{"title":"Two new alkaloids from the roots of Stemona parviflora","authors":"Si-Wei Luo, Qi-Fan Xu, Zhi-Qi Yin, Ke Pan","doi":"10.1016/j.phytol.2025.102993","DOIUrl":"10.1016/j.phytol.2025.102993","url":null,"abstract":"<div><div>Two previously undescribed stemofoline alkaloids, 11(<em>E</em>)-oxystemofoline (<strong>1</strong>) and 11(<em>E</em>)-17-hydroxystemofoline (<strong>2</strong>), and three known compounds, 11(<em>E</em>)-2′(<em>S</em>)-hydroxystemofoline (<strong>3</strong>), stemofoline (<strong>4</strong>), and isostemofoline (<strong>5</strong>), were isolated from the roots of <em>Stemona parviflora</em>. Their structures were elucidated by spectroscopic data analysis and single-crystal X-ray diffraction. <strong>2</strong> has unprecedented hydroxylation at C-17 of the stemofoline alkaloid skeleton. The inhibitory effects of all isolates on LPS-induced NO production in RAW 264.7 cells were evaluated. Although only <strong>4</strong> was active, the results showed that the <em>Z</em> configuration of the Δ<sup>11</sup> double bond was potentially beneficial for the anti-inflammatory effect of stemofoline alkaloids.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102993"},"PeriodicalIF":1.3,"publicationDate":"2025-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144090307","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"(±)-Laevigiol A, a pair of new enantiomeric phenylpropanoids from the leaves and twigs of Croton laevigatus Vahl. and their anti-Alzheimer’s disease activities","authors":"Yu-Bin Lu, Mi-Na Yang, Hui-Jie Li, Li-Jia Ye, Le-Le Guo, Miao Zhang, Chun-Min Liu, Xin Wang, Yi-Nan Yang, Zhan-Xin Zhang, Dong-Qing Fei","doi":"10.1016/j.phytol.2025.102982","DOIUrl":"10.1016/j.phytol.2025.102982","url":null,"abstract":"<div><div>(+)-Laevigiol A (<strong>1a</strong>) and (−)-Laevigiol A (<strong>1b</strong>), a pair of new enantiomeric phenylpropanoids, together with ten known compounds (<strong>2–11</strong>), were isolated from the ethanol extract of the leaves and twigs of <em>Croton laevigatus</em>. The racemic mixture <strong>1</strong> was separated through chiral HPLC. Their structures with absolute configurations were established by analysis of spectroscopic data (IR, HRESIMS, 1D and 2D NMR) and quantum chemical calculations of electronic circular dichroism (ECD) curves. Furthermore, all compounds were evaluated for their <em>in vivo</em> anti-Alzheimer’s disease (AD) activities by using <em>Caenorhabditis elegans</em> AD pathological model. Among them, compounds <strong>1</strong>, <strong>6</strong>, and <strong>9–11</strong> could delay AD-like symptoms of worm paralysis phenotype, indicating their potential anti-AD bioactivities.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102982"},"PeriodicalIF":1.3,"publicationDate":"2025-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072064","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Li-Hong Yan , Hao-Wei Chen , Peng Hu , Jiyang Li , Juan Xiong , Ze-Xin Jin , Jin-Feng Hu
{"title":"Diaporolide, a new 10-membered lactone derivative from the endophytic Diaporthe sp. RYF-Br-5 associated with the rare conifer Keteleeria pubescens","authors":"Li-Hong Yan , Hao-Wei Chen , Peng Hu , Jiyang Li , Juan Xiong , Ze-Xin Jin , Jin-Feng Hu","doi":"10.1016/j.phytol.2025.102981","DOIUrl":"10.1016/j.phytol.2025.102981","url":null,"abstract":"<div><div>A new 10-membered lactone derivative (diaporolide, <strong>1</strong>) and three known polyketides (<strong>2</strong>–<strong>4</strong>) were obtained from the endophytic fungus <em>Diaporthe</em> sp. RYF-Br-5, which was derived from the fresh branches of <em>Keteleeria pubescens</em>, a rare endemic conifer native to China. Through a detailed spectroscopic analysis and theoretical ECD calculations, the structure and absolute stereochemistry of compound <strong>1</strong> were confirmed. In antimicrobial assays, compound <strong>1</strong> exhibited an inhibitory effect against <em>Staphylococcus aureus</em> with an MIC value of 64 µg/mL.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102981"},"PeriodicalIF":1.3,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072063","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Irbaz Rehman , Alexandra King , Joey B. Tanney , Mark W. Sumarah , David R. McMullin
