{"title":"NMR-Guided Isolation of Anti-inflammatory Carabranolides from the Fruits of <i>Carpesium abrotanoides</i> L.","authors":"Lu Fu, Can-Can Wang, Wenyue Tian, Zhiyan Liu, Meng-Yu Bao, Jiazheng Liu, Wei Zhang, Li-Ping Bai, Zhi-Hong Jiang, Guo-Yuan Zhu","doi":"10.1021/acs.jnatprod.4c00338","DOIUrl":null,"url":null,"abstract":"<p><p>Carabranolides present characteristic NMR resonances for the cyclopropane moiety, which distinctly differ from those of other compounds and were used for an NMR-guided isolation in this study. As a result, 11 undescribed carabranolides (<b>1</b>-<b>11</b>), along with five known ones (<b>12</b>-<b>16</b>), were isolated from the fruits of <i>Carpesium abrotanoides</i> L. Compounds <b>1</b>-<b>11</b> are new esters of carabrol at C-4 with different carboxylic acids. Their structures were elucidated by HRESIMS and NMR spectroscopic data analysis. The biological evaluation showed that compounds <b>2</b>-<b>4</b>, <b>15</b>, and <b>16</b> exhibited significant inhibitory activity against LPS-induced NO release with an IC<sub>50</sub> value of 5.6-9.1 μM and dose-dependently decreased iNOS protein expression in RAW264.7 cells.</p>","PeriodicalId":3,"journal":{"name":"ACS Applied Electronic Materials","volume":null,"pages":null},"PeriodicalIF":4.3000,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11287756/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Applied Electronic Materials","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1021/acs.jnatprod.4c00338","RegionNum":3,"RegionCategory":"材料科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/7/10 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"ENGINEERING, ELECTRICAL & ELECTRONIC","Score":null,"Total":0}
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Abstract
Carabranolides present characteristic NMR resonances for the cyclopropane moiety, which distinctly differ from those of other compounds and were used for an NMR-guided isolation in this study. As a result, 11 undescribed carabranolides (1-11), along with five known ones (12-16), were isolated from the fruits of Carpesium abrotanoides L. Compounds 1-11 are new esters of carabrol at C-4 with different carboxylic acids. Their structures were elucidated by HRESIMS and NMR spectroscopic data analysis. The biological evaluation showed that compounds 2-4, 15, and 16 exhibited significant inhibitory activity against LPS-induced NO release with an IC50 value of 5.6-9.1 μM and dose-dependently decreased iNOS protein expression in RAW264.7 cells.
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