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Calcium-dependent regulation of anthraquinone biosynthesis by the sweet potato Ib-rolb/C gene in Rubia cordifolia callus cultures 甘薯Ib-rolB/C基因对甘薯愈伤组织中蒽醌合成的钙依赖性调控
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-02-01 Epub Date: 2025-10-21 DOI: 10.1016/j.phytochem.2025.114710
Yury Shkryl , Olga Grishchenko , Elena Vasileva , Natalia Mishchenko , Elena Vasyutkina , Egor Alaverdov , Olesya Kudinova , Galina Tchernoded , Alexandra Fialko , Zhargalma Tsydeneshieva , Maria Sorokina , Yulia Yaroshenko , Anton Degtyarenko , Sergey Fedoreyev , Victor Bulgakov , Yulia Yugay
{"title":"Calcium-dependent regulation of anthraquinone biosynthesis by the sweet potato Ib-rolb/C gene in Rubia cordifolia callus cultures","authors":"Yury Shkryl ,&nbsp;Olga Grishchenko ,&nbsp;Elena Vasileva ,&nbsp;Natalia Mishchenko ,&nbsp;Elena Vasyutkina ,&nbsp;Egor Alaverdov ,&nbsp;Olesya Kudinova ,&nbsp;Galina Tchernoded ,&nbsp;Alexandra Fialko ,&nbsp;Zhargalma Tsydeneshieva ,&nbsp;Maria Sorokina ,&nbsp;Yulia Yaroshenko ,&nbsp;Anton Degtyarenko ,&nbsp;Sergey Fedoreyev ,&nbsp;Victor Bulgakov ,&nbsp;Yulia Yugay","doi":"10.1016/j.phytochem.2025.114710","DOIUrl":"10.1016/j.phytochem.2025.114710","url":null,"abstract":"<div><div>This study investigates how the <em>Ib-rolB/C</em> (<u>ro</u>ot <u>l</u>ocus <em>B/C</em>) gene from sweet potato (<em>Ipomoea batatas</em>), a naturally transgenic plant, influences growth and secondary metabolism in <em>Rubia cordifolia</em> callus cultures. Specifically, its role in regulating anthraquinone (AQ) biosynthesis via calcium-dependent signaling pathways was examined. Transgenic callus lines expressing <em>Ib-rolB/C</em> exhibited robust growth and up to a sixfold increase in AQ production compared to non-transformed controls, particularly when cultured on cytokinin-enriched media. Gene expression analysis revealed strong upregulation of key biosynthetic genes (<em>RcICS</em>, <em>RcOSBS</em>, <em>RcOSBL</em>, and <em>RcIPPi</em>) as well as several calcium-dependent protein kinase (<em>CDPK</em>) isoforms, supporting the hypothesis that <em>Ib-rolB/C</em> modulates calcium-responsive pathways that contribute to the activation of secondary metabolism. Experiments under calcium-deficient and calcium-excess conditions in the culture medium, together with calcium channel inhibitor treatments, confirmed that AQ biosynthesis in transgenic lines is tightly coupled to calcium levels, whereas biomass accumulation was less affected. These findings highlight the regulatory function of <em>Ib-rolB/C</em> in linking calcium signaling with secondary metabolism and offer new insights into the molecular mechanisms of naturally transgenic systems.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114710"},"PeriodicalIF":3.4,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145355671","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Previously undescribed isoflavan-stilbene dimers from the roots of Sophora davidii (Franch.) skeels and their glucose transporter 4 translocation activities 先前未描述的苦荞麦根中异黄酮-二苯乙烯二聚体及其葡萄糖转运蛋白4转运活性
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-02-01 Epub Date: 2025-10-24 DOI: 10.1016/j.phytochem.2025.114715
Ruitao Yu , Shiwen Kang , Yuanren Ma , Haitao Cheng , Jinghua Chen , Yanduo Tao , Wei Xiong , Xinzhou Yang
{"title":"Previously undescribed isoflavan-stilbene dimers from the roots of Sophora davidii (Franch.) skeels and their glucose transporter 4 translocation activities","authors":"Ruitao Yu ,&nbsp;Shiwen Kang ,&nbsp;Yuanren Ma ,&nbsp;Haitao Cheng ,&nbsp;Jinghua Chen ,&nbsp;Yanduo Tao ,&nbsp;Wei Xiong ,&nbsp;Xinzhou Yang","doi":"10.1016/j.phytochem.2025.114715","DOIUrl":"10.1016/j.phytochem.2025.114715","url":null,"abstract":"<div><div>Eight previously undescribed compounds, davidinins B–G (<strong>1</strong>–<strong>4</strong>, <strong>5a</strong>, <strong>5b</strong>, <strong>6a</strong> and <strong>6b</strong>), including two sets of enantiomeric pairs (<strong>5a</strong>/<strong>5b</strong> and <strong>6a</strong>/<strong>6b</strong>) together