Phytochemistry最新文献

{"title":"Antithrombotic macrocyclic sesquiterpene pyridine alkaloids from Tripterygium hypoglaucum","authors":"Qiong Jin ,&nbsp;Jia-Shan Shen ,&nbsp;Xian-Run Wu ,&nbsp;Hui-Zhen Peng ,&nbsp;Zi-Hao Fu ,&nbsp;Li-Qiang Chen ,&nbsp;Yun-Li Zhao ,&nbsp;Min Ye ,&nbsp;Xiao-Dong Luo","doi":"10.1016/j.phytochem.2025.114516","DOIUrl":"10.1016/j.phytochem.2025.114516","url":null,"abstract":"<div><div>Six previously undescribed macrocyclic sesquiterpene pyridine alkaloids (SPAs) derivatives, named triptocumines A–F (<strong>1</strong>–<strong>6</strong>), as well as eighteen known analogs, were isolated from <em>Tripterygium hypoglaucum</em>. The structures were assigned based on analysis of spectroscopic data and electron circular dichroism calculations. Furthermore, compounds <strong>1</strong>−<strong>6</strong>, <strong>8</strong>, and <strong>24</strong> could effectively inhibit adenosine diphosphate-induced platelet aggregation, alleviate thrombosis and oxidative stress in zebrafish, reduce endothelin-1 level, protect endothelial cells from oxidative damage, and promote the formation of lumen structure.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"236 ","pages":"Article 114516"},"PeriodicalIF":3.2,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143859911","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}

{"title":"Nine undescribed pregnane glycosides from Gymnema sylvestre and their glucose uptake and GLUT4 translocation activities","authors":"Meiyu Liu ,&nbsp;Jinyan Zhang ,&nbsp;Yudi Yao ,&nbsp;Jinhua He ,&nbsp;Guangfeng Liao ,&nbsp;Xinzhou Yang ,&nbsp;Rumei Lu","doi":"10.1016/j.phytochem.2025.114513","DOIUrl":"10.1016/j.phytochem.2025.114513","url":null,"abstract":"<div><div>A phytochemical investigation on the ethyl acetate fraction of <em>Gymnema sylvestre</em> led to the production of nine previously undescribed C₂₁ steroidal glycosides sylvepregosides F–N (<strong>1</strong>−<strong>9</strong>), as well as ten known analogues, prosapogenin (<strong>10</strong>), 20-<em>O</em>-benzoyl-12-<em>O</em>-cinnamoyl-3<em>β</em>,5<em>α</em>,8<em>β</em>,12<em>β</em>,14<em>β</em>,17<em>β</em>,20-heptahydroxy-(20<em>S</em>)-pregn-6-ene (<strong>11</strong>), 12-<em>O</em>-cinnamoyl-3<em>β</em>,5<em>α</em>,8<em>β</em>,12<em>β</em>,14<em>β</em>,17<em>β</em>,20-heptahydroxy- (20<em>S</em>)-pregn-6-ene (<strong>12</strong>), stephanoside K (<strong>13</strong>), gymnepregoside C (<strong>14</strong>), gymnepregoside D (<strong>15</strong>), stephanoside O (<strong>16</strong>), isokidjoladinin (<strong>17</strong>), gymsyloside D (<strong>18</strong>) and gymsyloside C (<strong>19</strong>). The structures of these isolated compounds were elucidated based on extensive 1D and 2D nuclear magnetic resonance (NMR) spectra with mass spectrometry data. The biological activities screening demonstrated that compounds <strong>1</strong>, <strong>3</strong>−<strong>6</strong>, <strong>8</strong>−<strong>10</strong>, <strong>12</strong>−<strong>14</strong>, <strong>17</strong>, and <strong>18</strong> promoted glucose uptake by the range of 1.06–1.97 folds. In addition, compounds <strong>3</strong>−<strong>6</strong>, <strong>8</strong>, <strong>13</strong>, <strong>14</strong>, and <strong>19</strong> could promote GLUT-4 translocation to the plasma membrane in L6 cells.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"236 ","pages":"Article 114513"},"PeriodicalIF":3.2,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143886241","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}

