Pub Date : 2026-01-31DOI: 10.1016/j.phytochem.2026.114798
Nao Pang , Yafeng Wang , Shuyao Li , Guiqin Li , Li Ge , Zhangbin Liu , Ruijie He , Kedi Yang , Yonglin Huang
The first phytochemical study of Castanopsis choboensis Hickel & A. Camus (Paul Robert Hickel & Aimée Camus) leaves resulted in the isolation and structural characterization of nine previously undescribed glycosidic phenylpropanoid dimers and trimers, designated Choboensins A–I (1–9), along with nine known analogues (10–18). Comprehensive spectroscopic analysis, including HRESIMS and NMR spectroscopy, enabled full structural elucidation of these compounds. Absolute configurations were unambiguously assigned through comparison of experimental and calculated ECD spectra. Of particular structural significance, compound 8 represented the first reported glycosidic phenylpropanoid trimer featuring an unprecedented scaffold formed through the fusion of an aryltetralin-type lignan and a dihydrobenzofuran-type neolignan. Eyerin E exhibited moderate anti-inflammatory activity by inhibiting NO production (IC50 = 15.1 μM) in LPS-stimulated macrophages, highlighting its pharmacological potential.
对Castanopsis choboensis Hickel &； A. Camus （Paul Robert Hickel & aim Camus）叶片的首次植物化学研究导致了九种先前未描述的糖苷苯丙二聚体和三聚体的分离和结构表征，称为Choboensins A-I(1-9)，以及九种已知的类似物（10-18）。全面的光谱分析，包括hresms和NMR光谱，使这些化合物的完整结构阐明。通过比较实验和计算ECD谱，确定了绝对构型。具有特殊结构意义的是，化合物8代表了首次报道的糖苷苯丙类三聚体，其具有前所未有的支架，通过芳基四联素型木脂素和二氢苯并呋喃型新木脂素融合而形成。Eyerin E通过抑制lps刺激的巨噬细胞NO生成（IC50 = 15.1 μM）表现出中等的抗炎活性，显示出其药理潜力。
{"title":"Glycosidic phenylpropanoid dimers and trimers from Castanopsis choboensis and their anti-inflammatory activities","authors":"Nao Pang , Yafeng Wang , Shuyao Li , Guiqin Li , Li Ge , Zhangbin Liu , Ruijie He , Kedi Yang , Yonglin Huang","doi":"10.1016/j.phytochem.2026.114798","DOIUrl":"10.1016/j.phytochem.2026.114798","url":null,"abstract":"<div><div>The first phytochemical study of <em>Castanopsis choboensis</em> Hickel & A. Camus (Paul Robert Hickel & Aimée Camus) leaves resulted in the isolation and structural characterization of nine previously undescribed glycosidic phenylpropanoid dimers and trimers, designated Choboensins A–I (<strong>1</strong>–<strong>9</strong>), along with nine known analogues (<strong>10</strong>–<strong>18</strong>). Comprehensive spectroscopic analysis, including HRESIMS and NMR spectroscopy, enabled full structural elucidation of these compounds. Absolute configurations were unambiguously assigned through comparison of experimental and calculated ECD spectra. Of particular structural significance, compound <strong>8</strong> represented the first reported glycosidic phenylpropanoid trimer featuring an unprecedented scaffold formed through the fusion of an aryltetralin-type lignan and a dihydrobenzofuran-type neolignan. Eyerin E exhibited moderate anti-inflammatory activity by inhibiting NO production (IC<sub>50</sub> = 15.1 μM) in LPS-stimulated macrophages, highlighting its pharmacological potential.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"246 ","pages":"Article 114798"},"PeriodicalIF":3.4,"publicationDate":"2026-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146098689","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}
The 60 % EtOH-eluted fraction (60 %EF) from the roots and rhizomes of Clematis terniflora var. manshurica (Rupr.) Ohwi exhibited potent anti-inflammatory activity with minimal cytotoxicity compared to other fractions. A total of 88 compounds were identified from this fraction by UPLC-Q-TOF-MS analysis, with triterpenoid saponins found to be the most abundant class. Subsequently, nine previously undescribed oleanane-type triterpenoid saponins (1-9), along with twenty known analogues (10-29), were obtained from the 60 % EF. Their structures were elucidated through comprehensive spectroscopic analysis, employing HRESIMS, 1D and 2D NMR techniques. The plausible biosynthetic pathways of the compounds 1-9 were also proposed. All isolates were assessed for anti-inflammatory activity in LPS-stimulated RAW264.7 macrophages, among which 4 showed the strongest inhibition of NO and TNF-α production. Mechanistic studies using western blotting, molecular docking, and molecular dynamics simulations revealed that 4 suppresses NF-κB activation mainly by inhibiting IκBα phosphorylation and stabilizing IκBα protein levels, while also directly interacting with p65 to attenuate its phosphorylation. These findings provide new insights into the anti-inflammatory potential of triterpenoid saponins from C. terniflora var. mandshurica and highlight 4 as a promising NF-κB pathway modulator.
