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Phormidepistatin from the Cyanobacterium UIC 10484: Assessing the Phylogenetic Distribution of the Statine Pharmacophore
Journal of Natural Products ( IF 5.1 ) Pub Date : 2021-07-27 , DOI: 10.1021/acs.jnatprod.1c00334
Peter Sullivan 1 , Aleksej Krunic 1 , Lydia J Davis 1 , Hwan Seung Kim 1 , Joanna E Burdette 1 , Jimmy Orjala 1
Affiliation  

A new linear lipopeptide, phormidepistatin (1), containing an epi-statine amino acid was isolated from cf. Phormidium sp. strain UIC 10484. The planar structure was elucidated by 1D and 2D NMR experimentation. The relative configuration was determined by J-based configurational analysis and the absolute configuration by advanced Marfey’s analysis. Given that the statine moiety is an established pharmacophore known to inhibit aspartic proteases, phormidepistatin was evaluated against cathepsin D and displayed limited activity. With 1 containing a statine-like moiety, we sought to assess the distribution of this γ-amino acid within the phylum Cyanobacteria. In-depth MS/MS analysis identified the presence of phormidepistatin in cf. Phormidium sp. UIC 10045 and cf. Trichormus sp. UIC 10039. A structure database search identified 33 known cyanobacterial metabolites containing a statine or statine-like amino acid and, along with phormidepistatin, were grouped into 10 distinct compound classes. A phylogenetic tree was built comprising all cyanobacteria with established 16S rRNA sequences known to produce statine or statine-like-containing compound classes. This analysis suggests the incorporation of the γ-amino acid into secondary metabolites is taxonomically widespread within the phylum. Overall, it is our assessment that cyanobacteria are a potential source for statine or statine-like-containing compounds.

中文翻译:

来自蓝藻 UIC 10484 的 Phormidepistatin:评估他汀类药效团的系统发育分布

从cf. _ Phormidium sp。菌株 UIC 10484。平面结构通过 1D 和 2D NMR 实验阐明。相对构型由基于J的构型分析确定,绝对构型由高级 Marfey 分析确定。鉴于他汀部分是已知的抑制天冬氨酸蛋白酶的已确定的药效团,因此针对组织蛋白酶 D 评估了 phormidepistatin 并显示出有限的活性。由于1含有一个类似他汀的部分,我们试图评估这种 γ-氨基酸在蓝细菌门中的分布。深入的 MS/MS 分析确定了 phormidepistatin 在 cf.Phormidium sp。UIC 10045 和参见。Trihormus sp。UIC 10039. 结构数据库搜索确定了 33 种已知的蓝藻代谢物,其中含有一种他汀类或他汀类氨基酸,并与 phormidepistatin 一起被分为 10 个不同的化合物类别。建立了一个系统发育树,其中包括所有蓝藻,这些蓝细菌具有已知的产生他汀类或含他汀类化合物类别的 16S rRNA 序列。该分析表明,将 γ-氨基酸掺入次生代谢物在分类学上广泛存在于门内。总体而言,我们的评估是,蓝藻是他汀或含他汀类化合物的潜在来源。
更新日期:2021-08-27
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