Phytochemistry Letters最新文献

{"title":"The importance of verifying biological activity predictions in metabolomics studies of natural products: A case study on antimicrobial properties of Cannabis sativa (hemp)","authors":"Fridah C. Rotich,&nbsp;Joseph B. Mangun,&nbsp;Joëlle Houriet,&nbsp;Warren S. Vidar,&nbsp;Tyler N. Graf,&nbsp;Nicholas H. Oberlies,&nbsp;Nadja B. Cech","doi":"10.1016/j.phytol.2025.103014","DOIUrl":"10.1016/j.phytol.2025.103014","url":null,"abstract":"<div><div>Informatics-guided approaches involving untargeted mass spectrometry metabolomics to predict active compounds in natural products mixtures have become increasingly common. With such strategies, it is sometimes possible to target active compounds for isolation early in the fractionation process, thereby reducing effort and increasing hit rate success. However, such approaches require follow up studies to address the potential problem of false correlations. To demonstrate this, we employed the botanical <em>Cannabis sativa</em> (hemp) as a test case. A <em>C. sativa</em> extract was fractionated in several stages, and the ability of the fractions to inhibit the growth of Methicillin-resistant <em>Staphylococcus aureus</em> (MRSA) was evaluated in broth microdilution assays. Metabolomics data were collected for the extract and fractions using high performance liquid chromatography coupled to high resolution mass spectrometry on an Orbitrap mass spectrometer, and selectivity ratio analysis was employed as a statistical tool to predict the active compound from two different rounds of fractionation of the <em>C. sativa</em> extract. From the early stage of fractionation, we predicted that the cannabinoids cannabidiol (<strong>1,</strong> CBD) and cannabidiolic acid (<strong>2,</strong> CBDA) were major active constituents. These predictions, when verified with follow up minimum inhibitory concentration (MIC) assays of the pure compounds, proved to be accurate. However, in a later stage of fractionation using the same statistical approach, the previously reported <em>C. sativa</em> constituents <em>N</em>-<em>trans</em>-<em>p</em>-coumaroyltyramine (<strong>3</strong>, pCT) and <em>N</em>-<em>trans</em>-feruloyltyramine (<strong>4</strong>, FT) were predicted to be responsible for activity. Follow up assays with these pure compounds revealed that they possess no direct or synergistic antimicrobial activity against MRSA. This study highlights how statistical predictions of active compounds in untargeted metabolomics studies are inherently correlative and emphasizes the need for follow up studies to verify the accuracy of such predictions.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 103014"},"PeriodicalIF":1.3,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144694329","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":"A new benzoquinone and a new dihydroflavone from Fissistigma polyanthum and their bioactivity","authors":"Jian-Fen Xiao,&nbsp;Ming-Rui Yang,&nbsp;Pin-Xiang Fu,&nbsp;Rui Yang,&nbsp;Hong-Ping He,&nbsp;Hua-Yi Jiang","doi":"10.1016/j.phytol.2025.103012","DOIUrl":"10.1016/j.phytol.2025.103012","url":null,"abstract":"<div><div>A new benzoquinone and a new dihydroflavone, fispolyanins A (<strong>1</strong>) and B (<strong>2</strong>), along with four known compounds (<strong>3</strong>–<strong>6</strong>), were isolated from the ethyl acetate fraction of <em>Fissistigma polyanthum</em>. The structures of <strong>1</strong> and <strong>2</strong> were established primarily by a combination of NMR and MS methods. Compounds <strong>5</strong> and <strong>6</strong> were obtained from <em>F. polyanthum</em> for the first time. Compounds <strong>1</strong>, <strong>4</strong>, and <strong>6</strong> exhibited inhibitory activities against the production of nitric oxide (NO) in LPS-induced RAW 264.7 cells. Compounds <strong>2</strong> and <strong>4</strong> showed weak anti-oxidant activities.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 103012"},"PeriodicalIF":1.3,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144631742","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":"Structurally diverse alkaloids from stems and leaves of Baphicacanthus cusia and their neuraminidase inhibitory activity","authors":"Xiaofan Fan ,&nbsp;Yingzhe Li ,&nbsp;Min Jae Kim ,&nbsp;Zhihong Cheng","doi":"10.1016/j.phytol.2025.103013","DOIUrl":"10.1016/j.phytol.2025.103013","url":null,"abstract":"<div><div>Three new alkaloids, namely, ethyl 2-[(1<em>H</em>-indol-3-ylcarbonyl)amino]benzoate (<strong>1</strong>), 3-[(<em>R</em>)-1-benzyl-1-ethoxycarbonyl]-2,4(1<em>H</em>,3<em>H</em>)-quinazolinedione (<strong>2</strong>), and (±)-11-ethoxycarbonyl-baphicacanthcusine D (<strong>3</strong>), along with 21 known alkaloids (<strong>4</strong>–<strong>25</strong>), were isolated from the stems and leaves of <em>Baphicacanthus cusia</em>. Among these alkaloids, compounds <strong>1</strong>–<strong>3</strong> were proposed as new artifacts, and compounds <strong>4</strong> and <strong>16</strong>–<strong>18</strong> were identified as new natural products. The phytochemical investigation demonstrated that the herb has a high degree of structural diversity in alkaloids, with at least four types of alkaloids (e.g., indole-, quinazolone-, organic amine-, and quinoline-types) being present. All the alkaloids were assessed for their neuraminidase inhibitory activity using a fluorescence-based assay. Twelve alkaloids demonstrated the potential activity, with IC₅₀ values ranging from 40.16 to 144.73 μM.