Uniquely modified imidazole alkaloids from a calcareous Leucetta sponge
Uniquely modified imidazole alkaloids from a calcareous Leucetta sponge
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DOI：
10.1021/np020503d
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发表时间：
2003-07-01
影响因子：
5.1
通讯作者：
Crews, P
中科院分区：
文献类型：
--
作者：
Edrada, RA;Stessman, CC;Crews, P
斐济收集的石灰质海绵Leucetta属物种进行了调查，并产生了四个新的咪唑生物碱。一种化合物（+）-卡卡立定A（6）在其整体结构上是独特的，并且由成对取代的2-氨基咪唑啉酮组成。另一种化合物，（-）-螺calcaridine A（7），是独特的，其六氢环戊咪唑-2-亚基胺螺连接到环己烯酮。第三种化合物，（-）-螺卡胞定B（8），是7的OCH 3类似物。这些化合物具有前所未有的骨架和功能，是第一个从钙质海绵中分离的非有机手性氨基咪唑。这里讨论的两个问题包括与6和7的结构解析相关的挑战以及与以前遇到的Leucetta代谢物的关系。
A Fijian collection of the calcareous sponge Leucetta sp. was investigated and yielded four new imidazole alkaloids. One compound, (+)-calcaridine A (6), is unique in its overall structure and consists of a geminally substituted 2-aminoimidazolidinone. An additional compound, (-)-spirocalcaridine A (7), is distinctive in its hexahydrocyclopentamidazol-2-ylidenamine spiro-linked to a cyclohexenone. A third compound, (-)-spirocalcaridine B (8), is the OCH3 analogue of 7. These compounds have unprecedented skeletons and functionality and are the first nonorganometalic chiral aminoimidazoles isolated from calcareous sponges. The two issues discussed here include the challenges associated with the structure elucidations of 6 and 7 and the relationships to previously encountered Leucetta metabolites.