{"title":"Triterpenoid saponins from the roots and rhizomes of Clematis terniflora var. manshurica (Rupr.) Ohwi and their anti-inflammatory activities.","authors":"Sheng Dong, Anqi Lu, Kexin Li, Shiqing Zhao, Jialong Zhao, Jiuzhi Yuan, Chongning Lv, Jincai Lu","doi":"10.1016/j.phytochem.2026.114786","DOIUrl":"10.1016/j.phytochem.2026.114786","url":null,"abstract":"<p><p>The 60 % EtOH-eluted fraction (60 %EF) from the roots and rhizomes of Clematis terniflora var. manshurica (Rupr.) Ohwi exhibited potent anti-inflammatory activity with minimal cytotoxicity compared to other fractions. A total of 88 compounds were identified from this fraction by UPLC-Q-TOF-MS analysis, with triterpenoid saponins found to be the most abundant class. Subsequently, nine previously undescribed oleanane-type triterpenoid saponins (1-9), along with twenty known analogues (10-29), were obtained from the 60 % EF. Their structures were elucidated through comprehensive spectroscopic analysis, employing HRESIMS, 1D and 2D NMR techniques. The plausible biosynthetic pathways of the compounds 1-9 were also proposed. All isolates were assessed for anti-inflammatory activity in LPS-stimulated RAW264.7 macrophages, among which 4 showed the strongest inhibition of NO and TNF-α production. Mechanistic studies using western blotting, molecular docking, and molecular dynamics simulations revealed that 4 suppresses NF-κB activation mainly by inhibiting IκBα phosphorylation and stabilizing IκBα protein levels, while also directly interacting with p65 to attenuate its phosphorylation. These findings provide new insights into the anti-inflammatory potential of triterpenoid saponins from C. terniflora var. mandshurica and highlight 4 as a promising NF-κB pathway modulator.</p>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":" ","pages":"114786"},"PeriodicalIF":3.4,"publicationDate":"2026-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146097358","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}
Ophiobolins present characteristic 1H NMR resonances, which distinctly differ from other metabolites reported from Bipolaris maydis, and were used for an NMR-guided isolation in this research. As a result, 17 undescribed ophiobolin-sesterterpenoids, ophiobolinoids A-Q (1-17), were isolated from Bipolaris maydis. Ophiobolinoids A-C possessed a rare oxygen bridge connecting C-3 and C-21. Their structures were elucidated by comprehensive spectroscopic analyses, DP4+ calculations, ECD calculations, and X-ray diffraction analyses. Specifically, ophibolinoid C showed a weak inhibitory effect on NO production in LPS-induced RAW264.7 cells.
