TY - JOUR
T1 - Clerodane diterpenoids and an ursane triterpenoid from Salvia haenkei. Computer-assisted structural elucidation
AU - Almanza Vega, Giovanna Rocio Almanza Vega
AU - Balderrama, Luisa
AU - Labbé, Cecilia
AU - Lavaud, Catherine
AU - Massiot, Georges
AU - Nuzillard, Jean Marc
AU - Connolly, Joseph D.
AU - Farrugia, Louis J.
AU - Rycroft, David S.
PY - 1997/10/27
Y1 - 1997/10/27
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0030792724&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(97)00943-5
DO - 10.1016/S0040-4020(97)00943-5
M3 - Artículo
AN - SCOPUS:0030792724
VL - 53
SP - 14719
EP - 14728
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 43
ER -