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)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Salvia splendens Chemical synthesis Opioid receptor activity |
| Citations | 12 |
| Key findings | 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.
Comparable studies
Other experimental studies on salvia divinorum, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist. | 2002 | Experimental study | |
| Salvinorin A, an active component of the hallucinogenic sage salvia divinorum is a highly efficacious kappa-opioid receptor agonist: structural and functional considerations. Cloned human kappa-opioid receptors expressed in human embryonic kidney-293 cells and... | 2004 | Experimental study | |
| Synthesis and κ-opioid receptor activity of furan-substituted salvinorin A analogues. Animal model | 2014 | Experimental study | |
| Identification of the molecular mechanisms by which the diterpenoid salvinorin A binds to kappa-opioid receptors. | 2005 | Experimental study | |
| Dopamine D2High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil. Rat brain striatum homogenates | 2009 | Laboratory experiment |
Citations in the library
Cited by 2
Cites 4
- Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of Opioid Receptor affinity. Tetrahedron December 20, 2008
- Neoclerodane diterpenes as a novel scaffold for mu opioid receptor ligands. Journal of Medicinal Chemistry July 28, 2005
- Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2). Bioorganic & Medicinal Chemistry Letters June 1, 2005
- Studies toward the pharmacophore of salvinorin A, a potent kappa opioid receptor agonist. Journal of Medicinal Chemistry January 27, 2005