Phytochemistry最新文献

{"title":"Cytotoxic and anticoagulative diterpenoid glycosides from Pteris decrescens","authors":"Chenliang Zhao ,&nbsp;Yaxin Yang ,&nbsp;Abdullah Al Mamun ,&nbsp;Lei Wang ,&nbsp;Guangjie Li ,&nbsp;Jianghai Ye ,&nbsp;Jingjie Zhang ,&nbsp;Lutai Pan ,&nbsp;Kang He ,&nbsp;Juan Zou ,&nbsp;Hongjie Zhang","doi":"10.1016/j.phytochem.2025.114643","DOIUrl":"10.1016/j.phytochem.2025.114643","url":null,"abstract":"<div><div>Diterpenoids from the genus <em>Pteris</em> have demonstrated consistent anticancer properties. In the present study, five previously undescribed (<strong>1-5</strong>) and four known diterpenoids (<strong>6–9</strong>) were isolated from the 95 % methanol extract of <em>P. decrescens</em>. Among them, decrescensin A (<strong>1</strong>), represents the first naturally occurring example of a 15(8 → 9)-<em>abeo</em>-<em>ent</em>-kauranoid. The structures of these compounds were established based on their spectroscopic data and single-crystal X-ray diffraction. Compounds <strong>1</strong>–<strong>9</strong> have been evaluated for their cytotoxic effects against a panel of cancer cell lines including HeLa, HepG2, A549 and SW480. Compound <strong>1</strong> showed significant activity in SW480 cells with an IC₅₀ value of 0.46 μM. In addition, compounds <strong>4</strong> and <strong>6</strong> displayed a mild prolongation effect on activated partial thromboplastin time.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"240 ","pages":"Article 114643"},"PeriodicalIF":3.4,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144859499","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":"Investigating conserved aromatic residues in ent-copalyl pyrophosphate synthases required for gibberellin phytohormone biosynthesis","authors":"Ahmed M.A.A. Raslan,&nbsp;Cody Lemke ,&nbsp;Raymond Larsen,&nbsp;Reuben J. Peters","doi":"10.1016/j.phytochem.2025.114635","DOIUrl":"10.1016/j.phytochem.2025.114635","url":null,"abstract":"<div><div>Terpene synthases and cyclases catalyze carbocation cascade reactions, which have been hypothesized to be directed, in part, by aromatic residues via stabilization of specific intermediates through cation-π interactions towards specific product outcomes. Included in this are class II diterpene cyclases (DTCs), which are particularly widespread due to their role in initiating biosynthesis of gibberellin (GA) phytohormones but also function in production of a vast range of more specialized (labdane-related) diterpenoids. Indeed, the <em>ent</em>-copalyl pyrophosphate synthases (CPSs) required for GA biosynthesis are then conserved in all plants, with certain plant-associated bacteria that also produce GA containing potentially distantly related such CPSs as well. Building on the structure determined for the CPS from <em>Arabidopsis thaliana</em> (<em>At</em>CPS), sequence comparison reveals that all seven aromatic residues in the active sites are conserved, suggesting these may play important roles in the catalyzed reaction. The role of these aromatic residues in directing product outcome was then examined via a series of substitutions for each in two representative examples, one from plants (<em>At</em>CPS) and the other bacteria (<em>Et</em>CPS from <em>Erwinia tracheiphila</em>). Strikingly, substitution with even aliphatic residues had relatively little effect on product outcome, indicating more general structural roles for these aromatic groups. Accordingly, the role of aromatic residues in directing the carbocation cascade reactions catalyzed by at least such CPSs, if not also terpene cyclases and perhaps even synthases, requires additional evidence beyond simple presence in the active site, even when conserved.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"240 ","pages":"Article 114635"},"PeriodicalIF":3.4,"publicationDate":"2025-08-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144827721","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":"Tris- and tetrakis-iridoids: a review on their occurrence in plants, chemophenetic value and pharmacological activities","authors":"Claudio Frezza ,&nbsp;Daniela De Vita ,&nbsp;Alessandro Venditti ,&nbsp;Marcella Guiso ,&nbsp;Armandodoriano Bianco","doi":"10.1016/j.phytochem.2025.114633","DOIUrl":"10.1016/j.phytochem.2025.114633","url":null,"abstract":"<div><div>In this review paper, the occurrence in plants, structural variability, possible chemophenetic value and pharmacological activities of <em>tris</em>- and <em>tetrakis</em>-iridoids were reported altogether for the first time. In particular, the exact number of these compounds discovered so far was presented, listing their names and detailing the plant species of their recovery with their organs and belonging family as well as the methodologies adopted for their extraction, separation and identification. The structural characteristics of <em>tris</em>- and <em>tetrakis</em>-iridoids were displayed with a particular focus on their specific peculiarities. A chemophenetic