{"title":"六对具有细胞毒活性的淫羊藿烯酰化类黄酮对映体","authors":"Shuang-Shuang Xie, Xiang Yu, Qi-Mei Tie, Jing-Ke Zhang, Bei-Bei Zhang, Meng-Nan Zeng, Xiao-Ke Zheng, Wei-Sheng Feng","doi":"10.1007/s13659-025-00510-1","DOIUrl":null,"url":null,"abstract":"<div><p>In this work, six pairs of undescribed enantiomeric prenylated flavonoids, ( ±)-epimesatines J–O (<b>1a/1b–6a/6b</b>), were isolated from the aerial parts of <i>Epimedium sagittatum</i> Maxim. Their structures and absolute configurations were determined based on spectroscopic data, quantum chemical calculations of electronic circular dichroism (ECD) and <sup>13</sup>C NMR, as well as ECD experiments induced by Mo<sub>2</sub>(OAc)<sub>4</sub> and Rh<sub>2</sub>(OCOCF<sub>3</sub>)<sub>4</sub>. The cytotoxicity assay revealed that compounds<b> 1a/1b, 2a/2b</b>, and<b> 4a/4b–6a/6b</b> demonstrated significant inhibitory effects on the viability of human breast cancer cells MCF-7 while exhibiting no obvious toxicity towards human breast epithelial cells MCF-10A. Additionally, these compounds were found to decrease the expression of sphingosine kinase 1 (Sphk1) in MCF-7 cells. Notably, compounds<b> 4a</b> and<b> 5b</b> exhibited IC<sub>50</sub> values of 7.45 and 8.97 μM, respectively, in MCF-7 cells.</p><h3>Graphical Abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":718,"journal":{"name":"Natural Products and Bioprospecting","volume":"15 1","pages":""},"PeriodicalIF":4.8000,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s13659-025-00510-1.pdf","citationCount":"0","resultStr":"{\"title\":\"Six pairs of enantiomeric prenylated flavonoids with cytotoxic activities from Epimedium sagittatum Maxim\",\"authors\":\"Shuang-Shuang Xie, Xiang Yu, Qi-Mei Tie, Jing-Ke Zhang, Bei-Bei Zhang, Meng-Nan Zeng, Xiao-Ke Zheng, Wei-Sheng Feng\",\"doi\":\"10.1007/s13659-025-00510-1\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>In this work, six pairs of undescribed enantiomeric prenylated flavonoids, ( ±)-epimesatines J–O (<b>1a/1b–6a/6b</b>), were isolated from the aerial parts of <i>Epimedium sagittatum</i> Maxim. Their structures and absolute configurations were determined based on spectroscopic data, quantum chemical calculations of electronic circular dichroism (ECD) and <sup>13</sup>C NMR, as well as ECD experiments induced by Mo<sub>2</sub>(OAc)<sub>4</sub> and Rh<sub>2</sub>(OCOCF<sub>3</sub>)<sub>4</sub>. The cytotoxicity assay revealed that compounds<b> 1a/1b, 2a/2b</b>, and<b> 4a/4b–6a/6b</b> demonstrated significant inhibitory effects on the viability of human breast cancer cells MCF-7 while exhibiting no obvious toxicity towards human breast epithelial cells MCF-10A. Additionally, these compounds were found to decrease the expression of sphingosine kinase 1 (Sphk1) in MCF-7 cells. Notably, compounds<b> 4a</b> and<b> 5b</b> exhibited IC<sub>50</sub> values of 7.45 and 8.97 μM, respectively, in MCF-7 cells.</p><h3>Graphical Abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":718,\"journal\":{\"name\":\"Natural Products and Bioprospecting\",\"volume\":\"15 1\",\"pages\":\"\"},\"PeriodicalIF\":4.8000,\"publicationDate\":\"2025-05-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://link.springer.com/content/pdf/10.1007/s13659-025-00510-1.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Natural Products and Bioprospecting\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s13659-025-00510-1\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Natural Products and Bioprospecting","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s13659-025-00510-1","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Six pairs of enantiomeric prenylated flavonoids with cytotoxic activities from Epimedium sagittatum Maxim
In this work, six pairs of undescribed enantiomeric prenylated flavonoids, ( ±)-epimesatines J–O (1a/1b–6a/6b), were isolated from the aerial parts of Epimedium sagittatum Maxim. Their structures and absolute configurations were determined based on spectroscopic data, quantum chemical calculations of electronic circular dichroism (ECD) and 13C NMR, as well as ECD experiments induced by Mo2(OAc)4 and Rh2(OCOCF3)4. The cytotoxicity assay revealed that compounds 1a/1b, 2a/2b, and 4a/4b–6a/6b demonstrated significant inhibitory effects on the viability of human breast cancer cells MCF-7 while exhibiting no obvious toxicity towards human breast epithelial cells MCF-10A. Additionally, these compounds were found to decrease the expression of sphingosine kinase 1 (Sphk1) in MCF-7 cells. Notably, compounds 4a and 5b exhibited IC50 values of 7.45 and 8.97 μM, respectively, in MCF-7 cells.
期刊介绍：
Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects:
Natural products: isolation and structure elucidation
Natural products: synthesis
Biological evaluation of biologically active natural products
Bioorganic and medicinal chemistry
Biosynthesis and microbiological transformation
Fermentation and plant tissue cultures
Bioprospecting of natural products from natural resources
All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.
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