{"title":"Bioactive terpenoids and sterols from the fruiting bodies of Fomitopsis pinicola","authors":"Huan Yu ,&nbsp;Qian Chen ,&nbsp;Tian-Chi Xu ,&nbsp;Yue Wang ,&nbsp;Wen-Feng Xu ,&nbsp;Min Li ,&nbsp;Xu Zhang ,&nbsp;Chuan Zhao ,&nbsp;Dong-Li Zhang ,&nbsp;Peng-Fei Jin ,&nbsp;Shao-Yong Li ,&nbsp;Sheng-An Tang","doi":"10.1016/j.phytochem.2025.114510","DOIUrl":"10.1016/j.phytochem.2025.114510","url":null,"abstract":"<div><div>A chemical investigation of the fruiting bodies of <em>Fomitopsis pinicola</em> was conducted, resulting in the isolation of 51 compounds, which included 16 previously undescribed lanostane triterpenes (<strong>1</strong>–<strong>14, 16</strong>–<strong>17</strong>), 30 known analogs (<strong>15, 18</strong>–<strong>46</strong>) as well as two sterols (<strong>47</strong>–<strong>48</strong>) and three diterpenes (<strong>49</strong>–<strong>51</strong>). Comprehensive analyses utilizing 1D, 2D NMR, MS and IR spectroscopy and DFT calculations of ¹³C NMR chemical shifts have elucidated the structures of the compounds in question. Two undescribed compounds in addition to fomitosides F, G and K showed cytotoxicity against MCF-7 cell line with IC₅₀ values ranging from 11.01 to 31.92 μM. Meanwhile, these isolates showed <em>α</em>-glucosidase inhibitory activity, and compound <strong>7</strong> showed the IC₅₀ value of 9.22 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"236 ","pages":"Article 114510"},"PeriodicalIF":3.2,"publicationDate":"2025-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143868176","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}

{"title":"Diterpenoids from Marmoritis complanata and their anti-inflammatory activity in zebrafish","authors":"Ruifeng Liu ,&nbsp;Yongjie Wang ,&nbsp;Xiaobin Li ,&nbsp;Chengmin Zhang ,&nbsp;Peilin Wu ,&nbsp;Xiyue Wang ,&nbsp;Hongxiang Lou ,&nbsp;Jiaozhen Zhang","doi":"10.1016/j.phytochem.2025.114509","DOIUrl":"10.1016/j.phytochem.2025.114509","url":null,"abstract":"<div><div>In a phytochemical investigation of the Tibetan medicine <em>Marmoritis complanata</em> (Dunn) A. L. Budantzev, 30 compounds were identified: 9 undescribed abietane diterpenoids (<strong>1</strong>–<strong>9</strong>), 7 undescribed isopimarane diterpenoids (<strong>12</strong>–<strong>18</strong>) and 14 known compounds (<strong>10</strong>, <strong>11</strong> and <strong>19</strong>–<strong>30</strong>). The structures of the undescribed compounds were determined using one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, electronic circular dichroism and single-crystal X-ray diffraction. The concentration-gradient anti-inflammatory activity evaluation results indicated that most of the tested compounds exhibited concentration-dependent anti-inflammatory activity in the CuSO₄-induced zebrafish model. Abietane (<strong>7</strong>, <strong>9</strong> and <strong>10</strong>) and isopimarane diterpenoids (<strong>13</strong>, <strong>15</strong>, <strong>18</strong> and <strong>24</strong>) particularly showed the most significant anti-inflammatory activity, almost equal to that of a positive control. This study provides a basis for the development of anti-inflammatory drug lead compounds.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"236 ","pages":"Article 114509"},"PeriodicalIF":3.2,"publicationDate":"2025-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143864359","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}

