Pub Date : 2025-11-24DOI: 10.1016/j.phytochem.2025.114725
Wan-Qi Zhang, Xin-Yue Li, Ming-Hui Sun, Jie Zhou, Guo-Ru Shi, De-Quan Yu, Yan-Fei Liu
Eight previously undescribed cyclopentanoid monoterpene glycosides, paedosides A–H (1–8), and 19 known analogues were isolated from the aerial parts of Paederia foetida L. The structures of these compounds, especially their absolute configurations, were unequivocally established by comprehensive spectroscopic analysis, various quantum chemical calculations, and single-crystal X-ray diffraction analysis. Compound 1 contains a thiocarbonate group, with the aglycone C-1 linked via O-glycosidic bonds to both sugar C-1′ and C-6′, thereby forming a 7-membered ring. Compounds 2–4 feature a skeleton with three ortho-fused five-membered rings. Proposed biosynthetic pathways for compounds 1–4 are shown in Scheme 1. Compounds 1–27 were tested for cytotoxicity, hepatoprotective activity, and inhibitory effects on NO production in LPS-activated microglia, but all were inactive (IC50 > 10 μM or the compounds showed no significant cell protection at 10 μM).
{"title":"Cyclopentanoid monoterpene glycosides from the aerial parts of Paederia foetida L","authors":"Wan-Qi Zhang, Xin-Yue Li, Ming-Hui Sun, Jie Zhou, Guo-Ru Shi, De-Quan Yu, Yan-Fei Liu","doi":"10.1016/j.phytochem.2025.114725","DOIUrl":"10.1016/j.phytochem.2025.114725","url":null,"abstract":"<div><div>Eight previously undescribed cyclopentanoid monoterpene glycosides, paedosides A–H (<strong>1</strong>–<strong>8</strong>), and 19 known analogues were isolated from the aerial parts of <em>Paederia foetida</em> L. The structures of these compounds, especially their absolute configurations, were unequivocally established by comprehensive spectroscopic analysis, various quantum chemical calculations, and single-crystal X-ray diffraction analysis. Compound <strong>1</strong> contains a thiocarbonate group, with the aglycone C-1 linked via O-glycosidic bonds to both sugar C-1<em>′</em> and C-6<em>′</em>, thereby forming a 7-membered ring. Compounds <strong>2</strong>–<strong>4</strong> feature a skeleton with three <em>ortho</em>-fused five-membered rings. Proposed biosynthetic pathways for compounds <strong>1</strong>–<strong>4</strong> are shown in Scheme 1. Compounds <strong>1</strong>–<strong>27</strong> were tested for cytotoxicity, hepatoprotective activity, and inhibitory effects on NO production in LPS-activated microglia, but all were inactive (IC<sub>50</sub> > 10 <em>μ</em>M or the compounds showed no significant cell protection at 10 <em>μ</em>M).</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114725"},"PeriodicalIF":3.4,"publicationDate":"2025-11-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145616889","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 : 2025-11-24DOI: 10.1016/j.phytochem.2025.114721
Yongqi Tian , Junliang Zhang , Xuan Chen , Dengwei Zhang , Zengzhi Liu , Lisheng Li , Ying Xu , Yong-Xin Li
Genome mining of eight Kibdelosporangium genomes revealed previously untapped biosynthetic potential of diverse natural products. Among these, azicemicins, characterized by a unique aziridine moiety, drew considerable attention. Further genomic and metabolic analysis facilitated the identification of previously undescribed compounds from the K. phytohabitans XY-R10, including two angucyclines (1–2) and six azicemicins (3–8). Their structures were elucidated using comprehensive spectroscopic analyses, single-crystal X-ray diffraction, and electronic circular dichroism. Compounds 3–8 exhibited a distinctive ring-opened aziridine, likely originating from an acetylated aziridine precursor. Notably, compound 3 exhibited significant ferroptosis inhibition by decreasing RSL3-induced HMOX1 gene expression and upregulating GCH1 gene expression.