evaluation to individuate possible chemophenetic markers among <em>tris</em>- and <em>tetrakis</em>-iridoids was performed on the base of their occurrence at the species, genus and family levels along with a parallel discussion on the regularity of their distribution in the different plant organs. The pharmacological studies on <em>tris</em>- and <em>tetrakis</em>-iridoids were shown after a complete survey of literature data. All these data were widely compared with respect to simple iridoids and <em>bis-</em>iridoids when possible, too. This review paper clearly demonstrates that the research on <em>tris</em>- and <em>tetrakis</em>-iridoids is far from being exhaustive under several aspects and may indeed represent a starting point for future works.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"240 ","pages":"Article 114633"},"PeriodicalIF":3.4,"publicationDate":"2025-08-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144817268","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":"Uncrossing the ‘X’: Characterization of alternative alleles for KSLX in Oryza","authors":"Tristan Weers,&nbsp;Yiling Feng,&nbsp;Reuben J. Peters","doi":"10.1016/j.phytochem.2025.114634","DOIUrl":"10.1016/j.phytochem.2025.114634","url":null,"abstract":"<div><div>The widely cultivated Asian rice (<em>Oryza sativa</em>) produces a variety of physiologically relevant diterpenoid products, which range in effect from the phytohormone gibberellin, derived from <em>ent</em>-kaurene, to phytoalexins such as the momilactones, derived from <em>syn</em>-pimara-7,15-diene. Previous reports have shown functional variation in the kaurene synthase-like (KSL) genes responsible for synthesizing diterpene precursors to more specialized metabolites, leading to the creation of distinct diterpenoids from allelomorphic genes. Here is reported the product of two previously discovered but uncharacterized alleles of the unusual <em>KSLX</em>, representing a cross between (fusion of) the tandem pair <em>KSL8</em>-<em>KSL9p</em> found in most cultivars. The previously characterized allele (KSLXo) was reported to act on <em>syn</em>-copalyl pyrophosphate (<em>syn</em>-CPP) to produce <em>syn</em>-abieta-7,12-diene, precursor to the phytoalexin oryzalactone. However, at least one other functionally distinct allele was reported from the <em>O. sativa</em> pan-genome (KSLXn), along with another phylogenetically distinct allele found in <em>Oryza barthii</em> (KSLXb), but these were not further characterized. Here both KSLXn and KSLXb were found to selectively react with <em>syn</em>-CPP and produce <em>syn</em>-pimara-9(11),15-diene, a novel diterpene in rice. Additionally, evolution of this locus was investigated, with <em>KSLXb</em> hypothesized to be a functional <em>KSL9</em>. The striking complexity of this locus, which includes distinct composition (<em>KSL8-KSL9(p)</em> or <em>KSLX</em>) as well as allelomorphism of both <em>KSL8</em> and <em>KSLX</em>, suggests it is subject to balancing selection, consistent with the competing pressures exerted on phytoalexin biosynthesis. Regardless, the studies reported here clarify this additional example of allelomorphic variation in the rice KSL family, providing insight into the rice pan-genomic diterpenoid arsenal.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"240 ","pages":"Article 114634"},"PeriodicalIF":3.4,"publicationDate":"2025-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144813979","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":"HPLC-UV guided isolation of anti-inflammatory polyacetylene glucosides from Carthamus tinctorius L.","authors":"Yong-Xiang Wang ,&nbsp;Jia-Xu Bao ,&nbsp;Ran Wang ,&nbsp;Xian Zhang ,&nbsp;Yun-Fang Zhao ,&nbsp;Peng-Fei Tu ,&nbsp;Hui-Xia Huo ,&nbsp;Jun Li","doi":"10.1016/j.phytochem.2025.114629","DOIUrl":"10.1016/j.phytochem.2025.114629","url":null,"abstract":"<div><div>HPLC-UV guided fractionation led to the isolation of nineteen previously undescribed polyacetylene glucosides (<strong>1</strong>–<strong>19</strong>) from the florets of <em>Carthamus tinctorius</em> L. Their structures, including the absolute configurations, were established by analysis of UV, IR, HRESIMS, 1D and 2D NMR data, together with enzymatic hydrolysis and ECD calculations. Compounds <strong>1</strong> and <strong>2</strong> were polyacetylene glucosides bearing an unusual furan ring. Compounds <strong>3</strong>–<strong>6</strong> were rare polyacetylene glucosides with an <em>α</em>-<span><em>l</em></span>-arabinofuranosyl moiety, while compound <strong>3</strong> comprised a 1-O-<em>α</em>-<span><em>l</em></span>-arabinofuranosyl-(1 → 3)-<em>β</em>-<span><em>d</em></span>-glucopyranosyl disaccharide unit. Compounds <strong>2</strong>, <strong>4</strong>, <strong>5</strong>, <strong>8</strong>, <strong>11</strong>–<strong>13</strong>, <strong>16</strong>, and <strong>18</strong> showed inhibition of nitric oxide secretion in lipopolysaccharide-stimulated RAW264.7 cells with IC₅₀ values