{"title":"Polyketides from a marine medicinal brown alga-derived fungal strain Hypomontagnella monticulosa SC1047","authors":"Hsiao-Yang Hsi ,&nbsp;George Hsiao ,&nbsp;Shih-Wei Wang ,&nbsp;Wan-Ling Chang ,&nbsp;Shu-Jung Huang ,&nbsp;Shan-Chi Liu ,&nbsp;Guang-Wei Chen ,&nbsp;Tzong-Huei Lee","doi":"10.1016/j.phytochem.2025.114508","DOIUrl":"10.1016/j.phytochem.2025.114508","url":null,"abstract":"<div><div>In this study, a marine medicinal brown alga <em>Sargassum cristaefolium</em>-derived fungal strain <em>Hypomontagnella monticulosa</em> SC1047 was isolated and identified. The extracts from liquid-fermented products of the fungal strain were subjected to column chromatography, which yielded ten purified compounds. Their gross structures were characterized by spectroscopic analysis, and the absolute configurations were further established through modified Mosher's method and/or electronic circular dichroism spectroscopy. This analysis led to identification of six previously undescribed compounds, namely hypoketides A–F (<strong>1</strong>–<strong>6</strong>), along with four known compounds <strong>7</strong>–<strong>10</strong>. All the isolates were examined for anti-inflammatory and anti-angiogenic properties. Of the tested compounds, compounds <strong>2</strong> and <strong>7</strong> could moderately inhibit nitric oxide production in lipopolysaccharide-activated BV-2 microglial cells with IC₅₀ values of 4.9 ± 0.3 and 8.9 ± 0.1 μM compared to that of curcumin (IC₅₀ = 2.7 ± 0.3 μM). Compounds <strong>1</strong>, <strong>2</strong>, and <strong>7</strong> exhibited moderate to slight inhibitory effects on the growth of human endothelial progenitor cells with IC₅₀ values ranging from 21.6 ± 0.6 to 63.8 ± 1.8 μM compared to that of sorafenib (IC₅₀ = 4.8 ± 0.5 μM).</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"236 ","pages":"Article 114508"},"PeriodicalIF":3.2,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143855243","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}

{"title":"Antidiabetic constituents of Kaempferiae rhizoma: Previously undescribed O-linked diarylheptanoid dimers promoting GLP-1 secretion via PKA-CREB pathway","authors":"Sheng-Li Wu ,&nbsp;Tian Wang ,&nbsp;Xin-Yu Li ,&nbsp;Pianchou Gongpan ,&nbsp;Xiao-Yan Huang ,&nbsp;Yun-Bao Ma ,&nbsp;Chang-An Geng","doi":"10.1016/j.phytochem.2025.114496","DOIUrl":"10.1016/j.phytochem.2025.114496","url":null,"abstract":"<div><div>Glucagon-like peptide-1 (GLP-1) is a fascinating target for the treatment of diabetes to avoid hypoglycemia. Kaempferiae Rhizoma (KR), the dried rhizomes of <em>Kaempferia galanga</em>, is a famous pungent medicine used for activating Qi, warming interior, removing digestion and relieving pain in China. In order to characterize the antidiabetic effects of KR, 21 previously undescribed O-linked diarylheptanoid dimers, kaemgalangins A₁-A₄ (<strong>1</strong>–<strong>4</strong>), B₁–B₁₃ (<strong>5</strong>–<strong>17</strong>) and C₁–C₄ (<strong>18</strong>–<strong>21</strong>), were isolated from the ethyl acetate fraction. Their structures were determined by extensive spectroscopic analyses, quantum computation and chemical methods. All compounds were tested for their GLP-1 stimulating effects on NCI–H716 cells, most of which showed obvious activity representing a new type of antidiabetic constituents. Especially, compounds <strong>1</strong>, <strong>2</strong> and <strong>16</strong> showed spectacular GLP-1 stimulation with promoting rates of 146.6 ± 31.1 %, 159.0 ± 16.6 % and 142.9 ± 2.7 %, more potent than the positive control. Mechanism study manifested that kaemgalangin A₁ (<strong>1</strong>) promoted GLP-1 secretion through up-regulating the mRNA expression of <em>Gcg</em> and <em>Pc1/3</em>, and the phosphorylation of PKA and CREB, but independent on TGR5 and GPR119 receptors. Furthermore, network pharmacology analysis suggested that the GLP-1 secretion induced by <strong>1</strong> was closely related to MAPK and PI3K-Akt signaling pathways. This investigation first revealed that KR was rich in diarylheptanoid dimers with GLP-1 promoting effects, which provides scientific basis for the antidiabetic application of <em>K. galanga</em>.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"236 ","pages":"Article 114496"},"PeriodicalIF":3.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143776749","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}

