Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)

In the present study, in vitro techniques were used to investigate a range of biological activities of known natural quassinoids isobrucein B (1) and neosergeolide (2), known semi-synthetic derivative 1,12-diacetylisobrucein B (3), and a new semi-synthetic derivative, 12-acetylneosergeolide (4). The...

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Veröffentlicht in:Memórias do Instituto Oswaldo Cruz Jg. 104; H. 1; S. 48 - 56
Hauptverfasser: Silva, Ellen CC, Cavalcanti, Bruno C, Amorim, Rodrigo CN, Lucena, Jorcilene F, Quadros, Dulcimar S, Tadei, Wanderli P, Montenegro, Raquel C, Costa-Lotufo, Letícia V, Pessoa, Cláudia, Moraes, Manoel O, Nunomura, Rita CS, Nunomura, Sergio M, Melo, Marcia RS, de Andrade-Neto, Valter F, Silva, Luiz Francisco R, Vieira, Pedro Paulo R, Pohlit, Adrian M
Format: Journal Article
Sprache:Englisch
Veröffentlicht: Brazil Fundação Oswaldo Cruz, Fiocruz 01.02.2009
Instituto Oswaldo Cruz, Ministério da Saúde
Fundação Oswaldo Cruz (FIOCRUZ)
Schlagworte:
1,12-diacetylisobrucein B
12-acetylneosergeolide
Aedes - drug effects
Aedes aegypti
Animals
antimalarial
Artemia - drug effects
Artemia franciscana
cytotoxicity
Erythrocytes - drug effects
Hemolysis - drug effects
HL-60 Cells - drug effects
Humans
isobrucein B
larvicide
Lethal Dose 50
Mice
neosergeolide
neosergeolide - isobrucein B - 12-acetylneosergeolide - 1,12-diacetylisobrucein B - cytotoxicity - antimalarial - larvicide
PARASITOLOGY
Plants, Medicinal
Plasmodium falciparum
Plasmodium falciparum - drug effects
Quassins - isolation & purification
Quassins - pharmacology
Simaroubaceae
Simaroubaceae - chemistry
TROPICAL MEDICINE
12-acetylneosergeolide
1,12-diacetylisobrucein B
isobrucein B
antimalarial
neosergeolide
cytotoxicity
larvicide
ISSN:1678-8060, 0074-0276, 0074-0276, 1678-8060
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Zusammenfassung:In the present study, in vitro techniques were used to investigate a range of biological activities of known natural quassinoids isobrucein B (1) and neosergeolide (2), known semi-synthetic derivative 1,12-diacetylisobrucein B (3), and a new semi-synthetic derivative, 12-acetylneosergeolide (4). These compounds were evaluated for general toxicity toward the brine shrimp species Artemia franciscana, cytotoxicity toward human tumour cells, larvicidal activity toward the dengue fever mosquito vector Aedes aegypti , haemolytic activity in mouse erythrocytes and antimalarial activity against the human malaria parasite Plasmodium falciparum . Compounds 1 and 2 exhibited the greatest cytotoxicity against all the tumor cells tested (IC50 = 5-27 µg/L) and against multidrug-resistant P. falciparum K1 strain (IC50 = 1.0-4.0 g/L) and 3 was only cytotoxic toward the leukaemia HL-60 strain (IC50 = 11.8 µg/L). Quassinoids 1 and 2 (LC50 = 3.2-4.4 mg/L) displayed greater lethality than derivative 4 (LC50 = 75.0 mg/L) toward A. aegypti larvae, while derivative 3 was inactive. These results suggest a novel application for these natural quassinoids as larvicides. The toxicity toward A. franciscana could be correlated with the activity in several biological models, a finding that is in agreement with the literature. Importantly, none of the studied compounds exhibited in vitro haemolytic activity, suggesting specificity of the observed cytotoxic effects. This study reveals the biological potential of quassinoids 1 and 2 and to a lesser extent their semi-synthetic derivatives for their in vitro antimalarial and cytotoxic activities.
Bibliographie:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1678-8060
0074-0276
0074-0276
1678-8060
DOI:10.1590/s0074-02762009000100008