Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of Opioid Receptor affinity.
Gianfranco Fontana, Giuseppe Savona, Benjamín Rodríguez, Christina M Dersch, Richard B Rothman, Thomas E Prisinzano
Tetrahedron December 20, 2008 DOI: 10.1016/j.tet.2008.08.043 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Salvia splendens Salvia family Salvia genus Plant compounds Plant investigation Opioid receptors Kappa-opioid agonist Kappa receptors Opioid interactions Receptor binding Drug discovery Natural products Phytochemistry Plant-derived compounds Natural compounds Ethnopharmacology Pyrazoline structure Chemical scaffolds Synthetic compounds |
| Citations | 32 |
| Key findings | None of the tested compounds from Salvia splendens or semisynthetic derivatives showed high-affinity binding to human opioid receptors, though one compound showed modest kappa receptor affinity. |
Abstract
Salvinorin A (1), a neoclerodane diterpene from the hallucinogenic mint Salvia divinorum, is the only known non-nitrogenous and specific kappa-opioid agonist. Several structural congeners of 1 isolated from Salvia splendens (2 - 8) together with a series of semisynthetic derivatives (9 - 24), some of which possess a pyrazoline structural moiety (9, 19 - 22), have been tested for affinity at human mu, delta, and kappa opioid receptors. None of these compounds showed high affinity binding to these receptors. However, 10 showed modest affinity for kappa receptors suggesting other naturally neoclerodanes from different Salvia species may possess opioid affinity.