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 103013"},"PeriodicalIF":1.3,"publicationDate":"2025-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144604725","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":"New challenges for natural products in bioactive molecules discovery - PSE YSM 2023 - Special Issue - Editorial","authors":"","doi":"10.1016/j.phytol.2025.103009","DOIUrl":"10.1016/j.phytol.2025.103009","url":null,"abstract":"","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 103009"},"PeriodicalIF":1.3,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144588768","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":"Multi-target directed ligands design of 1-O-Acetylbritannilactone derivatives: Dual anti-neuroinflammatory and acetylcholinesterase inhibitory activities","authors":"Yan-Peng Liang ,&nbsp;Qian Gao ,&nbsp;Hong Chen ,&nbsp;Rui Ma ,&nbsp;Xiao-Bo Zhao ,&nbsp;Xiao-Jie Jin ,&nbsp;Jian Zhang ,&nbsp;Yan-Ping Shi ,&nbsp;Wei Ha","doi":"10.1016/j.phytol.2025.103011","DOIUrl":"10.1016/j.phytol.2025.103011","url":null,"abstract":"<div><div>Alzheimer’s disease, a progressive neurodegenerative disorder of the central nervous system, presents a complex pathological mechanism that limits the efficacy of conventional single-target drugs. Utilizing the unique advantages of natural products in multi-target intervention, this study employed the active component 1-<em>O</em>-acetylbritannilactone (ABL) from <em>Inula britannica</em> L. as the parent structure. Guided by the multi-target directed ligands (MTDLs) strategy, four novel derivatives (ABL-1 to ABL-4) were successfully designed and synthesized by introducing acetylcholinesterase (AChE) inhibitory pharmacophores into the ABL scaffold. <em>In vitro</em> pharmacological evaluation demonstrated that ABL-2, ABL-3, and ABL-4 not only preserved the anti-neuroinflammatory activity of the parent compound but also endowed compound ABL with AChE inhibitory potency. Notably, ABL-4 displayed the most promising dual efficacy profile, achieving an AChE inhibition rate of 40.09 ± 0.73 % at 30 μM and an anti-neuroinflammatory activity (EC₅₀ = 8.43 ± 0.5 μM). Molecular docking simulations revealed that the dual-target synergistic mechanism of ABL derivatives arises from hydrogen bonding and π-π stacking interactions with key residues of both AChE and inducible nitric oxide synthase (iNOS). This work not only validates the feasibility of the MTDLs strategy in optimizing natural product scaffolds but also provides a structurally novel lead compound with significant potential for developing multi-target anti-AD therapeutics.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 103011"},"PeriodicalIF":1.3,"publicationDate":"2025-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144570573","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":"Isolation and computational characterization of a novel cyanogenic glucoside from Centaurea microcarpa with antiviral potential against SARS-CoV-2: DFT, ADMET, and molecular docking analysis","authors":"Rachida Kerkour ,&nbsp;Samia Baatouche ,&nbsp;Abir Boublia ,&nbsp;Nadjib Chafai ,&nbsp;Ramadan Seghiri ,&nbsp;Djamel Sarri","doi":"10.1016/j.phytol.2025.103010","DOIUrl":"10.1016/j.phytol.2025.103010","url":null,"abstract":"<div><div>This study reports the isolation and structural elucidation of a novel cyanogenic glucoside, 6′-methacrylate prunasin (6-MPr), from <em>Centaurea microcarpa</em> Coss. &amp; Dur. The structure of 6-MPr was confirmed through spectroscopic techniques, including HRESI-MS NMR, and FTIR, revealing a molecular ion peak [M+Na]⁺ at <em>m/z</em> 364.1. Its antiviral potential against SARS-CoV-2 was assessed using in silico approach that integrates DFT calculations, ADMET profiling, and molecular docking. Results indicate that 6-MPr has good stability, favorable pharmacokinetic properties for oral administration, and strong binding affinities to key viral enzymes (Mpro, PLpro, RdRp, Nsp3). These findings highlight 6-MPr as a promising candidate for antiviral drug development, warranting further experimental validation.