RESUMO
Three new compounds, a bicyclogermacrene (1) and two 2,3-secoaromadendrane esters (2 and 3), together with (13S)-13-hydroxylabda-8,14-diene (4), fusicogigantone B (5), 3α,14-diacetoxy-2-hydoxybicyclogermacrene (6), fusicogigantone A (7), neofuranoplagiochilal (8), plagiochiline B (9), furanoplagiochilal (10), trans-nerolidol, spathulenol, α-tocopherol, and (+)-globulol were isolated from an Argentine collection of Plagiochila diversifolia. Their structures were elucidated by extensive mono and bidimensional NMR studies. Compounds 4, 5, and 6, incorporated to the larval diet at 100 µg per g of diet, reduced the larval growth of Spodoptera frugiperda (Lepidoptera: Noctuidae) by 70 ± 25, 57 ± 23, and 33 ± 16%, respectively. Compounds 4 and 5 produced 70% and 60% larval mortality at early instars. The latter also showed antifeedant properties in the Choice Test, with a feeding ratio of 0.54 ± 0.16.
Assuntos
Hepatófitas/química , Inseticidas/química , Animais , Argentina , Hepatófitas/metabolismo , Inseticidas/toxicidade , Larva/efeitos dos fármacos , Larva/crescimento & desenvolvimento , Espectroscopia de Ressonância Magnética , Conformação Molecular , Spodoptera/efeitos dos fármacos , Spodoptera/crescimento & desenvolvimentoRESUMO
The new 2,3-secoaromadendrane 1, together with the known compounds plagiochilines A and M (2 and 3, resp.), fusicogigantone A (4), and 1,4-dimethylazulene (5) were isolated from an Argentine collection of the liverwort Plagiochila bursata. Structures were elucidated by extensive 1D- and 2D-NMR studies. Compounds 2 and 4, incorporated to the larval diet at 100 microg per g of diet, reduced the larval growth of Spodoptera frugiperda (Lepidoptera: Noctuidae) by 66+/-29% and 25+/-8% and produced 55 and 75% larval mortality at early instars and 20 and 25% pupal mortality, respectively. Treatment with compound 2 also produced abdomen and wing malformation in adults leading to impossibility to mate.
Assuntos
Hepatófitas/química , Inseticidas/química , Inseticidas/farmacologia , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Spodoptera/crescimento & desenvolvimento , Animais , Inseticidas/isolamento & purificação , Larva/crescimento & desenvolvimento , Pupa/crescimento & desenvolvimento , Sesquiterpenos/isolamento & purificaçãoRESUMO
Seven africanes (1, 2a,b, 3-6), two of them new (1, 2a), three secoafricanes (7-9), one of them new (7), and two norsecoafricanes (10, 11a), one of them new (10), all of them swartzianin-type, have been isolated from an Argentine collection of the endemic liverwort Porella swartziana. The structures of the new compounds were established by extensive 1D and 2D NMR spectroscopic data. Absolute configurations of compounds 2a, 2b, and 10 were derived on the basis of CD spectra. The compounds were tested for activity against a variety of microbes, but none were found to exhibit significant antibacterial activity.
Assuntos
Antibacterianos/isolamento & purificação , Hepatófitas/química , Plantas Medicinais/química , Sesquiterpenos/isolamento & purificação , Antibacterianos/química , Antibacterianos/farmacologia , Argentina , Bactérias/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Dicroísmo Circular , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Staphylococcus aureus/efeitos dos fármacosRESUMO
Two eremophilanolides, 5-epidilatanolides A and B, as well as a new natural bibenzyl were isolated from an Argentine collection of the liverwort Frullania brasiliensis, along with the known eudesmane-type sesquiterpene lactones nepalensolide A, nepalensolide B, (+)-frullanolide, and (+)-dihydrofrullanolide, the hopanoid zeorin, the four sterols stigmasta-4,22-dien-3,6-dione, stigmasta-4,22-dien-3-one, stigmasterol, and sitosterol, and a trace amount of atraric acid. The structure and stereochemistry of the eremophilanolides and the bibenzyl were established by a combination of extensive NMR spectroscopy experiments and X-ray crystallographic analysis. Absolute configurations of the new compounds were derived on the basis of CD spectra.