Intramolecular transacetylation in salvinorins D and E.
Lukasz M Kutrzeba, Xing-Cong Li, Yuanqing Ding, Daneel Ferreira, Jordan K Zjawiony
Journal of natural products April 23, 2010 DOI: 10.1021/np900447w via PubMed
Summary
AI-generated from the abstractFresh Salvia divinorum leaves yielded salvinorins E and D, which may be natural precursors to salvinorin A, a potent hallucinogen. During HPLC purification, salvinorin E spontaneously converted into a mixture with its regioisomer salvinorin D in a 3:5 ratio, observable by NMR. This isomerization occurs through a dynamic intramolecular transacetylation process.
Study at a glance
| Characteristics | Experimental study Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Chemical equilibrium Natural products Chemical precursors |
| Citations | 23 |
| Key finding | Salvinorin E and D interconvert spontaneously via intramolecular transacetylation, forming a 3:5 equilibrium mixture. |
Abstract
Extraction of fresh Salvia divinorum leaves afforded salvinorins E and D as potential biosynthesis precursors of salvinorin A, a major metabolite and a potent hallucinogen. Attempts at HPLC purification of salvinorin E (2) with acetonitrile as a solvent revealed an equilibrium with its regioisomer, salvinorin D (3), in a 3:5 ratio. The presence of both compounds was readily observed in the (1)H NMR spectrum. This spontaneous formation of the mixture of isomers occurs via a dynamic intramolecular transacetylation process.