with six known compounds, were isolated from the ethyl acetate fractions of the roots of <em>Sophora davidii</em> (Franch.) Skeels. Using chiral HPLC, the enantiomers (+)-(3<em>R</em>,4<em>R</em>)-davidinin F (<strong>5a</strong>), (−)-(3<em>S</em>,4<em>S</em>)-davidinin F (<strong>5b</strong>), (+)-(<em>R</em>)-davidinin G (<strong>6a</strong>), and (−)-(<em>S</em>)-davidinin G (<strong>6b</strong>) were successfully separated and obtained. Their planer structures were established through analysis of 1D and 2D NMR and HRESIMS data. The absolute configurations of the previously undescribed compounds were mainly determined by NMR calculation and electronic circular dichroism (ECD) calculation. At a concentration of 20 μg/mL, compounds <strong>1</strong>–<strong>4</strong>, <strong>5a</strong>, <strong>5b</strong>, <strong>6a</strong>, <strong>6b</strong>, and <strong>7</strong>–<strong>9</strong> modulated GLUT4 translocation to 1.15–2.47-fold of the control; among them, compound <strong>4</strong> exhibited the strongest increase.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114715"},"PeriodicalIF":3.4,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145417757","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Phragmalin-type limonoid orthoesters from the twigs and leaves of Khaya ivorensis and their cytotoxic activities 海参细枝和叶片中的phragmalin型类柠檬素酯及其细胞毒活性。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-02-01 Epub Date: 2025-10-13 DOI: 10.1016/j.phytochem.2025.114703
Zong-Yi Zhang , Jia-Nan Wang , Peng Sun , Xiao-Cui Shi , Yi-Dian Xiao , Kai-Long Ji , Chun-Fen Xiao , Xiao-Nian Li , You-Kai Xu , Dong-Hua Cao
{"title":"Phragmalin-type limonoid orthoesters from the twigs and leaves of Khaya ivorensis and their cytotoxic activities","authors":"Zong-Yi Zhang ,&nbsp;Jia-Nan Wang ,&nbsp;Peng Sun ,&nbsp;Xiao-Cui Shi ,&nbsp;Yi-Dian Xiao ,&nbsp;Kai-Long Ji ,&nbsp;Chun-Fen Xiao ,&nbsp;Xiao-Nian Li ,&nbsp;You-Kai Xu ,&nbsp;Dong-Hua Cao","doi":"10.1016/j.phytochem.2025.114703","DOIUrl":"10.1016/j.phytochem.2025.114703","url":null,"abstract":"<div><div>Nine previously unreported phragmalin-type limonoid orthoesters, named ivorenoids G–O (<strong>1</strong>–<strong>9</strong>), together with seventeen known analogues (<strong>10</strong>–<strong>26</strong>) were isolated from the twigs and leaves of <em>Khaya ivorensis</em>. Their structures, including absolute configurations, were determined by extensive spectroscopic analyses, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Selected compounds were evaluated for cytotoxicity against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW480), and their structure–activity relationships were systematically analyzed. Notably, compound <strong>15</strong> exhibited cytotoxicity against A549 and SMMC-7721 cell lines, with IC<sub>50</sub> values of 14.0 ± 0.4 μM and 14.9 ± 0.6 μM, respectively. Compound <strong>22</strong> showed cytotoxicity against SW480 cells, with an IC<sub>50</sub> value of 7.5 ± 0.2 μM, while compound <strong>25</strong> displayed cytotoxicity against A549 cells, with an IC<sub>50</sub> of 14.6 ± 1.9 μM. These findings highlight the potential of limonoid orthesters derived from <em>K. ivorensis</em> as promising lead compounds for further anticancer drug development.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114703"},"PeriodicalIF":3.4,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145302736","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Euphorbia diterpenoids from Euphorbia peplus possessing anti-Alzheimer's activity via targeting PPARγ and upregulating the level of ABCA1 大戟二萜通过靶向PPARγ和上调ABCA1水平而具有抗阿尔茨海默病活性。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-02-01 Epub Date: 2025-10-22 DOI: 10.1016/j.phytochem.2025.114712
Yanlan Yang , Shoulun He , Yingting Lin, Junjie Chen, Renjing Yang, Xueli Li, Jingyu Sun, Guanghui Wang, Wenjing Tian, Haifeng Chen
