Synthetic studies of neoclerodane diterpenes from Salvia divinorum: semisynthesis of salvinicins A and B and other chemical transformations of salvinorin A.
Wayne W Harding, Matthew Schmidt, Kevin Tidgewell, Pavitra Kannan, Kenneth G Holden, Brian P Gilmour, Hernan Navarro, Richard B Rothman, Thomas E Prisinzano
Journal of Natural Products 2006 DOI: 10.1021/np050398i (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Intervention | chemical transformations of Salvinorin A |
| Topics | Salvia divinorum |
| Keywords | Salvinorin a research Unique hallucinogen Compound 10a Neoclerodane diterpene Opioid receptor ligands Receptor binding Chemical transformations Semisynthesizing Altering its structure |
| Citations | 59 |
| Key findings | Compound 10a is the first neoclerodane diterpene with delta opioid antagonist activity. |
Abstract
Salvinorin A (1) is a hallucinogenic neoclerodane diterpene isolated from the widely available psychoactive plant Salvia divinorum and is the first example of a non-nitrogenous opioid receptor ligand. At present, there is little information available as to why this compound is selective for kappa opioid receptors. One approach to better understanding the mode of binding of 1 at kappa receptors is to systematically alter the structure of 1 and examine the effects on opioid receptor affinity and activity. Currently, there is a paucity of methods described for the preparation of analogues derived from 1. Here, we report the investigation of several chemical transformations of 1 isolated from S. divinorum. In particular, this work provides a semisynthesis of salvinicins A (2) and B (3) and has identified 10a as the first neoclerodane diterpene with delta opioid antagonist activity.