title: A pyrimidine-beta-carboline and other alkaloids from Annona foetida with antileishmanial activity.
abstract: 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.
authors.affiliation: Departamento de Química, Universidade Federal do Amazonas, Avenida Gen. Rodrigo Otavio Jordão Ramos, 3000, Coroado, CEP 69077-000 Manaus, Amazonas, Brazil.
authors.forename: Emmanoel V
authors.initials: EV
authors.lastname: Costa
authors.forename: Maria Lúcia B
authors.initials: ML
authors.lastname: Pinheiro
authors.forename: Clahildek M
authors.initials: CM
authors.lastname: Xavier
authors.forename: Jefferson R A
authors.initials: JR
authors.lastname: Silva
authors.forename: Ana Cláudia F
authors.initials: AC
authors.lastname: Amaral
authors.forename: Afonso D L
authors.initials: AD
authors.lastname: Souza
authors.forename: Andersson
authors.initials: A
authors.lastname: Barison
authors.forename: Francinete R
authors.initials: FR
authors.lastname: Campos
authors.forename: Antonio G
authors.initials: AG
authors.lastname: Ferreira
authors.forename: Gérzia M C
authors.initials: GM
authors.lastname: Machado
authors.forename: Leonor L P
authors.initials: LL
authors.lastname: Leon
mesh_terms: 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*
chemical_list: D000470:Alkaloids; D000981:Antiprotozoal Agents; D002243:Carbolines; C508839:N-hydroxyannomontine; D011743:Pyrimidines; C508838:annomontine