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Synthesis and Biological Activity of Derivatives of (C-30)-Substituted Lupane Triterpenoids and Gallic Acid Bound Through a 1,2,3-Triazole Linker
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-02-04 DOI: 10.1007/s10600-025-04583-9
S. A. Popov, Z. Qi, G. Yang, C. Wang, M. D. Semenova, A. V. Shpatov, E. E. Shults
{"title":"Synthesis and Biological Activity of Derivatives of (C-30)-Substituted Lupane Triterpenoids and Gallic Acid Bound Through a 1,2,3-Triazole Linker","authors":"S. A. Popov,&nbsp;Z. Qi,&nbsp;G. Yang,&nbsp;C. Wang,&nbsp;M. D. Semenova,&nbsp;A. V. Shpatov,&nbsp;E. E. Shults","doi":"10.1007/s10600-025-04583-9","DOIUrl":"10.1007/s10600-025-04583-9","url":null,"abstract":"<p>New conjugates of lupane triterpenoids bound through a 1,2,3-triazole linker with gallate derivatives were prepared via Cu-catalyzed cycloaddition reactions of [3<i>β</i>,28-diacetoxy-20(29)-lupen-30-yl]azide and 3<i>β</i>-acetoxylup-20(29)-en-30-azido-28-oic acid with gallate derivatives with propargyl substituents in various positions. Conjugate <b>4</b> based on betulin with a modified gallate substituent containing a dioxolane moiety possessed potent antioxidant properties and anti-inflammatory activity (suppression of NO hyperexpression).</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 1","pages":"96 - 103"},"PeriodicalIF":0.8,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143475133","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 Naphtho[2,3-c]Furan-1(3H)-One Derivative and Anti-Inflammatory and Antioxidant Constituents from Rhamnus kanagusukii
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-02-04 DOI: 10.1007/s10600-025-04581-x
Chu-Wen Kuo, Zih-Rong Chen, Hsueh-Yang Huang, Chia-Ching Liaw, Ping-Jyun Sung, Ming-Jen Cheng, Fu-Sen Wu, Jih-Jung Chen
{"title":"A New Naphtho[2,3-c]Furan-1(3H)-One Derivative and Anti-Inflammatory and Antioxidant Constituents from Rhamnus kanagusukii","authors":"Chu-Wen Kuo,&nbsp;Zih-Rong Chen,&nbsp;Hsueh-Yang Huang,&nbsp;Chia-Ching Liaw,&nbsp;Ping-Jyun Sung,&nbsp;Ming-Jen Cheng,&nbsp;Fu-Sen Wu,&nbsp;Jih-Jung Chen","doi":"10.1007/s10600-025-04581-x","DOIUrl":"10.1007/s10600-025-04581-x","url":null,"abstract":"<p>A new naphtho[2,3-c]furan-1(3H)-one derivative, 6,8,9-trihydroxynaphtho[2,3-c]furan-1(3H)-one (<b>1</b>), has been isolated from the stem bark of <i>Rhamnus kanagusukii</i>, together with eight known compounds, chrysophanol (<b>2</b>), emodin (<b>3</b>), rhamnazin (<b>4</b>), kaempferol (<b>5</b>), apigenin (<b>6</b>), taxifolin (<b>7</b>), ferulic acid (<b>8</b>), and gallic acid (<b>9</b>). The structure of new compound <b>1</b> was determined using spectroscopic and MS analyses. Among the isolated compounds, 6,8,9-trihydroxynaphtho[2,3-c]furan-1(3H)-one (<b>1</b>), kaempferol (<b>5</b>), apigenin (<b>6</b>), and taxifolin (<b>7</b>) showed potent inhibition with IC<sub>50</sub> values of 19.48 ± 1.52, 20.48 ± 1.84, 16.47 ± 1.25, and 15.44 ± 1.02 μM, respectively, against LPS-induced NO generation. In addition, compounds <b>5</b>, <b>6</b>, <b>7</b>, <b>8</b>, and <b>9</b> also showed potent DPPH radical scavenging activities with IC<sub>50</sub> values of 21.11 ± 1.84, 22.47 ± 2.04, 13.02 ± 1.07, 14.54 ± 1.35, and 13.48 ± 1.16 μM respectively.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 1","pages":"86 - 90"},"PeriodicalIF":0.8,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143475152","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
Pectinic Substances from Scutellaria adenostegia and S. comosa and their Antimicrobial Activity
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-02-04 DOI: 10.1007/s10600-025-04589-3
A. A. Siddikova, M. Kh. Malikova, R. K. Rakhmanberdyeva
{"title":"Pectinic Substances from Scutellaria adenostegia and S. comosa and their Antimicrobial Activity","authors":"A. A. Siddikova,&nbsp;M. Kh. Malikova,&nbsp;R. K. Rakhmanberdyeva","doi":"10.1007/s10600-025-04589-3","DOIUrl":"10.1007/s10600-025-04589-3","url":null,"abstract":"","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 1","pages":"131 - 133"},"PeriodicalIF":0.8,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143475155","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 Cytotoxicity of Optically Pure Ester [1+2]-Conjugate of Castor Oil and Sebacic Acid