{"title":"Aziridine-ring-opened azicemicins with ferroptosis inhibitory activity from the Kibdelosporangium phytohabitans XY-R10","authors":"Yongqi Tian , Junliang Zhang , Xuan Chen , Dengwei Zhang , Zengzhi Liu , Lisheng Li , Ying Xu , Yong-Xin Li","doi":"10.1016/j.phytochem.2025.114721","DOIUrl":"10.1016/j.phytochem.2025.114721","url":null,"abstract":"<div><div>Genome mining of eight <em>Kibdelosporangium</em> genomes revealed previously untapped biosynthetic potential of diverse natural products. Among these, azicemicins, characterized by a unique aziridine moiety, drew considerable attention. Further genomic and metabolic analysis facilitated the identification of previously undescribed compounds from the <em>K. phytohabitans</em> XY-R10, including two angucyclines (<strong>1–2</strong>) and six azicemicins (<strong>3–8</strong>). Their structures were elucidated using comprehensive spectroscopic analyses, single-crystal X-ray diffraction, and electronic circular dichroism. Compounds <strong>3–8</strong> exhibited a distinctive ring-opened aziridine, likely originating from an acetylated aziridine precursor. Notably, compound <strong>3</strong> exhibited significant ferroptosis inhibition by decreasing RSL3-induced HMOX1 gene expression and upregulating GCH1 gene expression.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114721"},"PeriodicalIF":3.4,"publicationDate":"2025-11-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145637618","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 : 2025-11-24DOI: 10.1016/j.phytochem.2025.114723
Xin-Yi Hu , Lu Gan , Fei-Yu Zhang , Guang-Hai Zhu , Yi-Ling Liao , Guo-Sen Huang , De-an Guo , Wei Li
Ten previously undescribed nor-clerodane diterpenoids, teuvinoids A−J (1–10), were isolated from the whole plants of Teucrium viscidum. Comprehensive structural elucidation, including unambiguous determination of absolute configurations, was accomplished using spectroscopic analysis, electronic circular dichroism, and single-crystal X-ray diffraction. Teuvinoids A (1) and B (2) are particularly noteworthy for featuring an unusual 2,3,4,5-tetrahydroxylated tetrahydrofuran moiety. Compounds 1 and 2 exhibited anti-hepatic fibrosis effects in TGF-β1-induced LX-2 hepatic stellate cells, as demonstrated by downregulation of key fibrotic biomarkers including fibronectin, collagen I, and α-smooth muscle actin.
{"title":"Tetrahydrofuran- and dihydrofuran-containing nor-clerodane diterpenoids from Teucrium viscidum: Isolation, stereochemical assignment, and anti-hepatic fibrosis activity","authors":"Xin-Yi Hu , Lu Gan , Fei-Yu Zhang , Guang-Hai Zhu , Yi-Ling Liao , Guo-Sen Huang , De-an Guo , Wei Li","doi":"10.1016/j.phytochem.2025.114723","DOIUrl":"10.1016/j.phytochem.2025.114723","url":null,"abstract":"<div><div>Ten previously undescribed <em>nor</em>-clerodane diterpenoids, teuvinoids A−J (<strong>1</strong>–<strong>10</strong>), were isolated from the whole plants of <em>Teucrium viscidum</em>. Comprehensive structural elucidation, including unambiguous determination of absolute configurations, was accomplished using spectroscopic analysis, electronic circular dichroism, and single-crystal X-ray diffraction. Teuvinoids A (<strong>1</strong>) and B (<strong>2</strong>) are particularly noteworthy for featuring an unusual 2,3,4,5-tetrahydroxylated tetrahydrofuran moiety. Compounds <strong>1</strong> and <strong>2</strong> exhibited anti-hepatic fibrosis effects in TGF-<em>β</em>1-induced LX-2 hepatic stellate cells, as demonstrated by downregulation of key fibrotic biomarkers including fibronectin, collagen I, and <em>α</em>-smooth muscle actin.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114723"},"PeriodicalIF":3.4,"publicationDate":"2025-11-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145616887","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}
A phytochemical investigation of the roots of Premna herbacea Roxb. led to the isolation and characterization of ten abietane-type diterpenoids, including five previously undescribed compounds: premnaherbietones A and B (1 and 4), and premnaherbietanes A–C (5–7). Structural elucidation was achieved using comprehensive spectroscopic analysis (1D and 2D NMR, HRESIMS) and confirmed by electronic circular dichroism (ECD) calculations. The previously undescribed compounds possess diverse carbon skeletons, including quinonemethide abietane, 20(10 → 5)-abeo-abietane, and seco-4,5-abietane frameworks. Selected compounds (2, 3, 9, and 10) were evaluated for their α-glucosidase inhibitory and cytotoxic activities. Salvilenone (10) exhibited α-glucosidase inhibition with an IC50 value of 34.6 μM, significantly outperforming the positive control, acarbose (IC50 = 190.4 μM). In silico molecular docking revealed that compound 10 interacts with key active site residues of α-glucosidase through hydrogen bonding and π–π interactions, supporting its inhibitory potential. Bharangin (2) demonstrated notable cytotoxicity against A549 human lung adenocarcinoma cell lines with an IC50 value of 19.4 μM. A plausible biosynthetic pathway for the isolated diterpenoids is also proposed.