{"title":"<sup>1</sup>H NMR-guided isolation of ophiobolins from Bipolaris maydis and their bioactivities.","authors":"Yong Shen, Xiaotian Zhang, Qin Li, Mengru Yu, Yongqi Li, Luosheng Wan, Xing Sun, Chunmei Chen, Yonghui Zhang, Hucheng Zhu","doi":"10.1016/j.phytochem.2026.114802","DOIUrl":"10.1016/j.phytochem.2026.114802","url":null,"abstract":"<p><p>Ophiobolins present characteristic <sup>1</sup>H NMR resonances, which distinctly differ from other metabolites reported from Bipolaris maydis, and were used for an NMR-guided isolation in this research. As a result, 17 undescribed ophiobolin-sesterterpenoids, ophiobolinoids A-Q (1-17), were isolated from Bipolaris maydis. Ophiobolinoids A-C possessed a rare oxygen bridge connecting C-3 and C-21. Their structures were elucidated by comprehensive spectroscopic analyses, DP4+ calculations, ECD calculations, and X-ray diffraction analyses. Specifically, ophibolinoid C showed a weak inhibitory effect on NO production in LPS-induced RAW264.7 cells.</p>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":" ","pages":"114802"},"PeriodicalIF":3.4,"publicationDate":"2026-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146100578","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}
Pub Date : 2026-01-25DOI: 10.1016/j.phytochem.2026.114785
Zhenhua Wan, Huilin Peng, Chunping Tang, Jiangjiang Qin, Bintao Hu, Changqiang Ke, Sheng Yao, Ligen Lin, Yang Ye
A comprehensive chemical investigation of the rhizomes and roots of Ligularia hodgsonii Hook. was undertaken, which resulted in the identification of 11 previously undescribed eremophilane-type sesquiterpenes (1-4, 7-12, and 14), in addition to five known analogues (5-6, 13, and 15-16). The structures of previously undescribed compounds were fully characterized through comprehensive analysis of HRESIMS, 1D and 2D NMR spectroscopic data, single-crystal X-ray diffraction experiment, and time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculation. Compounds 1-12 represent six pairs of epimers at the C-11 position, and an empirical pattern to distinguish the C-11 stereochemistry was therefore established based on their characteristic Cotton effects in the ECD spectra, which was subsequently applied to revise the absolute configuration of the known compound 13. Furthermore, the pro-angiogenic activity of some isolated compounds was evaluated in human umbilical vein endothelial cells (HUVECs). Compound 14 exhibited potent effect by promoting HUVEC migration and facilitating the formation of capillary-like tubular networks, while compounds 7, 11, 13, and 15 interrupted wound healing in HUVECs. The findings provide the first insights into the bioactivity of eremophilane-type sesquiterpenes responsible for the wound-healing therapeutic effect of L. hodgsonii.
{"title":"Eremophilane-type sesquiterpenes from Ligularia hodgsonii: isolation, structural characterization, and pro-angiogenic potential.","authors":"Zhenhua Wan, Huilin Peng, Chunping Tang, Jiangjiang Qin, Bintao Hu, Changqiang Ke, Sheng Yao, Ligen Lin, Yang Ye","doi":"10.1016/j.phytochem.2026.114785","DOIUrl":"10.1016/j.phytochem.2026.114785","url":null,"abstract":"<p><p>A comprehensive chemical investigation of the rhizomes and roots of Ligularia hodgsonii Hook. was undertaken, which resulted in the identification of 11 previously undescribed eremophilane-type sesquiterpenes (1-4, 7-12, and 14), in addition to five known analogues (5-6, 13, and 15-16). The structures of previously undescribed compounds were fully characterized through comprehensive analysis of HRESIMS, 1D and 2D NMR spectroscopic data, single-crystal X-ray diffraction experiment, and time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculation. Compounds 1-12 represent six pairs of epimers at the C-11 position, and an empirical pattern to distinguish the C-11 stereochemistry was therefore established based on their characteristic Cotton effects in the ECD spectra, which was subsequently applied to revise the absolute configuration of the known compound 13. Furthermore, the pro-angiogenic activity of some isolated compounds was evaluated in human umbilical vein endothelial cells (HUVECs). Compound 14 exhibited potent effect by promoting HUVEC migration and facilitating the formation of capillary-like tubular networks, while compounds 7, 11, 13, and 15 interrupted wound healing in HUVECs. The findings provide the first insights into the bioactivity of eremophilane-type sesquiterpenes responsible for the wound-healing therapeutic effect of L. hodgsonii.</p>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":" ","pages":"114785"},"PeriodicalIF":3.4,"publicationDate":"2026-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146065997","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}
Pub Date : 2026-01-22DOI: 10.1016/j.phytochem.2026.114784
Yi-Fei Liao , George Hsiao , Shih-Wei Wang , Wei-Chiung Chi , Yuan-Chung Cheng , Shu-Jung Huang , Jyh-Yih Leu , Yung-Song Wang , Tzong-Huei Lee
In this study, a fungal strain Diaporthe middletonii Km3279, was isolated from the coralline alga Corallina declinata collected in Lieyu Township, Kinmen County, Taiwan, and subsequently identified. Liquid fermentation was carried out using the OSMAC (one strain, many compounds) strategy, with cultures grown in freshwater potato dextrose broth, brackish water (17 ‰) with malt extract (ME) medium, and freshwater ME medium supplemented with 0.03 % potassium iodide for 14–21 days. Following fermentation, all culture broths were extracted with ethyl acetate. The resulting dried extracts were then sequentially separated and purified by Sephadex LH-20 open-column chromatography, medium-pressure liquid chromatography, and high-performance liquid chromatography. This process led to the isolation and characterization of seven previously undescribed polyketides, designated diaportonicins A–G (1–7), along with five known compounds: periconsin D (8), cryptosporiopsinol (9), periconsin B (10), periconsin E (11), and (S)-6-hydroxymellein (12). In anti-neuroinflammatory assays, compounds 5, 8, 11, and 12 showed potent inhibitory effects on nitric oxide production in murine microglial BV-2 cells with IC50 values of 1.39 ± 0.26, 0.58 ± 0.07, 9.86 ± 1.91, and 6.19 ± 1.30 μM, respectively, and without detectable cytotoxicity. In addition, compounds 5, 7, and 9 exhibited moderate to strong anti-angiogenic activities by inhibiting tube formation in endothelial progenitor cells, with IC50 values of 8.00 ± 1.00, 5.00 ± 1.00, and 26.00 ± 2.00 μM, respectively. A putative biosynthetic pathway for compounds 1–11 is also proposed.
