RESUMO
The phytochemical investigation of Piptadenia gonoacantha (Mart.) J.F. Macbr. (Leguminosae-Mimosoideae), commonly known as "pau jacaré" (alligator stick), afforded sitosterol, campesterol, stigmasterol, the N-benzoylphenylalanine-2-benzoylamide-3-phenylpropyl ester, known as asperphenamate, sitosterol-3-O-β-D-glucopyranoside, besides three flavonoids, apigenin, 5-O-methylapigenin and 7,4'-dihydroxy-3',5-dimethoxyflavone from its branches. From its leaves, the methyl gallate and two flavonoids, vitexin and isovitexin, were isolated. From its bark, a mixture of sitosterol, campesterol, and stigmasterol, besides a mixture of cycloartenone, cycloartan-25-en-3-one, and 24-methylene-cycloartenone, and the pure triterpenes 24-methylenecycloartanol, friedelin, lupeol and lupenone, were isolated. Their structures were established on the basis of spectral analysis, comparison with literature data and GC-MS analysis of the mixtures. The ester, flavonoids and the cycloartanes are been identified for first time in the genus Piptadenia.
O estudo fitoquímico de galhos de Piptadenia gonoacantha (Mart.) J.F. Macbr. (Leguminosae-Mimosoideae), comumente conhecida como "pau jacaré", forneceu sitosterol, estigmasterol, o éster N-benzoilfenilalaninato de 2-N-benzoil-3-fenilpropila, conhecido como asperfenamato, 3-O-β-D-glicopiranosil-sitosterol, além de três flavonóides, apigenina (5,7,4'-triidroxiflavona), apigenina-5-O-metil éter e 7,4'-dihidroxi-3' , 5-dimetoxiflavona. Das folhas isolaram-se galato de metila e dois flavonóides, 8-C-glicopiranosil-5,7,4' -trihidroxiflavona e 6-C-glicopiranosil-5,7,4'-trihidroxiflavona, conhecidas como vitexina e isovitexina. Das cascas desta planta isolaram-se uma mistura de sitosterol, campesterol e estigmasterol; mistura de cicloartenona, cicloartan-25,26-en-3-ona e 24-metileno-cicloartanona, além dos triterpenos, 24-metilenocicloartenol, fridelina, lupeol e lupenona. As estruturas foram estabelecidas através de análise de espectros de IV, RMN ¹H e 13C e massas, além de análise com CG-EM para identificar os componentes das misturas de cicloartanos e esteróides. O éster conhecido como asperfenamato, os flavonóides e os cicloartanos estão sendo registrados pela primeira vez em Piptadenia.
Assuntos
Fabaceae/química , Casca de Planta/química , Extratos Vegetais/química , Folhas de Planta/química , Cromatografia em Gel , Fabaceae/classificação , Espectrometria de MassasRESUMO
The antimicrobial activity of copaiba oils was tested against Gram-positive and Gram-negative bacteria, yeast, and dermatophytes. Oils obtained from Copaifera martii, Copaifera officinalis, and Copaifera reticulata (collected in the state of Acre) were active against Gram-positive species (Staphylococcus aureus, methicillin-resistant S. aureus, Staphylococcus epidermidis, Bacillus subtilis, and Enterococcus faecalis) with minimum inhibitory concentrations ranging from 31.3-62.5 µg/ml. The oils showed bactericidal activity, decreasing the viability of these Gram-positive bacteria within 3 h. Moderate activity was observed against dermatophyte fungi (Trichophyton rubrum and Microsporum canis). The oils showed no activity against Gram-negative bacteria and yeast. Scannning electron microscopy of S. aureus treated with resin oil from C. martii revealed lysis of the bacteria, causing cellular agglomerates. Transmission electron microscopy revealed disruption and damage to the cell wall, resulting in the release of cytoplasmic compounds, alterations in morphology, and a decrease in cell volume, indicating that copaiba oil may affect the cell wall.