Salvinorins J from Salvia divinorum: Mutarotation in the Neoclerodane System
Lukasz Kutrzeba, Daneel Ferreira, Jordan Kordian Zjawiony
Journal of Natural Products May 27, 2009 DOI: 10.1021/np900181q (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Chemical isolation and structure elucidation study Peer reviewed |
|---|---|
| Population | Salvia divinorum leaf surface extract |
| Topics | Salvia divinorum |
| Citations | 27 |
| Key points | A new neoclerodane diterpenoid, salvinorins J, was isolated from Salvia divinorum leaves as a hemiacetal mixture that undergoes mutarotation to form an equilibrium mixture of C-17 epimers. The extract also contained 14 known analogues. The compound was found during a search for biosynthetic precursors of salvinorin A. |
Abstract
A search for biosynthetic precursors of salvinorin A (1) led to the isolation of a new neoclerodane diterpenoid hemiacetal mixture, salvinorins J (2), from the chloroform extract of Salvia divinorum. A leaf surface extraction method was used on S. divinorum, affording a chlorophyll-free extract containing predominantly neoclerodane diterpenoids, including the new salvinorins J (2) and 14 known analogues. Salvinorins J (2) represent an example of a neoclerodane hemiacetal (lactol) susceptible to mutarotation with the formation of an equilibrium mixture of C-17 epimers.
Citations in the library
Cited by 9
- Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A. Pharmacological Reviews June 1, 2011
- Biosynthesis of the psychotropic plant diterpene salvinorin A: Discovery and characterization of the Salvia divinorum clerodienyl diphosphate synthase The Plant Journal November 19, 2016
- From local to global-fifty years of research on Salvia divinorum. Journal of Ethnopharmacology February 3, 2014
- A unique natural selective kappa-opioid receptor agonist, salvinorin A, and its roles in human therapeutics. Phytochemistry May 1, 2017
- DARK Classics in Chemical Neuroscience: Salvinorin A. ACS Chemical Neuroscience December 2, 2020
and 4 more in the library
Cites 13
- Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist. Proceedings of the National Academy of Sciences September 3, 2002
- Opioid receptors and legal highs:Salvia divinorumand Kratom Clinical Toxicology 2008
- Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint, Salvia divinorum The Journal of Organic Chemistry November 1, 1984
- Ethnopharmacology of ska María Pastora (Salvia divinorum, Epling and Játiva-M.). Journal of Ethnopharmacology May 1, 1983
- Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum. Organic Letters November 29, 2001
and 8 more in the library