Phytochemistry Letters最新文献

{"title":"Antifungal Natural Products from the Culture Medium of Trichoderma orarium 18F0041","authors":"Hui-Tzu Ni ,&nbsp;Jih-Jung Chen ,&nbsp;Hsia-Wei Liu ,&nbsp;Jyh-Yih Leu ,&nbsp;Ming-Der Wu ,&nbsp;Yu-Hui Wei ,&nbsp;Min Tseng ,&nbsp;Yuan-Hsiang Yu ,&nbsp;Ming-Jen Cheng","doi":"10.1016/j.phytol.2025.102945","DOIUrl":"10.1016/j.phytol.2025.102945","url":null,"abstract":"<div><div>Fractionation of an EtOAc-soluble partition of a solid fermentation of the endophytic fungus <em>Trichoderma orarium</em> 18F0041 resulted in the isolation of two new compounds, a γ-butyrolactone, 5-hydroxy-3-(methoxymethyl)-4-methylfuran-2(5<em>H</em>)-one (<strong>1</strong>), and a methylpentanoid derivative, 5-ethoxy-4-hydroxy-3-methyl-5-oxopentanoic acid (<strong>2</strong>). Additionally, two further metabolites were also isolated for the first time from a natural source, namely 2-hydroxypyridin-3-yl acetate (<strong>3</strong>) and (+)-<em>rel</em>-(4<em>S</em>,5<em>S</em>)-4,5-dihydroxytetrahydro-2<em>H</em>-pyran-2-one (<strong>4</strong>). All structures were elucidated on the basis of extensive analyses of spectroscopic data and comparison with literature data. Their antifungal activity was also evaluated. Our results showed that some of the constituents possessed mild antifungal activity against <em>Fusarium</em> sp. LC8, <em>Neopestalotiopsis</em> sp. BCRC 35002, and <em>Colletotrichum gloeosporioides</em> BCRC 35178. Previously, δ-valerolactone derivatives were rarely reported in the genus <em>Trichoderma</em>. The discovery of these compounds in the fermentation products of this new <em>Trichoderma</em> species is therefore highly significant. Natural products of <em>Trichoderma</em> warrant further investigation as potential antifungal agents for biocontrol applications.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102945"},"PeriodicalIF":1.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143714958","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 coumarins from a hot water extract of Daphne mezereum bark","authors":"Hussain Shakeel Butt ,&nbsp;Lucía Bada ,&nbsp;Karl Egil Malterud ,&nbsp;Kari Tvete Inngjerdingen ,&nbsp;Helle Wangensteen","doi":"10.1016/j.phytol.2025.102954","DOIUrl":"10.1016/j.phytol.2025.102954","url":null,"abstract":"<div><div>This study aimed to investigate the low-molecular weight compounds in a hot water extract of the bark of <em>Daphne mezereum</em> L. (Thymelaceae), a medicinal plant with a longstanding medicinal use in Scandinavia. Among the fourteen isolated compounds, two coumarin glycosides are reported for the first time, and four known compounds were reported in <em>D. mezereum</em> for the first time. Their structures were elucidated by NMR, HRESIMS and methanolysis. The new compounds were identified as 3-(2-(β-<span>d</span>-glucopyranosyloxy)-4-[(7-hydroxy-6-methoxy-2-oxo-2H-chromen-3-yl)oxy]phenyl)propanoic acid (<strong>9</strong>), and 7-hydroxycoumarin-5,8-di-β-<span>d</span>-glucopyranoside (<strong>11</strong>). Cytotoxic effects were assessed by the MTT assay, while the anti-inflammatory effects were assessed by measuring the inhibition of NO-release by dendritic cells. The results revealed negligible cytotoxic effect and NO-inhibitory activity of compounds <strong>9</strong> and <strong>11</strong>.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102954"},"PeriodicalIF":1.3,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143706068","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Ginsenoside F2 inhibits MLCK to induce synthetic lethality in MYC-driven triple-negative breast cancer and pancreatic cancer","authors":"Rui Wu ,&nbsp;Dong Lu ,&nbsp;Xin Luan ,&nbsp;Weidong Zhang ,&nbsp;Zhe Sun","doi":"10.1016/j.phytol.2025.102949","DOIUrl":"10.1016/j.phytol.2025.102949","url":null,"abstract":"<div><div>Myosin Light Chain Kinase (MLCK) represents a synthetic lethal interaction with the “undruggable” oncoprotein MYC. In this study, we identified Ginsenoside F2 (GF2) as a novel MLCK inhibitor through molecular docking-based virtual screening of a natural compound library, followed by in vitro cellular validation. GF2 treatment inhibited MLCK