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 103010"},"PeriodicalIF":1.3,"publicationDate":"2025-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144570572","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":"Flavonoids and butanolides from the bark of Machilus robusta and their bioactivities","authors":"Rui-Qi Liu ,&nbsp;Shan-Shan Ling ,&nbsp;Xian-Da Hu ,&nbsp;Bing Peng ,&nbsp;Yan-Ru Li","doi":"10.1016/j.phytol.2025.103007","DOIUrl":"10.1016/j.phytol.2025.103007","url":null,"abstract":"<div><div>One new flavanone glycoside, named (2<em>R</em>,3<em>R</em>)-dihydrokaempferol-5-<em>O</em>-α-L-arabinopyranoside (<strong>1</strong>), together with 11 known compounds, was isolated from the ethanol extract of <em>Machilus robusta</em> bark. Their structures were elucidated by a combination of spectroscopic and chemical analysis. Compounds <strong>4</strong> and <strong>5</strong> showed neuroprotective activity against serum deprivation induced PC12 cell damage by increasing the cell viability from 66.6 ± 9.2 % to 81.96 ± 8.13 % and 78.38 ± 11.65 %, respectively, at a concentration of 10 µM. And at the same concentration, compound <strong>4</strong> showed stronger hepatoprotective activity against WB-F344 cell damage induced by DL-galactosamine than that of the positive drug bicyclol. In addition, compound <strong>3</strong> showed certain antioxidant activity inhibiting Fe^2 + -cystine-induced rat liver microsomal lipid peroxidation.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 103007"},"PeriodicalIF":1.3,"publicationDate":"2025-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144534356","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":"Natural drug discovery – Editorial","authors":"Didem Şöhretoğlu","doi":"10.1016/j.phytol.2025.103006","DOIUrl":"10.1016/j.phytol.2025.103006","url":null,"abstract":"","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 103006"},"PeriodicalIF":1.3,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144489335","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":"Corrigendum to “Antifungal natural products from the culture medium of Trichoderma orarium 18F0041” [Phytochem. Lett. 67 (2025) 102945]","authors":"Hui-Tzu Ni ,&nbsp;Jih-Jung Chen ,&nbsp;Hsia-Wei Liu ,&nbsp;Ming-Der Wu ,&nbsp;Yu-Hui Wei ,&nbsp;Min Tseng ,&nbsp;Yuan-Hsiang Yu ,&nbsp;Ming-Jen Cheng","doi":"10.1016/j.phytol.2025.103008","DOIUrl":"10.1016/j.phytol.2025.103008","url":null,"abstract":"","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 103008"},"PeriodicalIF":1.3,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144502763","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":"Two new neo-clerodane furanoditerpenoids and other bioactive constituents from the stem bark of the Cameroonian Croton macrostachyus (Euphorbiaceae)","authors":"Franck Landry Djila Possi ,&nbsp;Jean Koffi Garba ,&nbsp;Kevine Johane Jumeta Dongmo ,&nbsp;Billy Toussie Tchegnitegni ,&nbsp;Appolinaire Kene Dongmo ,&nbsp;Yannick Stéphane Fotsing Fongang ,&nbsp;Noella Molisa Efange ,&nbsp;Jean Jules Kezetas Bankeu ,&nbsp;Jean Rodolphe Chouna ,&nbsp;Lawrence Ayong ,&nbsp;Pépin Nkeng-Efouet-Alango ,&nbsp;Norbert Sewald ,&nbsp;Bruno Ndjakou Lenta","doi":"10.1016/j.phytol.2025.103004","DOIUrl":"10.1016/j.phytol.2025.103004","url":null,"abstract":"<div><div>In our continued search for potent bioactive agents with antiplasmodial activity from Cameroonian <em>Croton</em> species to roll back malaria, we undertook the chemical investigation of the stem bark of <em>C. macrostachyus</em>, a medicinal plant widely used in folk medicine to treat several diseases including malarial. Two previously undescribed <em>neo</em>-clerodane furanoditerpenoids named crotomaclerodane (<strong>1</strong>) and macrostaclerodane (<strong>2</strong>) along with 11 known compounds (<strong>3–13</strong>) were isolated from the methanol extract of the stem bark of <em>C. macrostachyus</em>. The structures of these compounds were characterized by spectroscopic (1D and 2D NMR) analyses, HRESIMS, and single-crystal X-ray diffraction techniques. The crude extract, fractions and isolated compounds were assessed <em>in vitro</em> for their antiplasmodial activity towards the chloroquine-sensitive (3D7) and the multidrug-resistant (Dd2) strains of <em>Plasmodium falciparum</em>. In addition, the antibacterial activity was also performed against some Gram-positive and Gram-negative strains. The results showed that neither the crude extract, nor the fractions were active towards both strains. Nevertheless, compounds <strong>4</strong>, <strong>6</strong>, <strong>7</strong>, and <strong>13</strong> showed good to moderate <em>in vitro</em> antiplasmodial activity with IC₅₀ values ranging from 8.40 <img> 51.39 <em>µ</em>g/mL against the two tested strains of <em>Plasmodium falciparum</em>. Furthermore, compound <strong>9</strong> showed good to moderate antibacterial activity on <em>Klebsiella pneumonia</em> clinical isolate, <em>Pseudomonas aeruginosa</em> HM801, <em>Staphylococcus aureus</em> 700698, <em>S. aureus</em> 12600 with MIC values ranging from 7.8<img>250 <em>µ</em>g/mL.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 103004"},"PeriodicalIF":1.3,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144297998","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}