6533b7ddfe1ef96bd12752b0

RESEARCH PRODUCT

Synthetic studies on neoclerodane diterpenes from Salvia splendens: oxidative modifications of ring A.

Thomas E. PrisinzanoBenjamín RodríguezRichard B. RothmanGiuseppe SavonaChristina M. DerschGianfranco Fontana

subject

chemistry.chemical_classificationbiologyStereochemistryOrganic ChemistryPharmacognosySalviabiology.organism_classificationBiochemistryTerpenoidSalvinorin AArticleTerpenechemistry.chemical_compoundchemistryDrug DiscoverySalvia divinorumSalvia splendens. Opioid receptors. Neoclerodane diterpenes. Semisynthetic derivativesDiterpeneLactone

description

Salvinorin A (1), a neoclerodane diterpene from the hallucinogenic mint Salvia divinorum, is the only known naturally occurring non-nitrogenous and specific κ-opioid agonist. Some oxidative modifications of the A ring in the congeners of 1 isolated from Salvia splendens salviarin, splenolide B, splendidin and in the non-natural 8-epi-salviarin gave new derivatives, some of which were tested as agonists at opioid receptors. However, none of these compounds were active. The presence of the C-18, C-19 lactone could be at the origin of the observed lack of binding affinity.

yearjournalcountryeditionlanguage
2011-05-06Tetrahedron
10.1016/j.tet.2008.12.009https://pubmed.ncbi.nlm.nih.gov/21544261