kinase activity, as demonstrated by the reduced phosphorylation of its substrate, myosin II regulatory light chain (MLC). The direct binding of GF2 to MLCK was confirmed using the cellular thermal shift assay (CETSA), which revealed decreased MLCK thermotolerance after GF2 treatment. Notably, GF2 selectively induced apoptosis in MYC-transformed cells while sparing normal counterparts. Triple-negative breast cancer (TNBC) and pancreatic cancer cells with high MYC expression are sensitive to GF2 treatment. Moreover, combining GF2 with the Bcl2 inhibitor venetoclax synergistically enhanced apoptosis in MYC-driven cancer cells. These findings establish GF2 as a novel MLCK inhibitor and underscore the therapeutic potential of targeting MLCK in MYC-driven malignancies, particularly TNBC and pancreatic cancer.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102949"},"PeriodicalIF":1.3,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143697892","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":"Chemical constituents from the stems of Erythropalum scandens","authors":"Qiao-dan Pan ,&nbsp;Yuan-he Huang ,&nbsp;Li-yang Zhao ,&nbsp;Wei-rui Wang ,&nbsp;Bing-an Wei ,&nbsp;Ying-ying Xu ,&nbsp;Xian Wei","doi":"10.1016/j.phytol.2025.102947","DOIUrl":"10.1016/j.phytol.2025.102947","url":null,"abstract":"<div><div>The phytochemical investigation on the EtOH extract of the stems of an ethnological herbal medicine <em>Erythropalum scandens</em> Blume led to the isolation thirteen secondary metabolites. The chemical structures of isolated compounds were elucidated by various spectroscopic techniques. Among them, compound <strong>1</strong>, named scandenoside A (<strong>1</strong>), is a previously unreported aromatic glycoside. Compounds (<strong>3</strong>-<strong>7</strong>,<strong>9</strong>-<strong>10</strong>,<strong>12</strong>) were isolated from this plant for the first time. The inhibitory activity of the isolates against xanthine oxidase (XOD) was evaluated, with compound <strong>11</strong> exhibiting strong inhibitory activity and a half inhibitory concentration (IC₅₀) value of 706.35 ± 18.36 µM. Molecular docking analyses revealed that the compound could bind within the active pocket of the XOD enzyme through hydrogen bonding and hydrophobic interactions. These results suggest that the stems of <em>E. scandens</em> may have a potentially beneficial effect on hyperuricemia.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102947"},"PeriodicalIF":1.3,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143680559","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":"Investigation of antibacterial activity and mechanism of action: Design and synthesis of coumarin derivatives containing sulfonamide groups","authors":"Song Bai ,&nbsp;Miaohe Zhang ,&nbsp;Miao Li ,&nbsp;Suran Wan ,&nbsp;Fang Wang ,&nbsp;Shouyin Tang ,&nbsp;Lijun Chen ,&nbsp;Xian Wei ,&nbsp;Rong Wu","doi":"10.1016/j.phytol.2025.102948","DOIUrl":"10.1016/j.phytol.2025.102948","url":null,"abstract":"<div><div>In this innovative study, we combined coumarin with a sulfonamide group and synthesized a series of coumarin derivatives. I<em>n vitro</em> antibacterial activity tests, these derivatives demonstrated antibacterial potential, especially compound <strong>27</strong>, whose antibacterial effect was particularly remarkable. Our experimental results revealed that compound <strong>27</strong> enhanced bacterial cell membrane permeability by disrupting the cell membrane of <em>Xanthomonas oryzae pv. oryzicola</em>, thereby effectively inhibiting its growth and reproduction. This not only provides insights into our understanding of the mechanism of action of compound <strong>27</strong>, but also represents a breakthrough in the development of novel antibacterial agents, offering unlimited possibilities for the future of agriculture and medicine.