Phytochemistry Letters最新文献

{"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}

{"title":"Daphnicalycinones A and B, Daphniphyllum alkaloids from the roots of Daphniphyllum calycinum with anti-inflammatory activity","authors":"Jiaqi Guo ,&nbsp;Wenlong Li ,&nbsp;Runchao Ma ,&nbsp;Lizhu Han ,&nbsp;Jiani Ying ,&nbsp;Xiongyu Meng ,&nbsp;Huaqiang Li ,&nbsp;Qi Shi ,&nbsp;Luping Qin","doi":"10.1016/j.phytol.2025.102946","DOIUrl":"10.1016/j.phytol.2025.102946","url":null,"abstract":"<div><div>Two undescribed <em>Daphniphyllum</em> alkaloids, daphnicalycinones A and B (<strong>1</strong> and <strong>2</strong>), together with three known analogues, daphnezomine D (<strong>3</strong>), calycindaphine H (<strong>4</strong>) and calycindaphine A (<strong>5</strong>) were isolated from the roots of <em>Daphniphyllum calycinum</em>. Their planar structures and stereo-structures were determined by extensively spectral analyses, including HRESIMS, NMR, DP4 + computational method and single-crystal X-ray crystallography. The anti-inflammatory activities of compounds <strong>1</strong>−<strong>5</strong> were tested on LPS-induced RAW 264.7 cells, and the results showed that <strong>2</strong> and <strong>5</strong> exhibited potent inhibitory effects with the IC₅₀ values of 1.53 ± 0.35 <em>μ</em>M and 10.13 ± 0.72 <em>μ</em>M, respectively.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102946"},"PeriodicalIF":1.3,"publicationDate":"2025-03-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644597","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":"Ultrasound-assisted deep eutectic solvent extraction of kukoamine A and kukoamine B from Lycii cortex","authors":"Xiaomei Wang ,&nbsp;Jinxia Hu ,&nbsp;Ling Ma ,&nbsp;Zhiming Han ,&nbsp;Jianfei Liu ,&nbsp;Zhibin Lu ,&nbsp;Dong Pei ,&nbsp;Ningli Wang ,&nbsp;Duolong Di","doi":"10.1016/j.phytol.2025.02.013","DOIUrl":"10.1016/j.phytol.2025.02.013","url":null,"abstract":"<div><div>Deep eutectic solvents (DES), are new environmentally friendly and efficient extraction solvents, and have considerable importance for environmental protection and sustainable development. In this study, ultrasound-assisted extraction (UAE) using DES was carried out to extract kukoamine A (KuA) and kukoamine B (KuB) from <em>Lycii cortex</em> (LyC). The DES was synthesised using a magnetic stirring method. A novel approach to extract KuA and KuB from LyC was developed by combining UAE with DES. Different DES formulations were tested to evaluate the efficiency of KuA and KuB extraction. Among them, choline chloride-lactic acid (ChCl-LA) DES had the best effect, and its extraction rate was much higher than that of methanol, which was 8.5 times that of methanol. Both single factorial experiments and response surface methodology (RSM) were used to optimise and model the extraction process. Density functional theory was also used to discuss the extraction mechanism. It was found that HBD and HBA will interact with hydrogen bonding and van der Waals interactions during the formation of DES, and these interactions will also affect the decrease in electron density. Taking ChCl-LA and ChCl-urea as examples, it was found that the binding energy of ChCl-LA was lower than that of ChCl-urea, indicating that ChCl-LA had a stronger interaction with the target substance and a higher extraction rate. The combination of UAE-DES proved to be a sustainable, effective, and simple extraction technique for the recovery of KuA and KuB from LyC.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 136-143"},"PeriodicalIF":1.3,"publicationDate":"2025-03-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143577708","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 cytosporin derivatives from the deep-sea-derived fungus Eutypella scoparia FS716","authors":"TingYue Wen ,&nbsp;YuChan Chen ,&nbsp;JiaXi Li ,&nbsp;HongXin Liu ,&nbsp;WeiMin Zhang ,&nbsp;XiaoXia Gao","doi":"10.1016/j.phytol.2025.02.014","DOIUrl":"10.1016/j.phytol.2025.02.014","url":null,"abstract":"<div><div>Two new cytosporin derivatives, cytosporin Y₄ (<strong>1</strong>) and cytosporin Y₅ (<strong>2</strong>), together with seven known compounds (<strong>3–9</strong>) were isolated from <em>Eutypella scoparia</em> FS716, a fungus from the deep-sea sediment in South China Sea. The chemical structures of compounds <strong>1</strong> and <strong>2</strong> were established by 1D, 2D NMR, HRESIMIS, IR and UV spectroscopic data analyses. All the isolated compounds were evaluated for cytotoxic and anti-inflammatory activities. As a result, compounds <strong>3–6, 8</strong> and <strong>9</strong> showed significant anti-inflammatory activities.