{"title":"Abietane diterpenoids and their biological activities from Premna herbacea Roxb.","authors":"Passakorn Teerapongpisan , Angkana Doungsanit , Wuttichai Jaidee , Waroton Paisuwan , Virayu Suthiphasilp , Sarawut Tontapha , Natcha Injan , Somkiat Nokbin , Pakit Kumboonma , Rawiwan Charoensup , Siau Hui Mah , Sarot Cheenpracha , Surat Laphookhieo , Tharakorn Maneerat","doi":"10.1016/j.phytochem.2025.114722","DOIUrl":"10.1016/j.phytochem.2025.114722","url":null,"abstract":"<div><div>A phytochemical investigation of the roots of <em>Premna herbacea</em> Roxb. led to the isolation and characterization of ten abietane-type diterpenoids, including five previously undescribed compounds: premnaherbietones A and B (<strong>1</strong> and <strong>4</strong>), and premnaherbietanes A–C (<strong>5</strong>–<strong>7</strong>). Structural elucidation was achieved using comprehensive spectroscopic analysis (1D and 2D NMR, HRESIMS) and confirmed by electronic circular dichroism (ECD) calculations. The previously undescribed compounds possess diverse carbon skeletons, including quinonemethide abietane, 20(10 → 5)-<em>abeo</em>-abietane, and <em>seco</em>-4,5-abietane frameworks. Selected compounds (<strong>2</strong>, <strong>3</strong>, <strong>9</strong>, and <strong>10</strong>) were evaluated for their <em>α</em>-glucosidase inhibitory and cytotoxic activities. Salvilenone (<strong>10</strong>) exhibited <em>α</em>-glucosidase inhibition with an IC<sub>50</sub> value of 34.6 μM, significantly outperforming the positive control, acarbose (IC<sub>50</sub> = 190.4 μM). In silico molecular docking revealed that compound <strong>10</strong> interacts with key active site residues of <em>α</em>-glucosidase through hydrogen bonding and π–π interactions, supporting its inhibitory potential. Bharangin (<strong>2</strong>) demonstrated notable cytotoxicity against A549 human lung adenocarcinoma cell lines with an IC<sub>50</sub> value of 19.4 μM. A plausible biosynthetic pathway for the isolated diterpenoids is also proposed.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114722"},"PeriodicalIF":3.4,"publicationDate":"2025-11-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145637592","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 : 2025-11-20DOI: 10.1016/j.phytochem.2025.114719
Xishan Bai , Li Zhang , Qiarebati Tuerkesitan , Ziyao Yan , Yuxiao Li , Ziliang Wang , Hongcheng Liu , Liqun Guo , Yanhong Li , Xiangzhong Huang
Five undescribed sesquiterpenes, including a dimeric sesquiterpene lactone with an unreported rare framework, neoversicolactone (1), and four sesquiterpenes, yunnadolins A–D (3–6), and a reidentified dimeric sesquiterpene lactone, versicolactone D (2), were obtained from the roots of Isotrema yunnanense, together with twelve known compounds. Their structures were established by spectroscopic analysis, single-crystal X-ray diffraction, and calculated electronic circular dichroism. Moreover, their analgesic and anti-inflammatory activities were evaluated in vivo and in vitro. All compounds exhibited significant anti-nociceptive activity, up to 59.5 % inhibition, except compounds 1 and 2. Meanwhile, compounds 6 and 15–17 showed better NO inhibition effects with IC50 values of 17.4 ± 2.9, 14.1 ± 2.0, 18.4 ± 0.3, and 12.8 ± 3.0 μM, respectively. Further investigation of the anti-inflammatory effect and mechanism shows that 6 exhibits a distinct anti-inflammatory effect by inhibiting the activation of MAPK/NF-κB pathways. Additionally, it also demonstrated effective anti-rheumatoid arthritis activity.