{"title":"Euphorbia diterpenoids from Euphorbia peplus possessing anti-Alzheimer's activity via targeting PPARγ and upregulating the level of ABCA1","authors":"Yanlan Yang ,&nbsp;Shoulun He ,&nbsp;Yingting Lin,&nbsp;Junjie Chen,&nbsp;Renjing Yang,&nbsp;Xueli Li,&nbsp;Jingyu Sun,&nbsp;Guanghui Wang,&nbsp;Wenjing Tian,&nbsp;Haifeng Chen","doi":"10.1016/j.phytochem.2025.114712","DOIUrl":"10.1016/j.phytochem.2025.114712","url":null,"abstract":"<div><div>Four previously undescribed <em>Euphorbia</em> diterpenoids (<strong>1–3</strong>, <strong>13</strong>), along with 19 known derivatives (<strong>4</strong>–<strong>12</strong>, <strong>14</strong>–<strong>23</strong>), were isolated from the whole plant of <em>Euphorbia peplus</em>. Their structures were characterized by a combination of spectroscopic studies, single-crystal X-ray diffraction and ECD calculations. In this study, all isolates were investigated for their effects on the expression of ABCA1 protein in BV-2 cells. Compound <strong>4</strong> increased ABCA1 levels in a dose-dependent manner. Network pharmacology analysis predicted that PPAR<em>γ</em> might be the potential target for the anti-AD effect of compound <strong>4</strong>. Binding of <strong>4</strong> to the PPAR<em>γ</em> was further confirmed by the fluorescence quenching assay, surface plasmon resonance, fluorescein-labeled differential scanning fluorimetry method, and molecular docking technology. Thus, compound <strong>4</strong> may exert anti-AD effect by targeting PPAR<em>γ</em> and upregulating the level of ABCA1.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114712"},"PeriodicalIF":3.4,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145368542","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Metabolomic analysis of macromycetes from French Guiana reveals chemodiversity in Xylariales order 法属圭亚那大型菌的代谢组学分析揭示了木菌目的化学多样性。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-02-01 Epub Date: 2025-10-20 DOI: 10.1016/j.phytochem.2025.114709
Jonathan Sorres , Juliette Segret , Elsa Van-Elslande , David Touboul , Véronique Eparvier
{"title":"Metabolomic analysis of macromycetes from French Guiana reveals chemodiversity in Xylariales order","authors":"Jonathan Sorres ,&nbsp;Juliette Segret ,&nbsp;Elsa Van-Elslande ,&nbsp;David Touboul ,&nbsp;Véronique Eparvier","doi":"10.1016/j.phytochem.2025.114709","DOIUrl":"10.1016/j.phytochem.2025.114709","url":null,"abstract":"<div><div>An original approach was undertaken to explore the metabolomic variability of macroscopic fungi collected in French Guiana. Extracts from 160 specimens, representing 13 fungal orders, were analyzed using liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS). The resulting metabolomic profiles enabled the construction of chemotaxonomic dendrograms, which successfully grouped most samples assigned to the order Xylariales and highlighted chemodiversity at both the genus and species levels within this lineage. Principal Component Analysis based on molecular family presence/absence revealed 35 discriminant clusters, including specific markers distinguishing <em>Thamnomyces chordalis</em> and <em>Phylacia</em> sp. Five previously undescribed natural products were isolated and structurally characterized: four polyketides—prochordapyrone (<strong>1</strong>) and chordapyrones A–C (<strong>2</strong>–<strong>4</strong>)—and one terpenoid, chordapyranone (<strong>5</strong>). Structural elucidation was accomplished through a combination of nuclear magnetic resonance (NMR) spectroscopy, circular dichroism and single-crystal X-ray diffraction. Based on structural and mechanistic considerations, a putative biosynthetic pathway was proposed for the formation of the polyketide compounds.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114709"},"PeriodicalIF":3.4,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145346430","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Integrated multi-omics demonstrates DNA demethylation-driven activation of the RgMYB2-RgG10H4 axis enhancing iridoid glycoside biosynthesis in Rehmannia glutinosa 综合多组学研究表明,DNA去甲基化驱动的rggmyb2 - rgg10h4轴激活促进了地黄环烯醚萜苷的生物合成。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-02-01 Epub Date: 2025-10-14 DOI: 10.1016/j.phytochem.2025.114705
