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Journal of the Mexican Chemical Society

Print version ISSN 1870-249X

J. Mex. Chem. Soc vol.50 n.2 México Apr./Jun. 2006

 

Article

 

New Prenylated Flavanones from Esenbeckia berlandieri ssp. acapulcensis

 

Arturo Cano,1* Marina Espinoza,1 Clara H. Ramos2 and Guillermo Delgado3*

 

1 Facultad de Estudios Superiores Zaragoza, Universidad Nacional Autónoma de México. Av. Guelatao No. 66 (Eje 7 Oriente). Col. Ejército de Oriente. Iztapalapa 09230. México D. F. Email: aecanomx@correo.unam.mx

2 Instituto de Biología, Universidad Nacional Autónoma de México. Ciudad Universitaria, Circuito Exterior, Coyoacán 04510, México D. F.

3 Instituto de Química, Universidad Nacional Autónoma de México. Ciudad Universitaria, Circuito Exterior, Coyoacán 04510, México D. F. Email: delgado@servidor.unam.mx

 

Recibido el 12 de enero del 2006.
Aceptado el 29 de junio del 2006
.

 

Abstract

Three new (1-3) and four known prenylated flavanones as well as friedelin were isolated from the aerial parts of Esenbeckia berlandieri ssp acapulcensis (Rutaceae). The structures of the new compounds were elucidated as 5,7-dihydroxy-8-(2,3-epoxy-3-methyl-butyl)flavanone (1), 5,4'-dihydroxy-7-methoxy-8-(2,3-dihydroxy-3-methylbutyl)flavanone (2), and 5,7,4'-trihydroxy-8-(2,3-dihydroxy-3-methylbutyl)flavanone (3). The isolated flavanones possess diferentially functionalized isoprene units at C-8, and this is the first report of flavanones isolated from Esenbeckia species.

Keywords: Esenbeckia berlandieri ssp. acapulcensis, Rutaceae, prenylflavanones.

 

Resumen

Tres flavanonas preniladas novedosas (1-3), cuatro conocidas así como friedelina fueron aisladas de las partes aéreas de Esenbeckia berlandieri ssp acapulcensis (Rutaceae). Las estructuras de los compuestos nuevos fueron determinadas como 5,7-dihidroxi-8-(2,3-epoxi-3-metilbutil)flavanona (1), 5,4'-dihidroxi-7-metoxi-8-(2,3-dihidroxi-3-metilbutil) flavanona (10) y 5,7,4'-trihidroxi-8-(2,3-dihidroxi-3-metilbutil) flavanona (11). Las flavanonas aisladas poseen isoprenilos con diferente funcionalidad unidos a C-8, y este es el primer reporte de flavanonas aisladas de especies de Esenbeckia.

Palabras clave: Esenbeckia berlandieri ssp. acapulcensis, Rutaceae, prenilflavanonas.

 

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