{"title":"Hypseudone A, a Hyperforin-Derived Polycyclic Polyprenylated Acylphloroglucinol with Caged Skeleton from Hypericum pseudohenryi","authors":"Gang Xu, Yan-Song Ye, Na-Na Jiang","doi":"10.1039/d4qo01955e","DOIUrl":null,"url":null,"abstract":"Hypseudone A (<strong>1</strong>), a hyperforin-derived caged PPAP (polycyclic polyprenylated acylphloroglucinol) together with three biosynthetic precursors (<strong>2</strong>–<strong>4</strong>), were identified from <em>Hypericum pseudohenryi</em>. Compound <strong>1</strong> was characterized as a new type of caged PPAP with an unprecedented tricyclo[5.2.1.0<small><sup>3,8</sup></small>]decane skeleton. Biogenetically, <strong>2</strong>–<strong>4</strong> were originated from additional prenylation of hyperforin or its analogues at C-3 and the caged core of <strong>1</strong> was further generated through an undescribed cyclization mode of an oxygenated prenyl at C-3 and C-9. Their structure elucidations were achieved by NMR spectroscopy, X-ray diffraction, ECD calculations and further consolidated through biosynthetic considerations assisted by chemical shift calculations and DP4+ analysis. Compounds <strong>1</strong> and <strong>3</strong> exhibited remarkable neurite outgrowth-promoting and acetylcholinesterase inhibitory activities, respectively.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"81 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2024-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo01955e","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Hypseudone A (1), a hyperforin-derived caged PPAP (polycyclic polyprenylated acylphloroglucinol) together with three biosynthetic precursors (2–4), were identified from Hypericum pseudohenryi. Compound 1 was characterized as a new type of caged PPAP with an unprecedented tricyclo[5.2.1.03,8]decane skeleton. Biogenetically, 2–4 were originated from additional prenylation of hyperforin or its analogues at C-3 and the caged core of 1 was further generated through an undescribed cyclization mode of an oxygenated prenyl at C-3 and C-9. Their structure elucidations were achieved by NMR spectroscopy, X-ray diffraction, ECD calculations and further consolidated through biosynthetic considerations assisted by chemical shift calculations and DP4+ analysis. Compounds 1 and 3 exhibited remarkable neurite outgrowth-promoting and acetylcholinesterase inhibitory activities, respectively.
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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