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

TETRAHEDRON

卷:64

Article

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

[1] Univ Palermo, Dipartimento 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.2008.08.043

来源: Elsevier

【 摘 要 】

Salvinorin A (1), a neoclerodane diterpene from the hallucinogenic mint Salvia divinorum, is the only known non-nitrogenous and specific x-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 mu, delta, and kappa opioid receptors. None of these compounds showed high affinity binding to these receptors. However, 10 showed modest affinity for kappa receptors suggesting that other natural neoclerodanes from different Salvia species may possess opioid affinity. (C) 2008 Elsevier Ltd. All rights reserved.

【 授权许可】

Free