{"title":"从意大利黄刺玫果实中提取的具有细胞毒性的黄烷内酯倍半萜。","authors":"Yu-Tong Li, Cheng-Yong Tan, Jiang Fu, Hai-Qiang Wang, Yun-Bao Liu, Shuang-Gang Ma, Yong Li, Jing Qu, Shi-Shan Yu","doi":"10.1016/j.phytochem.2024.114196","DOIUrl":null,"url":null,"abstract":"<div><p>One previously undescribed xanthanolide sesquiterpene dimer pungiolide P (<strong>1</strong>), possessing an unprecedented scaffold with a 5/7/5/7/5 ring system skeleton and its intermediate pungiolide Q (<strong>2</strong>), ten xanthanolide sesquiterpenes (<strong>3</strong>–<strong>12</strong>), two eudesmene sesquiterpene derivatives (<strong>13</strong>–<strong>14</strong>), one phenylpropionic acid derivative (<strong>15</strong>), together with eleven known compounds (<strong>16</strong>–<strong>26</strong>) were obtained from the fruits of <em>Xanthium italicum</em> Moretti. A possible biosynthetic pathway for pungiolide P (<strong>1</strong>) was also proposed, which was supported by its bio-synthetic intermediate (<strong>2</strong>). Compounds <strong>1</strong>, <strong>4</strong>–<strong>5</strong>, <strong>18</strong>–<strong>21</strong>, and <strong>25</strong> exhibited cytotoxic activity against a variety of human cancer cell lines. Furthermore, compounds <strong>1</strong>, <strong>4</strong>–<strong>5</strong>, could cause blockage of the cell cycle in the G2/M phase and induce apoptosis in H460 cells. Notably, pungiolide P (<strong>1</strong>) exhibited significantly superior cytotoxicity compared to previously reported compounds, providing valuable insights for natural anti-tumor sources.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Cytotoxic xanthanolide sesquiterpenes from the fruits of Xanthium italicum Moretti\",\"authors\":\"Yu-Tong Li, Cheng-Yong Tan, Jiang Fu, Hai-Qiang Wang, Yun-Bao Liu, Shuang-Gang Ma, Yong Li, Jing Qu, Shi-Shan Yu\",\"doi\":\"10.1016/j.phytochem.2024.114196\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>One previously undescribed xanthanolide sesquiterpene dimer pungiolide P (<strong>1</strong>), possessing an unprecedented scaffold with a 5/7/5/7/5 ring system skeleton and its intermediate pungiolide Q (<strong>2</strong>), ten xanthanolide sesquiterpenes (<strong>3</strong>–<strong>12</strong>), two eudesmene sesquiterpene derivatives (<strong>13</strong>–<strong>14</strong>), one phenylpropionic acid derivative (<strong>15</strong>), together with eleven known compounds (<strong>16</strong>–<strong>26</strong>) were obtained from the fruits of <em>Xanthium italicum</em> Moretti. A possible biosynthetic pathway for pungiolide P (<strong>1</strong>) was also proposed, which was supported by its bio-synthetic intermediate (<strong>2</strong>). Compounds <strong>1</strong>, <strong>4</strong>–<strong>5</strong>, <strong>18</strong>–<strong>21</strong>, and <strong>25</strong> exhibited cytotoxic activity against a variety of human cancer cell lines. Furthermore, compounds <strong>1</strong>, <strong>4</strong>–<strong>5</strong>, could cause blockage of the cell cycle in the G2/M phase and induce apoptosis in H460 cells. Notably, pungiolide P (<strong>1</strong>) exhibited significantly superior cytotoxicity compared to previously reported compounds, providing valuable insights for natural anti-tumor sources.</p></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-06-25\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phytochemistry\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0031942224002334\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942224002334","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Cytotoxic xanthanolide sesquiterpenes from the fruits of Xanthium italicum Moretti
One previously undescribed xanthanolide sesquiterpene dimer pungiolide P (1), possessing an unprecedented scaffold with a 5/7/5/7/5 ring system skeleton and its intermediate pungiolide Q (2), ten xanthanolide sesquiterpenes (3–12), two eudesmene sesquiterpene derivatives (13–14), one phenylpropionic acid derivative (15), together with eleven known compounds (16–26) were obtained from the fruits of Xanthium italicum Moretti. A possible biosynthetic pathway for pungiolide P (1) was also proposed, which was supported by its bio-synthetic intermediate (2). Compounds 1, 4–5, 18–21, and 25 exhibited cytotoxic activity against a variety of human cancer cell lines. Furthermore, compounds 1, 4–5, could cause blockage of the cell cycle in the G2/M phase and induce apoptosis in H460 cells. Notably, pungiolide P (1) exhibited significantly superior cytotoxicity compared to previously reported compounds, providing valuable insights for natural anti-tumor sources.
期刊介绍:
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.