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 131-135"},"PeriodicalIF":1.3,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143563724","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":"Antiplasmodial-guided isolation of constituents from the stem bark of Balanites aegyptiaca","authors":"Sylvestre Saidou Tsila ,&nbsp;Claire Christine Waleguele ,&nbsp;Noella Molisa Efange ,&nbsp;Billy Toussie Tchegnitegni ,&nbsp;Jean Rodolphe Chouna ,&nbsp;Angelbert Fusi Awantu ,&nbsp;Yannick Stéphane Fotsing Fongang ,&nbsp;Lawrence Ayong ,&nbsp;Norbert Sewald ,&nbsp;Bruno Ndjakou Lenta","doi":"10.1016/j.phytol.2025.02.016","DOIUrl":"10.1016/j.phytol.2025.02.016","url":null,"abstract":"<div><div>The CH₂Cl₂/MeOH (1:1, v/v) extract of the stem bark of <em>Balanites aegyptiaca</em> showed moderate antiplasmodial activity against both the chloroquine sensitive <em>Plasmodium falciparum</em> 3D7 (<em>Pf</em>3D7) and multidrug-resistant <em>Plasmodium falciparum</em> Dd2 (<em>Pf</em>Dd2) strains with IC₅₀ values of 14.20 ± 1.92 and 42.14 ± 2.83 <em>µ</em>g/mL, respectively. The extract was successively subjected to liquid-liquid partition with <em>n-</em>hexane, ethyl acetate, and <em>n-</em>butanol, and the fractions obtained were assessed for their antiplasmodial activity against the same strains. The ethyl acetate soluble fraction was the most active one with IC₅₀ values of 7.74 ± 0.74 and 19.27 ± 2.15 <em>µ</em>g/mL against <em>Pf</em>3D7 and <em>Pf</em>Dd2, respectively, followed by the <em>n-</em>hexane fraction (IC₅₀ = values of 31.06 ± 2.60 and 90.67 ± 0.07 <em>µ</em>g/mL against <em>Pf</em>3D7 and <em>Pf</em>Dd2, respectively). The <em>n-</em>butanol fraction was inactive (IC₅₀ &gt; 50 <em>µ</em>g/mL). Successive column chromatography of the active fractions led to the isolation of fifteen compounds including two new lignans [balanitals A (<strong>1</strong>) and B (<strong>2</strong>)], together with 13 known compounds (<strong>3</strong>–<strong>15</strong>). Their structures were established by means of spectroscopic methods. The isolated compounds were also assessed for their antiplasmodial activity against both <em>Pf</em>3D7 and <em>Pf</em>Dd2. Compound <strong>4</strong> exhibited a good antiplasmodial activity with an IC₅₀ value of 4.95 ± 0.70 <em>µ</em>M against <em>Pf</em>3D7, while it was not active against <em>Pf</em>Dd2 (IC₅₀ &gt; 100 <em>µ</em>M).</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 126-130"},"PeriodicalIF":1.3,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143550766","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 compounds from Pentadesma butyracea and their biological activities","authors":"Yue Yang,&nbsp;Li Hua Gong,&nbsp;Fu Hua Peng,&nbsp;Tao Jiang,&nbsp;Jian Guo Hu,&nbsp;Hong Dong Liu,&nbsp;Bin Li,&nbsp;Yin Xia Yang,&nbsp;Jing Ying Peng,&nbsp;Xue Mei Gao","doi":"10.1016/j.phytol.2025.02.012","DOIUrl":"10.1016/j.phytol.2025.02.012","url":null,"abstract":"<div><div>Two new compounds (<strong>1</strong>-<strong>2</strong>) and twenty-two known compounds (<strong>3</strong>-<strong>24</strong>) were isolated from the ethanol extract of the stems and leaves of <em>Pentadesma butyracea</em> Sabine (Clusiaceae). The structures of compounds <strong>1</strong>-<strong>2</strong> were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR spectroscopy and HRMS techniques. According to previous literature research and molecular docking, we tested antiproliferative and <em>α</em>-glucosidase inhibitory activities of these compounds. Compounds <strong>1</strong>, <strong>5</strong>, and <strong>6</strong> showed good <em>α</em>-glucosidase inhibitory activities with IC₅₀ values of 23.12, 3.60, and 16.83 <em>μ</em>M, respectively. Molecular docking results showed that compounds <strong>1</strong>, <strong>5</strong>, and <strong>6</strong> have strong binding affinities with <em>α</em>-glucosidase. In addition, the antiproliferative activities of compounds <strong>1</strong>, <strong>5</strong>, and <strong>6</strong> against human cancer A549 cells exhibited IC₅₀ values of 41.47, 19.46 and 45.75 <em>μ</em>M, respectively. Except for compound <strong>14</strong>, all the compounds were isolated from the genus <em>Pentadesma</em> for the first time. The findings propose that xanthones with isoprenyl groups may be effective lead compounds for the development of <em>α</em>-glucosidase inhibitors and anticancer therapies.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"66 ","pages":"Pages 119-125"},"PeriodicalIF":1.3,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143550767","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}