{"title":"(±)-Salvicatone A: A Pair of C<sub>27</sub>-Meroterpenoid Enantiomers with Skeletons from the Roots and Rhizomes of <i>Salvia castanea</i> Diels f. <i>tomentosa</i> Stib.","authors":"Dong-Dong Wang, Rui Zhang, Lian-Yu Tang, Guo-Qing Long, Hui Yan, Yong-Cheng Yang, Zi-Feng Guo, Ying-Ying Zheng, Yong Wang, Jing-Ming Jia, An-Hua Wang","doi":"10.1021/acs.joc.3c01664","DOIUrl":null,"url":null,"abstract":"<p><p>(±)-Salvicatone A (<b>1</b>), a C<sub>27</sub>-meroterpenoid featuring a unique 6/6/6/6/6-pentacyclic carbon skeleton with a 7,8,8a,9,10,10a-hexahydropyren-1 (<i>6H</i>)-one motif, was isolated from the roots and rhizomes of <i>Salvia castanea</i> Diels <i>f. tomentosa</i> Stib. Its structure was characterized by comprehensive spectroscopic analyses along with computer-assisted structure elucidation, including ACD/structure elucidator and quantum chemical calculations with <sup>1</sup>H/<sup>13</sup>C NMR and electronic circular dichroism. Biogenetically, compound <b>1</b> was constructed from decarboxylation following [4 + 2] Diels-Alder cycloaddition reaction between caffeic acid and miltirone analogue. Bioassays showed that (-)-<b>1</b> and (+)-<b>1</b> inhibited nitric oxide production in lipopolysaccharide-induced RAW264.7 macrophage cells with an IC<sub>50</sub> value of 6.48 ± 1.25 and 15.76 ± 5.55 μM, respectively. The structure-based virtual screening based on the pharmacophores in ePharmaLib, as well as the molecular docking and molecular dynamics simulations study, implied that (-)-<b>1</b> and (+)-<b>1</b> may potentially bind to retinoic acid receptor-related orphan receptor C to exert anti-inflammatory activities.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.3c01664","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2023/11/17 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
(±)-Salvicatone A (1), a C27-meroterpenoid featuring a unique 6/6/6/6/6-pentacyclic carbon skeleton with a 7,8,8a,9,10,10a-hexahydropyren-1 (6H)-one motif, was isolated from the roots and rhizomes of Salvia castanea Diels f. tomentosa Stib. Its structure was characterized by comprehensive spectroscopic analyses along with computer-assisted structure elucidation, including ACD/structure elucidator and quantum chemical calculations with 1H/13C NMR and electronic circular dichroism. Biogenetically, compound 1 was constructed from decarboxylation following [4 + 2] Diels-Alder cycloaddition reaction between caffeic acid and miltirone analogue. Bioassays showed that (-)-1 and (+)-1 inhibited nitric oxide production in lipopolysaccharide-induced RAW264.7 macrophage cells with an IC50 value of 6.48 ± 1.25 and 15.76 ± 5.55 μM, respectively. The structure-based virtual screening based on the pharmacophores in ePharmaLib, as well as the molecular docking and molecular dynamics simulations study, implied that (-)-1 and (+)-1 may potentially bind to retinoic acid receptor-related orphan receptor C to exert anti-inflammatory activities.
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.