RESUMO
Salinaphthoquinones A-E (1-5) were isolated from a marine Salininispora arenicola strain, recovered from sediments of the St. Peter and St. Paul Archipelago, Brazil. The structures of the compounds were elucidated using a combination of spectroscopic (NMR, IR, HRESIMS) data, including single-crystal X-ray diffraction analysis. A plausible biosynthetic pathway for 1-5 is proposed. Compounds 1 to 4 displayed moderate activity against Staphylococcus aureus and Enterococcus faecalis with MIC values of 125 to 16 µg/mL.
Assuntos
Antibacterianos/farmacologia , Sedimentos Geológicos/química , Micromonosporaceae/química , Naftoquinonas/farmacologia , Água do Mar/química , Antibacterianos/química , Brasil , Sedimentos Geológicos/microbiologia , Estrutura Molecular , Naftoquinonas/química , Água do Mar/microbiologiaRESUMO
From the leaves of Solanum campaniforme (Solanaceae), eight solanidane alkaloids were isolated, four of which contain a p-hydroxyphenylethylamine unit. Their structures were established as: 22ß,23ß-epoxy-solanida-1,4-dien-3-one; 22α,23α-epoxy-10-epi-solanida-1,4,9-trien-3-one; 22α,23α-epoxy-solanida-4-en-3-one; 22ß,23ß-epoxy-solanida-4-en-3-one; (E)-N-[8'(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4,9-trien-3-imine; (E)-N-[8'(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4-dien-3-imine; (Z)-N-[8'(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4,9-trien-3-imine and (Z)-N-[8'(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4-dien-3-imine. All structures were determined using spectroscopic techniques, such as 1D and 2D NMR, and HRESIMS. The cytotoxicity and the antiophidic activities of the alkaloids were evaluated. The alkaloids did not show any cytotoxicity, but inhibited the main toxic actions of Bothrops pauloensis venom.
Assuntos
Alcaloides/isolamento & purificação , Solanum/química , Alcaloides/química , Alcaloides/farmacologia , Brasil , Venenos de Crotalídeos/antagonistas & inibidores , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , EstereoisomerismoRESUMO
From the leaves of Solanum campaniforme, two new spirosolane alkaloids ß-acetoxyl-(25S)-22ßN-spirosol-4-en-3-one (1) and ß-hydroxyl-(25S)-22ßN-spirosol-4-en-3-one (4) were isolated along with two other known alkaloids of the same class (25S)-22ßN-spirosol-1,4-dien-3-one (2) and (25S)-22ßN-spirosol-4-en-3-one (3), which are reported for the first time as natural products. The structures of all alkaloids were established after an extensive analysis by 1D and 2D NMR spectroscopy (COSY, HSQC, HMBC and NOESY) as well as HRESIMS.
Assuntos
Alcaloides/química , Solanum/química , Alcaloides/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Fitosteróis/química , Fitosteróis/isolamento & purificação , Folhas de Planta/química , Padrões de Referência , Alcaloides de Solanáceas/química , Alcaloides de Solanáceas/isolamento & purificaçãoRESUMO
Three new solanidane alkaloids bearing a 22,23-epoxy ring (1-3) and four known compounds were isolated from leaves of Solanum campaniforme. The structures were determined using spectroscopic techniques, including 1D and 2D NMR, and HRESIMS experiments. The antiophidic activity of the alkaloids was tested against Bothrops pauloensis venom. Compounds 1-3 completely inhibited myotoxicity without inhibiting phospholipase A2 activity of the venom, while hemorrhage and skin necrosis were significantly reduced in the presence of alkaloids 1 and 2.
Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Venenos de Crotalídeos/toxicidade , Solanum/química , Esteroides/isolamento & purificação , Esteroides/farmacologia , Alcaloides/química , Alcaloides/imunologia , Animais , Bothrops/fisiologia , Brasil , Venenos de Crotalídeos/sangue , Venenos de Crotalídeos/metabolismo , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , Esteroides/químicaRESUMO
Croton regelianus Muell. Arg., popularly known as 'velame-de-cheiro', is a native plant from the Northeast of Brazil used in folk medicine to treat diseases of different kinds, including malignant tumors. In this study, the in vitro and in vivo antitumor effects of the essential oil from the leaves of C. regelianus and ascaridole, one of the main constituents, were investigated. In vitro, the essential oil and ascaridole displayed cytotoxicity, showing IC(50) values in the range of 22.2 to 48.0 microg/ml in HL-60 and SF-295 cell lines for the essential oil, and 6.3 to 18.4 microg/ml in HL-60 and HCT-8 cells lines for ascaridole, respectively. The in vivo study, using sarcoma 180 as a tumor model, demonstrated inhibition rates of 28.1 and 31.8% for essential oil, at the 50 and 100 mg/kg, while ascaridole inhibition rates were 33.9% at 10 mg/kg and 33.3% at 20-mg/kg doses. Histopathological examination showed that the organs were only weakly affected by the treatment. In conclusion, ascaridole has an interesting antitumor activity in sarcoma 180 murine model, probably related to the described cytotoxic activity, and, moreover, its presence in the essential oil from the leaves of C. regelianus could explain, at least in part, the ethnopharmacological use of this plant in the treatment of cancer.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Monoterpenos/farmacologia , Óleos Voláteis/farmacologia , Peróxidos/farmacologia , Óleos de Plantas/farmacologia , Animais , Linhagem Celular Tumoral , Croton/química , Monoterpenos Cicloexânicos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Camundongos , Folhas de Planta/química , Sarcoma 180RESUMO
The chemical composition of the leaf essential oil of Croton regelianus collected from wild plants growing in two different sites at Ceará State (Brazil) was analyzed by GC/MS and GC-FID. Twenty monoterpenoids, representing more than 96% of the chemical composition of the oils, were identified and quantified. The oils showed similar chemical composition but considerable variation in the levels of each constituent. Ascaridole (33.9-17.0%), p-cymene (22.3-21.6%), and camphor (13.0-3.1%) were the predominant constituents. The monoterpene ascaridole was isolated and characterized by spectroscopic data. The essential oils and the isolated compounds were tested against Aedes aegypti and Artemia sp. larvae, and the root knot nematode Meloidogyne incognita. The bioassay results show that the essential oil of C. regelianus and ascaridole were moderately active against the M. incognita, but strongly effective against both A. aegypti and Artemia sp. larvae.