Five new indolizidine alkaloids, grandisines C, D, E, F, and G (4-8), and one known indolizidine alkaloid, (-)-isoelaeocarpiline (3), were isolated from the leaves of Elaeocarpus grandis and their structures determined by 1D and 2D NMR spectroscopy. Grandisine C (4) is isomeric with the known compound rudrakine (1). The absolute configuration of grandisine D (5) was deduced by its conversion to (-)-isoelaeocarpiline. Grandisine E (6) contains a novel tetracyclic ring system. Grandisine F (7) is the 14-amino analogue of grandisine C. Grandisine G (8) contains the novel combination of a piperidine attached to an indolizidine. Grandisines C, D, F, and G and (-)-isoelaeocarpiline showed receptor binding affinity for the human delta-opioid receptor with IC(50) values of 14.6, 1.65, 1.55, 75.4, and 9.9 microM, respectively.

中文翻译：

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Grandisines CG，来自澳大利亚雨林树Elaeocarpus grandis的吲哚并立生物碱。

从大叶胡杨叶中分离出5种新的吲哚并立定生物碱，大地碱C，D，E，F和G（4-8）和一种已知的吲哚并立定生物碱（-）-异松果碱（3），其结构通过1D和2D NMR光谱。Grandisine C（4）与已知的化合物rudrakine（1）是异构体。通过将其转化为（-）-异古朴碱，推导出金刚烷D（5）的绝对构型。Grandisine E（6）包含一个新颖的四环系统。Grandisine F（7）是Grandisine C的14个氨基酸类似物。GrandisineG（8）包含哌啶与吲哚并立唑的新颖组合。大丁胺C，D，F和G以及（-）-异古皮碱显示出对人类δ-阿片类受体的受体结合亲和力，其IC（50）值分别为14.6、1.65、1.55、75.4和9.9 microM。