{"title":"从内生真菌 Pseudoplectania sp. EL000327 中分离出的三种新的二萜类化合物，plectalibertellenones A-C","authors":"","doi":"10.1016/j.tetlet.2024.155227","DOIUrl":null,"url":null,"abstract":"<div><p>Three new pimarane diterpenoids, plectalibertellenones A−C (<strong>1–3</strong>), along with six known compounds, 9α-hydroxy-1,8(14),15-isopimaratrien-3,7,11-trione (<strong>4</strong>), 9α-hydroxy-1,8(14),15-isopimaratrien-3,11-dione (<strong>5</strong>), phomenone B (<strong>6</strong>), (−)-pestalotin (<strong>7</strong>), (+)-pestalotin (<strong>8</strong>), and 6-pentyl-4-methoxy-pyran-2-one (<strong>9</strong>) were isolated from the crude extract of an endolichenic fungus, <em>Pseudoplectania</em> sp. EL000327. The planar structures of metabolites <strong>1–3</strong> were elucidated using UV, mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopic data. The relative and absolute configurations of <strong>1–3</strong> were deduced from an interpretation of circular dichroism (CD) spectroscopic data, application of an advanced Mosher’s method, DP4<sup>+</sup> calculations, and combination of NMR spectroscopic methods. Compounds <strong>1–9</strong> did not display any significant anti-bacterial activity; however, compounds <strong>1–4</strong> were cytotoxic to Caco2 cells, with IC<sub>50</sub> values 54.8, 80.7, 76.4, and 19.6 µM, respectively.</p></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Three new diterpenoids, plectalibertellenones A–C, isolated from endolichenic fungi Pseudoplectania sp. EL000327\",\"authors\":\"\",\"doi\":\"10.1016/j.tetlet.2024.155227\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Three new pimarane diterpenoids, plectalibertellenones A−C (<strong>1–3</strong>), along with six known compounds, 9α-hydroxy-1,8(14),15-isopimaratrien-3,7,11-trione (<strong>4</strong>), 9α-hydroxy-1,8(14),15-isopimaratrien-3,11-dione (<strong>5</strong>), phomenone B (<strong>6</strong>), (−)-pestalotin (<strong>7</strong>), (+)-pestalotin (<strong>8</strong>), and 6-pentyl-4-methoxy-pyran-2-one (<strong>9</strong>) were isolated from the crude extract of an endolichenic fungus, <em>Pseudoplectania</em> sp. EL000327. The planar structures of metabolites <strong>1–3</strong> were elucidated using UV, mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopic data. The relative and absolute configurations of <strong>1–3</strong> were deduced from an interpretation of circular dichroism (CD) spectroscopic data, application of an advanced Mosher’s method, DP4<sup>+</sup> calculations, and combination of NMR spectroscopic methods. Compounds <strong>1–9</strong> did not display any significant anti-bacterial activity; however, compounds <strong>1–4</strong> were cytotoxic to Caco2 cells, with IC<sub>50</sub> values 54.8, 80.7, 76.4, and 19.6 µM, respectively.</p></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-08-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403924003228\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924003228","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
三种新的皮马兰二萜--折衷贝特烯酮 A-C（）以及六种已知化合物--9α-羟基-1,8(14),15-异异戊二烯-3,7,11-三酮（）、9α-羟基-1,8(14)、15-isopimaratrien-3,11-dione (), phomenone B (), (-)-pestalotin (), (+)-pestalotin (), and 6-pentyl-4-methoxy-pyran-2-one () were isolated from the crude extract of an endolichenic fungus, sp.EL000327。利用紫外光谱、质谱（MS）和核磁共振（NMR）光谱数据阐明了代谢物的平面结构。通过解释圆二色性（CD）光谱数据、应用先进的 Mosher 方法、DP4 计算以及结合核磁共振光谱方法，推导出了代谢物的相对和绝对构型。化合物没有显示出明显的抗菌活性；但是，化合物对 Caco2 细胞具有细胞毒性，IC 值分别为 54.8、80.7、76.4 和 19.6 µM。
Three new diterpenoids, plectalibertellenones A–C, isolated from endolichenic fungi Pseudoplectania sp. EL000327
Three new pimarane diterpenoids, plectalibertellenones A−C (1–3), along with six known compounds, 9α-hydroxy-1,8(14),15-isopimaratrien-3,7,11-trione (4), 9α-hydroxy-1,8(14),15-isopimaratrien-3,11-dione (5), phomenone B (6), (−)-pestalotin (7), (+)-pestalotin (8), and 6-pentyl-4-methoxy-pyran-2-one (9) were isolated from the crude extract of an endolichenic fungus, Pseudoplectania sp. EL000327. The planar structures of metabolites 1–3 were elucidated using UV, mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopic data. The relative and absolute configurations of 1–3 were deduced from an interpretation of circular dichroism (CD) spectroscopic data, application of an advanced Mosher’s method, DP4+ calculations, and combination of NMR spectroscopic methods. Compounds 1–9 did not display any significant anti-bacterial activity; however, compounds 1–4 were cytotoxic to Caco2 cells, with IC50 values 54.8, 80.7, 76.4, and 19.6 µM, respectively.
期刊介绍：
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
