STUDIES OF AUSTRALIAN ASCIDIANS .1. 6 NEW LAMELLARIN-CLASS ALKALOIDS FROM A COLONIAL ASCIDIAN, DIDEMNUM-SP
STUDIES OF AUSTRALIAN ASCIDIANS .1. 6 NEW LAMELLARIN-CLASS ALKALOIDS FROM A COLONIAL ASCIDIAN, DIDEMNUM-SP
复制标题
DOI：
10.1071/ch9930489
复制
发表时间：
1993-01-01
影响因子：
1.1
通讯作者：
COLL, JC
中科院分区：
文献类型：
--
作者：
CARROLL, AR;BOWDEN, BF;COLL, JC
从海洋海鞘Didemnum sp.中分离得到6个新的多环芳香族生物碱，即片螺素I（3）、J（6）、K（7）、L（9）、MR（11）和片螺素N的三乙酸酯（13），以及4个已知生物碱，即片螺素A（1）、B（15）、C（16）和片螺素D的三乙酸酯（14）。光谱学，包括C-13-H-1位移相关二维（2D）核磁共振。实验和n.O.e.测量.两种化合物，片螺素K（7）和片螺素L（9）的三乙酸酯（8）和（10），通过在加热回流的乙醇中用2，3-二氯-5，6-二氰基-1，4-苯醌处理，以高产率脱氢。所得产物在所有方面分别与片螺素MR和N的三乙酸酯相同。重新分离以前从前鳃类软体动物Lamellaria sp.获得的片层蛋白A-D，进一步支持了这些软体动物从海鞘中提取化合物作为食物来源的想法。
Six new polyaromatic alkaloids, lamellarin I (3), J (6), K (7), L (9), MR (11) and the triacetate (13) of lamellarin N, and four known alkaloids, lamellarin A (1), B (15), C (16) and the triacetate (14) of lamellarin D, have been isolated from the marine ascidian Didemnum sp. The structures were deduced by high-field n.mr.r. spectroscopy including C-13-H-1 shift-correlated two-dimensional (2D) n.mr.r. experiments and n.O.e. measurements. The triacetates (8) and (10) of two of the compounds, lamellarin K (7) and lamellarin L (9), were dehydrogenated in high yield by treatment with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in ethanol heated under reflux. The products obtained were identical in all respects to the triacetates of lamellarin MR and N, respectively. The re-isolation of lamellarins A-D, which were previously obtained from the prosobranch mollusc Lamellaria sp., lends further support for the idea that these molluscs sequester the compounds from ascidians as food sources.