Tianyu Dong , Yajie Du , Tingting Huang , Jiuchang Su , Qingxiang Yang , Jie Guo , Peilei Chen , Jingjing Xing , Hongying Duan
{"title":"Integrated multi-omics demonstrates DNA demethylation-driven activation of the RgMYB2-RgG10H4 axis enhancing iridoid glycoside biosynthesis in Rehmannia glutinosa","authors":"Tianyu Dong ,&nbsp;Yajie Du ,&nbsp;Tingting Huang ,&nbsp;Jiuchang Su ,&nbsp;Qingxiang Yang ,&nbsp;Jie Guo ,&nbsp;Peilei Chen ,&nbsp;Jingjing Xing ,&nbsp;Hongying Duan","doi":"10.1016/j.phytochem.2025.114705","DOIUrl":"10.1016/j.phytochem.2025.114705","url":null,"abstract":"<div><div><em>Rehmannia glutinosa</em> roots produce a group of lipophilic bioactive components known as iridoid glycosides. However, the molecular mechanisms by which DNA methylation regulates the biosynthesis of iridoid glycosides in <em>R</em>. <em>glutinosa</em> remain unknown. Herein, the development of <em>R</em>. <em>glutinosa</em> roots and the content of iridoid glycosides in the Wenxian region were significantly higher than those in Xinxiang. Low methylation level contributed to the accumulation of iridoid glycosides and the expression of related enzyme genes. Demethylation promoted both roots growth and development, as well as the accumulation of iridoid glycosides. Up-regulated genes including aldehyde dehydrogenase (<em>RgALDH13</em>), 1-hydroxy-2-methyl-2-butenyl 4-diphosphate reductase (<em>RgHDR1</em>), geraniol 10-hydroxylases (<em>RgG10H3</em> and <em>RgG10H4</em>), 1-deoxy-<span>d</span>-xylulose 5-phosphate reductoisomerase (<em>RgDXR1</em>), uroporphyrinogen decarboxylase (<em>RgUPD1</em>), and various transcription factors, collectively form the regulatory network for iridoid glycoside biosynthesis. Furthermore, the primary active region of the <em>RgG10H4</em> promoter is located in the −164 bp region, where the RgMYB2 protein specifically binds to the TAACCA motif in the <em>RgG10H4</em> promoter. Collectively, low DNA methylation enhances core gene expression, promoting iridoid glycoside accumulation, with <em>RgMYB2</em>-<em>RgG10H4</em> positively regulating this process. The study provides new insights into the regulation of iridoid glycosides biosynthesis in plants by DNA methylation.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114705"},"PeriodicalIF":3.4,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145308904","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Rare and underexplored lobane- and prenyleudesmane-type diterpenes primarily from corals with additional plant sources—Biosynthesis and pharmacological perspectives 稀有和未开发的主要来自珊瑚和其他植物来源的Lobane和prenyleudesmane型二萜-生物合成和药理学观点。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-02-01 Epub Date: 2025-11-07 DOI: 10.1016/j.phytochem.2025.114717
Lo-Yun Chen , Bo-Rong Peng , You-Ying Chen , Huong-Giang Le , Ngoc-Thac Pham , Yi-Ying Lin , Hung-Yi Chen , Pei-Jhen Hsieh , Mohamed El-Shazly , Kuei-Hung Lai
{"title":"Rare and underexplored lobane- and prenyleudesmane-type diterpenes primarily from corals with additional plant sources—Biosynthesis and pharmacological perspectives","authors":"Lo-Yun Chen ,&nbsp;Bo-Rong Peng ,&nbsp;You-Ying Chen ,&nbsp;Huong-Giang Le ,&nbsp;Ngoc-Thac Pham ,&nbsp;Yi-Ying Lin ,&nbsp;Hung-Yi Chen ,&nbsp;Pei-Jhen Hsieh ,&nbsp;Mohamed El-Shazly ,&nbsp;Kuei-Hung Lai","doi":"10.1016/j.phytochem.2025.114717","DOIUrl":"10.1016/j.phytochem.2025.114717","url":null,"abstract":"<div><div>Lobane- and prenyleudesmane-type diterpenoids represent structurally unique and biologically diverse natural products, predominantly isolated from soft corals in the genera <em>Lobophytum</em> and <em>Sinularia</em>. This review comprehensively covers the literature from 1978 to 2025, isolation methods, structural elucidation, biological evaluations, and proposed biosynthetic pathways. Based on their reported bioactivities, the compounds were systematically classified, and their potential biosynthetic pathways were proposed. Additionally, a structure–activity relationship (SAR) analysis was conducted to further elucidate the functional groups responsible for their anti-inflammatory, toxicity and anti-fungal properties. To address the challenge of insufficient supply for biological assays, recent total syntheses of representative compounds were also highlighted, providing alternative solutions for future drug discovery and mechanistic studies. This review not only consolidates current knowledge but also provides perspectives for future biosynthetic studies and the development of marine-derived diterpenoids as therapeutic leads.