本研究从台湾金门县列屿乡采集的珊瑚藻中分离到一株真菌，并对其进行鉴定。采用OSMAC（一株多化合物）发酵策略，分别在淡水马铃薯葡萄糖肉液、含麦芽提取物（ME）培养基的微淡水（17‰）和添加0.03%碘化钾的淡水ME培养基中培养14 ~ 21 d。发酵后，用乙酸乙酯提取所有培养液。然后用Sephadex LH-20开柱层析、中压液相层析和高效液相层析进行分离纯化。这一过程导致了7个先前未描述的聚酮的分离和表征，命名为diaportonicins A-G(1-7)，以及5个已知化合物：periconsin D (8), cryptosporiopsinol (9), periconsin B (10), periconsin E（11）和(S)-6-hydroxymellein（12）。在抗神经炎实验中，化合物5、8、11和12对小鼠小胶质BV-2细胞的一氧化氮产生有明显的抑制作用，IC50值分别为1.39±0.26、0.58±0.07、9.86±1.91和6.19±1.30 μM，且无细胞毒性。化合物5、7、9通过抑制内皮祖细胞成管表现出中强的抗血管生成活性，IC50值分别为8.00±1.00、5.00±1.00和26.00±2.00 μM。还提出了化合物1-11的推定生物合成途径。
{"title":"Chloro-containing polyketides with anti-neuroinflammatory and anti-angiogenic activities from a coralline algicolous fungal strain Diaporthe middletonii Km3279","authors":"Yi-Fei Liao , George Hsiao , Shih-Wei Wang , Wei-Chiung Chi , Yuan-Chung Cheng , Shu-Jung Huang , Jyh-Yih Leu , Yung-Song Wang , Tzong-Huei Lee","doi":"10.1016/j.phytochem.2026.114784","DOIUrl":"10.1016/j.phytochem.2026.114784","url":null,"abstract":"<div><div>In this study, a fungal strain <em>Diaporthe middletonii</em> Km3279, was isolated from the coralline alga <em>Corallina declinata</em> collected in Lieyu Township, Kinmen County, Taiwan, and subsequently identified. Liquid fermentation was carried out using the OSMAC (one strain, many compounds) strategy, with cultures grown in freshwater potato dextrose broth, brackish water (17 ‰) with malt extract (ME) medium, and freshwater ME medium supplemented with 0.03 % potassium iodide for 14–21 days. Following fermentation, all culture broths were extracted with ethyl acetate. The resulting dried extracts were then sequentially separated and purified by Sephadex LH-20 open-column chromatography, medium-pressure liquid chromatography, and high-performance liquid chromatography. This process led to the isolation and characterization of seven previously undescribed polyketides, designated diaportonicins A–G (<strong>1</strong>–<strong>7</strong>), along with five known compounds: periconsin D (<strong>8</strong>), cryptosporiopsinol (<strong>9</strong>), periconsin B (<strong>10</strong>), periconsin E (<strong>11</strong>), and (<em>S</em>)-6-hydroxymellein (<strong>12</strong>). In anti-neuroinflammatory assays, compounds <strong>5</strong>, <strong>8</strong>, <strong>11</strong>, and <strong>12</strong> showed potent inhibitory effects on nitric oxide production in murine microglial BV-2 cells with IC<sub>50</sub> values of 1.39 ± 0.26, 0.58 ± 0.07, 9.86 ± 1.91, and 6.19 ± 1.30 μM, respectively, and without detectable cytotoxicity. In addition, compounds <strong>5</strong>, <strong>7</strong>, and <strong>9</strong> exhibited moderate to strong anti-angiogenic activities by inhibiting tube formation in endothelial progenitor cells, with IC<sub>50</sub> values of 8.00 ± 1.00, 5.00 ± 1.00, and 26.00 ± 2.00 μM, respectively. A putative biosynthetic pathway for compounds <strong>1</strong>–<strong>11</strong> is also proposed.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"245 ","pages":"Article 114784"},"PeriodicalIF":3.4,"publicationDate":"2026-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146044052","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}
Pub Date : 2026-01-22DOI: 10.1016/j.phytochem.2026.114787
Yu Zhang , Yu-Chen Zhang , Yu-Chen Fan , Chen-Sen Xu , Hao-Lin Yu , Chao Wang , Jing Zhang , Yi-Lin Liu , Yi-Bo Shen , Chao Liu , Jin-Yue Sun , Jin-Zhong Hu , Zhi-Xin Liao