从云南异trema yunnanense的根中获得了5种未被描述的倍半萜，包括具有未报道的罕见结构的二聚倍半萜内酯，neosicolactone(1)， 4种倍半萜，yunnadolins a -D(3-6)，以及重新鉴定的二聚倍半萜内酯，versicolactone D(2)，以及12种已知化合物。通过光谱分析、单晶x射线衍射和计算电子圆二色性确定了它们的结构。此外，对其体内和体外的镇痛和抗炎活性进行了评价。除化合物1和2外，其余化合物均表现出显著的抗伤害活性，抑制率达59.5%。同时，化合物6和15-17的IC50分别为17.4±2.9 μM、14.1±2.0 μM、18.4±0.3 μM和12.8±3.0 μM，具有较好的NO抑制作用。对其抗炎作用和机制的进一步研究表明，6通过抑制MAPK/NF-κB通路的激活而具有明显的抗炎作用。此外，它还显示出有效的抗类风湿关节炎活性。
{"title":"Structurally diverse sesquiterpenes from the roots of Isotrema yunnanense and their analgesic and anti-inflammatory activity","authors":"Xishan Bai , Li Zhang , Qiarebati Tuerkesitan , Ziyao Yan , Yuxiao Li , Ziliang Wang , Hongcheng Liu , Liqun Guo , Yanhong Li , Xiangzhong Huang","doi":"10.1016/j.phytochem.2025.114719","DOIUrl":"10.1016/j.phytochem.2025.114719","url":null,"abstract":"<div><div>Five undescribed sesquiterpenes, including a dimeric sesquiterpene lactone with an unreported rare framework, neoversicolactone (<strong>1</strong>), and four sesquiterpenes, yunnadolins A–D (<strong>3</strong>–<strong>6</strong>), and a reidentified dimeric sesquiterpene lactone, versicolactone D (<strong>2</strong>), were obtained from the roots of <em>Isotrema yunnanense</em>, together with twelve known compounds. Their structures were established by spectroscopic analysis, single-crystal X-ray diffraction, and calculated electronic circular dichroism. Moreover, their analgesic and anti-inflammatory activities were evaluated <em>in vivo</em> and <em>in vitro</em>. All compounds exhibited significant anti-nociceptive activity, up to 59.5 % inhibition, except compounds <strong>1</strong> and <strong>2</strong>. Meanwhile, compounds <strong>6</strong> and <strong>15</strong>–<strong>17</strong> showed better NO inhibition effects with IC<sub>50</sub> values of 17.4 ± 2.9, 14.1 ± 2.0, 18.4 ± 0.3, and 12.8 ± 3.0 μM, respectively. Further investigation of the anti-inflammatory effect and mechanism shows that <strong>6</strong> exhibits a distinct anti-inflammatory effect by inhibiting the activation of MAPK/NF-<em>κ</em>B pathways. Additionally, it also demonstrated effective anti-rheumatoid arthritis activity.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"243 ","pages":"Article 114719"},"PeriodicalIF":3.4,"publicationDate":"2025-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145582521","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 : 2025-11-07DOI: 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
Lobane- and prenyleudesmane-type diterpenoids represent structurally unique and biologically diverse natural products, predominantly isolated from soft corals in the genera Lobophytum and Sinularia. 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.
