Synthetic studies on neoclerodane diterpenes from Salvia splendens: oxidative modifications of ring A.
Tetrahedron – February 21, 2009
Source: PubMed
Summary
A unique natural compound, Salvinorin A, stands alone as a non-nitrogenous κ-opioid agonist. Inspired by this, researchers investigated related plant compounds from *Salvia splendens*, aiming to synthesize novel derivatives through oxidative modifications of their A ring. They successfully generated several new molecules. However, subsequent testing revealed these newly formed compounds did not show activity at opioid receptors, possibly due to a specific lactone structure.
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.