From the rhizomes of Paris polyphylla var. yunnanensis (Franch.) Hand.-Mazz., five novel steroidal saponins (Polyphyllozsides A-E, 1–5) and four known steroidal saponins (6–9) were isolated. The biological activities of the nine compounds against human hematologic malignancy cell lines (U-937, THP-1 and Jurkat) was evaluated using a cytotoxicity assay. The results demonstrated that compound 9 significantly inhibited the proliferation of Jurkat cells, with an IC50 value of 0.25 ± 0.03 μM. Compound 9 likely induces tumor cell apoptosis and inhibits cell cycle progression via targeting the PI3K/AKT/GSK3β signaling pathway, providing critical molecular evidence for the development of target-specific anti-leukemia therapeutics.
源自云南多叶巴黎（Paris polyphylla var. yunnanensis）根状茎Hand.-Mazz。共分离得到5个新的甾体皂苷（多叶黄苷A-E， 1-5）和4个已知的甾体皂苷（6-9）。用细胞毒法评价9种化合物对人血液恶性肿瘤细胞株（U-937、THP-1和Jurkat）的生物活性。结果表明，化合物9能显著抑制Jurkat细胞的增殖，IC50值为0.25±0.03 μM。化合物9可能通过靶向PI3K/AKT/GSK3β信号通路诱导肿瘤细胞凋亡并抑制细胞周期进程，为靶向特异性抗白血病治疗药物的开发提供关键的分子证据。
{"title":"Anti-leukemia steroidal saponins from Paris polyphylla var. yunnanensis","authors":"Yu Zhang , Yu-Chen Zhang , Yu-Chen Fan , Chen-Sen Xu , Hao-Lin Yu , Chao Wang , Jing Zhang , Yi-Lin Liu , Yi-Bo Shen , Chao Liu , Jin-Yue Sun , Jin-Zhong Hu , Zhi-Xin Liao","doi":"10.1016/j.phytochem.2026.114787","DOIUrl":"10.1016/j.phytochem.2026.114787","url":null,"abstract":"<div><div>From the rhizomes of <em>Paris polyphylla</em> var. <em>yunnanensis</em> (Franch.) Hand.-Mazz., five novel steroidal saponins (Polyphyllozsides A-E, <strong>1</strong>–<strong>5</strong>) and four known steroidal saponins (<strong>6</strong>–<strong>9</strong>) were isolated. The biological activities of the nine compounds against human hematologic malignancy cell lines (U-937, THP-1 and Jurkat) was evaluated using a cytotoxicity assay. The results demonstrated that compound <strong>9</strong> significantly inhibited the proliferation of Jurkat cells, with an IC<sub>50</sub> value of 0.25 ± 0.03 μM. Compound <strong>9</strong> likely induces tumor cell apoptosis and inhibits cell cycle progression via targeting the PI3K/AKT/GSK3<em>β</em> signaling pathway, providing critical molecular evidence for the development of target-specific anti-leukemia therapeutics.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"245 ","pages":"Article 114787"},"PeriodicalIF":3.4,"publicationDate":"2026-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146043737","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}
Pub Date : 2026-01-22DOI: 10.1016/j.phytochem.2026.114788
Wenxiang Xu , Qian Zhang , Xinyuan Li , Zhenyun Liu , Peng Jiang , Yiqiang Zhang , Yumeng Luo , Wei Guan , Mengmeng Li , Qingyue Bu , Qingshan Chen , Lili Zhang , Xiaochi Ma , Haixue Kuang , Yan Liu
In total, 14 undescribed triterpenoid saponins (1–14), along with three known ones (15–17), were isolated from the leaves of Astragalus membranaceus (Fisch.) Bge. In the case of previously unknown compounds, it was observed that dehydration occurred between the hydroxyl group at C-24 and the hydroxyl group at C-16 in compounds 1–3. This resulted in the formation of an ether bond, leading to the creation of a previously undescribed seven-membered structure. The structures were elucidated based on comprehensive spectroscopic analysis, encompassing HRESIMS, 1D and 2D NMR data, X-ray diffraction, DP4+ analysis, electron circular dichroism (ECD) calculations as well as comparison with published literature data. Additionally, HT22 cells induced with d-galactose were employed to evaluate the neuroprotective potential of all isolated triterpenoids. Results showed that triterpenoids 1–3 as well as 12–14 demonstrated notable neuroprotective benefits.
