Intramolecular Transacetylation in Salvinorins D and E

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• 作者：Lukasz M. Kutrzeba ; Xing-Cong Li ; Yuanqing Ding ; Daneel Ferreira ; Jordan K. Zjawiony
• 刊名：Journal of Natural Products
• 出版年：2010
• 出版时间：April 23, 2010
• 年：2010
• 卷：73
• 期：4
• 页码：707-708
• 全文大小：84K
• 年卷期：v.73,no.4(April 23, 2010)
• ISSN：1520-6025

文摘

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 ¹H NMR spectrum. This spontaneous formation of the mixture of isomers occurs via a dynamic intramolecular transacetylation process.