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 Gilmour, Hernan Navarro, Richard B. Rothman, Thomas E. Prisinzano

Research output: Contribution to journalArticlepeer-review

50 Scopus citations

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 κ opioid receptors. One approach to better understanding the mode of binding of 1 at κ 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 δ opioid antagonist activity.

Original languageEnglish
Pages (from-to)107-112
Number of pages6
JournalJournal of Natural Products
Volume69
Issue number1
DOIs
StatePublished - Jan 2006

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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