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102948"},"PeriodicalIF":1.3,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143680696","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":"Chemopreventive properties of naturally occurring methoxylated resveratrol analogues","authors":"Federico Brucoli ,&nbsp;Gael N.N. Neba Ambe ,&nbsp;Avninder S. Bhambra ,&nbsp;Randolph R.J. Arroo","doi":"10.1016/j.phytol.2025.03.001","DOIUrl":"10.1016/j.phytol.2025.03.001","url":null,"abstract":"<div><div>Whereas thousands of papers have been published on the cancer chemopreventive properties of resveratrol (3,5,4′-trihydroxy-<em>trans</em>-stilbene) and related monomeric stilbenoids, there still is no consensus on their mechanism of action in a dietary setting. A widely held assumption is that the naturally occurring <em>trans</em> stilbenoids act as phytoestrogens, and thus affect cell metabolism of estrogen sensitive cells. This is known to be the mechanism of action for Tamoxifen, a synthetic drug with a stilbene moiety at its core, which is now approved as a chemopreventive agent. The bioavailability of resveratrol is low, which means that the doses known to inhibit cell proliferation <em>in vitro</em> (IC₅₀ in the range 3–30 µM) are never reached <em>in vivo</em>. The cytotoxic activity of a methoxylated analogue of resveratrol, pterostilbene (3,5-dimethoxy-4’-hydroxy <em>trans</em> stilbene), is in the same range as resveratrol. However, the methoxylated <em>trans</em> stilbenoid appears have better pharmacokinetic properties. Still, its overall bioavailability <em>in vivo</em> seems insufficient to make it have any significant effect on modulation of carcinogenesis. Polymethoxylated <em>cis</em>-stilbenoids (combretastatins), in contrast to the <em>trans</em>-stilbenoids, are too cytotoxic to be considered as chemopreventive agents. Combretastatin A4 has been considered as a cancer therapeutic agent; it inhibits tubulin polymerization by interacting at the colchicine binding site of microtubules, a mechanism of action that is fundamentally different from that of the <em>trans</em>-stilbenoids. It may be speculated that naturally occurring <em>trans</em> stilbenoids selectively accumulate in precancerous cells, thus locally reaching sufficiently high levels. This hypothesis may be difficult to prove experimentally. Further clues on the material properties of stilbenoids will most likely come from synthetic chemistry, where a wide range of analogues can be investigated for structure–activity relationships.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102943"},"PeriodicalIF":1.3,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143680558","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Antioxidant capacity prediction: Combining individual compound capacities to predict plant-extract capacities","authors":"Jamie Selby-Pham ,&nbsp;Kimber Wise ,&nbsp;Sophie Selby-Pham","doi":"10.1016/j.phytol.2025.102951","DOIUrl":"10.1016/j.phytol.2025.102951","url":null,"abstract":"<div><div>The antioxidant activity of plant extracts offer potential for preventing and managing degenerative diseases linked to oxidative stress. Whilst the structure-function relationship of individual compound antioxidant capacities is well-established, accurate prediction of the overall antioxidant capacity of complex mixtures such as plant extracts, remains challenging. In this study, we sourced a data set of 68 plant extracts with empirically determined antioxidant capacities via the 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt assay (ABTS assay) and paired quantitatively determined metabolite profiles. Using a previously developed Trolox equivalent antioxidant capacity (TEAC) model, we predicted the antioxidant capacities of each phytochemical within these profiles. We then employed polynomial regression with k-fold cross-validation (k = 10) to develop a model predicting the antioxidant capacity of the plant extracts. The model, which utilised the count and sum of individual compound capacities of antioxidant-capable phytochemicals to predict log₁₀(TEAC), achieved an R² of 92.28 % and a 10-fold cross-validated R² of 74.49 %. When transformed back to TEAC (mM), the model resulted in an R² of 94.59 %, with 77.9 % of predictions within 20 % of their true values. These results demonstrate the utility of statistical models in predicting individual phytochemical antioxidant capacities and their contributions to food functional properties. Our model represents a significant advancement in predicting plant-extract antioxidant capacities from their phytochemical compositions, with implications for optimising functional food value through targeted modulation of phytochemical profiles or strategic blending (fortification) of plant extracts.