(2R-trans)-2-Butyl-5-heptylpyrrolidine as a Potent Sigma Receptor Ligand Produced by Streptomyces longispororuber

Abstract

A potent sigma (σ) receptor ligand was isolated from the culture broth of Streptomyces longispororuber #525. The active compound was identified to be (2R-trans)-2-butyl-5-heptylpyrrolidine by spectroscopic and chemical studies. The compound exhibited high affinity and selectivity for σ receptors. The IC50 values toward σ₁, σ₂ and dopamine D₂ receptors were 2.0, 22.7 and more than 40, 000 nM, respectively. Its (2S-trans)- and (±)-cis-isomers, both synthesized, were also found to be high affinity σ ligands.