A pyrimidine-beta-carboline and other alkaloids from Annona foetida with antileishmanial activity.
Bioassay-guided fractionation of the bark extract of Annona foetida afforded a new antileishmanial pyrimidine-beta-carboline alkaloid, N-hydroxyannomontine (1), together with the previously reported annomontine (2), O-methylmoschatoline (3), and liriodenine (4). The structure of compound 1 was established on the basis of extensive 1D and 2D NMR and MS analyses. This is the third reported pyrimidine-beta-carboline-type alkaloid and is particularly important for Annona genus chemotaxonomy. In addition, all compounds exhibit in vitro antileishmanial activity against promastigote forms of Leishmania braziliensis. Compounds 2 and 4 showed better activity than compounds 1 and 3 against L. braziliensis. Compound 2 was not active against L. guyanensis.
Costa
Emmanoel V
EV
Departamento de Química, Universidade Federal do Amazonas, Avenida Gen. Rodrigo Otavio Jordão Ramos, 3000, Coroado, CEP 69077-000 Manaus, Amazonas, Brazil.
Pinheiro
Maria Lúcia B
ML
Xavier
Clahildek M
CM
Silva
Jefferson R A
JR
Amaral
Ana Cláudia F
AC
Souza
Afonso D L
AD
Barison
Andersson
A
Campos
Francinete R
FR
Ferreira
Antonio G
AG
Machado
Gérzia M C
GM
Leon
Leonor L P
LL
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D031041:Annona / Q000737:chemistry*; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001938:Brazil; D002243:Carbolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007891:Leishmania / Q000187:drug effects*; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
D000470:Alkaloids; D000981:Antiprotozoal Agents; D002243:Carbolines; C508839:N-hydroxyannomontine; D011743:Pyrimidines; C508838:annomontine