{"title":"Oleanane-type triterpenoids from Sabia limoniacea with nitric oxide inhibitory activity","authors":"Ping Hou ,&nbsp;Liwei Pan ,&nbsp;Liuting Peng ,&nbsp;Chunqiu Gan ,&nbsp;Chenyang Ren ,&nbsp;Ruiyun Yang ,&nbsp;Weifeng Xu ,&nbsp;Chaowen He ,&nbsp;Yanlin Cui ,&nbsp;Wen Tang ,&nbsp;Jun Li ,&nbsp;Yan Huang","doi":"10.1016/j.phytochem.2025.114497","DOIUrl":"10.1016/j.phytochem.2025.114497","url":null,"abstract":"<div><div>Fourtheen undescribed oleanane-type triterpenoids (Sabialimons S-Z₆), including five nortriterpenoids (<strong>1</strong>−<strong>5</strong>) and nine normal triterpenoids (<strong>6</strong>−<strong>14</strong>), along with five previously described analogs (<strong>15</strong>−<strong>19</strong>) were isolated and characterized from the stems of <em>Sabia limoniacea.</em> Their structures were fully elucidated via extensive spectroscopic analyses, including 1D and 2D NMR, HRESIMS. Compounds <strong>1</strong>−<strong>3</strong> are oleanane-type triterpenoids which the rings A are broken and the carbons of position 2 are absent to form the five-membered ring-A contracted nortriterpenoids, resulting in the establishment of a 5/6/6/6/6 pentacyclic skeleton. Compounds <strong>4</strong> and <strong>5</strong> represent the interesting variation in which the C-1/C-3 bonds have been oxidatively cleaved to generate ring-A-<em>seco</em> triterpenoids, leading to establishment of a 0/6/6/6/6 tetracyclic skeleton. Biological evaluation revealed that compounds <strong>9</strong> and <strong>10</strong> can inhibited nitric oxide production in lipopolysaccharide stimulated RAW264.7 cells with IC₅₀ values of 36.40 and 36.52 μM, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"236 ","pages":"Article 114497"},"PeriodicalIF":3.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143780808","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}

{"title":"A series of meroterpenoids with highly oxygenated skeletons from the endophytic fungus Penicillium sp. and their anti-inflammatory activities","authors":"Tu-Xiang Mo ,&nbsp;Liu-Xia Lv ,&nbsp;Xi-Shan Huang,&nbsp;Jia-Tong Zhou,&nbsp;Qian Wu,&nbsp;Xian-Hua He,&nbsp;Li-Qi Liang,&nbsp;Wei-Feng Xu,&nbsp;Jun Li,&nbsp;Rui-Yun Yang","doi":"10.1016/j.phytochem.2025.114493","DOIUrl":"10.1016/j.phytochem.2025.114493","url":null,"abstract":"<div><div>Four undescribed meroterpenoids, peniclactone D (<strong>1</strong>) and penichrodrimanins A−C (<strong>5</strong>−<strong>7</strong>), along with five known analogues (<strong>2</strong>−<strong>4</strong>, <strong>8</strong>, and <strong>9</strong>), were isolated from the fungus <em>Penicillium</em> sp. GDGJ-285. Their structures and absolute configurations were established on the basis of spectroscopic analyses and single-crystal X-ray diffraction. Compound <strong>1</strong> represents a highly oxygenated 6/5/6/5/5/5 polycyclic ring system, and <strong>7</strong> is a chrodrimanin-type meroterpenoid with a rare ether linkage between rings A and B <em>via</em> C-3 and C-9. Compound <strong>5</strong> exhibited notable inhibitory effect on nitric oxide (NO) production in LPS-induced RAW 264.7 cells, with the IC₅₀ value of 18.50 ± 1.26 μM compared to dexamethasone (33.61 ± 4.45 μM). The further investigation indicated that <strong>5</strong> could suppress LPS-induced TNF-<em>α</em>, IL-1<em>β</em>, and iNOS expression <em>via</em> inhibition of NF-<em>κ</em>B signaling pathway.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"236 ","pages":"Article 114493"},"PeriodicalIF":3.2,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143746945","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}

