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
{"title":"β-Carboline alkaloids from the roots of Peganum harmala L.","authors":"Shengge LI ,&nbsp;Qin ZHANG ,&nbsp;Yuetong WANG ,&nbsp;Bin LIN ,&nbsp;Dahong LI ,&nbsp;Huiming HUA ,&nbsp;Xu HU","doi":"10.1016/S1875-5364(24)60583-2","DOIUrl":null,"url":null,"abstract":"<div><p>This study reports the isolation of four new <em>β</em>-carboline alkaloids (<strong>1</strong>−<strong>4</strong>) and six previously identified alkaloids (<strong>5</strong>−<strong>10</strong>) from the roots of <em>Peganum harmala</em> L. Among these compounds, <strong>1</strong> and <strong>2</strong> were characterized as rare <em>β</em>-carboline-quinazoline dimers exhibiting axial chirality. Compound <strong>3</strong> possessed a unique 6/5/6/7 tetracyclic ring system with an azepine ring, and compound <strong>4</strong> was a novel annomontine <em>β</em>-carboline. The structures of these compounds were elucidated by spectroscopic data and quantum mechanical calculations. The biosynthetic pathways of <strong>1</strong>−<strong>3</strong> 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 <strong>4</strong> exhibited significant cytotoxicity against HL-60, A549, and DU145 cells with IC<sub>50</sub> values of 12.39, 12.80, and 30.65 μmol·L<sup>−1</sup>, respectively. Furthermore, compound <strong>2</strong> demonstrated selective cytotoxicity against HL-60 cells with an IC<sub>50</sub> value of 17.32 μmol·L<sup>−1</sup>.</p></div>","PeriodicalId":10002,"journal":{"name":"Chinese Journal of Natural Medicines","volume":"22 2","pages":"Pages 171-177"},"PeriodicalIF":4.0000,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chinese Journal of Natural Medicines","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1875536424605832","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"INTEGRATIVE & COMPLEMENTARY MEDICINE","Score":null,"Total":0}
引用次数: 0

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.

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
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。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
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.
期刊最新文献
NO inhibitory constituents from Glycosmis craibii var. glabra Multioxidized polyketides from an endophytic Penicillium sp. YUD17006 associated with Gastrodia elata Dual-function natural products: Farnesoid X receptor agonist/inflammation inhibitor for metabolic dysfunction-associated steatotic liver disease therapy Loganin inhibits the ROS-NLRP3-IL-1β axis by activating the NRF2/HO-1 pathway against osteoarthritis Luteolin ameliorates ulcerative colitis in mice via reducing the depletion of NCR+ILC3 through Notch signaling pathway
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1