{"title":"Rare and underexplored lobane- and prenyleudesmane-type diterpenes primarily from corals with additional plant sources—Biosynthesis and pharmacological perspectives","authors":"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","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":"2025-11-07","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}
Pub Date : 2025-11-04DOI: 10.1016/j.phytochem.2025.114716
Su Hui Seong , Bohyun Yun , Jin-Ho Kim , Chan Seo , Seahee Han , Tae-Su Kim , Bo-Ram Kim , Ha-Nul Lee , Sua Im , Jung Eun Kim , Ji-Min Jung , Kyung-Min Choi , Jin-Woo Jeong
The genus Sedum is recognized for its diverse biological activities; however, the potential anti-depressive properties of Sedum kamtschaticum Fisch. & C. A. Mey. and S. takesimense Nakai, along with their bioactive constituents, remain unexplored. Therefore, this study was conducted to profile the phytochemicals of SK and ST and evaluate their antioxidant, anti-aging, and anti-monoamine oxidase potential in vitro. The 70 % ethanolic extracts of SK and ST showed radical-scavenging, anti-aging, and monoamine oxidase inhibitory activities. Through ultra-performance liquid chromatography–electrospray ionization–high-resolution quadrupole time-of-flight mass spectrometry, three phenolic acids, 12 phenolic glucosides, one ellagic acid, and 14 flavonoids were identified. Notably, four flavonoids were reported for the first time: gossypetin-3,5-di-O-β-d-glucopyranoside-8-O-β-d-xylopyranoside (7), gossypetin-3,5-di-O-β-d-glucopyranoside-8-O-α-l-arabinopyranoside (8), herbacetin-3,5-di-O-β-d-glucopyranoside-8-O-β-d-xylopyranoside (10), and herbacetin-3,5-di-O-β-d-glucopyranoside-8-O-α-l-arabinopyranoside (11), as characterized through mass spectrometry, ultraviolet, electronic circular dichroism, and nuclear magnetic resonance analyses. The biological activity assay revealed that most flavonoids exhibited significant antioxidant and lifespan-extending activities. Moreover, their aglycones—gossypetin and herbacetin—exhibited potent and selective inhibition of monoamine oxidase-B. These findings suggest that gossypetin- and herbacetin-based flavonols, the main active compounds in S. kamtschaticum Fisch. & C. A. Mey. and S. takesimense Nakai, may be employed as lead structures in the development of functional foods or drugs to prevent diseases caused by aging and neurotransmitter imbalances.
景天属以其多样的生物活性而闻名；然而，景天潜在的抗抑郁特性。& C. A.好的。和S. takesimense Nakai及其生物活性成分仍未被探索。因此，本研究对其植物化学成分进行了分析，并对其体外抗氧化、抗衰老和抗单胺氧化酶活性进行了评价。70%乙醇提取物具有清除自由基、抗衰老和抑制单胺氧化酶活性。通过超高效液相色谱-电喷雾电离-高分辨率四极杆飞行时间质谱分析，鉴定出3种酚类酸、12种酚类糖苷、1种鞣花酸和14种黄酮类化合物。值得注意的是，通过质谱、紫外、电子圆二色性和核磁共振分析，首次报道了四种黄酮类化合物：棉苷-3,5-二- o -β- d -葡萄糖吡喃苷-8- o -α- l -阿拉伯糖吡喃苷(7)、棉苷-3,5-二- o -β- d -葡萄糖吡喃苷-8- o -α- l -阿拉伯糖吡喃苷(8)、草糖苷-3,5-二- o -β- d -葡萄糖吡喃苷-8- o -α- l -阿拉伯糖吡喃苷（10）和草糖苷-3,5-二- o -β- d -葡萄糖吡喃苷-8- o -α- l -阿拉伯糖吡喃苷（11）。生物活性分析表明，大多数黄酮类化合物具有显著的抗氧化和延寿活性。此外，它们的糖基——棉籽苷和草菌素——表现出对单胺氧化酶- b的有效和选择性抑制。这些结果表明，棉黄酮醇和草黄酮醇是金缕草的主要活性化合物。& C. A.好的。和S. takesimense Nakai，可能被用作开发功能食品或药物的先导结构，以预防由衰老和神经递质失衡引起的疾病。
{"title":"Herbacetin and gossypetin glycosides from Sedum kamtschaticum Fisch. & C. A. Mey. and S. takesimense Nakai, and their antioxidant, anti-aging, and monoamine oxidase inhibitory activities","authors":"Su Hui Seong , Bohyun Yun , Jin-Ho Kim , Chan Seo , Seahee Han , Tae-Su Kim , Bo-Ram Kim , Ha-Nul Lee , Sua Im , Jung Eun Kim , Ji-Min Jung , Kyung-Min Choi , Jin-Woo Jeong","doi":"10.1016/j.phytochem.2025.114716","DOIUrl":"10.1016/j.phytochem.2025.114716","url":null,"abstract":"<div><div>The genus <em>Sedum</em> is recognized for its diverse biological activities; however, the