Antimalarial ß-carbolines from the New Zealand ascidian Pseudodistoma opacum.
J Nat Prod
; 74(9): 1972-9, 2011 Sep 23.
Article
em En
| MEDLINE
| ID: mdl-21846091
ABSTRACT
One tetrahydro-ß-carboline, (-)-7-bromohomotrypargine (1), and three alkylguanidine-substituted ß-carbolines, opacalines A, B, and C (2-4), have been isolated from the New Zealand ascidian Pseudodistoma opacum. The structures of the metabolites were determined by analysis of mass spectrometric and 2D NMR spectroscopic data. Natural products 2 and 3, synthetic debromo analogues 8 and 9, and intermediate 16 exhibited moderate antimalarial activity toward a chloroquine-resistant strain of Plasmodium falciparum, with an IC50 range of 2.5-14 µM. The biosynthesis of 1-4 is proposed to proceed via a Pictet-Spengler condensation of 6-bromotryptamine and the α-keto acid transamination product of either arginine or homoarginine. Cell separation and 1H NMR analysis of P. opacum identified tetrahydro-ß-carboline 1 to be principally located in the zooids, while fully aromatized analogues 2-4 were localized to the test.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Plasmodium falciparum
/
Urocordados
/
Carbolinas
/
Antimaláricos
Limite:
Animals
País como assunto:
Oceania
Idioma:
En
Ano de publicação:
2011
Tipo de documento:
Article