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Compounds Isolated from the Pericarp of Zanthoxylum bungeanum and Their Antibacterial Activity 花椒果皮中分离的化合物及其抑菌活性研究
IF 0.9 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-07-25 DOI: 10.1007/s10600-025-04745-9
Jing-Zhi Zhao, Xiao-Juan Huang, Khalid Hassan Mohamed, Bang-Yin Tan, Wei-Yan Hu, Rong-Ping Zhang, Hao-Fei Yu, Ying Guo, Lan-Chun Zhang
{"title":"Compounds Isolated from the Pericarp of Zanthoxylum bungeanum and Their Antibacterial Activity","authors":"Jing-Zhi Zhao,&nbsp;Xiao-Juan Huang,&nbsp;Khalid Hassan Mohamed,&nbsp;Bang-Yin Tan,&nbsp;Wei-Yan Hu,&nbsp;Rong-Ping Zhang,&nbsp;Hao-Fei Yu,&nbsp;Ying Guo,&nbsp;Lan-Chun Zhang","doi":"10.1007/s10600-025-04745-9","DOIUrl":"10.1007/s10600-025-04745-9","url":null,"abstract":"<p>A previously unreported acyclic monoterpene, zanthungeanumol A (<b>1</b>), and eleven known alkaloids <b>2</b>–<b>12</b> were isolated from the pericarps of <i>Zanthoxylum bungeanum</i>. The activity evaluation showed that compound <b>7</b> exhibited potent antibacterial activities against Staphylococcus aureus, while compound <b>8</b> exhibited significant antimicrobial activity against Escherichia coli 140 with a MIC value of 6.25 μg/mL, and their activities were comparable to the plant-derived antibacterial drug berberine.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 4","pages":"724 - 730"},"PeriodicalIF":0.9,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145169251","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 Cytotoxic Properties of N-Substituted Derivatives of Quinolizidine Alkaloid (–)-Cytisine and Their Thioanalogues 喹诺嗪类生物碱(-)-胱氨酸及其硫代类似物n -取代衍生物的合成及细胞毒性
IF 0.9 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-07-25 DOI: 10.1007/s10600-025-04741-z
Alena Koval’skaya, Alexander Lobov, Vener Vakhitov, Yulia Vakhitova, Inna Tsypysheva
{"title":"Synthesis and Cytotoxic Properties of N-Substituted Derivatives of Quinolizidine Alkaloid (–)-Cytisine and Their Thioanalogues","authors":"Alena Koval’skaya,&nbsp;Alexander Lobov,&nbsp;Vener Vakhitov,&nbsp;Yulia Vakhitova,&nbsp;Inna Tsypysheva","doi":"10.1007/s10600-025-04741-z","DOIUrl":"10.1007/s10600-025-04741-z","url":null,"abstract":"<p><i>N</i>-Substituted derivatives of the alkaloid (–)-cytisine and its thioanalogue were synthesized via a two-step ‘alkylation-thionation’ chemical transformation sequence. The ability of the obtained compounds to inhibit metabolic activity of conditionally normal (HEK293, human embryonic kidney cells) and cancerous cells (A549, lung adenocarcinoma; MCF-7, breast cancer) was assessed. It was found that <i>N</i>-hexyl-, -nonylcytisine and <i>N</i>-heptyl-, -octyl-, -nonyl- and -benzyl-thiocytisine demonstrated moderate cytotoxic properties. The hit-compound (1<i>R</i>,5<i>S</i>)-3-benzyl-1,2,3,4,5,6-hexahydro-8<i>H</i>-1,5-methanopyrido[1,2-a][1,5]diazocine-8- thione (<b>22</b>) was identified with IC<sub>50</sub> values of 12.83 ± 1.2 μM (A-549) and 35.75 ± 7.43 μM (MCF-7). It was shown that the antiproliferative properties of compound <b>22</b> might be associated with alterations of cell cycle regulation in tumor cells (A549 and MCF-7), exhibiting mainly cytostatic effect, whereas in conditionally normal cells (HEK293), <b>22</b> promotes apoptosis, thus triggering the cytotoxic mechanisms.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 4","pages":"705 - 712"},"PeriodicalIF":0.9,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145169252","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
