Synthetic studies on neoclerodane diterpenes from Salvia splendens: oxidative modifications of ring A

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

Research output: Contribution to journalArticlepeer-review

7 Scopus citations


Salvinorin A (1), a neoclerodane diterpene from the hallucinogenic mint Salvia divinorum, is the only known naturally occurring non-nitrogenous and specific κ-opioid agonist. Some oxidative modifications of the A ring in the congeners of 1 isolated from Salvia splendens salviarin, splenolide B, splendidin, and in the non-natural 8-epi-salviarin gave new derivatives, some of which were tested as agonists at opioid receptors. However, none of these compounds was active. The presence of the C-18, C-19 lactone could be at the origin of the observed lack of binding affinity.

Original languageEnglish
Pages (from-to)1708-1715
Number of pages8
Issue number8
StatePublished - Feb 21 2009

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, and from the Italian ‘Università degli Studi di Palermo’, grant ‘Ex 60%-2005’, and R01DA018151 (to TEP) 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. Portions of this work were also supported by the Intramural Research Program, National Institute on Drug Abuse (NIDA), NIH, DHHS (RBR and CMD).


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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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