Shengge LI , Qin ZHANG , Yuetong WANG , Bin LIN , Dahong LI , Huiming HUA , Xu HU
{"title":"从Peganum harmala L.根中提取的β-咔啉生物碱","authors":"Shengge LI , Qin ZHANG , Yuetong WANG , Bin LIN , Dahong LI , Huiming HUA , 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":null,"pages":null},"PeriodicalIF":4.0000,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"β-Carboline alkaloids from the roots of Peganum harmala L.\",\"authors\":\"Shengge LI , Qin ZHANG , Yuetong WANG , Bin LIN , Dahong LI , Huiming HUA , 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\":null,\"pages\":null},\"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}","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}
β-Carboline alkaloids from the roots of Peganum harmala L.
This study reports the isolation of four new β-carboline alkaloids (1−4) and six previously identified alkaloids (5−10) 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 1−3 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.
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.