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Synthetic Transformations of Higher Terpenoids. 44#. Synthesis of New Derivatives of 18-Nor-4-Amino-8(17),13,14-Labdatriene and Evaluation of Their Cytotoxicity for MCF7, HepG2, and HeLa Tumor Cell Lines 高等萜类化合物的合成转化。44#.18-Nor-4-Amino-8(17),13,14-Labdatriene 新衍生物的合成及其对 MCF7、HepG2 和 HeLa 肿瘤细胞系的细胞毒性评估
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-03-28 DOI: 10.1007/s10600-024-04299-2
Yu. V. Kharitonov, V. I. Antipova, M. K. Marenina, Yu. V. Meshkova, T. G. Tolstikova, E. E. Shults
{"title":"Synthetic Transformations of Higher Terpenoids. 44#. Synthesis of New Derivatives of 18-Nor-4-Amino-8(17),13,14-Labdatriene and Evaluation of Their Cytotoxicity for MCF7, HepG2, and HeLa Tumor Cell Lines","authors":"Yu. V. Kharitonov, V. I. Antipova, M. K. Marenina, Yu. V. Meshkova, T. G. Tolstikova, E. E. Shults","doi":"10.1007/s10600-024-04299-2","DOIUrl":"https://doi.org/10.1007/s10600-024-04299-2","url":null,"abstract":"<p>Various <i>N</i>-containing 18-norlabdanoids were synthesized via reactions of 18-nor-4-amino-15,16-epoxy-8(17),13(16),14-labdatriene with methyl iodide, aromatic aldehydes, acetic and trifluoroacetic acid anhydrides, benzoyl chloride, sulfonyl chlorides, bromoacetic acid chloride, and methyl bromoacetate and condensation with azidobenzoic acids. The cytotoxic activity (MTT assay) against MCF7, HepG2, and HeLa tumor cell lines was shown to increase significantly if the lambertianic acid carboxylic group was replaced by an amine. Subsequent modification of the <i>N</i>-containing substituent by addition of an <i>N</i>′-substituted glycylamide moiety altered the cytotoxicity and selectivity. The synthesized compounds had the greatest effect on the viability of MCF7 cell line. The IC<sub>50</sub> value for the most active compound was 8 μM.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140325681","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Protein from the Aerial Part of Arundo donax and its Hypoglycemic Activity 一种来自 Arundo donax 药用部分的蛋白质及其降血糖活性
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-03-27 DOI: 10.1007/s10600-024-04331-5
S. Rakhimova, L. G. Meshlumyan, D. Narbutaeva, U. Ishimov, B. U. Aytjanov, I. Jalolov, S. Aripova
{"title":"A Protein from the Aerial Part of Arundo donax and its Hypoglycemic Activity","authors":"S. Rakhimova, L. G. Meshlumyan, D. Narbutaeva, U. Ishimov, B. U. Aytjanov, I. Jalolov, S. Aripova","doi":"10.1007/s10600-024-04331-5","DOIUrl":"https://doi.org/10.1007/s10600-024-04331-5","url":null,"abstract":"","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140376303","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chemical Compounds from of Aconitum rockii and Anti-Cancer Activity 岩乌头的化学成分和抗癌活性
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-03-27 DOI: 10.1007/s10600-024-04330-6
Dan Lv, Li-mei Zhang, Hong-Bo Lou, Jing Zhou, Jiang-Rui He, Yong Shen
{"title":"Chemical Compounds from of Aconitum rockii and Anti-Cancer Activity","authors":"Dan Lv, Li-mei Zhang, Hong-Bo Lou, Jing Zhou, Jiang-Rui He, Yong Shen","doi":"10.1007/s10600-024-04330-6","DOIUrl":"https://doi.org/10.1007/s10600-024-04330-6","url":null,"abstract":"","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140375233","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthetic Transformations of Lappaconitine 拉帕康尼汀的合成转化
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-03-27 DOI: 10.1007/s10600-024-04289-4
E. M. Tsyrlina, Sh. Sh. Sagdullaev, M. S. Yunusov
