Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of opioid receptor affinity

Gianfranco Fontana, Giuseppe Savona, Benjamín Rodríguez, Christina M. Dersch, Richard B. Rothman, Thomas E. Prisinzano

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

Salvinorin A (1), a neoclerodane diterpene from the hallucinogenic mint Salvia divinorum, is the only known non-nitrogenous and specific κ-opioid agonist. Several structural congeners of 1 isolated from Salvia splendens (2-8) together with a series of semisynthetic derivatives (9-24), some of which possess a pyrazoline structural moiety (9, 19-22), have been tested for affinity at human μ, δ, and κ opioid receptors. None of these compounds showed high affinity binding to these receptors. However, 10 showed modest affinity for κ receptors suggesting that other natural neoclerodanes from different Salvia species may possess opioid affinity.

Original languageEnglish
Pages (from-to)10041-10048
Number of pages8
JournalTetrahedron
Volume64
Issue number43
DOIs
StatePublished - Oct 20 2008

Bibliographical note

Funding Information:
This work was supported in part by funds from the Spanish ‘Comisión Interministerial de Ciencia y Tecnología’ (CICYT), grant No. CTQ2006-15279-C02-02, Italian ‘Università degli Studi di Palermo’, grant ‘Ex 60%-2005’, and R01DA018151 (to T.E.P.) from the National Institute on Drug Abuse. The content is the sole responsibility of the authors and does not necessarily represent the official views of the National Institute on Drug Abuse or the National Institutes of Health.

Keywords

  • Neoclerodane diterpenes
  • Opioid receptors
  • Salvia splendens
  • Semisynthetic derivatives

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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