Stereochemical insights into enantioselective antiplasmodial lignanamides from the twigs and leaves of Solanum erianthum.
Phytochemistry
; 224: 114163, 2024 Aug.
Article
em En
| MEDLINE
| ID: mdl-38815883
ABSTRACT
Stereochemical investigations on the twigs and leaves of Solanum erianthum afforded five pairs of lignanamide enantiomers and a previously undescribed phenolic amide (3). Particularly, two pairs of previously undescribed lignanamide racemates (1a/1b-2a/2b) represent the first case of natural products that feature an unreported 5/5-fused N/O-biheterocyclic core. Their structures, including the absolute configurations, were determined unambiguously by using spectroscopic analyses and electronic circular dichroism calculations. A speculative biogenetic pathway for 1-3 was proposed. Interestingly, these lignanamides exhibited enantioselective antiplasmodial activities against drug-sensitive Plasmodium falciparum 3D7 strain and chloroquine-resistant Plasmodium falciparum Dd2 strain, pointing out that chirality plays an important role in drug development.
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Base de dados:
MEDLINE
Assunto principal:
Plasmodium falciparum
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Folhas de Planta
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Solanum
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Antimaláricos
Idioma:
En
Ano de publicação:
2024
Tipo de documento:
Article