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

TETRAHEDRON

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Article

Fontana, Gianfranco¹  Savona, Giuseppe¹  Rodriguez, Benjamin²  Dersch, Christina M.³  Rothman, Richard B.³  Prisinzano, Thomas E.⁴ 

[1] Univ Palermo, Dept Chim Organ E Paterno, I-90128 Palermo, Italy

[2] CSIC, Inst Quim Organ, E-28006 Madrid, Spain

[3] NIDA, Clin Psychopharmacol Sect, IRP, NIH,DHHS, Baltimore, MD 21224 USA

[4] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA

关键词: Salvia splendens;    Opioid receptors;    Neoclerodane diterpenes;    Semisynthetic derivatives;   

DOI  :  10.1016/j.tet.2008.12.009

来源: Elsevier

【 摘 要 】

Salvinorin A (1), a neoclerodane diterpene from the hallucinogenic mint Salvia divinorum, is the only known naturally occurring non-nitrogenous and specific K-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. (C) 2008 Elsevier Ltd. All rights reserved.

【 授权许可】

Free