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Solvolysis Artifacts: Leucettazoles as Cryptic Macrocyclic Alkaloid Dimers from a Southern Australian Marine Sponge Leucetta sp.

机译:溶剂分解伪像:亮氨唑类化合物是来自澳大利亚南部海洋海绵Leucetta sp。的隐性大环生物碱二聚体。

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摘要

Chemical analysis of a southern Australian sponge, Leucetta sp., led to the discovery of a pair of solvolysis adducts, leucettazoles A1 (>1a) and B1 (>2a), as artifacts of an unprecedented family of 15-membered macrocyclic alkaloid dimers featuring a pair of imino bridged 2-aminoimidazoles, together with a putative monomeric precursor, leucettazine A (>3). The dimeric alkaloids >1a and >2a, and monomer >3, were identified by detailed spectroscopic analysis, supported by chemical transformations, analytical mass spectrometry, and biosynthetic considerations. Global natural product social networking (GNPS) molecular analysis of crude sponge extracts and solvent partitions, supported by single ion extraction (SIE) and diagnostic MS/MS fragmentations, revealed the associated natural products, leucettazoles A (>1) and B (>2). This study highlights that the study of natural product artifacts can be useful, and can on occasion serve as a pathway to discover cryptic new classes of natural products.
机译:对澳大利亚南部海绵Leucetta sp。的化学分析导致​​发现了一对溶剂分解加合物,即亮叶酸唑A1(> 1a )和B1(> 2a )作为人工制品。是史无前例的15元大环生物碱二聚体家族,其特征是一对亚氨基桥连的2-氨基咪唑,以及假定的单体前体亮氨蝶呤A(> 3 )。通过详细的光谱分析鉴定了二聚生物碱> 1a 和> 2a 以及单体> 3 ,并进行了化学转化,分析质谱和生物合成的支持注意事项。全球天然产物社交网络(GNPS)对粗海绵提取物和溶剂分配区进行分子分析,并通过单离子提取(SIE)和诊断性MS / MS碎片技术支持,揭示了相关的天然产物亮三唑A(> 1 )和B(> 2 )。这项研究强调,对天然产物人工制品的研究可能是有用的,并且有时可以用作发现神秘的新型天然产物的途径。

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