Volatile Components of Mesua racemosa and Tyrosinase Inhibitory Effect 总状Mesua挥发性成分及酪氨酸酶抑制作用
IF 0.9 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-07-24 DOI: 10.1007/s10600-025-04767-3
Abubakar Siddiq Salihu, Wan Mohd Nuzul Hakimi Wan Salleh, Nurunajah Ab Ghani, Wirginia Kukula-Koch
{"title":"Volatile Components of Mesua racemosa and Tyrosinase Inhibitory Effect","authors":"Abubakar Siddiq Salihu,&nbsp;Wan Mohd Nuzul Hakimi Wan Salleh,&nbsp;Nurunajah Ab Ghani,&nbsp;Wirginia Kukula-Koch","doi":"10.1007/s10600-025-04767-3","DOIUrl":"10.1007/s10600-025-04767-3","url":null,"abstract":"","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 4","pages":"810 - 811"},"PeriodicalIF":0.9,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145168951","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 of Amino-Acid Conjugates of 18β-Glycyrrhetic Acid Methyl Ester 3-O-Hemisuccinate 半琥珀酸18β-甘草酸甲酯氨基酸缀合物的合成
IF 0.9 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-07-24 DOI: 10.1007/s10600-025-04738-8
L. A. Baltina, E. R. Karimova, S. F. Petrova, P. A. Ilyina, I. S. Balashova, V. V. Zarubaev
{"title":"Synthesis of Amino-Acid Conjugates of 18β-Glycyrrhetic Acid Methyl Ester 3-O-Hemisuccinate","authors":"L. A. Baltina,&nbsp;E. R. Karimova,&nbsp;S. F. Petrova,&nbsp;P. A. Ilyina,&nbsp;I. S. Balashova,&nbsp;V. V. Zarubaev","doi":"10.1007/s10600-025-04738-8","DOIUrl":"10.1007/s10600-025-04738-8","url":null,"abstract":"<p>Hybrid molecules based on 18<i>β</i>-glycyrrhetic acid (GLA), i.e., conjugates of GLA methyl ester 3-<i>O</i>-hemisuccinate with methyl/ethyl esters of <i>L</i>-amino acids (isoleucine, leucine, phenylalanine), were synthesized in 50–55% yields using <i>N</i>-hydroxysuccinimide–<i>N,N</i>′-dicyclohexylcarbodiimide. The conjugate with <i>L</i>-leucine methyl ester (<b>5</b>) showed pronounced antiviral activity against human adenovirus type 5.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 4","pages":"692 - 697"},"PeriodicalIF":0.9,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145168954","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
Pyrrolizidine Alkaloids from Heliotropium lasiocarpum and Insecticidal Activity of Their Extracts 龙葵中吡咯利西啶类生物碱及其提取物的杀虫活性
IF 0.9 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-07-24 DOI: 10.1007/s10600-025-04748-6
Kh. N. Olimova, U. Kh. Kurbanov, R. Ya. Okmanov, B. Tashkhodzhaev, N. I. Mukarramov, S. M. Turaeva
{"title":"Pyrrolizidine Alkaloids from Heliotropium lasiocarpum and Insecticidal Activity of Their Extracts","authors":"Kh. N. Olimova,&nbsp;U. Kh. Kurbanov,&nbsp;R. Ya. Okmanov,&nbsp;B. Tashkhodzhaev,&nbsp;N. I. Mukarramov,&nbsp;S. M. Turaeva","doi":"10.1007/s10600-025-04748-6","DOIUrl":"10.1007/s10600-025-04748-6","url":null,"abstract":"<p>The new pyrrolizidine alkaloid helasine (<b>1</b>) and known heliotrine (<b>2</b>), lasiocarpine N-oxide (<b>3</b>), trachelanthamine (<b>4</b>), and echinatine (<b>5</b>) were isolated from the plant Heliotropium lasiocarpum. Alkaloids <b>4</b> and <b>5</b> were observed for the first time in H. lasiocarpum. The absolute configurations of isolated alkaloids <b>2</b>–<b>4</b> were established by X-ray crystal structure analyses. The insecticidal activity of the CHCl<sub>3</sub>, n-BuOH, and H<sub>2</sub>O parts of the H. lasiocarpum extract against Callosobruchus maculates and Sitophilus oryzae was examined. The CHCl<sub>3</sub> extract at a dose of 10 mg/L had the highest activity.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 4","pages":"748 - 754"},"PeriodicalIF":0.9,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145168952","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
