity against breast cancer cell line, while the alkaloid-free fractions did not show significant activity against cancer cell lines.
ABSTRACT
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.
ABSTRACT
Conchocarpus fontanesianus (A. St.-Hill.) Kallunki & Pirani, Rutaceae, popularly known as pitaguará, is a native and endemic tree from São Paulo and Rio de Janeiro States, Brazil. Based in the information that anticholinesterasic derivatives could act as new prototypes to treatment of Alzheimer disease, this work describes the fractionation guided by evaluation of the anticholinesterase activity of the ethanolic stems extract from C. fontanesianus. This procedure afforded the alkaloids dictamnine (1), γ-fagarine (2), skimianine (3), and 2-phenyl-1-methyl-4-quinolone (4), as well as the coumarin marmesin (5).
ABSTRACT
The essential oil of the leaves from Annona coriacea Mart., Annonaceae, was extracted by hydrodistillation in a Clevenger apparatus and analyzed by GC/MS and GC/FID. The oil yield was 0.05 percent m/m. Sixty compounds were identified, in a complex mixture of sesquiterpenes (76.7 percent), monoterpenes (20.0 percent) and other constituents (3.3 percent). Bicyclogermacrene was its major compound (39.8 percent) followed by other sesquiterpenes. Most of the monoterpenes were in low concentration (<1 percent). Only β-pinene and pseudolimonene presented the highest level of 1.6 percent. The volatile oil presented anti-leishmanial and trypanocidal activity against promastigotes of four species of Leishmania and trypomastigotes of Trypanosoma cruzi, showing to be more active against Leishmania (L.) chagasi (IC50 39.93 µ g/mL) (95 percent CI 28.00-56.95 µ g/mL).
ABSTRACT
The chemical composition of volatile oils from two Myrtaceae species, Myrceugenia myrcioidesand Eugenia riedeliana, both native from the Brazilian Atlantic Rain Forest, was analyzed by GC-MS. Acetylcholinesterase inhibitory activity was colorimetrically evaluated for these oils. For M. myrcioides, monoterpene hydrocarbons represented the major class in the volatile oil, with α-pinene as the most abundant component and a weak inhibitory activity was observed, whilst for E. riedeliana sesquiterpenes were found in higher amounts, being valerianol the major compound, and this oil presented a strong acetylcholinesterase inhibition.
A composição química dos óleos voláteis de duas espécies de Myrtaceae, Myrceugenia myrcioidese Eugenia riedeliana, ambas nativas da Mata Atlântica, foi analisada por CG-EM. A atividade inibidora de acetilcolinesterase foi determinada colorimetricamente para estes óleos. Em M. myrcioides, hidrocarbonetos monoterpênicos representaram a classe majoritária de compostos presentes no óleo volátil, sendo α-pineno o componente mais abundante e a atividade inibidora de acetilcolinesterase foi baixa, enquanto para E. riedelianaos sesquiterpenos foram observados em maiores concentrações, sendo o valerianol o componente majoritário, e este óleo apresentou uma forte atividade inibidora da enzima.
ABSTRACT
A necessidade da introdução de novos agentes quimioterápicos é uma realidade no controle de doenças infecciosas. O Brasil é o país mais rico em biodiversidade, e o Laboratório de Extração da Universidade Paulista tem coletado plantas na Amazônia e Mata Atlântica com a finalidade de identificar extratos vegetais antibacterianos e antitumorais. Estudos prévios demonstraram que a fração etanólica obtida do extrato bruto orgânico do caule de Tabernaemontana angulata Mart. ex Müll. Arg. apresentou atividade antimicrobiana significante contra Staphylococcus aureus ATCC6538, no ensaio de diluição em caldo. Verificou-se por cromatografia em camada delgada que os compostos majoritários presentes na fração ativa eram alcalóides. No presente trabalho, foi obtida a fração de alcalóides totais a partir do extrato bruto, da qual os compostos majoritários foram isolados por sucessivas cromatografias e, posteriormente, identificados por CG-EM e ¹H-RMN como os alcalóides indólicos coronaridina e voacangina. As frações obtidas do isolamento foram testadas no ensaio biológico, porém não demonstraram atividade antimicrobiana.
Introducing new chemotherapeutic agents is a great demand in the control of infectious diseases. Brazil is one of the richest countries in biodiversity and the Laboratório de Extração at UNIP has been collecting plants from the Amazon and Atlantic Rain Forests with the aim of screening for new antibacterial and antitumor plant extracts. Previous studies demonstrated that the ethanol fraction obtained from the crude extract of Tabernaemontana angulata stems showed an antibacterial activity against Staphylococcus aureus (ATCC 6538) in the microdilution broth assay. Two alkaloids were the major compounds in the active fraction, verified by thin layer chromatography analysis. In the present study, the total alkaloids were obtained from the crude extract and were fractionated by preparative thin layer chromatography for the isolation of the main components. The isolated compounds were identified by GC/MS and ¹H-NMR as coronaridine and voacangine. The alkaloid fractions obtained from the isolation procedure were tested for antibacterial activity, but no activity was detected.
ABSTRACT
Cissus verticillata L. (Vitaceae) tem sido empregada popularmente como anti-diabética. Nessa espécie foi também detectada atividade fungitóxica. O objetivo do presente trabalho foi realizar a identificação dos compostos fungitóxicos em extratos de folhas. O extrato etanólico foi submetido a fracionamento com solventes de diferentes polaridades (hexano, clorofórmio, acetato de etila e butanol) e seu efeito antifúngico foi analisado frente a Cladosporium sphaerospermum. Os extratos em clorofórmio e acetato de etila mostraram atividade, e foram fracionados por cromatografia em coluna e cromatografia preparativa em placas de sílica, respectivamente. Três terpenóides foram isolados do extrato em clorofórmio; um deles foi identificado, por análise em CG-EM, como um sesquiterpeno, o biciclogermacreno. O composto ativo do extrato em acetato de etila foi identificado, por análises em CLAE, como o estilbeno resveratrol.
Cissus verticillata L. (Vitaceae) is popularly employed as hypoglicemic and it shows fungitoxic activity. This work aims at identification of fungitoxic compounds on extracts of leaves. The ethanol extract was partitioned using solvents of different polarities (hexane, chloroform, ethyl acetate and butanol) and its fungitoxic activity was analysed upon Cladosporium sphaerospermum. The chloroform and ethyl acetate extracts showed activity and they were fractionated by column chromatography and preparative TLC, respectively. Three terpenoids were isolated from the chloroform extract, one of them identified by GLC-MS analysis as sesquiterpene bicyclogermacrene. The active compound of the ethyl acetate extract was identified by HPLC analyses as stilbene resveratrol.