{"title":"Isolation of pentasaccharide resin glycosides from the whole plants of Ipomoea biflora and their cytotoxic activities","authors":"Jin-Ping Gu ,&nbsp;Tian-Zi Qi ,&nbsp;Dong-Rong Zhu ,&nbsp;Xu-Jia He ,&nbsp;Su-Peng Guo ,&nbsp;Xin Lan ,&nbsp;Hong Gu ,&nbsp;Jia-Lie Luo ,&nbsp;Min Yang ,&nbsp;Yu-Cheng Gu ,&nbsp;Wen-Li Wang ,&nbsp;Guang-Tong Chen ,&nbsp;Bo-Yi Fan","doi":"10.1016/j.phytochem.2025.114494","DOIUrl":"10.1016/j.phytochem.2025.114494","url":null,"abstract":"<div><div>A total of eight previously undescribed pentasaccharide resin glycosides, named ipomofins I-VIII (<strong>1</strong>–<strong>8</strong>), along with five known ones (<strong>9</strong>–<strong>13</strong>), were isolated from the whole plants of <em>Ipomoea biflora</em>. Their structural elucidation was achieved through a comprehensive application of spectroscopic and chemical techniques. All these resin glycosides were characterized as partially acylated pentasaccharides, originating from operculinic acids A or D, containing <span>l</span>-rhamnose, <span>d</span>-glucose, <span>d</span>-xylose or <span>d</span>-fucose units, and 11<em>S</em>-hydroxyhexadecanoic acid serving as the aglycone. Notably, compounds <strong>1</strong> and <strong>2</strong> represent the first resin glycosides with operculinic acid D as their core structure, while compounds <strong>3</strong> and <strong>4</strong> are the first derivatives of operculinic acid A featuring a 23-membered ring. Compounds <strong>1</strong>, <strong>2</strong>, and <strong>4–6</strong> exhibited apparent cytotoxic effects against certain cancer cell lines. Particularly, compound <strong>5</strong> demonstrated the ability to impair colony formation, reduce the proportion of EdU-positive cells, and enhance the expression of proteins related to endoplasmic reticulum stress (ERS) in HCT-15 cells, indicating that its cytotoxicity might be driven by the activation of ERS pathways. Collectively, this research identified 13 resin glycosides from <em>I. biflora</em>, including eight previously undescribed compounds, with compound <strong>5</strong> emerging as a potential anticancer agent due to its induction of ERS.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"236 ","pages":"Article 114494"},"PeriodicalIF":3.2,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143725970","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}

{"title":"Phenanthrenoid monomers and dimers from Juncus alatus: Isolation, structural characterization, and anti-inflammatory potential","authors":"Jingyi Deng ,&nbsp;Chang-Qiang Ke ,&nbsp;Zheling Feng ,&nbsp;Chunping Tang ,&nbsp;Yang Ye","doi":"10.1016/j.phytochem.2025.114495","DOIUrl":"10.1016/j.phytochem.2025.114495","url":null,"abstract":"<div><div>A systematic investigation of the whole plant of <em>Juncus alatus</em> Franch. et Sav. resulted in the identification of seven novel phenanthrene dimers named alatusins A-G (<strong>1</strong>–<strong>7</strong>) and 11 undescribed monomers (<strong>8</strong>–<strong>9</strong>, <strong>11</strong>–<strong>14</strong> and <strong>18</strong>–<strong>22</strong>), in addition to six known analogues (<strong>10</strong>, <strong>15</strong>–<strong>17</strong> and <strong>23</strong>–<strong>24</strong>). The structures of new 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 <strong>1</strong>–<strong>4</strong> feature a methylene tethering two phenanthrene/9,10-dihydrophenanthrene monomers, while <strong>5</strong> possesses an undescribed linkage of C-5/C-5′. Compound <strong>6</strong> was constructed by forming a six-membered ring spiroed at C-5′. Compound <strong>7</strong> possesses a furan ring to connect two monomeric halves. All the connection patterns have never or rarely been reported before. The racemates of compounds <strong>5</strong>, <strong>6</strong>, <strong>7</strong>, and <strong>14</strong> were separated via chiral HPLC, and their stereochemistry was characterized on-line by circular dichroism (CD) spectroscopy (LC-CD coupling) and comparison of the calculated and experimental ECD spectra. Most compounds were tested for their inhibition of NO on LPS stimulated murine RAW 264.7 cells. Compounds <strong>13</strong> and <strong>18</strong>–<strong>21</strong> exhibited potent inhibitory activity, with IC₅₀ values of 4.11 ± 0.59, 2.89 ± 0.90, 5.98 ± 1.86, 5.77 ± 1.36, and 5.68 ± 0.14 μM, respectively. In the ELISA assays, compound <strong>18</strong> significantly redused the production of pro-inflammatory cytokines, including TNF-α, IL-6, and MCP-1, in LPS-stimulated macrophages. Possible biosynthetic pathways of new dimeric compounds <strong>1</strong>−<strong>7</strong> were proposed.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"236 ","pages":"Article 114495"},"PeriodicalIF":3.2,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143743446","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}