{"title":"Synthetic Transformations of Lappaconitine","authors":"E. M. Tsyrlina, Sh. Sh. Sagdullaev, M. S. Yunusov","doi":"10.1007/s10600-024-04289-4","DOIUrl":"https://doi.org/10.1007/s10600-024-04289-4","url":null,"abstract":"<p>Synthetic transformations of lappaconitine, <i>N</i>-norlappaconitine, and <i>N</i>-deacetyllappaconitine are reviewed.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140313855","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Phytochemical Investigation and Biological Characterization of Hedysarum pallidum 苍耳子的植物化学研究和生物学特征
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-03-27 DOI: 10.1007/s10600-024-04317-3
Amina Dob, Naima Rahmouni, C. Bensouici, Diana C. G. A. Pinto, Artur M. S. Silva, Z. Djerrou, O. Boumaza
{"title":"Phytochemical Investigation and Biological Characterization of Hedysarum pallidum","authors":"Amina Dob, Naima Rahmouni, C. Bensouici, Diana C. G. A. Pinto, Artur M. S. Silva, Z. Djerrou, O. Boumaza","doi":"10.1007/s10600-024-04317-3","DOIUrl":"https://doi.org/10.1007/s10600-024-04317-3","url":null,"abstract":"","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140376537","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Analysis of Essential Oil from Syzygium cerinum 茜草精油分析
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-03-27 DOI: 10.1007/s10600-024-04320-8
Faezatul Alwani Mohd Rahim, Wan Salleh, N. Ghani, A. Salihu
{"title":"Analysis of Essential Oil from Syzygium cerinum","authors":"Faezatul Alwani Mohd Rahim, Wan Salleh, N. Ghani, A. Salihu","doi":"10.1007/s10600-024-04320-8","DOIUrl":"https://doi.org/10.1007/s10600-024-04320-8","url":null,"abstract":"","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140373878","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Composition and Anticancer Activity of the Essential Oil of Aglaia rufinervis Aglaia rufinervis 精油的成分和抗癌活性
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-03-27 DOI: 10.1007/s10600-024-04319-1
Wan Salleh, A. Salihu, S. Khamis, M. Juhari
{"title":"Composition and Anticancer Activity of the Essential Oil of Aglaia rufinervis","authors":"Wan Salleh, A. Salihu, S. Khamis, M. Juhari","doi":"10.1007/s10600-024-04319-1","DOIUrl":"https://doi.org/10.1007/s10600-024-04319-1","url":null,"abstract":"","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140377158","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis and Antiviral Activity of 21β-Acetyl-20β,28-Epoxy-18α,19βH-Ursane Derivatives Against Influenza H1N1 and SARS-Cov-2 Spike Pseudovirus 21β-Acetyl-20β,28-Epoxy-18α,19βH-Ursane 衍生物的合成及其对 H1N1 流感和 SARS-Cov-2 Spike 伪病毒的抗病毒活性
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-03-26 DOI: 10.1007/s10600-024-04302-w
E. F. Khusnutdinova, Z. I. Galimova, A. V. Petrova, E. V. Tretyakova, I. E. Smirnova, A. V. Slita, S. V. Fedij, V. V. Zarubaev, S. Xiao, X. Ma, D. Zhou, T. V. Rybalova, D. N. Polovyanenko, O. B. Kazakova
{"title":"Synthesis and Antiviral Activity of 21β-Acetyl-20β,28-Epoxy-18α,19βH-Ursane Derivatives Against Influenza H1N1 and SARS-Cov-2 Spike Pseudovirus","authors":"E. F. Khusnutdinova, Z. I. Galimova, A. V. Petrova, E. V. Tretyakova, I. E. Smirnova, A. V. Slita, S. V. Fedij, V. V. Zarubaev, S. Xiao, X. Ma, D. Zhou, T. V. Rybalova, D. N. Polovyanenko, O. B. Kazakova","doi":"10.1007/s10600-024-04302-w","DOIUrl":"https://doi.org/10.1007/s10600-024-04302-w","url":null,"abstract":"<p>Allobetulin derivatives with rearranged <i>E</i>-ring exhibit important pharmacological properties against various viral pathogens. Basing on 3<i>β</i>-acetoxy-21<i>β</i>-acetyl-20<i>β</i>,28-epoxy-18<i>α</i>,19<i>βH</i>-ursane triterpenoid, obtained from allobetulin in one stage, a series of new derivatives have been synthesized and their antiviral activity against both influenza virus A (H1N1) and SARS-CoV-2 pseudovirus was evaluated. Among them, 2,3-indolo-allobetulone <i>N</i>-propargyl derivatives were the most efficacious against influenza virus with low toxicity (CC<sub>50</sub> × 300 μM) and IC<sub>50</sub> values of 7.04 to 3.5 μM and high selectivity indexes (SI 43 and 86). Compared with amodiaquine, a derivative with 3-pyridinylidene fragment <b>12</b> showed a weak antiviral activity against SARS-CoV-2 pseudovirus with an inhibition rate of 57.3% at a concentration of 20 μM. Further optimization to increase the cellular antiviral activity seems to be necessary to develop this series of triterpenoids as antiviral agents.