Indolizidine Alkaloids with δ-Opioid Receptor Binding Affinity from the Leaves of Elaeocarpus fuscoides

Citations Over TimeTop 17% of 2007 papers

Abstract

In the first chemical investigation of the Papua New Guinean plant Elaeocarpus fuscoides, one new indolizidine alkaloid, elaeocarpenine (1), and three known alkaloids, isoelaeocarpicine (2), isoelaeocarpine (3), and elaeocarpine (4), were isolated from the leaves. Their structures were determined by 1D and 2D NMR spectroscopy. Since treatment of elaeocarpenine (1) with ammonia produced a 1:1 mixture of the diastereomers 3 and 4, we propose that elaeocarpenine (1) is the biogenetic precursor of isoelaeocarpine (3) and elaeocarpine (4). Compounds 1-4 demonstrated binding affinity for the human delta-opioid receptor with IC50 values of 2.7, 35.1, 13.6, and 86.4 microM, respectively.

Related Papers

• → A concise asymmetric synthesis of 5,8-disubstituted indolizidine alkaloids. Total synthesis of (−)-indolizidine 209B(2002)33 cited
• → A General Approach to 3-n-Butyl-5-alkylindolizidines: Total Synthesis of (−)-Indolizidine 195B(2007)21 cited
• → The Study of Several Synthesis Methods of Indolizidine (±)-209I and (±)-209B as Natural Alkaloids(2020)7 cited
• → Compound Separation by Cyclic, Selective Dissolution. Isolation of Diastereomeric, 1β-Methylcarbapenem Key Intermediates(1993)3 cited
• → Synthesis of threo-4,5-dihydroxy diastereomers of sphinganine(1975)