Antimalarial (+)-trans-hexahydrodibenzopyran derivatives from Machaerium multiflorum.
J Nat Prod
; 64(10): 1322-5, 2001 Oct.
Article
em En
| MEDLINE
| ID: mdl-11678659
Bioassay-guided fractionation of Machaerium multiflorum yielded the hitherto unreported (+)-trans-hexahydrodibenzopyrans machaeriol A (1) and machaeriol B (2), as well as the known guaiane sesquiterpene (-)-kessane. Structure elucidation was based on (1)H and (13)C NMR data, mainly 2D NMR (1)H-(1)H COSY, (1)H-(13)C HMQC, (1)H-(13)C HMBC, and (1)H-(1)H NOESY experiments. This is the first report of the hexahydrodibenzopyrans from a higher plant other than the genus Cannabis. The cannabimimetic activity was thus evaluated by radioligand binding assay for cannabinoid receptor CB1, which indicated, notably, that both 1 and 2 were inactive. In addition, the cross reactivity of 1 and 2 toward antibodies designed for urinary metabolites of cannabinoids was evaluated with the EMIT and On Line cannabinoids assays. Both compounds showed no response at 100 000 ng/mL in both assays. Machaeriol B (2) demonstrated in vitro antimalarial activity (IC(50) = 120 ng/mL) against Plasmodium falciparum W-2 clone.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Plantas Medicinais
/
Sesquiterpenos
/
Benzopiranos
/
Fabaceae
/
Anti-Infecciosos
/
Antimaláricos
País/Região como assunto:
America do sul
/
Peru
Idioma:
En
Revista:
J Nat Prod
Ano de publicação:
2001
Tipo de documento:
Article
País de afiliação:
Estados Unidos
País de publicação:
Estados Unidos