ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES

Quimica nova

Dutra, Lívia M.¹  Bomfim, Larissa M.²  Santos, Maria de Fátima C.³  Costa, Cinara O. D.⁴  Fontes, José Eraldo N.⁵  Moraes, Valéria R. S.⁶  Barison, Andersson⁷ 

[1] Fundação Oswaldo Cruz, Salvador, Brasil;Hospital São Rafael, Salvador, Brasil;Universidade Federal de Sergipe, São Cristóvão, Brasil;Universidade Federal do Amazonas, Manaus, Brasil;Universidade Federal do Paraná, Curitiba, Brasil;Universidade Federal do Vale do São Francisco, Petrolina, Brasil;Universidade do Estado do Amazonas, Manaus, Brasil

关键词: alkaloids;    Guatteria pogonopus;    leaves;    Annonaceae;    NMR;    cytotoxicity.;   

DOI  :  10.21577/0100-4042.20170258

学科分类：化学（综合）

来源: Sociedade Brasileira de Quimica

【 摘 要 】

The phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatteria pogonopus Mart. (Annonaceae) allowed the isolation and identification for the first time in this species of: (+)-nornuciferine (1), a mixture of 1 and (+)-anonaine (2), (+)-isocorydine (3), (+)-nuciferine (4), (+)-roemerine (5), (-)-tetrahydropseudocolumbamine (6), a mixture of 6, liriodenine (9) and lysicamine (10), a mixture of 1,2,9-trimethoxy-10-hydroxyaporphine (7) and bulbocapnine (8), 9, 10, and (+)-N-methyllindicarpine (11). Compounds 6, 7, 8, and 11 have not been previously reported in the family Annonaceae. Furthermore, the formerly synthetic 1,2,9-trimethoxyaporfin-10-ol (7) is described for the first time as a natural aporphine alkaloid herein. The chemical structures were established by 1D and 2D NMR as well as in comparison with data previously reported in the literature. The cytotoxic activity of the alkaloids was evaluated against tumor (B16-F10, HepG2, HL-60, and K562) and non-tumor (PBMC) cell lines. Alkaloid 1 presented significant activity against HepG2 cell lines with IC50 of 9.60 µmol L-1 while the mixture of 6, 9 and 10 displayed strong cytotoxic activity against HL-60 and K562 cell lines with IC50 values of 3.41 an 8.50 µmol L-1, respectively.

【 授权许可】

CC BY