Clerodane diterpenoids and an ursane triterpenoid from Salvia haenkei. Computer-assisted structural elucidation

Giovanna Rocio Almanza Vega Almanza Vega, Luisa Balderrama, Cecilia Labbé, Catherine Lavaud, Georges Massiot, Jean Marc Nuzillard, Joseph D. Connolly, Louis J. Farrugia, David S. Rycroft

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

27 Citas (Scopus)

Resumen

Five ent-clerodane diterpenoids, four new, and a new ursane triterpenoid have been isolated from Salvia haenkei collected in Bolivia. The structures of two ent-clerodanes ent-(4S,5R)-7α-acetoxy-15,16-epoxy-10-oxo-9,10-sccocleroda-1,8,13(16),14 -tetraene-17,12S;18,19-diolide 1 (salvianduline B) and ent-(5R,9R)-15,16-epoxy-10S-hydroxy-cleroda-3,7,13(16),14-tetraene-17,12S;18,19 -diolide 2, were elucidated from HMQC and HMBC data using an automatic structure elucidation computer program. The structures of the other clerodanes, ent-(5R,9R)-15,16-epoxy-10S-hydroxy-cleroda-3,13(16),14-triene-17,12S;18,19 -diolide 6, ent-(4S,5R,9S,10R)-15,16-epoxycleroda-1,13(16),14-triene-17,12S;18,19-diolide 7 and ent-(5R,9R,10S)-7S-acetoxy-15,16-epoxy-1S,2S,12ξ-trihydroxycleroda-3,13(16),14 -trien-18,19-olide 8, were derived in the usual manner from 1H and 13C NMR data. The stereochemistry of 2 was confirmed by an X-ray crystal structure analysis. The triterpenoid is 3-oxours-12-ene-1β,11α-diol 9.

Idioma originalInglés
Páginas (desde-hasta)14719-14728
Número de páginas10
PublicaciónTetrahedron
Volumen53
N.º43
DOI
EstadoPublicada - 27 oct. 1997

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