Chung-Wei Fu , Atallah F. Ahmed , Lin Chiang , Shu-Fen Chiou , Hui-Chun Wang , Jyh-Horng Sheu
{"title":"一种新的天然溴吡咯生物碱agenakasine、一种生物合成相关代谢物laughine和从中村海苔中分离出的去虫anemonin","authors":"Chung-Wei Fu , Atallah F. Ahmed , Lin Chiang , Shu-Fen Chiou , Hui-Chun Wang , Jyh-Horng Sheu","doi":"10.1016/j.phytol.2025.102975","DOIUrl":null,"url":null,"abstract":"<div><div>Chemical investigation of the secondary metabolites of a Formosan sponge, <em>Agelas nakamurai</em>, has led to the isolation of one undescribed natural bromopyrrole alkaloidal ester, agenakasine (<strong>1</strong>), along with known alkaloids, laughine (<strong>2</strong>) and norzooanemonin (<strong>3</strong>). The structures of these compounds were determined by detailed spectroscopic analysis, including 2D NMR spectroscopy, and literature data comparison. Compound <strong>3</strong> was crystallized as a TFA salt, with the structure confirmed by single-crystal X-ray diffraction analysis. Laughine and norzooanemonin were isolated for the first time from <em>Agelas</em> genus. The biosynthesis pathway of agenakasine and laughine was proposed in this study. Agenakasine demonstrated effective inhibitory activity against <em>Klebsiella pneumoniae</em>.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102975"},"PeriodicalIF":1.3000,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Isolation of a new natural bromopyrrole alkaloid agenakasine, a biosynthetically related metabolite laughine, and norzooanemonin from a marine sponge Agelas nakamurai\",\"authors\":\"Chung-Wei Fu , Atallah F. Ahmed , Lin Chiang , Shu-Fen Chiou , Hui-Chun Wang , Jyh-Horng Sheu\",\"doi\":\"10.1016/j.phytol.2025.102975\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Chemical investigation of the secondary metabolites of a Formosan sponge, <em>Agelas nakamurai</em>, has led to the isolation of one undescribed natural bromopyrrole alkaloidal ester, agenakasine (<strong>1</strong>), along with known alkaloids, laughine (<strong>2</strong>) and norzooanemonin (<strong>3</strong>). The structures of these compounds were determined by detailed spectroscopic analysis, including 2D NMR spectroscopy, and literature data comparison. Compound <strong>3</strong> was crystallized as a TFA salt, with the structure confirmed by single-crystal X-ray diffraction analysis. Laughine and norzooanemonin were isolated for the first time from <em>Agelas</em> genus. The biosynthesis pathway of agenakasine and laughine was proposed in this study. Agenakasine demonstrated effective inhibitory activity against <em>Klebsiella pneumoniae</em>.</div></div>\",\"PeriodicalId\":20408,\"journal\":{\"name\":\"Phytochemistry Letters\",\"volume\":\"68 \",\"pages\":\"Article 102975\"},\"PeriodicalIF\":1.3000,\"publicationDate\":\"2025-05-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phytochemistry Letters\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S187439002501064X\",\"RegionNum\":4,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry Letters","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S187439002501064X","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Isolation of a new natural bromopyrrole alkaloid agenakasine, a biosynthetically related metabolite laughine, and norzooanemonin from a marine sponge Agelas nakamurai
Chemical investigation of the secondary metabolites of a Formosan sponge, Agelas nakamurai, has led to the isolation of one undescribed natural bromopyrrole alkaloidal ester, agenakasine (1), along with known alkaloids, laughine (2) and norzooanemonin (3). The structures of these compounds were determined by detailed spectroscopic analysis, including 2D NMR spectroscopy, and literature data comparison. Compound 3 was crystallized as a TFA salt, with the structure confirmed by single-crystal X-ray diffraction analysis. Laughine and norzooanemonin were isolated for the first time from Agelas genus. The biosynthesis pathway of agenakasine and laughine was proposed in this study. Agenakasine demonstrated effective inhibitory activity against Klebsiella pneumoniae.
期刊介绍:
Phytochemistry Letters invites rapid communications on all aspects of natural product research including:
• Structural elucidation of natural products
• Analytical evaluation of herbal medicines
• Clinical efficacy, safety and pharmacovigilance of herbal medicines
• Natural product biosynthesis
• Natural product synthesis and chemical modification
• Natural product metabolism
• Chemical ecology
• Biotechnology
• Bioassay-guided isolation
• Pharmacognosy
• Pharmacology of natural products
• Metabolomics
• Ethnobotany and traditional usage
• Genetics of natural products
Manuscripts that detail the isolation of just one new compound are not substantial enough to be sent out of review and are out of scope. Furthermore, where pharmacology has been performed on one new compound to increase the amount of novel data, the pharmacology must be substantial and/or related to the medicinal use of the producing organism.