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 via PubMed
Summary
AI-generated from the abstractSalvinorin A, a compound from the hallucinogenic mint Salvia divinorum, is the only known non-nitrogenous and specific kappa-opioid agonist. Several related compounds from Salvia splendens and a series of semisynthetic derivatives, including some with a pyrazoline structural moiety, were tested for their ability to bind to human mu, delta, and kappa opioid receptors. None of these compounds showed high-affinity binding to these receptors. However, one compound (10) showed modest affinity for kappa receptors, suggesting that other naturally occurring neoclerodanes from different Salvia species may have opioid affinity.
Study at a glance
| Characteristics | Experimental study Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Salvia splendens Salvia family Salvia genus Plant compounds |
| Citations | 32 |
| Key finding | 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.