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102951"},"PeriodicalIF":1.3,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143680695","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Three new polyketide metabolites from the endophytic fungus Trichoderma protrudens of Hibiscus tiliaceus","authors":"Yan-Mei Wu ,&nbsp;Jing-Ya Mo ,&nbsp;Yong-Yan Mei ,&nbsp;Quan Liu ,&nbsp;Yuan-Yuan Huang ,&nbsp;Bei Zhou ,&nbsp;Yi-Hang Li ,&nbsp;Yan-Chun Wu ,&nbsp;Jing-Quan Yuan","doi":"10.1016/j.phytol.2025.102950","DOIUrl":"10.1016/j.phytol.2025.102950","url":null,"abstract":"<div><div>Trichodones D-F (<strong>1</strong>-<strong>3</strong>), three previously undescribed polyketide compounds featuring conjugated <em>α</em>-<em>β</em>-unsaturated ketone moieties, were isolated from the endophytic fungus <em>Trichoderma protrudens</em> associated with the semi-mangrove plant <em>Hibiscus tiliaceus</em> Linn. The structural elucidation of these compounds was accomplished through the analysis of 1D and 2D NMR spectra, complemented by HR-ESI-MS data. The absolute configurations were determined through comparative analysis of experimental CD and calculated ECD spectra. Additionally, the cytotoxic activities of compounds <strong>1</strong>-<strong>3</strong> against the human breast cancer cell line MCF-7 and the human hepatocellular carcinoma cell line HepG2 were evaluated using the CCK8 assay. Notably, compound <strong>3</strong> exhibited moderate inhibitory activity against HepG2 and MCF-7 cell lines with IC₅₀ values of 22.7 μM and 55.1 μM, respectively.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102950"},"PeriodicalIF":1.3,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143680694","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":"Announcements of the Phytochemical Society of Europe","authors":"","doi":"10.1016/S1874-3900(25)01039-0","DOIUrl":"10.1016/S1874-3900(25)01039-0","url":null,"abstract":"","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages I-V"},"PeriodicalIF":1.3,"publicationDate":"2025-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143642981","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"α-Pyrones, root growth inhibitors from a mesophotic zone sponge-associated fungus Purpureocillium sp. NBUF263","authors":"Yu-Ying Liu ,&nbsp;Ting-Ting Wei ,&nbsp;Guang-Jun Ran ,&nbsp;Xiao-Hui Li ,&nbsp;Salman Khan ,&nbsp;Tao Cai ,&nbsp;Chan-Ting Lai ,&nbsp;Hong-Kun Wang ,&nbsp;Bin Wu ,&nbsp;Hai-Xiao Jin ,&nbsp;Wei-Yan Zhang ,&nbsp;Ting-Ting Wang ,&nbsp;Shan He","doi":"10.1016/j.phytol.2025.102944","DOIUrl":"10.1016/j.phytol.2025.102944","url":null,"abstract":"<div><div>Two new <em>α</em>-pyrones, pureones A (<strong>1</strong>) and B (<strong>2</strong>), one analog 6-carbomethoxymethyl-4-hydroxy-2-pyrone (<strong>3</strong>) (isolated as a natural product for the first time), together with 8-acetoxy pestalopyrone (<strong>4</strong>), 6-[(7<em>S</em>,8 <em>R</em>)-8-propyloxiran-1-yl]-4-methoxy-pyran-2-one (<strong>5</strong>), 6-pentyl-4-methoxy-pyran-2-one (<strong>6</strong>), pestalotin (LL-P880<em>α</em>) (<strong>7</strong>), LL-P880<em>β</em> (<strong>8</strong>) and annularin D (<strong>9</strong>) were identified from <em>Purpureocillium</em> sp. NBUF263, associated with an <em>Ircinia</em> sp. sponge from the mesophotic zone. The structures of all isolated compounds were elucidated by spectroscopic data analysis, and the absolute stereochemistry of <strong>2</strong> was determined by the modified Mosher's method. Compounds <strong>2</strong> and <strong>3</strong> exhibited root growth inhibition activities in <em>Arabidopsis thaliana</em> Columbia-0 model at 2.5 and 10.0 μM, respectively.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102944"},"PeriodicalIF":1.3,"publicationDate":"2025-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143680697","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}