Structurally Diverse Flavonolignans with Hepatoprotective Activities from the Fruits of Hippophae rhamnoides 沙棘果实中具有保肝活性的结构多样性黄酮木脂素
IF 0.9 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-07-24 DOI: 10.1007/s10600-025-04729-9
Qinge Ma, Wenmin Liu, Rongrui Wei
{"title":"Structurally Diverse Flavonolignans with Hepatoprotective Activities from the Fruits of Hippophae rhamnoides","authors":"Qinge Ma,&nbsp;Wenmin Liu,&nbsp;Rongrui Wei","doi":"10.1007/s10600-025-04729-9","DOIUrl":"10.1007/s10600-025-04729-9","url":null,"abstract":"<p>A novel flavonolignan, named 3,3′,4′,5-tetrahydroxy-3′′′,5′′′-dimethoxy-9′,9′′′dihydroxymethyl-4- hydroxyphenyl-4′′′-hydroxy-3′′′,5′′′-dimethoxyphenylflavonolignan (<b>1</b>), together with five known flavonolignan derivatives (<b>2–6</b>) were isolated from <i>Hippophae rhamnoides</i> L. for the first time. Their structures were determined by extensive and comprehensive IR, UV, NMR, MS spectra, as well as reported references. Compounds <b>1–6</b> were evaluated for their hepatoprotective activities on APAP-treated HepG2 cells. As a result, compounds <b>1</b> and <b>2</b> exhibited moderate hepatoprotective activities.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 4","pages":"648 - 652"},"PeriodicalIF":0.9,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145168953","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 New Cyclopentenone Derivative from an Endophytic Fungus Aspergillus sp. 内生真菌曲霉（Aspergillus sp.）新环戊烯酮衍生物。
IF 0.9 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-07-23 DOI: 10.1007/s10600-025-04761-9
Qian Wu, Jia-Tong Zhou, Zhuo-Jian Zhi, Lan-Fang Zou, Min Liang, Xian-Hua He, Li-Qi Liang, Wei-Feng Xu, Rui-Yun Yang
{"title":"A New Cyclopentenone Derivative from an Endophytic Fungus Aspergillus sp.","authors":"Qian Wu,&nbsp;Jia-Tong Zhou,&nbsp;Zhuo-Jian Zhi,&nbsp;Lan-Fang Zou,&nbsp;Min Liang,&nbsp;Xian-Hua He,&nbsp;Li-Qi Liang,&nbsp;Wei-Feng Xu,&nbsp;Rui-Yun Yang","doi":"10.1007/s10600-025-04761-9","DOIUrl":"10.1007/s10600-025-04761-9","url":null,"abstract":"","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 4","pages":"791 - 793"},"PeriodicalIF":0.9,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145169068","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 of Conjugates of 9-(Hydroxymethyl)Methylcytisine with 1,2,3-Triazoles 9-（羟甲基）甲基胞氨酸与1,2,3-三唑缀合物的合成
IF 0.9 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-07-23 DOI: 10.1007/s10600-025-04747-7
A. V. Koval’skaya, V. A. Sorokina, A. N. Lobov, I. P. Tsypysheva
{"title":"Synthesis of Conjugates of 9-(Hydroxymethyl)Methylcytisine with 1,2,3-Triazoles","authors":"A. V. Koval’skaya,&nbsp;V. A. Sorokina,&nbsp;A. N. Lobov,&nbsp;I. P. Tsypysheva","doi":"10.1007/s10600-025-04747-7","DOIUrl":"10.1007/s10600-025-04747-7","url":null,"abstract":"<p>1,3-Dipolar cycloaddition of benzyl azides to the propargyl ether of the 9-hydroxymethyl derivative of the quinolizidine alkaloid methylcytisine under CuAAC conditions synthesized 9-conjugates of it with 1-benzyl-, 1-(4-methoxybenzyl)-, 1-(2,3-dimethoxybenzyl)-, 1-(3,4-dimethoxybenzyl)-, 1-(2-fluorobenzyl)-, 1-(2-chlorobenzyl)-, 1-(4-bromobenzyl)-, 1-(2,4-dichlorobenzyl)-, and 1-(3-nitrobenzyl)-substituted 1,2,3-triazoles. The structures of the synthesized compounds were confirmed by physicochemical analysis, including elemental analysis and NMR spectroscopy.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 4","pages":"742 - 747"},"PeriodicalIF":0.9,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145168573","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