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114717"},"PeriodicalIF":3.4,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145482705","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
NMR-guided isolation of alkaloids from Nigella glandulifera seeds and their bioactivities 核磁共振引导下黑穗槐种子生物碱的分离及其生物活性研究。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-02-01 Epub Date: 2025-10-08 DOI: 10.1016/j.phytochem.2025.114693
Tuernisan Tudi , Ruxianguli Rouzimaimaiti , Deng Zang , Jiangyu Zhao , Haji Akber Aisa
{"title":"NMR-guided isolation of alkaloids from Nigella glandulifera seeds and their bioactivities","authors":"Tuernisan Tudi ,&nbsp;Ruxianguli Rouzimaimaiti ,&nbsp;Deng Zang ,&nbsp;Jiangyu Zhao ,&nbsp;Haji Akber Aisa","doi":"10.1016/j.phytochem.2025.114693","DOIUrl":"10.1016/j.phytochem.2025.114693","url":null,"abstract":"<div><div>NMR-guided investigation of <em>Nigella glandulifera</em> Freyn et Sint seeds led to the isolation and characterization of 11 previously undescribed alkaloids, designated nigelladine D–N (<strong>1</strong>–<strong>11</strong>). These include three skeletons: (+)/(−)-nigelladine D (<strong>1a/1b</strong>), and nigelladine E–F (<strong>2</strong>–<strong>3</strong>); three piperidines: nigelladine G (<strong>4</strong>), (+)/(−)-nigelladine H (<strong>5a/5b</strong>), and nigelladine I (<strong>6</strong>); three indole alkaloids: (+)/(−)-nigelladine J (<strong>7a/7b</strong>) and nigelladine K–L (<strong>8</strong>–<strong>9</strong>); as well as two pyrrole alkaloids: nigelladine M–N (<strong>10</strong>–<strong>11</strong>). In addition, three known 1,4-diazaindane-type pyrrole alkaloids were obtained: agrocybenine (<strong>12</strong>), the enantiomeric pairs (±)-flavascensine (<strong>13a/13b</strong>), and (±)-howlumine (<strong>14a/14b</strong>). Their structures were elucidated using 1D and 2D NMR (Nuclear Magnetic Resonance) spectroscopic analyses, electronic circular dichroism (ECD), quantum chemical calculations, and single-crystal X-ray diffraction (Cu Kα) analysis. Nigelladine D (<strong>1</strong>) skeleton arises from a piperidine ring and a pyrrole ring fusion through a shared nitrogen atom. Nigelladine E (<strong>2</strong>) exhibits an unprecedented 6/6/6/6 dipiperidine-condensed cyclopentane framework, likely formed through dimerization of two piperidine derivatives, whereas nigelladine F (<strong>3</strong>) consists of two piperidine units linked by a pyrrole ring. Furthermore, all compounds exhibited weak inhibitory activity against phosphodiesterase 5 (PDE5) and menin–mixed lineage leukemia 1 (menin–MLL1) protein–protein interaction. Compound <strong>2</strong> significantly increased the melanin content, comparable to that of the positive control 8-methoxypsoralen (8-MOP) (134.50 ± 3.91 % and 134.80 ± 10.24 %, respectively).</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114693"},"PeriodicalIF":3.4,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145275584","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Diterpenoids and sesquiterpenoids from Euphorbia helioscopia and their neuroprotective activity 大戟二萜和倍半萜及其神经保护活性
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-01-01 Epub Date: 2025-08-23 DOI: 10.1016/j.phytochem.2025.114653
Dong-Kun Zheng , Xue-Jin Liu , Xi Chen , Lin Liu , Shui-Chun Mao
