{"title":"从 Siraitia grosvenorii 的根中提取的不同寻常的葫芦巴苷。","authors":"","doi":"10.1016/j.phytochem.2024.114230","DOIUrl":null,"url":null,"abstract":"<div><p><em>Siraitia grosvenorii</em> Swingle is one of the first approved medicine food homology species in China, and it has been used as a natural sweetener in the food industry and as a traditional medicine to relieve cough and reduce phlegm. However, many <em>S. grosvenorii</em> roots are discarded yearly, which results in a great waste of resources. Twelve undescribed norcucurbitacin-type triterpenoid glycosides, siraitiaosides A-L (<strong>1</strong>–<strong>12</strong>), and six known analogs (<strong>13</strong>–<strong>18</strong>) were isolated from the roots of <em>S. grosvenorii</em>. The structures of isolated norcucurbitacin glycosides were elucidated by comprehensive data analyses, including HRESIMS, UV, IR, NMR, ECD calculations, and X-ray crystallography analysis. Siraitiaosides A-E (<strong>1</strong>–<strong>5</strong>) featured an unusual 19,29-norcucurbitacin framework while siraitiaosides F-L (<strong>6</strong>–<strong>12</strong>) featured a rare 29-norcucurbitacin framework. Notably, compound <strong>4</strong> displayed moderate anti-acetylcholinesterase (AChE) activity with an IC<sub>50</sub> of 21.0 μM, meanwhile, compounds <strong>16</strong> and <strong>18</strong> exhibited pronounced cytotoxic activities against MCF-7, CNE-1, and HeLa cancer cell lines with IC<sub>50</sub> values of 2.1–15.2 μM. <em>In silico</em> studies showed that compound <strong>4</strong> bound closely to AChE with a binding energy of −5.04 kcal/mol, and compound <strong>18</strong> could tightly bind to PI3K, AKT1, ERK2, and MMP9 proteins that related to autophagy, apoptosis, migration/invasion, and growth/proliferation. In summary, the roots of <em>Siraitia grosvenorii</em> have potential medicinal values due to the multiple bioactive components.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Unusual norcucurbitacin glycosides from the roots of Siraitia grosvenorii\",\"authors\":\"\",\"doi\":\"10.1016/j.phytochem.2024.114230\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p><em>Siraitia grosvenorii</em> Swingle is one of the first approved medicine food homology species in China, and it has been used as a natural sweetener in the food industry and as a traditional medicine to relieve cough and reduce phlegm. However, many <em>S. grosvenorii</em> roots are discarded yearly, which results in a great waste of resources. Twelve undescribed norcucurbitacin-type triterpenoid glycosides, siraitiaosides A-L (<strong>1</strong>–<strong>12</strong>), and six known analogs (<strong>13</strong>–<strong>18</strong>) were isolated from the roots of <em>S. grosvenorii</em>. The structures of isolated norcucurbitacin glycosides were elucidated by comprehensive data analyses, including HRESIMS, UV, IR, NMR, ECD calculations, and X-ray crystallography analysis. Siraitiaosides A-E (<strong>1</strong>–<strong>5</strong>) featured an unusual 19,29-norcucurbitacin framework while siraitiaosides F-L (<strong>6</strong>–<strong>12</strong>) featured a rare 29-norcucurbitacin framework. Notably, compound <strong>4</strong> displayed moderate anti-acetylcholinesterase (AChE) activity with an IC<sub>50</sub> of 21.0 μM, meanwhile, compounds <strong>16</strong> and <strong>18</strong> exhibited pronounced cytotoxic activities against MCF-7, CNE-1, and HeLa cancer cell lines with IC<sub>50</sub> values of 2.1–15.2 μM. <em>In silico</em> studies showed that compound <strong>4</strong> bound closely to AChE with a binding energy of −5.04 kcal/mol, and compound <strong>18</strong> could tightly bind to PI3K, AKT1, ERK2, and MMP9 proteins that related to autophagy, apoptosis, migration/invasion, and growth/proliferation. In summary, the roots of <em>Siraitia grosvenorii</em> have potential medicinal values due to the multiple bioactive components.</p></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-08-03\",\"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/S003194222400267X\",\"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/S003194222400267X","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}
Unusual norcucurbitacin glycosides from the roots of Siraitia grosvenorii
Siraitia grosvenorii Swingle is one of the first approved medicine food homology species in China, and it has been used as a natural sweetener in the food industry and as a traditional medicine to relieve cough and reduce phlegm. However, many S. grosvenorii roots are discarded yearly, which results in a great waste of resources. Twelve undescribed norcucurbitacin-type triterpenoid glycosides, siraitiaosides A-L (1–12), and six known analogs (13–18) were isolated from the roots of S. grosvenorii. The structures of isolated norcucurbitacin glycosides were elucidated by comprehensive data analyses, including HRESIMS, UV, IR, NMR, ECD calculations, and X-ray crystallography analysis. Siraitiaosides A-E (1–5) featured an unusual 19,29-norcucurbitacin framework while siraitiaosides F-L (6–12) featured a rare 29-norcucurbitacin framework. Notably, compound 4 displayed moderate anti-acetylcholinesterase (AChE) activity with an IC50 of 21.0 μM, meanwhile, compounds 16 and 18 exhibited pronounced cytotoxic activities against MCF-7, CNE-1, and HeLa cancer cell lines with IC50 values of 2.1–15.2 μM. In silico studies showed that compound 4 bound closely to AChE with a binding energy of −5.04 kcal/mol, and compound 18 could tightly bind to PI3K, AKT1, ERK2, and MMP9 proteins that related to autophagy, apoptosis, migration/invasion, and growth/proliferation. In summary, the roots of Siraitia grosvenorii have potential medicinal values due to the multiple bioactive components.
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.