RESUMO
A systematic molecular fragmentation pathway (SMFP) was designed as an identifier to detect swartziarboreols (abieta-8,11,13-triene diterpenoid derivatives) in Swartzia extracts. The SMFP was rationalised through the interpretation of the EI/MS of swartziarboreols isolated from S. arborescens and S. langasdorffii and by analogy with the fragmentations observed for previously isolated compounds. Two pairs of swartziarboreol epimers were identified by GC-MS in an extract of S. langsdorffii using SMFP. Acetylation and methylation of the dichloromethane extract furnished, respectively, 3 and 4, which suggested the occurrence of a new natural orthodiphenolic swartziarboreol.
Assuntos
Abietanos/química , Fabaceae/química , Espectrometria de Massas por Ionização por Electrospray , Estrutura Molecular , Extratos Vegetais/químicaRESUMO
The presence of saponins and the molluscicidal activity of the roots, leaves, seeds and fruits of Swartzia langsdorffii Raddi (Leguminosae) against Biomphalaria glabrata adults and eggs were investigated. The roots, seeds and fruits were macerated in 95% ethanol. These extracts exerted a significant molluscicidal activity against B. glabrata, up to a dilution of 100 mg/l. Four mixtures (A2, B2, C and D) of triterpenoid oleanane type saponins were chromatographically isolated from the seed and fruit extracts. Two known saponins (1 and 2) were identified as beta-D-glucopyranosyl-[alpha-L-rhamnopyranosyl-(1->3)- beta-D-glucuronopyranosyl-(1->3)]-3beta-hydroxyolean-12-ene-28 -oate, and beta-D-glucopyranosyl-(1->3)-beta-D-glucuronopyranosyl-(1 ->3)]-3beta-hydroxyolean-12-ene-28-oate, respectively. These two saponins were present in all the mixtures, together with other triterpenoid oleane type saponins, which were shown to be less polar, by reversed-phase HPLC. The saponin identifications were based on spectral evidence, including H- H two-dimensional correlation spectroscopy, nuclear Overhauser and exchange spectroscopy, heteronuclear multiple quantum coherence, and heteronuclear multiple-bond connectivity experiments. The toxicity of S. langsdorffii saponins to non-target organisms was prescreened by the brine shrimp lethality test.
Assuntos
Biomphalaria/efeitos dos fármacos , Fabaceae/química , Moluscocidas/isolamento & purificação , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Animais , Cromatografia em Camada Fina , Dose Letal Mediana , Moluscocidas/química , Moluscocidas/toxicidade , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Saponinas/química , Saponinas/toxicidade , Triterpenos/química , Triterpenos/toxicidadeRESUMO
The presence of saponins and the molluscicidal activity of the roots, leaves, seeds and fruits of Swartzia langsdorffii Raddi (Leguminosae) against Biomphalaria glabrata adults and eggs were investigated. The roots, seeds and fruits were macerated in 95 percent ethanol. These extracts exerted a significant molluscicidal activity against B. glabrata, up to a dilution of 100 mg/l. Four mixtures (A2, B2, C and D) of triterpenoid oleanane type saponins were chromatographically isolated from the seed and fruit extracts. Two known saponins (1 and 2) were identified as beta-D-glucopyranosyl-[alpha-L-rhamnopyranosyl-(1->3)- beta-D-glucuronopyranosyl-(1->3)]-3beta-hydroxyolean-12-ene-28 -oate, and beta-D-glucopyranosyl-(1->3)-beta-D-glucuronopyranosyl-(1 ->3)]-3beta-hydroxyolean-12-ene-28-oate, respectively. These two saponins were present in all the mixtures, together with other triterpenoid oleane type saponins, which were shown to be less polar, by reversed-phase HPLC. The saponin identifications were based on spectral evidence, including H- H two-dimensional correlation spectroscopy, nuclear Overhauser and exchange spectroscopy, heteronuclear multiple quantum coherence, and heteronuclear multiple-bond connectivity experiments. The toxicity of S. langsdorffii saponins to non-target organisms was prescreened by the brine shrimp lethality test