potential anti-depressive properties of <em>Sedum kamtschaticum</em> Fisch. & C. A. Mey. and <em>S</em>. <em>takesimense</em> Nakai, along with their bioactive constituents, remain unexplored. Therefore, this study was conducted to profile the phytochemicals of SK and ST and evaluate their antioxidant, anti-aging, and anti-monoamine oxidase potential <em>in vitro</em>. The 70 % ethanolic extracts of SK and ST showed radical-scavenging, anti-aging, and monoamine oxidase inhibitory activities. Through ultra-performance liquid chromatography–electrospray ionization–high-resolution quadrupole time-of-flight mass spectrometry, three phenolic acids, 12 phenolic glucosides, one ellagic acid, and 14 flavonoids were identified. Notably, four flavonoids were reported for the first time: gossypetin-3,5-di-<em>O</em>-β-<span>d</span>-glucopyranoside-8-<em>O</em>-β-<span>d</span>-xylopyranoside (<strong>7</strong>), gossypetin-3,5-di-<em>O</em>-β-<span>d</span>-glucopyranoside-8-<em>O</em>-α-<span>l</span>-arabinopyranoside (<strong>8</strong>), herbacetin-3,5-di-<em>O</em>-β-<span>d</span>-glucopyranoside-8-<em>O</em>-β-<span>d</span>-xylopyranoside (<strong>10</strong>), and herbacetin-3,5-di-<em>O</em>-β-<span>d</span>-glucopyranoside-8-<em>O</em>-α-<span>l</span>-arabinopyranoside (<strong>11</strong>), as characterized through mass spectrometry, ultraviolet, electronic circular dichroism, and nuclear magnetic resonance analyses. The biological activity assay revealed that most flavonoids exhibited significant antioxidant and lifespan-extending activities. Moreover, their aglycones—gossypetin and herbacetin—exhibited potent and selective inhibition of monoamine oxidase-B. These findings suggest that gossypetin- and herbacetin-based flavonols, the main active compounds in <em>S</em>. <em>kamtschaticum</em> Fisch. & C. A. Mey. and <em>S</em>. <em>takesimense</em> Nakai, may be employed as lead structures in the development of functional foods or drugs to prevent diseases caused by aging and neurotransmitter imbalances.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114716"},"PeriodicalIF":3.4,"publicationDate":"2025-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145459487","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 : 2025-10-26DOI: 10.1016/j.phytochem.2025.114713
Ming Hu , Run-Cheng Yan , Qiao-Ling Wei, Jiang-Li Su, Bi-Juan Yang, Wen-Chao Tu, Gan-Peng Li, Xing-De Wu
Chemical investigation of the plant pathogen Alternaria solani, associated with Hypoestes phyllostachya, led to the isolation of alternsolain A (1), an unprecedented alternariol-zinnol hybrid, and alternsolains B-G (2–7), six previously undescribed zinnol derivatives containing two pairs of enantiomers, (±)-alternsolains E (5) and F (6), along with five known compounds (8–12). Their structures were elucidated using comprehensive spectral analysis, single-crystal X-ray diffraction, NMR computational techniques, and electronic circular dichroism calculations. Compound 1 possessed a previously unreported carbon skeleton formed through the linkage of alternariol and zinnol via C-8-C-4′ bond. Compound 2 featured a rare dimeric skeleton composed of two zinnol units connected by an ether bond. Plausible biosynthetic pathways for 1 and 2 were also postulated. Additionally, compound 9 showed potent cytotoxic activities against HL-60, MDA-MB-231, and SW480 human cancer cell lines, with IC50 values of 10.73 ± 0.08, 19.40 ± 0.97, and 29.72 ± 1.61 μM, respectively. These results enrich the diversity of zinnols and may provide active compounds for the development of new anticancer drugs.