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140298215","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
New Flavonoids of the Genus Scutellaria. II. Baicalein and Wogonin Glycosides from S. baicalensis 黄芩属的新黄酮类化合物。II.黄芩中的黄芩素和黄芩苷
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-03-26 DOI: 10.1007/s10600-024-04294-7
D. N. Olennikov, N. K. Chirikova
{"title":"New Flavonoids of the Genus Scutellaria. II. Baicalein and Wogonin Glycosides from S. baicalensis","authors":"D. N. Olennikov, N. K. Chirikova","doi":"10.1007/s10600-024-04294-7","DOIUrl":"https://doi.org/10.1007/s10600-024-04294-7","url":null,"abstract":"<p>New glycosides of baicalein (<b>1–4</b>) and wogonin (<b>5</b> and <b>6</b>) were found by studying phenolic compounds from roots of <i>Scutellaria baicalensis</i> Georgi (Lamiaceae) grown with treatment by 24-epibrassinolide. The new compounds were baicalein 7-O-(2′′-O-<i>β</i>-D-glucosyl)-<i>β</i>-D-glucuronopyranoside (scutellariside III, <b>1</b>), baicalein 6-O-<i>β</i>-D-glucopyranoside-7-O-(2′′-O-<i>β</i>-D-glucosyl)-<i>β</i>-D-glucoronopyranoside (scutellariside IV, <b>2</b>), baicalein 6-O-<i>β</i>-D-glycopyranosyl-7-O-<i>β</i>-D-glucuronopyranoside (scutellariside V, <b>3</b>), baicalein 7-O-(2′′-O-malonyl)-<i>β</i>-D-glucuronopyranoside (scutellariside VI, <b>4</b>), wogonin 7-O-(2′′-O-<i>β</i>-D-glucosyl)-<i>β</i>-D-glucuronopyranoside (scutellariside VII, <b>5</b>), and wogonin 7-O-(2′′-O-malonyl)-<i>β</i>-D-glucuronopyranoside (scutellariside VIII, <b>5</b>) according to UV and NMR spectroscopic and mass spectrometric data.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140298331","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
New Hopanoid, Chemical Profiling Using UPLC-ESI-MS/MS and Biological Activities of Centaurea pumilio 新藿香类化合物、UPLC-ESI-MS/MS 化学成分分析以及积雪草的生物活性
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-03-26 DOI: 10.1007/s10600-024-04300-y
Rasha A. Attia, Asmaa Gamal, Amal A. Al-Gendy, Samia S. Hafez
{"title":"New Hopanoid, Chemical Profiling Using UPLC-ESI-MS/MS and Biological Activities of Centaurea pumilio","authors":"Rasha A. Attia, Asmaa Gamal, Amal A. Al-Gendy, Samia S. Hafez","doi":"10.1007/s10600-024-04300-y","DOIUrl":"https://doi.org/10.1007/s10600-024-04300-y","url":null,"abstract":"<p>Few studies have been conducted on phytochemical constituents and biological activities of <i>Centaurea pumilio</i> L. Hence, fractions of root ethanolic extract were subjected to chromatographic separation. Eight compounds were isolated for the first time from the roots – one is new, hop-17(21)-ene-3β-ylformate (<b>1</b>) and seven are known. Fifty-three compounds were tentatively identified in the fractions of the root and aerial parts using UPLC-ESI-MS/MS analysis. Moreover, the ethyl acetate fraction of the roots exhibited an in vitro hypoglycemic effect in that it inhibited the α-amylase enzyme compared to acarbose. Additionally, total ethanolic extracts as well as different soluble fractions of the root and aerial parts were examined for their cytotoxic activity.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140298407","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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