Piperidine Alkaloids with Diverse Skeletons from Anacyclus pyrethrum,Journal of Natural Products

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Piperidine Alkaloids with Diverse Skeletons from Anacyclus pyrethrum
Journal of Natural Products ( IF 3.3 ) Pub Date : 2018-05-18 00:00:00 , DOI: 10.1021/acs.jnatprod.8b00239
Qi-Bin Chen ₁ , Jie Gao ₁ , Guo-An Zou ₁ , Xue-Lei Xin ₁ , Haji Akber Aisa ₁

Affiliation

Fifteen new piperidine derivatives, pyracyclumines A–J (1–10), including five pairs of enantiomers, (+)-1/(−)-1 to (+)-5/(−)-5, together with three known compounds, agrocybenine (11), 4,6,6-trimethyl-5,6-dihydro-2(1H)-pyridone (12), and 3,5,5-trimethyl-1,5-dihydro-2H-pyrrol-2-one (13), were isolated from the roots of Anacyclus pyrethrum. Pyracyclumines A, B, and H (1, 2, and 8) possess a novel 6/5/6/6 dimeric piperidine skeleton, a unique 6/5/6 dimeric piperidine skeleton, and a 1,4,6-triazaindan skeleton, respectively. Pyracyclumine C (3) is based on a rare cyclopentane–piperidine framework. The structures of the isolated compounds were established by analysis of their NMR and HRESIMS data. The racemic pyracyclumines A–E (1–5) were further separated by chiral HPLC to give the enantiomers (+)-1/(−)-1 to (+)-5/(−)-5, for which the absolute configurations were determined by comparison of their experimental and calculated ECD spectra. The plausible biogenetic pathways of these piperidine alkaloids were proposed starting from the basic units of compounds 12 and 13. All of the isolated compounds were tested for their inhibitory effects on menin–mixed lineage leukemia 1 protein–protein interaction.

中文翻译：

拟除虫菊酯具有不同骨架的哌啶生物碱

15个新的哌啶衍生物，pyracyclumines甲-J（1 - 10），包括五对对映体，（+） - 1 /（ - ） - 1到（+） - 5 /（ - ） - 5，有三个已知的化合物一起，农用贝宁（11），4,6,6-三甲基-5,6-二氢-2（1 H）-吡啶酮（12）和3,5,5-三甲基-1,5-二氢-2 H-吡咯从除虫菊柳的根中分离出-2--1（13）。Pyracyclumines A，B，和H（1，2，和8）分别具有新颖的6/5/6/6二聚哌啶骨架，独特的6/5/6二聚哌啶骨架和1,4,6-三氮杂丹骨架。Pyracyclumine C（3）基于罕见的环戊烷-哌啶骨架。通过分析其NMR和HRESIMS数据确定分离出的化合物的结构。外消旋pyracyclumines A-E（1 - 5）通过手性HPLC进一步分离，得到对映异构体（+） - 1 /（ - ） - 1到（+） - 5 /（ - ） - 5，其绝对构型是通过比较实验和计算出的ECD光谱来确定的。从化合物12和13的基本单元开始，提出了这些哌啶生物碱的可能的生物发生途径。测试了所有分离出的化合物对脑膜混合血统白血病1蛋白与蛋白相互作用的抑制作用。

更新日期：2018-05-18

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