{"title":"Antifungal naphthalenes and related polyketides from the cranberry (Vaccinium macrocarpon) endophyte Protoventuria sp.","authors":"Irbaz Rehman , Alexandra King , Joey B. Tanney , Mark W. Sumarah , David R. McMullin","doi":"10.1016/j.phytol.2025.102974","DOIUrl":"10.1016/j.phytol.2025.102974","url":null,"abstract":"<div><div>Ericaceous plants, including high-value fruit crops, harbor phylogenetically diverse fungal endophytes. A collection of ∼350 fungal endophytes from Canadian fruit-bearing plants was generated to investigate the taxonomic and secondary metabolite diversity of these poorly studied fungi. A putatively novel species of <em>Protoventuria</em> was isolated as an endophyte from a cranberry (<em>Vaccinium macrocarpon</em>) leaf in Central Ontario promoting an investigation of its secondary metabolites. From this fungus, two new naphthalenes, protoventurenes A and B (<strong>1</strong>–<strong>2</strong>), were characterized by LC-HRMS and NMR spectroscopy. Two additional structurally similar metabolites were also identified, the naphtalenone fragranone (<strong>3</strong>), previously reported from a shrub in Thailand, and the phenalenone derivative lamellicolic anhydride (<strong>4</strong>) originally from <em>Verticillium lamellicola</em>. Metabolites <strong>1</strong>–<strong>4</strong> inhibited the growth of the plant pathogen <em>Botrytis cinerea</em> with a 100-µg dose, and protoventurene B (<strong>2</strong>) inhibited <em>Colletotrichum gloeosporioides</em> at the same concentration. The investigation of ericaceous endophytes continues to reveal ecologically unique fungi and their new secondary metabolites.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102974"},"PeriodicalIF":1.3,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144068270","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Lin-Fen Ding , Xiang-Yue Zhang , Qiu-Hua Wang , Qiu-Ye Zhao , Shi-Huan Yin , Liu-Dong Song , Xing-De Wu
{"title":"Two new phenolic derivatives with neuroprotective activities from the fruits of Magnolia denudata","authors":"Lin-Fen Ding , Xiang-Yue Zhang , Qiu-Hua Wang , Qiu-Ye Zhao , Shi-Huan Yin , Liu-Dong Song , Xing-De Wu","doi":"10.1016/j.phytol.2025.102980","DOIUrl":"10.1016/j.phytol.2025.102980","url":null,"abstract":"<div><div>Two new phenolic derivatives, magnodatins A and B (<strong>1</strong> and <strong>2</strong>), were isolated from the fruits of <em>Magnolia denudata</em> Desr., along with two known compounds, denudalide (<strong>3</strong>) and lettowipyraquinol (<strong>4</strong>). The structures of <strong>1</strong> and <strong>2</strong> were determined through comprehensive analysis using NMR, HR-ESI-MS, and IR data. Notably, compound <strong>1</strong> featured a 3,7-dimethylocta-2,6-dienyl chain motif. Additionally, the neuroprotective effects of compounds <strong>1</strong> and <strong>2</strong> were evaluated <em>in vitro</em> against corticosterone-induced damage in PC12 cells. Compounds <strong>1</strong> and <strong>2</strong> showed weak neuroprotective activities at a concentration of 20 <em>μ</em>mol/L with PC12 cell viability of 62.39 % for <strong>1</strong> and 61.79 % for <strong>2</strong>, compared to 60.09 ± 0.04 % for the model group.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102980"},"PeriodicalIF":1.3,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143948549","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Shan-Xuan Zhang , Meng-Fei Liu , Yu-Ling Tan , Jin-Long Duan , Qiao-Lin Xu , Jian-Wen Tan
