{"title":"HR-LC/MS Guided Separation and Identification of Acyl-Migrated Sucrose Esters From Physalis Calyx seu Fructus.","authors":"Chuanyang Zhang, Lujia Yang, Lishi Jiang, Yuting Mu, Xianglian Mao, Qian Liu, Fang Deng, Dale Guo","doi":"10.1002/pca.70028","DOIUrl":null,"url":null,"abstract":"<p><strong>Introduction: </strong>Physalis Calyx seu Fructus is a commonly used traditional Chinese medicine with recognized effects of clearing heat, detoxifying, soothing the throat, and resolving phlegm. Previous studies have identified it as a rich source of sucrose fatty acid esters (SEs).</p><p><strong>Objectives: </strong>The aim of this study was to isolate structurally novel SEs with biological activity.</p><p><strong>Material and methods: </strong>HR-LC/MS guided isolation was conducted, followed by unequivocal structural characterization of all compounds through comprehensive spectroscopic analysis. All compounds were evaluated for anti-inflammatory activity using an LPS-stimulated RAW 264.7 macrophage model, and their antibacterial activity was assessed against three clinically relevant bacterial strains. Simultaneously, isotope labeling experiments were conducted to elucidate the role of H<sub>2</sub>O in the acyl migration process of the SEs.</p><p><strong>Results: </strong>Ten new SEs, designated Phyalkfranose A-J (1-10), were isolated; six of them were unstable and underwent intramolecular acyl migration. Experimental results demonstrated that these 6 SEs underwent slow intramolecular acyl migration in aqueous solution, a process that was significantly accelerated under conditions of elevated temperature and high water content. Isotope labeling studies confirmed that H<sub>2</sub>O facilitates, but does not participate in the migration. Compounds 8 and 10 inhibited the production of pro-inflammatory cytokines (IL-1β, IL-6, TNF-α). All compounds exhibited negligible antimicrobial activity.</p><p><strong>Conclusion: </strong>This study represents the first report on the acyl migration phenomenon of naturally occurring SEs from the plant source. These findings not only enrich the structural diversity of SEs but also offer novel strategies and methodologies for the isolation of such components.</p>","PeriodicalId":20095,"journal":{"name":"Phytochemical Analysis","volume":" ","pages":""},"PeriodicalIF":2.6000,"publicationDate":"2025-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemical Analysis","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1002/pca.70028","RegionNum":3,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMICAL RESEARCH METHODS","Score":null,"Total":0}
引用次数: 0
Abstract
Introduction: Physalis Calyx seu Fructus is a commonly used traditional Chinese medicine with recognized effects of clearing heat, detoxifying, soothing the throat, and resolving phlegm. Previous studies have identified it as a rich source of sucrose fatty acid esters (SEs).
Objectives: The aim of this study was to isolate structurally novel SEs with biological activity.
Material and methods: HR-LC/MS guided isolation was conducted, followed by unequivocal structural characterization of all compounds through comprehensive spectroscopic analysis. All compounds were evaluated for anti-inflammatory activity using an LPS-stimulated RAW 264.7 macrophage model, and their antibacterial activity was assessed against three clinically relevant bacterial strains. Simultaneously, isotope labeling experiments were conducted to elucidate the role of H2O in the acyl migration process of the SEs.
Results: Ten new SEs, designated Phyalkfranose A-J (1-10), were isolated; six of them were unstable and underwent intramolecular acyl migration. Experimental results demonstrated that these 6 SEs underwent slow intramolecular acyl migration in aqueous solution, a process that was significantly accelerated under conditions of elevated temperature and high water content. Isotope labeling studies confirmed that H2O facilitates, but does not participate in the migration. Compounds 8 and 10 inhibited the production of pro-inflammatory cytokines (IL-1β, IL-6, TNF-α). All compounds exhibited negligible antimicrobial activity.
Conclusion: This study represents the first report on the acyl migration phenomenon of naturally occurring SEs from the plant source. These findings not only enrich the structural diversity of SEs but also offer novel strategies and methodologies for the isolation of such components.
期刊介绍：
Phytochemical Analysis is devoted to the publication of original articles concerning the development, improvement, validation and/or extension of application of analytical methodology in the plant sciences. The spectrum of coverage is broad, encompassing methods and techniques relevant to the detection (including bio-screening), extraction, separation, purification, identification and quantification of compounds in plant biochemistry, plant cellular and molecular biology, plant biotechnology, the food sciences, agriculture and horticulture. The Journal publishes papers describing significant novelty in the analysis of whole plants (including algae), plant cells, tissues and organs, plant-derived extracts and plant products (including those which have been partially or completely refined for use in the food, agrochemical, pharmaceutical and related industries). All forms of physical, chemical, biochemical, spectroscopic, radiometric, electrometric, chromatographic, metabolomic and chemometric investigations of plant products (monomeric species as well as polymeric molecules such as nucleic acids, proteins, lipids and carbohydrates) are included within the remit of the Journal. Papers dealing with novel methods relating to areas such as data handling/ data mining in plant sciences will also be welcomed.
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