RESUMO
Two new mexicanolides, named xylomexicanolides A and B, were isolated from the seeds of an Indian mangrove, Xylocarpus moluccensis, together with four known limonoids, khayasin, angolensic acid methyl ester, khayasin T, and 2'S-methylbutanoylproceranolide. The structures of these limonoids were established on the basis of spectroscopic data. The (13)C-NMR data of khayasin were reported for the first time. Khayasin was found to exhibit marked insecticidal activity against the fifth instar larvae of Brontispa longissima (GESTRO) at a concentration of 10 mg/l.
Assuntos
Inseticidas/química , Inseticidas/farmacologia , Limoninas/química , Limoninas/farmacologia , Meliaceae/química , Sementes/química , Animais , Besouros/efeitos dos fármacos , Inseticidas/isolamento & purificação , Larva/efeitos dos fármacos , Limoninas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Estrutura MolecularRESUMO
Six new phragmalins, moluccensins H-M (1-6), two new andirobin-type limonoids, moluccensins N and O (7, 8), and two new tirucallane derivatives, moluccensins P and Q (9, 10), were isolated from seeds of an Indian mangrove, Xylocarpus moluccensis, together with the known compound 3beta,22S-dihydroxytirucalla-7,24-dien-23-one. The structures of these compounds were established on the basis of spectroscopic data. Moluccensins H-L were phragmalins with a C-30 carbonyl group, and moluccensin M was a unique ring-D-opened 16-norphragmalin. Moluccensins H-J possess conjugated Delta(8,9) and Delta(14,15) double bonds, moluccensins K and L contain a Delta(8,14) double bond, and moluccensin M has a characteristic C(15)-C(30) linked five-membered lactone ring. Moluccensins H and I showed moderate insecticidal activity against the fifth instar larvae of Brontispa longissima (Gestro) at a concentration of 100 mg/L.
Assuntos
Limoninas/isolamento & purificação , Rhizophoraceae/química , Triterpenos/isolamento & purificação , Animais , Besouros/efeitos dos fármacos , Larva/efeitos dos fármacos , Limoninas/química , Limoninas/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sementes/química , Triterpenos/química , Triterpenos/farmacologiaRESUMO
Seven new phragmalins with a C-30 carbonyl moiety, named moluccensins A-G (1-7), among which moluccensins A-F, possessing a Delta(8,14) double bond, and moluccensin G (7), containing conjugated Delta(8,9) and Delta(14,15) double bonds, were isolated from the seeds of an Indian mangrove, Xylocarpus moluccensis. The structures of these compounds were established on the basis of single-crystal X-ray diffraction analysis and spectroscopic data. This is the first report of phragmalins with a conjugated C-30 carbonyl group.