{"title":"Two new ursane type triterpenoids from adult leaves of Cyclocarya paliurus","authors":"Shan-Xuan Zhang , Meng-Fei Liu , Yu-Ling Tan , Jin-Long Duan , Qiao-Lin Xu , Jian-Wen Tan","doi":"10.1016/j.phytol.2025.102976","DOIUrl":"10.1016/j.phytol.2025.102976","url":null,"abstract":"<div><div>A phytochemical study on the adult leaves of <em>Cyclocarya paliurus</em> led to the isolation of two new ursane type triterpenoids 2<em>α</em>,3<em>β</em>,23-trihydroxy-taraxastan-28,20<em>β</em>-olide (<strong>1</strong>) and 3<em>β</em>,11<em>α</em>,19<em>α</em>,24,30-pentahydroxy-20<em>β</em>,28-epoxy-28<em>β</em>-ethoxy-ursane (<strong>2</strong>), along with four known analogs, 2<em>α</em>,3<em>α</em>-23-trihydroxyurs-12-en-28-oic acid (<strong>3</strong>), hederagenin (<strong>4</strong>), quinatic acid (<strong>5</strong>) and arjunolic acid (<strong>6</strong>). Their structures were elucidated on the basis of extensive spectroscopic analysis including 1D, 2D NMR and MS techniques. These triterpenoids were tested for their <em>in vitro α</em>-glucosidase inhibitory activity with acarbose and corosolic acid as references. All of these compounds, except <strong>2</strong>, were found to show obvious <em>in vitro α</em>-glucosidase inhibitory activity with MIC values ranging from 0.017 to 0.106 mM, which were much stronger than acarbose (IC<sub>50</sub> 0.408 mM). Especially, <strong>3</strong>, <strong>4</strong> and <strong>6</strong> showed <em>in vitro α</em>-glucosidase inhibitory activity with MIC values (IC<sub>50</sub> 0.034, 0.017 and 0.041 mM) close or even more potent than corosolic acid (IC<sub>50</sub> 0.033 mM). The present result supported that the adult leaves of <em>C. paliurus</em> was also a rich resource for potential anti-diabetic chemicals worthy of further investigation.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102976"},"PeriodicalIF":1.3,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143941883","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ang Li , Xiu-Wei Li , Huan Guo, Qiang Guo, Xia Wu, Xiao-Qing Chen
{"title":"Two new alkamides and a new polyacetylene glucoside from Achillea alpina L.","authors":"Ang Li , Xiu-Wei Li , Huan Guo, Qiang Guo, Xia Wu, Xiao-Qing Chen","doi":"10.1016/j.phytol.2025.102968","DOIUrl":"10.1016/j.phytol.2025.102968","url":null,"abstract":"<div><div>In this study, nine compounds were isolated and identified from the <em>Achillea alpina</em> L. Among them, compounds <strong>1</strong> and <strong>2</strong> were new alkamides, named achilleamide E and achilleamide F, compound <strong>3</strong> was a polyacetylene glycoside, named achillneoside A, and compounds <strong>4</strong>-<strong>9</strong> were known as polyacetylene alkamides. In addition, compounds <strong>1</strong>-<strong>3</strong>, <strong>8</strong> and <strong>9</strong> exhibited good neuroprotective activities against 6-OHDA-induced cell death on human neuroblastoma SH-SY5Y cells at 20 μM.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102968"},"PeriodicalIF":1.3,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143948561","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dan Wang , Ming Zhao , Xiaoxue Li , Shujun Zhang , Liqiu Sun , Jinlan Wang , Zhichun Shi , Jun Li , Yingnan Zhao
