Yi Chen , Xu-Lan Bai , Ting-Ting Du , Hong-Tao Xu , Yong-Li Wang , Le-Yi Huang , Xu-Dong Mao , Gui-Xin Chou
{"title":"从 Schnabelia terniflora 中提取的新-5,10-seco-clerodane 二萜。","authors":"Yi Chen , Xu-Lan Bai , Ting-Ting Du , Hong-Tao Xu , Yong-Li Wang , Le-Yi Huang , Xu-Dong Mao , Gui-Xin Chou","doi":"10.1016/j.fitote.2024.106190","DOIUrl":null,"url":null,"abstract":"<div><p>Three new <em>neo</em>-5,10-<em>seco</em>-clerodane diterpenoids (<strong>1</strong>–<strong>3</strong>), four previously undescribed ethoxy/methoxy acetal analogues (<strong>4</strong>–<strong>7</strong>), one new etherified labdane diterpenoid (<strong>8</strong>), and seven known diterpenoids (<strong>9</strong>–<strong>15</strong>) were isolated from the whole plant of <em>Schnabelia terniflora</em>. Their structures were established on the basis of extensive spectroscopic analysis, single-crystal X-ray diffraction data, calculated electronic circular dichroism (ECD), and Mo<sub>2</sub>(OAc)<sub>4</sub>-induced circular dichroism. Compounds <strong>2</strong> and <strong>3</strong> represent the first examples of <em>neo</em>-5,10-<em>seco</em>-clerodane diterpenoids containing a 1<em>H</em>-pyrrole-2,5-dione and a pyrrolidine-2,5-dione moiety, respectively. A plausible biosynthetic pathway for <strong>1</strong>–<strong>3</strong> is proposed. All diterpenoids were evaluated for their cytotoxic activity against non-small-cell lung cancer lines (A549 and H460) and gastric cancer lines (HGC27 and AGS). Among them, <strong>2</strong> and <strong>14</strong> showed moderate cytotoxicity against four cell lines.</p></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"178 ","pages":"Article 106190"},"PeriodicalIF":2.5000,"publicationDate":"2024-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Neo-5,10-seco-clerodane diterpenoids from Schnabelia terniflora\",\"authors\":\"Yi Chen , Xu-Lan Bai , Ting-Ting Du , Hong-Tao Xu , Yong-Li Wang , Le-Yi Huang , Xu-Dong Mao , Gui-Xin Chou\",\"doi\":\"10.1016/j.fitote.2024.106190\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Three new <em>neo</em>-5,10-<em>seco</em>-clerodane diterpenoids (<strong>1</strong>–<strong>3</strong>), four previously undescribed ethoxy/methoxy acetal analogues (<strong>4</strong>–<strong>7</strong>), one new etherified labdane diterpenoid (<strong>8</strong>), and seven known diterpenoids (<strong>9</strong>–<strong>15</strong>) were isolated from the whole plant of <em>Schnabelia terniflora</em>. Their structures were established on the basis of extensive spectroscopic analysis, single-crystal X-ray diffraction data, calculated electronic circular dichroism (ECD), and Mo<sub>2</sub>(OAc)<sub>4</sub>-induced circular dichroism. Compounds <strong>2</strong> and <strong>3</strong> represent the first examples of <em>neo</em>-5,10-<em>seco</em>-clerodane diterpenoids containing a 1<em>H</em>-pyrrole-2,5-dione and a pyrrolidine-2,5-dione moiety, respectively. A plausible biosynthetic pathway for <strong>1</strong>–<strong>3</strong> is proposed. All diterpenoids were evaluated for their cytotoxic activity against non-small-cell lung cancer lines (A549 and H460) and gastric cancer lines (HGC27 and AGS). Among them, <strong>2</strong> and <strong>14</strong> showed moderate cytotoxicity against four cell lines.</p></div>\",\"PeriodicalId\":12147,\"journal\":{\"name\":\"Fitoterapia\",\"volume\":\"178 \",\"pages\":\"Article 106190\"},\"PeriodicalIF\":2.5000,\"publicationDate\":\"2024-08-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Fitoterapia\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0367326X24003733\",\"RegionNum\":3,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Fitoterapia","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0367326X24003733","RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Neo-5,10-seco-clerodane diterpenoids from Schnabelia terniflora
Three new neo-5,10-seco-clerodane diterpenoids (1–3), four previously undescribed ethoxy/methoxy acetal analogues (4–7), one new etherified labdane diterpenoid (8), and seven known diterpenoids (9–15) were isolated from the whole plant of Schnabelia terniflora. Their structures were established on the basis of extensive spectroscopic analysis, single-crystal X-ray diffraction data, calculated electronic circular dichroism (ECD), and Mo2(OAc)4-induced circular dichroism. Compounds 2 and 3 represent the first examples of neo-5,10-seco-clerodane diterpenoids containing a 1H-pyrrole-2,5-dione and a pyrrolidine-2,5-dione moiety, respectively. A plausible biosynthetic pathway for 1–3 is proposed. All diterpenoids were evaluated for their cytotoxic activity against non-small-cell lung cancer lines (A549 and H460) and gastric cancer lines (HGC27 and AGS). Among them, 2 and 14 showed moderate cytotoxicity against four cell lines.
期刊介绍:
Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas:
1. Characterization of active ingredients of medicinal plants
2. Development of standardization method for bioactive plant extracts and natural products
3. Identification of bioactivity in plant extracts
4. Identification of targets and mechanism of activity of plant extracts
5. Production and genomic characterization of medicinal plants biomass
6. Chemistry and biochemistry of bioactive natural products of plant origin
7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.