{"title":"Discovery of Anti-Inflammatory Alkaloids from Sponge <i>Stylissa massa</i> Suggests New Biosynthetic Pathways for Pyrrole-Imidazole Alkaloids.","authors":"Xiaojing Liu, Qi Wang, Yun Zhang, Hanting Zhang","doi":"10.3390/md22100477","DOIUrl":null,"url":null,"abstract":"<p><p>Pyrrole-imidazole alkaloids (PIAs) are a class of marine sponge derived natural products which have complex carbon frameworks and broad bioactivities. In this study, four new alkaloids, stylimassalins A-B (<b>1</b>-<b>2</b>), <b>3</b>, and <b>5</b>, together with two known compounds (<b>4</b> and <b>6</b>), were isolated from <i>Stylissa massa</i>. Compounds <b>2</b>, <b>4</b>, and <b>6</b> are the C-2 brominated analogues of <b>1</b>, <b>3</b>, and <b>5</b>, respectively. Their structures display three different scaffolds, of which scaffold 1 (compounds <b>1</b>,<b>2</b>) is new. A new biosynthetic pathway from oroidin, through spongiacidin, to latonduine and scaffold 1 was proposed by our group, in which the C12-N13-cleavaged compounds of spongiacidin (scaffold 2), dubbed seco-spongiacidins (<b>3</b> and <b>4</b>), are recognized as a key bridged scaffold, to afford PIA analogues (<b>1</b>,<b>2</b> and <b>5</b>,<b>6</b>). An anti-inflammatory evaluation in a zebrafish inflammation model induced by copper sulphate (CuSO<sub>4</sub>) demonstrated that stylimassalins A and B (<b>1</b> and <b>2</b>) could serve as a promising lead scaffold for treating inflammation.</p>","PeriodicalId":18222,"journal":{"name":"Marine Drugs","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11509139/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Marine Drugs","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.3390/md22100477","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0
Abstract
Pyrrole-imidazole alkaloids (PIAs) are a class of marine sponge derived natural products which have complex carbon frameworks and broad bioactivities. In this study, four new alkaloids, stylimassalins A-B (1-2), 3, and 5, together with two known compounds (4 and 6), were isolated from Stylissa massa. Compounds 2, 4, and 6 are the C-2 brominated analogues of 1, 3, and 5, respectively. Their structures display three different scaffolds, of which scaffold 1 (compounds 1,2) is new. A new biosynthetic pathway from oroidin, through spongiacidin, to latonduine and scaffold 1 was proposed by our group, in which the C12-N13-cleavaged compounds of spongiacidin (scaffold 2), dubbed seco-spongiacidins (3 and 4), are recognized as a key bridged scaffold, to afford PIA analogues (1,2 and 5,6). An anti-inflammatory evaluation in a zebrafish inflammation model induced by copper sulphate (CuSO4) demonstrated that stylimassalins A and B (1 and 2) could serve as a promising lead scaffold for treating inflammation.
期刊介绍:
Marine Drugs (ISSN 1660-3397) publishes reviews, regular research papers and short notes on the research, development and production of drugs from the sea. Our aim is to encourage scientists to publish their experimental and theoretical research in as much detail as possible, particularly synthetic procedures and characterization information for bioactive compounds. There is no restriction on the length of the experimental section.