{"title":"Undescribed triterpenoid saponins from the leaves of Astragalus membranaceus (Fisch.) Bge. and their neuroprotective effects","authors":"Wenxiang Xu , Qian Zhang , Xinyuan Li , Zhenyun Liu , Peng Jiang , Yiqiang Zhang , Yumeng Luo , Wei Guan , Mengmeng Li , Qingyue Bu , Qingshan Chen , Lili Zhang , Xiaochi Ma , Haixue Kuang , Yan Liu","doi":"10.1016/j.phytochem.2026.114788","DOIUrl":"10.1016/j.phytochem.2026.114788","url":null,"abstract":"<div><div>In total, 14 undescribed triterpenoid saponins (<strong>1</strong>–<strong>14</strong>), along with three known ones (<strong>15</strong>–<strong>17</strong>), were isolated from the leaves of <em>Astragalus membranaceus</em> (Fisch.) Bge. In the case of previously unknown compounds, it was observed that dehydration occurred between the hydroxyl group at C-24 and the hydroxyl group at C-16 in compounds <strong>1</strong>–<strong>3</strong>. This resulted in the formation of an ether bond, leading to the creation of a previously undescribed seven-membered structure. The structures were elucidated based on comprehensive spectroscopic analysis, encompassing HRESIMS, 1D and 2D NMR data, X-ray diffraction, DP4+ analysis, electron circular dichroism (ECD) calculations as well as comparison with published literature data. Additionally, HT22 cells induced with <span>d</span>-galactose were employed to evaluate the neuroprotective potential of all isolated triterpenoids. Results showed that triterpenoids <strong>1</strong>–<strong>3</strong> as well as <strong>12</strong>–<strong>14</strong> demonstrated notable neuroprotective benefits.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"245 ","pages":"Article 114788"},"PeriodicalIF":3.4,"publicationDate":"2026-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146044096","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}
Pub Date : 2026-01-21DOI: 10.1016/j.phytochem.2026.114783
Trung Huy Ngo , Ngoc Duy Le , Kibria Gulam , Hyukjae Choi , Jong Oh Kim , Joo-Won Nam
Flowers of Inula japonica Thunb., a rich source of sesquiterpenoids, have long been used in traditional medicine to improve inflammatory conditions. To explore previously unreported anti-inflammatory sesquiterpenoids, isolation and structural elucidation were performed on this plant material, yielding 18 compounds (1−18), including 6 previously undescribed sesquiterpenoids (1−3 and 6−8). The structures of these compounds, including their absolute configurations, were assigned based on one- and two-dimensional nuclear magnetic resonance experiments, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism spectral calculations and measurements, and chemical derivatization. Compounds 3, 8−11, 14, and 18 significantly inhibited NO production in lipopolysaccharide-stimulated macrophages. Network pharmacology analysis suggested the involvement of the MAPK signaling pathway, along with key targets such as AKT1, EGFR, JUN, CASP3, CCND1, and IL1B, in the biological action of the active compounds. This outcome is supported by a molecular docking model, which proposes binding patterns between the active compounds and key targets. The results of this study improve our understanding of the anti-inflammatory mechanisms of I. japonica flowers and contribute to the structural diversity of bioactive sesquiterpenoids.
