Katavic Peter L, Venables Debra A, Rali Topul, Carroll Anthony R
Natural Product Discovery, Eskitis Institute, Griffith University, Brisbane, Queensland, Australia.
J Nat Prod. 2007 May;70(5):872-5. doi: 10.1021/np060607e. Epub 2007 Apr 24.
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.
在对巴布亚新几内亚植物褐毛杜英（Elaeocarpus fuscoides）进行的首次化学研究中，从其叶子中分离出一种新的吲哚里西啶生物碱——杜英宁（1），以及三种已知生物碱——异杜英辛（2）、异杜英碱（3）和杜英碱（4）。它们的结构通过一维和二维核磁共振光谱确定。由于用氨处理杜英宁（1）会产生非对映异构体3和4的1:1混合物，我们推测杜英宁（1）是异杜英碱（3）和杜英碱（4）的生物合成前体。化合物1 - 4对人δ-阿片受体表现出结合亲和力，其IC50值分别为2.7、35.1、13.6和86.4微摩尔。
