β-Carboline alkaloids from the roots of Peganum harmala L.

IF 4 2区 医学 Q1 INTEGRATIVE & COMPLEMENTARY MEDICINE Chinese Journal of Natural Medicines Pub Date : 2024-02-01 DOI:10.1016/S1875-5364(24)60583-2
Shengge LI , Qin ZHANG , Yuetong WANG , Bin LIN , Dahong LI , Huiming HUA , Xu HU
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Abstract

This study reports the isolation of four new β-carboline alkaloids (14) and six previously identified alkaloids (510) from the roots of Peganum harmala L. Among these compounds, 1 and 2 were characterized as rare β-carboline-quinazoline dimers exhibiting axial chirality. Compound 3 possessed a unique 6/5/6/7 tetracyclic ring system with an azepine ring, and compound 4 was a novel annomontine β-carboline. The structures of these compounds were elucidated by spectroscopic data and quantum mechanical calculations. The biosynthetic pathways of 13 were proposed. Additionally, the cytotoxicity of some isolates against four cancer cell lines (HL-60, A549, MDA-MB-231, and DU145) was evaluated. Notably, compound 4 exhibited significant cytotoxicity against HL-60, A549, and DU145 cells with IC50 values of 12.39, 12.80, and 30.65 μmol·L−1, respectively. Furthermore, compound 2 demonstrated selective cytotoxicity against HL-60 cells with an IC50 value of 17.32 μmol·L−1.

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从Peganum harmala L.根中提取的β-咔啉生物碱
在这些化合物中,化合物 1 和 2 是罕见的β-咔啉-喹唑啉二聚体,具有轴向手性。化合物 3 具有独特的 6/5/6/7 四环环状体系,其中含有一个氮杂环,而化合物 4 则是一种新型的环状 β-咔啉。光谱数据和量子力学计算阐明了这些化合物的结构。提出了 1-3 个化合物的生物合成途径。此外,还评估了一些分离物对四种癌细胞株(HL-60、A549、MDA-MB-231 和 DU145)的细胞毒性。值得注意的是,化合物 4 对 HL-60、A549 和 DU145 细胞具有显著的细胞毒性,IC50 值分别为 12.39、12.80 和 30.65 μmol-L-1。此外,化合物 2 对 HL-60 细胞具有选择性细胞毒性,IC50 值为 17.32 μmol-L-1。
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来源期刊
Chinese Journal of Natural Medicines
Chinese Journal of Natural Medicines INTEGRATIVE & COMPLEMENTARY MEDICINE-PHARMACOLOGY & PHARMACY
CiteScore
7.50
自引率
4.30%
发文量
2235
期刊介绍: The Chinese Journal of Natural Medicines (CJNM), founded and sponsored in May 2003 by China Pharmaceutical University and the Chinese Pharmaceutical Association, is devoted to communication among pharmaceutical and medical scientists interested in the advancement of Traditional Chinese Medicines (TCM). CJNM publishes articles relating to a broad spectrum of bioactive natural products, leading compounds and medicines derived from Traditional Chinese Medicines (TCM). Topics covered by the journal are: Resources of Traditional Chinese Medicines; Interaction and complexity of prescription; Natural Products Chemistry (including structure modification, semi-and total synthesis, bio-transformation); Pharmacology of natural products and prescription (including pharmacokinetics and toxicology); Pharmaceutics and Analytical Methods of natural products.
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