Siyu Qin , Jianbing Tan , Yuting Zheng , Shujuan Zhu , Bin Jiang , Chen Chen , Linjie Wei , Xuanxuan Weng , Zhenxing Zou
{"title":"Phyllanfranins A-F, anti-inflammatory ent-cleistanthane diterpenoids from Phyllanthus franchetianus","authors":"Siyu Qin , Jianbing Tan , Yuting Zheng , Shujuan Zhu , Bin Jiang , Chen Chen , Linjie Wei , Xuanxuan Weng , Zhenxing Zou","doi":"10.1016/j.phytochem.2025.114422","DOIUrl":null,"url":null,"abstract":"<div><div>A comprehensive chemical investigation of the EtOAc extract derived from the dried branches and leaves of <em>Phyllanthus franchetianus</em> H. Lév had successfully resulted to the isolation of six undescribed cleistanthane diterpenoids phyllanfranins A-F (<strong>1</strong>–<strong>6</strong>), along with three known compounds phyllarheophol C (<strong>7</strong>), phyacioid C (<strong>8</strong>), and spruceanol (<strong>9</strong>). The chemical structures of these compounds were elucidated by combined means of HRESIMS, 1D and 2D NMR spectra, together with ECD calculations. The absolute configuration of phyllanfranin A (<strong>1</strong>) was established by single crystal X-ray diffraction analysis. Notably, phyllanfranin F (<strong>6</strong>) represents the first <em>ent</em>-cleistanthane diterpenoid with the unique 6/6/6/6 tetracyclic system occurring in nature. Additionally, all the isolates were evaluated for anti-inflammatory activities. As a result, compounds <strong>4</strong> and <strong>8</strong> showed notable inhibitory activity against NO production in LPS-stimulated macrophages RAW264.7 cells, with IC<sub>50</sub> values of 19.03 and 18.14 μM, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"234 ","pages":"Article 114422"},"PeriodicalIF":3.2000,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942225000457","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
A comprehensive chemical investigation of the EtOAc extract derived from the dried branches and leaves of Phyllanthus franchetianus H. Lév had successfully resulted to the isolation of six undescribed cleistanthane diterpenoids phyllanfranins A-F (1–6), along with three known compounds phyllarheophol C (7), phyacioid C (8), and spruceanol (9). The chemical structures of these compounds were elucidated by combined means of HRESIMS, 1D and 2D NMR spectra, together with ECD calculations. The absolute configuration of phyllanfranin A (1) was established by single crystal X-ray diffraction analysis. Notably, phyllanfranin F (6) represents the first ent-cleistanthane diterpenoid with the unique 6/6/6/6 tetracyclic system occurring in nature. Additionally, all the isolates were evaluated for anti-inflammatory activities. As a result, compounds 4 and 8 showed notable inhibitory activity against NO production in LPS-stimulated macrophages RAW264.7 cells, with IC50 values of 19.03 and 18.14 μM, respectively.
期刊介绍：
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.
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