Synthetic studies on neoclerodane diterpenes from Salvia splendens: oxidative modifications of ring A.
Gianfranco Fontana, Giuseppe Savona, Benjamín Rodríguez, Christina M Dersch, Richard B Rothman, Thomas E Prisinzano
Tetrahedron February 21, 2009 DOI: 10.1016/j.tet.2008.12.009 (opens in new tab) via PubMed
Summary
AI-generated from the abstractSalvinorin A is a unique naturally occurring compound that activates κ-opioid receptors without containing nitrogen. Researchers modified the A ring of salvinorin A and related compounds from Salvia splendens and a non-natural derivative, producing new molecules. When tested for opioid receptor activity, none of these derivatives were active. The absence of activity may be due to the presence of a lactone group at specific positions in the molecular structure.
Study at a glance
| Characteristics | Experimental study Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Salvia splendens Chemical synthesis Opioid receptor activity |
| Citations | 12 |
| Key finding | None of the tested derivatives of salvinorin A and related compounds showed agonist activity at opioid receptors. |
Abstract
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.