{"title":"Discovery of and mechanistic insights into anti-inflammatory sesquiterpenoids from flowers of Inula japonica Thunb","authors":"Trung Huy Ngo , Ngoc Duy Le , Kibria Gulam , Hyukjae Choi , Jong Oh Kim , Joo-Won Nam","doi":"10.1016/j.phytochem.2026.114783","DOIUrl":"10.1016/j.phytochem.2026.114783","url":null,"abstract":"<div><div>Flowers of <em>Inula japonica</em> Thunb., a rich source of sesquiterpenoids, have long been used in traditional medicine to improve inflammatory conditions. To explore previously unreported anti-inflammatory sesquiterpenoids, isolation and structural elucidation were performed on this plant material, yielding 18 compounds (<strong>1</strong>−<strong>18</strong>), including 6 previously undescribed sesquiterpenoids (<strong>1</strong>−<strong>3</strong> and <strong>6</strong>−<strong>8</strong>). The structures of these compounds, including their absolute configurations, were assigned based on one- and two-dimensional nuclear magnetic resonance experiments, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism spectral calculations and measurements, and chemical derivatization. Compounds <strong>3</strong>, <strong>8</strong>−<strong>11</strong>, <strong>14</strong>, and <strong>18</strong> significantly inhibited NO production in lipopolysaccharide-stimulated macrophages. Network pharmacology analysis suggested the involvement of the MAPK signaling pathway, along with key targets such as AKT1, EGFR, JUN, CASP3, CCND1, and IL1B, in the biological action of the active compounds. This outcome is supported by a molecular docking model, which proposes binding patterns between the active compounds and key targets. The results of this study improve our understanding of the anti-inflammatory mechanisms of <em>I. japonica</em> flowers and contribute to the structural diversity of bioactive sesquiterpenoids.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"245 ","pages":"Article 114783"},"PeriodicalIF":3.4,"publicationDate":"2026-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146041229","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}
Pub Date : 2026-01-20DOI: 10.1016/j.phytochem.2026.114781
Sheng-Zhi Wang , Hong Zhu , Xiao-Po Zhang , De-Li Chen
Natural cadinene-type sesquiterpenoids (CTSs) exhibit diverse structures and a wide range of pharmacological activities, including anti-tumor, anti-inflammatory, and antibacterial effects. They represent an important source for new drug discovery and development. By searching the PubMed, Web of Science, and the China National Knowledge Infrastructure (CNKI) databases, this review summarizes the research progress on 283 naturally occurring CTSs isolated and identified from plants, terrestrial fungi, marine organisms, and bacteria between 2015 and 2025. Based on their structural characteristics, these CTSs were classified into 145 bicyclic CTSs, 76 tricyclic CTSs, 37 carbon-bridged CTS dimers, 13 oxygen-bridged CTS dimers, 2 CTS trimers, and 10 heterocyclic CTSs. In addition, the biological activities and biosynthetic pathways of selected compounds are summarized. This work may facilitate the discovery and development of therapeutic agents derived from natural CTSs.