{"title":"Isolation of macrocarpene-type sesquiterpenes from stigma maydis (Zea mays)","authors":"Dan Wang , Ming Zhao , Xiaoxue Li , Shujun Zhang , Liqiu Sun , Jinlan Wang , Zhichun Shi , Jun Li , Yingnan Zhao","doi":"10.1016/j.phytol.2025.102977","DOIUrl":"10.1016/j.phytol.2025.102977","url":null,"abstract":"<div><div>Two new sesquiterpenes, zeaol C (<strong>1</strong>) and zeaone A (<strong>2</strong>), along with four known related analogues, were isolated from the styles and stigmas of <em>Zea mays</em>. The structures and absolute configurations of compounds <strong>1</strong> and <strong>2</strong> were elucidated through extensive spectroscopic techniques, including 1D- and 2D-NMR, HR-ESI-MS, and ECD. Compounds <strong>1</strong> and <strong>2</strong> exhibited weak cytotoxic activities against the SK-OV-3 cancer cell line, while compounds <strong>1</strong>−<strong>6</strong> enhanced glucose consumption in HepG2 cells.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102977"},"PeriodicalIF":1.3,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143941884","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chung-Wei Fu , Atallah F. Ahmed , Lin Chiang , Shu-Fen Chiou , Hui-Chun Wang , Jyh-Horng Sheu
{"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":"10.1016/j.phytol.2025.102975","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":1.3,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143937681","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kate Tolan , Mohammed Ali Selo , Ismael Obaidi , Peter O’Connell , Michael Carty , Shipra Nagar , Anne Marie Healy , Helen Sheridan
{"title":"The effects of upstream processing on the chemical profile and immunomodulating activity of Echinacea purpurea tinctures","authors":"Kate Tolan , Mohammed Ali Selo , Ismael Obaidi , Peter O’Connell , Michael Carty , Shipra Nagar , Anne Marie Healy , Helen Sheridan","doi":"10.1016/j.phytol.2025.102971","DOIUrl":"10.1016/j.phytol.2025.102971","url":null,"abstract":"<div><div><em>Echinacea purpurea</em> (L.) Moench is a medicinal plant that is widely known for its immunomodulating properties. There is a lack of understanding regarding how <em>E. purpurea</em> tinctures should be prepared to ensure the most favourable biological activity. To address this gap, a total of 24 tinctures of <em>E. purpurea</em> were prepared with fresh or dried plant material, that was chopped (>2000 µm) or shredded (500–2000 µm), and that was 2 or 3-years-old at the time of harvest. Tinctures contained herba or radix or a combination of both. The chemical profile of the tinctures was determined using HPLC coupled with a principal component analysis of <sup>1</sup>H NMR data. This analysis revealed that tinctures prepared with dried plant material (n = 8) had significantly higher concentrations of caffeic acid derivatives than tinctures prepared with fresh plant material, with the exception of 4 tinctures. The immunomodulating ability of tincture extracts, at a concentration of 100 µg/mg, was evaluated <em>in vitro</em> using non stimulated and lipopolysaccharide (LPS)-stimulated immortalised bone marrow derived macrophages (iBMDM) and THP-1 cell lines. Tincture extracts containing dried plant material reduced IL-6 production in LPS-stimulated iBMDM and THP-1 cells and increased production of TNF-α in THP-1 cells to a greater extent than tincture extracts prepared with fresh plant material. Despite the absence of caffeic acid derivatives, a number of tincture extracts prepared with fresh and shredded plant material had significant anti-inflammatory activity. The inclusion of herba in the tincture was seen to significantly inhibited IL-6 in both iBMDM and THP-1 cells. This study highlights the importance of selecting appropriate upstream processing methods to ensure the production of quality <em>E. purpurea</em> tinctures.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102971"},"PeriodicalIF":1.3,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143937680","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}