Intramolecular transacetylation in salvinorins D and E.
Journal of natural products – April 23, 2010
Source: PubMed
Summary
Compounds can spontaneously transform into each other, a fascinating chemical secret revealed in nature. Two compounds from *Salvia divinorum*, salvinorin E and D, were discovered to dynamically interconvert. While attempting to purify salvinorin E, scientists observed it spontaneously rearranging into salvinorin D, forming a constant 3:5 mixture. This internal chemical shift, a dynamic equilibrium, is key to understanding their potential as precursors to other potent substances.
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.