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

被引:60
作者
Costa, Emmanoel Vilaca [2 ]
Belem Pinheiro, Maria Lucia [1 ]
Leao de Souza, Afonso Duarte [1 ]
Barison, Andersson [3 ]
Campos, Francinete Ramos [4 ]
Valdez, Rodrigo Hinojosa [5 ]
Ueda-Nakamura, Tania [5 ]
Dias Filho, Benedito Prado [5 ]
Nakamura, Celso Vataru [5 ]
机构
[1] Univ Fed Amazonas, Dept Chem, BR-69077000 Manaus, AM, Brazil
[2] Univ Fed Sergipe, Dept Chem, LABORGAN, BR-49100000 Sao Cristovao, SE, Brazil
[3] Univ Fed Parana, Dept Chem, BR-81531990 Curitiba, PR, Brazil
[4] Univ Fed Parana, Dept Pharm, BR-81531990 Curitiba, PR, Brazil
[5] Univ Estadual Maringa, Dept Basic Hlth Sci, BR-87020900 Maringa, PR, Brazil
关键词
annonaceae; Annona foetida; alkaloids; oxoaporphine alkaloids; pyrimidine-beta-carboline alkaloids; trypanocidal activity; ANTILEISHMANIAL ACTIVITY; TRYPANOSOMA-CRUZI; METHOXYANNOMONTINE; DITERPENOIDS; CONSTITUENTS; ANNOMONTINE; MONTANA; LEAVES; STEM;
D O I
10.3390/molecules16119714
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Phytochemical investigation of the branches of Annona foetida Mart. led to isolation from the CH(2)Cl(2) 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.
引用
收藏
页码:9714 / 9720
页数:7
相关论文
共 23 条
[1]   Annonaceous acetogenins: Recent progress [J].
Alali, FQ ;
Liu, XX ;
McLaughlin, JL .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540
[2]  
BRENER Z., 1962, REV INST MED TROP SAO PAULO, V4, P389
[3]   Two new 7-dehydroaporphine alkaloids and antiplatelet action aporphines from the leaves of Annona purpurea [J].
Chang, FR ;
Wei, JL ;
Teng, CM ;
Wu, YC .
PHYTOCHEMISTRY, 1998, 49 (07) :2015-2018
[4]   Flanking regions of monomorphic microsatellite loci provide a new source of data for plant species-level phylogenetics [J].
Chatrou, Lars W. ;
Pilar Escribano, M. ;
Viruel, Maria A. ;
Maas, Jan W. ;
Richardson, James E. ;
Hormaza, Jose I. .
MOLECULAR PHYLOGENETICS AND EVOLUTION, 2009, 53 (03) :726-733
[5]   The constituents from the stems of Annona cherimola [J].
Chen, CY ;
Chang, FR ;
Wu, YC .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1997, 44 (03) :313-319
[6]  
Correa M.P., 1984, DICIONARIO PLANTAS U, P687
[7]   Full NMR analysis of annomontine, methoxyannomontine and N-hydroxyannomontine pyrimidine-β-carboline alkaloids [J].
Costa, Emmanoel Vilaca ;
Pinheiro, Maria Lucia Belem ;
de Souza, Afonso Duarte Leao ;
dos Santos, Adriane Gama ;
Campos, Francinete Ramos ;
Ferreira, Antonio Gilberto ;
Barison, Andersson .
MAGNETIC RESONANCE IN CHEMISTRY, 2008, 46 (01) :69-74
[8]  
Costa EV, 2011, NAT PROD COMMUN, V6, P907
[9]   7,7-Dimethylaporphine Alkaloids from the Stem of Guatteriopsis friesiana [J].
Costa, Emmanoel Vilaca ;
Marques, Francisco A. ;
Pinheiro, Maria Lucia B. ;
Vaz, Nelissa P. ;
Duarte, Marta Cristina T. ;
Delarmelina, Camila ;
Braga, Raquel M. ;
Sales Maia, Beatriz Helena L. N. .
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (08) :1516-1519
[10]   ANTIMICROBIAL AND ANTILEISHMANIAL ACTIVITY OF ESSENTIAL OIL FROM THE LEAVES OF Annona foetida (ANNONACEAE) [J].
Costa, Emmanoel Vilaca ;
Belem Pinheiro, Maria Lucia ;
de Andrade Silva, Jefferson Rocha ;
de Noronha Sales Maia, Beatriz Helena Lameiro ;
Teixeira Duarte, Marta Cristina ;
Fernandes Amaral, Ana Claudia ;
de Carvalho Machado, Gerzia Maria ;
Leon, Leonor Laura .
QUIMICA NOVA, 2009, 32 (01) :78-81