Eight new withanolides were isolated from the aerial parts of Vassobia lorentzii and characterized by spectroscopic methods and with the aid of molecular modeling. The compounds were identified as (17S,20R,22R)-5β,6β:18,20-diepoxy-18-hydroxy-1-oxowitha-2,5,24-trienolide (1); (17S,20R,22R)-18,20-epoxy-4β,18-dihydroxy-1-oxowitha-2,5,24-trienolide (2); (17S,18R,20R,22R)-4β-hydroxy-18,20-epoxy-18-methoxy-1-oxowitha-2,5,24-trieno lide (3); (17S,18S,20R,22R)-4β-hydroxy-18,20-epoxy-18-methoxy-1-oxowitha-2,5,24-trieno lide (4); (17S,20R,22R)-4β-hydroxy-18,20-epoxy-1,18-dioxowitha-2,5,24-trienolide (5); (17S,18R,20R,22R)-18,20-epoxy-18-methoxy-1,4-dioxowitha-2,5,24-trienolide (6); (17S,18S,20R,22R)-18,20-epoxy-18-methoxy-1,4-dioxowitha-2,5,24-trienolide (7); and (17S,20R,22R)-5β,6β-epoxy-4β,18,20-trihydroxy-1-oxowitha-2,24-dienolide (8). Compounds 1 and 2 were obtained as epimeric mixtures at C-18.
Documento: | Artículo |
Título: | Withanolides from Vassobia lorentzii |
Autor: | Misico, R.I.; Gil, R.R.; Oberti, J.C.; Veleiro, A.S.; Burton, G. |
Filiación: | Departamento de Química Orgánica and IMBIV, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, 5000 Córdoba, Argentina Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina |
Palabras clave: | 18,20 epoxy 18 methoxy 1,4 dioxowitha 2,5,24 trienolide; 18,20 epoxy 4beta,18 dihydroxy 1 oxowitha 2,5,24 trienolide; 4beta hydroxy 18,20 epoxy 1,18 dioxowitha 2,5,24 trienolide; 4beta hydroxy 18,20 epoxy 18 methoxy 1 oxowitha 2,5,24 trienolide; 5beta,6beta epoxy 4beta,18,20 trihydroxy 1 oxowitha 2,24 dienolide; 5beta,6beta:18,20 diepoxy 18 hydroxy 1 oxowitha 2,5,24 trienolide; plant extract; unclassified drug; Vassobia lorentzii extract; withanolide; article; chemical structure; chemotaxonomy; extraction; isomer; molecular model; nonhuman; spectroscopy; Animals; Antimalarials; Ergosterol; Humans; Lactones; Magnetic Resonance Spectroscopy; Plasmodium falciparum; Solanaceae; Vassobia |
Año: | 2000 |
Volumen: | 63 |
Número: | 10 |
Página de inicio: | 1329 |
Página de fin: | 1332 |
DOI: | http://dx.doi.org/10.1021/np000022z |
Título revista: | Journal of Natural Products |
Título revista abreviado: | J. Nat. Prod. |
ISSN: | 01633864 |
CODEN: | JNPRD |
CAS: | withanolide, 40326-62-3; Antimalarials; Ergosterol, 57-87-4; Lactones |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v63_n10_p1329_Misico |