天然鸡丁烯型倍半萜类化合物（CTSs）具有多种结构和广泛的药理活性，包括抗肿瘤、抗炎和抗菌作用。它们是新药发现和开发的重要来源。通过检索PubMed、Web of Science和中国知网（CNKI）数据库，总结了2015 ~ 2025年从植物、陆生真菌、海洋生物和细菌中分离鉴定的283种天然CTSs的研究进展。根据结构特征，将这些CTSs分为145个双环CTSs、76个三环CTSs、37个碳桥CTS二聚体、13个氧桥CTS二聚体、2个CTS三聚体和10个杂环CTS。此外，还对所选化合物的生物活性和生物合成途径进行了综述。这项工作可能有助于从天然CTSs衍生的治疗剂的发现和开发。
{"title":"Natural cadinane-type sesquiterpenoids and their bioactivity: a review (2015–2025)","authors":"Sheng-Zhi Wang , Hong Zhu , Xiao-Po Zhang , De-Li Chen","doi":"10.1016/j.phytochem.2026.114781","DOIUrl":"10.1016/j.phytochem.2026.114781","url":null,"abstract":"<div><div>Natural cadinene-type sesquiterpenoids (CTSs) exhibit diverse structures and a wide range of pharmacological activities, including anti-tumor, anti-inflammatory, and antibacterial effects. They represent an important source for new drug discovery and development. By searching the PubMed, Web of Science, and the China National Knowledge Infrastructure (CNKI) databases, this review summarizes the research progress on 283 naturally occurring CTSs isolated and identified from plants, terrestrial fungi, marine organisms, and bacteria between 2015 and 2025. Based on their structural characteristics, these CTSs were classified into 145 bicyclic CTSs, 76 tricyclic CTSs, 37 carbon-bridged CTS dimers, 13 oxygen-bridged CTS dimers, 2 CTS trimers, and 10 heterocyclic CTSs. In addition, the biological activities and biosynthetic pathways of selected compounds are summarized. This work may facilitate the discovery and development of therapeutic agents derived from natural CTSs.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"245 ","pages":"Article 114781"},"PeriodicalIF":3.4,"publicationDate":"2026-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146024156","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}
Pub Date : 2026-01-13DOI: 10.1016/j.phytochem.2026.114780
An Jin , Zhuocan Huang , Hui Li , Jinling Chang , Hanli Ruan , Wenming Wu
A detailed phytochemical analysis of the dried, ripe fruits of Kadsura coccinea led to the isolation and structural characterization of eleven undescribed lignans, designated kadcolignan K–U (1–11), together with thirteen previously documented compounds (12–24). Notably, kadcolignan U (11) is particularly distinctive, representing a rare dearomatized lignan with a dienone moiety and an uncommon 7, 2′–oxygen bridge. Mechanistic evaluation of the most potent isolates, kadcolignan O (5) and kadcolignan Q (7), revealed their capacity to trigger apoptosis in activated mice B lymphocytes through mitochondrial-dependent pathways, as evidenced by dose-dependent elevation of pro-apoptotic Bax, suppression of anti-apoptotic Bcl-2/Bcl-xL, and release of cleaved caspase-3 and caspase-9. Additionally, both metabolites were found to disrupt the PI3K/AKT/mTOR signaling axis by inhibiting the phosphorylation of PI3K, AKT, and mTOR in a dose-dependent manner. Our findings highlight K. coccinea as a source of B cell-targeted immunosuppressants, with 5 and 7 emerging as promising candidates for further development in autoimmune disease therapy.
{"title":"Dibenzocyclooctadiene lignans from Kadsura coccinea and their immunosuppressive activities","authors":"An Jin , Zhuocan Huang , Hui Li , Jinling Chang , Hanli Ruan , Wenming Wu","doi":"10.1016/j.phytochem.2026.114780","DOIUrl":"10.1016/j.phytochem.2026.114780","url":null,"abstract":"<div><div>A detailed phytochemical analysis of the dried, ripe fruits of <em>Kadsura coccinea</em> led to the isolation and structural characterization of eleven undescribed lignans, designated kadcolignan K–U (<strong>1</strong>–<strong>11</strong>), together with thirteen previously documented compounds (<strong>12</strong>–<strong>24</strong>). Notably, kadcolignan U (<strong>11</strong>) is particularly distinctive, representing a rare dearomatized lignan with a dienone moiety and an uncommon 7, 2′–oxygen bridge. Mechanistic evaluation of the most potent isolates, kadcolignan O (<strong>5</strong>) and kadcolignan Q (<strong>7</strong>), revealed their capacity to trigger apoptosis in activated mice B lymphocytes through mitochondrial-dependent pathways, as evidenced by dose-dependent elevation of pro-apoptotic Bax, suppression of anti-apoptotic Bcl-2/Bcl-xL, and release of cleaved caspase-3 and caspase-9. Additionally, both metabolites were found to disrupt the PI3K/AKT/mTOR signaling axis by inhibiting the phosphorylation of PI3K, AKT, and mTOR in a dose-dependent manner. Our findings highlight <em>K. coccinea</em> as a source of B cell-targeted immunosuppressants, with <strong>5</strong> and <strong>7</strong> emerging as promising candidates for further development in autoimmune disease therapy.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"245 ","pages":"Article 114780"},"PeriodicalIF":3.4,"publicationDate":"2026-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145979583","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}
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