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-02-04 DOI: 10.1007/s10600-025-04590-w
M. P. Yakovleva, K. M. Saitov, I. S. Nazarov, A. A. Kravchenko, A. A. Kovalenko, D. V. Ishmetova, V. A. Vakhitov, G. Yu. Ishmuratov
{"title":"Synthesis and Cytotoxicity of Optically Pure Ester [1+2]-Conjugate of Castor Oil and Sebacic Acid","authors":"M. P. Yakovleva,&nbsp;K. M. Saitov,&nbsp;I. S. Nazarov,&nbsp;A. A. Kravchenko,&nbsp;A. A. Kovalenko,&nbsp;D. V. Ishmetova,&nbsp;V. A. Vakhitov,&nbsp;G. Yu. Ishmuratov","doi":"10.1007/s10600-025-04590-w","DOIUrl":"10.1007/s10600-025-04590-w","url":null,"abstract":"","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 1","pages":"134 - 137"},"PeriodicalIF":0.8,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143475131","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, Complexation with Pd(II), and Cytotoxicity of Pyridin-3-Ylmethylylidene Derivatives of Methyl Betulonate
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-02-04 DOI: 10.1007/s10600-025-04584-8
M. S. Denisov, A. O. Voronina, O. A. Maiorova
{"title":"Synthesis, Complexation with Pd(II), and Cytotoxicity of Pyridin-3-Ylmethylylidene Derivatives of Methyl Betulonate","authors":"M. S. Denisov,&nbsp;A. O. Voronina,&nbsp;O. A. Maiorova","doi":"10.1007/s10600-025-04584-8","DOIUrl":"10.1007/s10600-025-04584-8","url":null,"abstract":"<p>Pyridin-3-ylmethylylidene derivatives of methyl betulonate were synthesized. Six new Pd(II) complexes of them were obtained. The effects of these compounds on A549 (non-small-cell lung carcinoma) and HCT116 cell lines (colon cancer) were assessed by the MTT assay. 3-{(<i>E</i>)-[28-Methoxy-3,28-dioxolup-20(29)-en-2-ylidene]methyl}-1-methylpyridinium tetrafluoroborate exhibited potent cytotoxic activity on HCT116 cell line (IC<sub>50</sub> = 7.21 μM).</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 1","pages":"104 - 110"},"PeriodicalIF":0.8,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143475148","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 Ester from the Male Flowers of Carica papaya
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-02-04 DOI: 10.1007/s10600-025-04564-y
Do Thi Thuy Van, Giang Thi Kim Lien
{"title":"A New Ester from the Male Flowers of Carica papaya","authors":"Do Thi Thuy Van,&nbsp;Giang Thi Kim Lien","doi":"10.1007/s10600-025-04564-y","DOIUrl":"10.1007/s10600-025-04564-y","url":null,"abstract":"<p>A new ester compound, ethyl-(9<i>E</i>)-8,11,12-trihydroxyoctadecenoat (<b>1</b>), and five known compounds comprising a mixture of 3-hydroxy-3-methyl-5-hexanolide (<b>2A</b>) and leucine (<b>2B</b>), indole-3-aldehyde (<b>3</b>), 3<i>β</i>,7<i>α</i>-dihydroxy-6-cholest-5-ene (<b>4</b>), cholest-5-ene-3<i>β</i>,7<i>β</i>-diol (<b>5</b>), and saringosterol (<b>6</b>) were isolated from the dichloromethane extract of male <i>Carica papaya</i> flowers. Their structures were determined by NMR, MS spectra and comparison with the reported data.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 1","pages":"8 - 10"},"PeriodicalIF":0.8,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143475149","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
Polysaccharides from Scutellaria. I. Structure of Glucoarabinogalactan from S. adenostegia
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-02-03 DOI: 10.1007/s10600-025-04562-0
A. A. Siddikova, R. K. Rakhmanberdyeva, M. Kh. Malikova
{"title":"Polysaccharides from Scutellaria. I. Structure of Glucoarabinogalactan from S. adenostegia","authors":"A. A. Siddikova,&nbsp;R. K. Rakhmanberdyeva,&nbsp;M. Kh. Malikova","doi":"10.1007/s10600-025-04562-0","DOIUrl":"10.1007/s10600-025-04562-0","url":null,"abstract":"<p>A water-soluble polysaccharide based on glucoarabinogalactan GAG-Sa was isolated from the aerial part of <i>Scutellaria adenostegia</i>. The monosaccharide composition of the glucoarabinogalactan included arabinose, glucose, and galactose in a 1.0:10.9:7.6 mole ratio. GAG-Sa was characterized as a branched polysaccharide with a main chain of <i>β</i>-1,6-bound <i>β</i>-D-galactopyranose residues. The side chains of GAG-Sa consisted of 1,3-bound <i>β</i>-D-galactopyranose, α-D-glucopyranose, and <i>α</i>-L-arabinofuranose residues. The aqueous extract of the aerial part of <i>S</i>. <i>adenostegia</i> was shown to have anti-inflammatory activity.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 1","pages":"1 - 4"},"PeriodicalIF":0.8,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143475128","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, Anticancer Evaluation and Structure–Activity Relationship of Taiwanin a Derivatives
