Indolizidine Alkaloids with δ-Opioid Receptor Binding Affinity from the Leaves of Elaeocarpus fuscoides
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In the first chemical investigation of the Papua New Guinean plant Elaeocarpus fuscoides Knuth, 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 d-opioid receptor with IC50 values of 2.7, 35.1, 13.6 and 86.4 卬 respectively.
Journal of Natural Products