{"title":"An unprecedented alternariol-zinnol hybrid and six undescribed zinnol derivatives from the phytopathogen Alternaria solani and their cytotoxic activities","authors":"Ming Hu , Run-Cheng Yan , Qiao-Ling Wei, Jiang-Li Su, Bi-Juan Yang, Wen-Chao Tu, Gan-Peng Li, Xing-De Wu","doi":"10.1016/j.phytochem.2025.114713","DOIUrl":"10.1016/j.phytochem.2025.114713","url":null,"abstract":"<div><div>Chemical investigation of the plant pathogen <em>Alternaria solani</em>, associated with <em>Hypoestes phyllostachya</em>, led to the isolation of alternsolain A (<strong>1</strong>), an unprecedented alternariol-zinnol hybrid, and alternsolains B-G (<strong>2</strong>–<strong>7</strong>), six previously undescribed zinnol derivatives containing two pairs of enantiomers, (±)-alternsolains E (<strong>5</strong>) and F (<strong>6</strong>), along with five known compounds (<strong>8</strong>–<strong>12</strong>). Their structures were elucidated using comprehensive spectral analysis, single-crystal X-ray diffraction, NMR computational techniques, and electronic circular dichroism calculations. Compound <strong>1</strong> possessed a previously unreported carbon skeleton formed through the linkage of alternariol and zinnol via C-8-C-4′ bond. Compound <strong>2</strong> featured a rare dimeric skeleton composed of two zinnol units connected by an ether bond. Plausible biosynthetic pathways for <strong>1</strong> and <strong>2</strong> were also postulated. Additionally, compound <strong>9</strong> showed potent cytotoxic activities against HL-60, MDA-MB-231, and SW480 human cancer cell lines, with IC<sub>50</sub> values of 10.73 ± 0.08, 19.40 ± 0.97, and 29.72 ± 1.61 μM, respectively. These results enrich the diversity of zinnols and may provide active compounds for the development of new anticancer drugs.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114713"},"PeriodicalIF":3.4,"publicationDate":"2025-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145392166","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 : 2025-10-24DOI: 10.1016/j.phytochem.2025.114715
Ruitao Yu , Shiwen Kang , Yuanren Ma , Haitao Cheng , Jinghua Chen , Yanduo Tao , Wei Xiong , Xinzhou Yang
Eight previously undescribed compounds, davidinins B–G (1–4, 5a, 5b, 6a and 6b), including two sets of enantiomeric pairs (5a/5b and 6a/6b) together with six known compounds, were isolated from the ethyl acetate fractions of the roots of Sophora davidii (Franch.) Skeels. Using chiral HPLC, the enantiomers (+)-(3R,4R)-davidinin F (5a), (−)-(3S,4S)-davidinin F (5b), (+)-(R)-davidinin G (6a), and (−)-(S)-davidinin G (6b) 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 1–4, 5a, 5b, 6a, 6b, and 7–9 modulated GLUT4 translocation to 1.15–2.47-fold of the control; among them, compound 4 exhibited the strongest increase.
从苦参（Sophora davidii）根的乙酸乙酯部分分离得到8个先前未被描述的化合物，davidinins B-G (1 - 4,5a, 5b, 6a， 6a和6b)，包括两组对映体对（5a/5b和6a/6b）和6个已知化合物。斯基尔。采用手性高效液相色谱法成功分离得到(+)-(3R,4R)-davidinin F (5a),(−)-(3S,4S)-davidinin F (5b), (+)-(R)-davidinin G (6a),(−)-(S)-davidinin G （6b）对映体。通过分析一维和二维NMR和hremsims数据，建立了它们的平面结构。上述化合物的绝对构型主要通过核磁共振计算和电子圆二色性（ECD）计算确定。在浓度为20 μg/mL时，化合物1-4、5a、5b、6a、6b和7-9调节GLUT4易位为对照的1.15 - 2.47倍；其中化合物4增幅最大。
{"title":"Previously undescribed isoflavan-stilbene dimers from the roots of Sophora davidii (Franch.) skeels and their glucose transporter 4 translocation activities","authors":"Ruitao Yu , Shiwen Kang , Yuanren Ma , Haitao Cheng , Jinghua Chen , Yanduo Tao , Wei Xiong , 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":"2025-10-24","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}
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