关键词: Penicillium simplicissimum acetylcholinesterase inhibition computational chemistry nitrogen-containing compounds polyketide structural elucidation

Mesh : Molecular Structure Polyketides / chemistry Acetylcholinesterase / metabolism Penicillium / chemistry Peptides / metabolism Alkaloids / chemistry

来  源:   DOI:10.3390/molecules29030613   PDF(Pubmed)

Abstract:
In this study, two previously undescribed nitrogen-containing compounds, penisimplicins A (1) and B (2), were isolated from Penicillium simplicissimum JXCC5. The structures of 1 and 2 were elucidated on the basis of comprehensive spectroscopic data analysis, including 1D and 2D NMR and HRESIMS data. The absolute configuration of 2 was determined by Marfey\'s method, ECD calculation, and DP4+ analysis. Both structures of 1 and 2 feature an unprecedented manner of amino acid-derivatives attaching to a polyketide moiety by C-C bond. The postulated biosynthetic pathways for 1 and 2 were discussed. Additionally, compound 1 exhibited significant acetylcholinesterase inhibitory activity, with IC50 values of 6.35 μM.
摘要:
在这项研究中,两种先前未描述的含氮化合物,penisimplicinsA(1)和B(2),从单纯青霉JXCC5中分离出。在全面的光谱数据分析的基础上阐明了1和2的结构,包括1D和2DNMR和HRESIMS数据。2的绝对构型由Marfey's方法确定,ECD计算,和DP4+分析。1和2的结构都具有前所未有的氨基酸衍生物通过C-C键连接到聚酮化合物部分的方式。讨论了1和2的假定生物合成途径。此外,化合物1表现出显著的乙酰胆碱酯酶抑制活性,IC50值为6.35μM。
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