Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Preparation and Opioid Receptor Activity of Salvinicin Analogues

Authors

Denise S. Simpson, Cedarville UniversityFollow
Peter L. Katavic
Anthony Lozama
Wayne W. Harding
Damon Parrish
Jeffrey R. Deschamps
Christina M. Dersch
John S. Partilla
Richard B. Rothman
Hernan Navarro
Thomas E. Prisinzano

Document Type

Article

Publication Date

7-26-2007

Journal Title

Journal of Medicinal Chemistry

Volume

50

Issue

15

First Page

3596

Last Page

3603

Abstract

Further modification of salvinorin A (1a), the major active component of Salvia divinorum, has resulted in the synthesis of novel neoclerodane diterpenes with opioid receptor affinity and activity. We report in this study that oxadiazole 11a and salvidivin A (12a), a photooxygenation product of 1a, have been identified as the first neoclerodane diterpenes with κ antagonist activity. This indicates that additional structural modifications of 1a may lead to analogues with higher potency and utility as drug abuse medications.

Keywords

Terpenes, Terpenoids

Recommended Citation

Simpson, D. S., Katavic, P. L., Lozama, A., Harding, W. W. , Parrish, D., Deschamps, Jeffrey R.; Dersch, Christina M.; Partilla, John S.; Rothman, Richard B.; Navarro, H.; Prisinzano, T. E., (2007). Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Preparation and Opioid Receptor Activity of Salvinicin Analogues. Journal of Medicinal Chemistry, 50, 3596-3603.