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

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)14719-14728
Number of pages10
JournalTetrahedron
Volume53
Issue number43
DOIs
StatePublished - 27 Oct 1997

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