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-02-03 DOI: 10.1007/s10600-025-04565-x
Chi-I Chang, Ching-Chuan Kuo, Yung-Shung Wein, Che-Yi Chao, Yu-Chang Chen, Jang-Yang Chang, Yueh-Hsiung Kuo
{"title":"Synthesis, Anticancer Evaluation and Structure–Activity Relationship of Taiwanin a Derivatives","authors":"Chi-I Chang,&nbsp;Ching-Chuan Kuo,&nbsp;Yung-Shung Wein,&nbsp;Che-Yi Chao,&nbsp;Yu-Chang Chen,&nbsp;Jang-Yang Chang,&nbsp;Yueh-Hsiung Kuo","doi":"10.1007/s10600-025-04565-x","DOIUrl":"10.1007/s10600-025-04565-x","url":null,"abstract":"<p>Taiwanin A, a natural naphthalide lignan isolated from the heartwoods of <i>Taiwania cryptomerioides</i> Hayata, has previously been reported to have cytotoxicity against human tumor cells. In this study, a series of taiwanin A derivatives were synthesized and evaluated for their structure–activity relationship. Among the eleven taiwanin A derivatives, four compounds showed higher in vitro cytotoxic activity than taiwanin A. The biological evaluation of the synthesized compounds illustrated that the introduction of an electron-donating group in aryl ring A contributed to the antiproliferative potency, while in aryl ring B, it attenuated the cytotoxic activity. Compound <b>20</b> demonstrated excellent anticancer activity with an IC<sub>50</sub> value of 0.5 μM against HONE-1 human carcinoma cell lines, indicating that it could be a promising lead compound for further drug development studies.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 1","pages":"11 - 18"},"PeriodicalIF":0.8,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143475127","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 Terpenoid from the Leaves of Aphanamixis polystachya
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-02-03 DOI: 10.1007/s10600-025-04566-w
Jian Su, He Mi, Xin-Yue Zhang, Yu-Qing Xie, Yan Fu, Zhi-Yu Ni, Yi-Bing Wu
{"title":"A New Terpenoid from the Leaves of Aphanamixis polystachya","authors":"Jian Su,&nbsp;He Mi,&nbsp;Xin-Yue Zhang,&nbsp;Yu-Qing Xie,&nbsp;Yan Fu,&nbsp;Zhi-Yu Ni,&nbsp;Yi-Bing Wu","doi":"10.1007/s10600-025-04566-w","DOIUrl":"10.1007/s10600-025-04566-w","url":null,"abstract":"<p>A new terpenoid, nornemoralisin D was isolated from the leaves of <i>Aphanamixis polystachya</i>. The structure of the isolated compound was elucidated by various spectroscopic methods, including 1D and 2D NMR experiments.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 1","pages":"19 - 21"},"PeriodicalIF":0.8,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143475119","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
Hepatoprotective Flavonolignan from Citrus medica var. sarcodactylis
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2025-02-03 DOI: 10.1007/s10600-025-04570-0
Qinge Ma, Jiazeng Guo, Wenmin Liu, Rongrui Wei
{"title":"Hepatoprotective Flavonolignan from Citrus medica var. sarcodactylis","authors":"Qinge Ma,&nbsp;Jiazeng Guo,&nbsp;Wenmin Liu,&nbsp;Rongrui Wei","doi":"10.1007/s10600-025-04570-0","DOIUrl":"10.1007/s10600-025-04570-0","url":null,"abstract":"<p>A novel flavonolignan, named 3-hydroxy-7-O-<i>β</i>-D-glucopyranosyl-7′′-(4′′-methoxyphenyl)-8′′-(9′′-ethyl acetate)-flavonolignan (<b>1</b>), along with eight known flavonolignan derivatives (<b>2</b>–<b>9</b>) were isolated from <i>Citrus medica</i> var. sarcodactylis (Siebold ex Hoola van Nooten) Swingle for the first time. These compounds (<b>1</b>–<b>9</b>) were determined by extensive and comprehensive IR, UV, NMR, MS spectral analyses and compared with the reported references. Compounds <b>1</b>–<b>9</b> were evaluated for their inhibitory effects against the increases in AST and ALT levels on H<sub>2</sub>O<sub>2</sub>-induced HepG2 cells. As a result, compounds <b>1</b> and <b>2</b> displayed moderate hepatoprotective activities.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 1","pages":"37 - 41"},"PeriodicalIF":0.8,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143475129","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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