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海洋被囊动物 sp. 中的罕见海鞘六元环生物碱

Rare Caulamidine Hexacyclic Alkaloids from the Marine Ascidian sp.

机构信息

College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.

Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, Maryland 21702-1201, United States.

出版信息

J Nat Prod. 2023 Jul 28;86(7):1855-1861. doi: 10.1021/acs.jnatprod.3c00393. Epub 2023 Jun 27.

Abstract

Two new caulamidines C () and D () and three isocaulamidines B, C, and D (, , and ) along with the known compound caulamidine B () were isolated from the marine ascidian sp. Their structures were elucidated by analysis of nuclear magnetic resonance (NMR) and electronic circular dichroism (ECD) data. Isocaulamidines have an altered pattern of -methyl substitution (N-15 vs N-13 in the caulamidines) with a concomitant double-bond rearrangement to provide a new C-14/N-13 imine functionality. Caulamidine C () and isocaulamidine C () are the first members of this alkaloid family with two chlorine substituents in the core 6-2,6-naphthyridine ring system.

摘要

从海洋海鞘 中分离得到两个新的 Caulamidines C()和 D()和三个 Isocaulamidines B、C 和 D(),以及已知化合物 Caulamidine B()。通过核磁共振 (NMR) 和电子圆二色性 (ECD) 数据分析确定了它们的结构。Isocaulamidines 的-N-15 取代模式发生了变化(与 Caulamidines 中的 N-13 相比),同时发生双键重排,提供了新的 C-14/N-13 亚胺官能团。Caulamidine C()和 Isocaulamidine C()是该生物碱家族中第一个在核心 6-2,6-萘啶环系统中有两个氯取代基的成员。

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