Trypanocidal Activity of Oxoaporphine and Pyrimidine-β-Carboline Alkaloids from the Branches of Annona foetida Mart. (Annonaceae)

Abstract

Phytochemical investigation of the branches of Annona foetida Mart. led to isolation from the CH2Cl2 extract of four alkaloids: Atherospermidine (1), described for the first time in this species, liriodenine (2), O-methylmoschatoline (3), and annomontine (4). Their chemical structures were established on the basis of spectroscopic data from IR, MS, NMR (1D and 2D), and comparison with the literature. Compounds 2–4 showed potent trypanocidal effect when evaluated against epimastigote and trypomastigote forms of Trypanosoma cruzi.

Alkaloids from leaves of Annona salzmannii and Annona vepretorum (Annonaceae)

“…However, anonaine, asimilobine and liriodenine were described in the stem bark of A. salzmannii (Da Cruz et al, 2011). These compounds are very common in Annonaceae species, mainly in the genus Annona (Guinaudeau et al, 1975, 1979Leboeuf et al, 1982;Chang et al, 2000;Pinheiro et al, 2009;Costa et al, 2009Costa et al, , 2010Costa et al, , 2011b. Anonaine have been described in Annona glabra L. and Annona montana Macfad.…”

“…eluted with CH 2 Cl 2 :MeOH (95:05, v/v, three times), giving oxonantenine (3.6 mg: Yang et al, 2010) and1,3,6,6-tetramethyl-5,6,7,8-tetrahydro-isoquinolin-8-one (2.4 mg: Demole andDemole, 2004;Daopeng et al, 2010), respectively. Group GF9 (44.6 mg) was subjected to a preparative TLC eluted with n-hexane:acetone (60:40, v/v, four times), affording of liriodenine (1.4 mg: Costa et al, 2009Costa et al, , 2011b and lanuginosine (2.3 mg: Wirasathien et al, 2006). Group GF10 (10.0 mg) was subjected to a preparative TLC eluted with CH 2 Cl 2 :MeOH (95:05, v/v, one time), resulting again in lanuginosine (2.8 mg; Wirasathien et al, 2006).…”

“…These fractions were evaluated and pooled according to TLC analysis yielding fifteen groups (GF1eGF15). Group GF7 (18.5 mg) was subjected to a preparative TLC eluted with CH 2 Cl 2 :MeOH (90:10, v/v), giving liriodenine (5.8 mg: Costa et al, 2009Costa et al, , 2011b, and anonaine (7.9 mg: Chang et al, 2000), respectively. Group GF8 (303.0 mg) was submitted to a new silica gel CC previously treated with a 10% NaHCO 3 solution, eluted with the same solvent system as described above, affording 47 fractions (25 mL each) that were pooled in six groups (GF8.1 to GF8.6), according to TLC analysis.…”

“…Group GF8 (303.0 mg) was submitted to a new silica gel CC previously treated with a 10% NaHCO 3 solution, eluted with the same solvent system as described above, affording 47 fractions (25 mL each) that were pooled in six groups (GF8.1 to GF8.6), according to TLC analysis. Group GF8.1 (18.6 mg) was subjected to a preparative TLC eluted with CH 2 Cl 2 :MeOH (95:05, v/v, two times), affording liriodenine (1.8 mg: Costa et al, 2009Costa et al, , 2011b Dried and powdered leaves of A. vepretorum (800.0 g) were extracted with petroleum ether (3.5 L, five times), followed by MeOH (3.5 L, five times), yielding of petroleum ether (30.94 g) and MeOH (124.06 g) extracts, after each solvent removal.…”

N -Butyl-[1-(4-Methoxy)Phenyl-9 H -β-Carboline]-3-Carboxamide Prevents Cytokinesis in Leishmania amazonensis

“…␤-Carboline alkaloids have drawn attention because of their biological activities against parasites of the Trypanosomatidae family, including antitrypanosomal activity (6)(7)(8)(9)(10) and antileishmanial activity (8,(11)(12)(13). A recent study demonstrated the antileishmanial and antitrypanosomal activity of a series of N-alkyl-(1-phenyl-substituted-tetrahydro-␤-carboline)-3-carboxamides, showing that compounds containing Nbutylcarboxamide groups were the most active, suggesting that these groups may improve the biological activity of these compounds (8).…”