Antibacterial Pyrroloquinolines from Cigar-Tobacco-Derived Endophytic Fungus Aspergillus puniceus 雪茄烟草内生真菌曲霉的抗菌吡咯喹啉类
IF 0.9 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-07-23 DOI: 10.1007/s10600-025-04750-y
Guang-Hui Kong, Hua-Yin Liu, Guang-Hai Zhang, Yu-Long Su, Xue-Ru Song, Wei Li, Wei-Guang Wang, Qiu-Fen Hu, Yu-Ping Wu, Ling-Duo Bu
{"title":"Antibacterial Pyrroloquinolines from Cigar-Tobacco-Derived Endophytic Fungus Aspergillus puniceus","authors":"Guang-Hui Kong,&nbsp;Hua-Yin Liu,&nbsp;Guang-Hai Zhang,&nbsp;Yu-Long Su,&nbsp;Xue-Ru Song,&nbsp;Wei Li,&nbsp;Wei-Guang Wang,&nbsp;Qiu-Fen Hu,&nbsp;Yu-Ping Wu,&nbsp;Ling-Duo Bu","doi":"10.1007/s10600-025-04750-y","DOIUrl":"10.1007/s10600-025-04750-y","url":null,"abstract":"<p>In this study, two new pyrroloisoquinolines, cigarpyrro A and B (<b>1</b> and <b>2</b>), together with five known pyrroloisoquinolines (<b>3–7</b>) were isolated from the cigar-tobacco-derived endophytic fungus <i>Aspergillus puniceus</i>. Their structures were determined by means of HR-ESI-MS and extensive 1D and 2D NMR spectroscopic studies. Compounds <b>1</b> and <b>2</b> were evaluated for their antibacterial activities against five pathogenic strains (<i>Staphylococcus aureus</i> (SEA), <i>Escherichia coli</i> (EPEC), <i>Streptococcus pyogenes</i> (GAS), <i>Bacillus subtilis</i> (QST713), and <i>Proteus</i> spp.). Interestingly, compounds <b>1</b> and <b>2</b> exhibited notable antibacterial activity with a bacteriostatic diameter within the range 15.4 ± 1.8 – 25.2 ± 1.6 mm against the above strains, and most of the bacteriostatic diameters are higher than that of the positive control. In addition, the potential values for compounds <b>1</b> and <b>2</b> used as antiseptic agents were also evaluated, and they have the potential value for use as antiseptic agents for cigarette-tipping paper.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 4","pages":"731 - 736"},"PeriodicalIF":0.9,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145168576","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
Deciphering the Chemical Composition of the Volatile Oil of Cratoxylum maingayi 梅茄挥发油的化学成分分析
IF 0.9 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-07-23 DOI: 10.1007/s10600-025-04769-1
Abubakar Siddiq Salihu, Wan Mohd Nuzul Hakimi Wan Salleh, Nurunajah Ab Ghani, Nesteve John Agosto
{"title":"Deciphering the Chemical Composition of the Volatile Oil of Cratoxylum maingayi","authors":"Abubakar Siddiq Salihu,&nbsp;Wan Mohd Nuzul Hakimi Wan Salleh,&nbsp;Nurunajah Ab Ghani,&nbsp;Nesteve John Agosto","doi":"10.1007/s10600-025-04769-1","DOIUrl":"10.1007/s10600-025-04769-1","url":null,"abstract":"","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 4","pages":"815 - 816"},"PeriodicalIF":0.9,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145168574","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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