Chemical constituents of the underground stem bark of Duguetia furfuracea (Annonaceae)

Abstract

In the present investigation the underground parts of Duguetia furfuracea (Annonaceae) were used to conduct a phytochemical study that included the brine shrimp (Artemia salina) lethality bioassay. The substances (-)-duguetine β-N-oxide, (-)-duguetine, dicentrinone, (-)-N-methyltetrahydropalmatine, and (+)-N-methylglaucine were isolated from the alkaloid extract of the bark of the underground stem, and the ureide allantoin was also isolated by precipitation from the ethanol extract of the wood of the underground stem. A fresh volatile oil and a nonpolar extract were also obtained from the underground stem bark. The substances 2,4,5-trimethoxystyrene, α-gurjunene, aromadendrene, bicyclogermacrene, (E)-methylisoeugenol, and α-asarone were isolated from the fresh volatile oil and polycarpol, β-caryophyllene oxide, 2,4,5-trimethoxystyrene, β-asarone, and asaraldehyde were obtained from the petroleum ether extract. The present study describes for the first time the alkaloid (-)-duguetine β-N-oxide and the occurrence of (-)-N-methyltetrahydropalmatine and (+)-N-methylglaucine in the family Annonaceae. All extracts were active in the brine shrimp lethality bioassay. ©2007 Sociedade Brasileira de Química.