{"title":"Diterpenoids and sesquiterpenoids from Euphorbia helioscopia and their neuroprotective activity","authors":"Dong-Kun Zheng ,&nbsp;Xue-Jin Liu ,&nbsp;Xi Chen ,&nbsp;Lin Liu ,&nbsp;Shui-Chun Mao","doi":"10.1016/j.phytochem.2025.114653","DOIUrl":"10.1016/j.phytochem.2025.114653","url":null,"abstract":"<div><div><em>Euphorbia helioscopia</em> L., also known as “Zeqi” in China, has been used for decades as a traditional Chinese medicine to treat various diseases. In this study, a phytochemical investigation of the whole plant of <em>E. helioscopia</em> resulted in the isolation and structural elucidation of two undescribed lathyrane-type diterpenoids, euphohelioscopids A (<strong>1</strong>) and B (<strong>2</strong>), and one unreported megastigmane-type sesquiterpenoid, euphohelioscopid C (<strong>3</strong>), along with 20 known congeners (<strong>4−23</strong>). Their structures with absolute configurations were elucidated, based on a combination of extensive spectroscopic data analyses, ECD, and calculated NMR with the STS strategy, as well as comparison with previously reported NMR data. The isolated compounds were evaluated for their neuroprotective activities against glutamate-induced damage in HT22 cells. Compounds <strong>1</strong>, <strong>3</strong>, <strong>5−8</strong>, <strong>13</strong>, and <strong>17</strong> exhibited varying degrees of neuroprotective effects. Notably, compound <strong>1</strong>, at a low concentration of 5 μM, demonstrated potent activity comparable to that of the positive control, D/L-3-<em>n</em>-butylphthalide (racemic NBP), elevating the cell survival rate from 48.4 % to 82.6 %. Further biological evaluations, including flow cytometric analysis and assessments of the expression of apoptosis-related proteins Bcl-2 and Bax, revealed that compound <strong>1</strong> mitigated glutamate-induced neuronal cell death through an anti-apoptotic pathway. These findings suggested that compound <strong>1</strong> may serve as a valuable lead scaffold for the development of novel neuroprotective agents.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"241 ","pages":"Article 114653"},"PeriodicalIF":3.4,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144908400","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Euphebranes A−G: higher diterpenoids from the radix of Euphorbia ebracteolata 大戟膜A−G:大戟根中的高级二萜
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-01-01 Epub Date: 2025-08-27 DOI: 10.1016/j.phytochem.2025.114657
Shu-Qi Wu , Lei-Ming Wu , Jia-Qian Chen , Fang-Yu Yuan , Dong Huang , Jia-Luo Huang , Yun-Yun Chen , Tao Yuan , Xin Chen , Zhang-Hua Sun , Gui-Hua Tang , Sheng Yin
{"title":"Euphebranes A−G: higher diterpenoids from the radix of Euphorbia ebracteolata","authors":"Shu-Qi Wu ,&nbsp;Lei-Ming Wu ,&nbsp;Jia-Qian Chen ,&nbsp;Fang-Yu Yuan ,&nbsp;Dong Huang ,&nbsp;Jia-Luo Huang ,&nbsp;Yun-Yun Chen ,&nbsp;Tao Yuan ,&nbsp;Xin Chen ,&nbsp;Zhang-Hua Sun ,&nbsp;Gui-Hua Tang ,&nbsp;Sheng Yin","doi":"10.1016/j.phytochem.2025.114657","DOIUrl":"10.1016/j.phytochem.2025.114657","url":null,"abstract":"<div><div>Phytochemical investigation of roots of <em>Euphorbia ebracteolata</em> Hayata led to ten higher diterpenoids including seven undescribed ones (<strong>1</strong>–<strong>7</strong>) and three analogues (<strong>8</strong>−<strong>10</strong>), accompanied by four derivatives (<strong>7a</strong> and <strong>9a</strong>−<strong>9c</strong>) obtained <em>via</em> chemical correlation. Notably, compound <strong>1</strong> represents a rare di<em>nor</em>-<em>ent</em>-isopimarane diterpenoid. Their structures were fully characterized using a combination of spectroscopic, ECD, chemical, and single-crystal X-ray diffraction means. Cytotoxicity screening suggested that the oxidized derivative of <strong>7</strong> (<strong>7a</strong>) displayed the most potent activity against non-small-cell lung cancer (NSCLC) cell line HCC827, comparable to the positive control, cisplatin. Mechanistic study revealed that <strong>7a</strong> could arrest cell cycle at G1/S phase and induce apoptosis.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"241 ","pages":"Article 114657"},"PeriodicalIF":3.4,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144911748","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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