ranging from 5.0 to 40.0 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"240 ","pages":"Article 114629"},"PeriodicalIF":3.4,"publicationDate":"2025-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144749804","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 constituents from Salacia obovatilimba as potential in vitro hSGLT2 inhibitors","authors":"Zhi-Yong Jiang ,&nbsp;Lin Chen ,&nbsp;Hong-Xi Xie ,&nbsp;Jun-Jie Hao ,&nbsp;Rong Chen ,&nbsp;Chun-Qiu Huang ,&nbsp;Hong-Lei Zhang ,&nbsp;Ai-Xue Zuo","doi":"10.1016/j.phytochem.2025.114626","DOIUrl":"10.1016/j.phytochem.2025.114626","url":null,"abstract":"<div><div>Sixteen compounds including twelve previously undescribed sesquiterpenes were isolated from <em>Salacia obovatilimba</em>. Based on HRESIMS, IR, NMR and electronic circular dichroism (ECD) spectroscopic analysis, the previously undescribed compounds were characterized as twelve undescribed dihydro-<em>β</em>-agarofuran sesquiterpenoids (compounds <strong>1</strong>–<strong>12</strong>). The structures of compounds <strong>1</strong> and <strong>6</strong> were confirmed by single-crystal X-ray diffraction. All compounds were assayed for their inhibitory effect on <em>h</em>SGLT2 in vitro, results suggested compounds <strong>11</strong> and <strong>13</strong> exhibited significant <em>h</em>SGLT2 inhibitory activity, with IC₅₀ values of 11.9 and 9.45 nM, respectively. The probable binding potency were predicted through molecular docking by accurate models of protein-ligand complex.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"240 ","pages":"Article 114626"},"PeriodicalIF":3.4,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144720977","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":"Defence induction and identification of key genes associated with Lymantria dispar oral secretions in Populus davidiana × P. bolleana on the basis of transcriptome and hormone levels","authors":"Yuan Gao ,&nbsp;Mengyuan Wang ,&nbsp;Qingjun Xie ,&nbsp;Lili Sun ,&nbsp;Chuanwang Cao","doi":"10.1016/j.phytochem.2025.114625","DOIUrl":"10.1016/j.phytochem.2025.114625","url":null,"abstract":"<div><div>In the constant battle with herbivorous insects, plants have evolved sophisticated recognition and adaptation mechanisms to fight insect attacks. Insect infestation is a major challenge in poplar afforestation production. In this study, we mimicked insect feeding by applying insect oral secretions (OS) to the leaf mechanical wounds of <em>Populus davidiana</em> × <em>P. bolleana</em> and combined transcriptome and hormone analyses to investigate the effects of OS from <em>Lymantria dispar</em> on defence responses and to identify the key genes involved in <em>Populus davidiana</em> × <em>P. bolleana</em> defence. Our results revealed that 3067 differentially expressed genes were involved in the OS-induced response to wounding in <em>Populus davidiana</em> × <em>P. bolleana</em>. OS treatment can rapidly induce the expression of genes related to the jasmonic acid (JA) biosynthetic and signal transduction pathways. The contents of JA, jasmonoyl-<span>l</span>-isoleucine, indole-3-acetic acid and salicylic acid significantly increased in response to OS. To construct a coexpression gene network, a hub gene annotated as <em>WRKY22</em> was identified in <em>Populus davidiana</em> × <em>P. bolleana.</em> To investigate the function of the <em>PdbWRKY22</em> gene against pests, <em>PdbWRKY22</em> was successfully transformed into <em>Populus davidiana × P. bolleana.</em> Transient overexpression of <em>PdbWRKY22</em> induced JA-related gene expression and suppressed the feeding behaviour of <em>L. dispar</em> larvae under OS treatment. These results suggested the defence mechanism of <em>Populus davidiana</em> × <em>P. bolleana</em> against <em>L. dispar</em> at the transcriptional and hormonal levels, and revealed that <em>PdbWRKY22</em> plays a crucial physiological role in <em>Populus davidiana</em> × <em>P. bolleana</em>.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"240 ","pages":"Article 114625"},"PeriodicalIF":3.4,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144724858","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":"Cassane diterpenoids with hepatic gluconeogenesis inhibitory activity from the seeds of Caesalpinia decapetala (Roth) Alston","authors":"De-Sheng Wang ,&nbsp;Yu Shen ,&nbsp;Lin-Fen Ding ,&nbsp;Run-Cheng Yan ,&nbsp;Ming Hu ,&nbsp;Wen-Chao Tu ,&nbsp;Liu-Dong Song ,&nbsp;Suling Huang ,&nbsp;Xing-De Wu","doi":"10.1016/j.phytochem.2025.114628","DOIUrl":"10.1016/j.phytochem.2025.114628","url":null,"abstract":"<div><div>A chemical investigation of the seeds of <em>Caesalpinia decapetala</em> (Roth) Alston led to the isolation of fifteen cassane diterpenoids, including ten previously undescribed compounds (<strong>1</strong>–<strong>10</strong>) and five known analogues (<strong>11</strong>–<strong>15</strong>). The structures of <strong>1</strong>–<strong>10</strong> were determined using ¹H, ¹³C, and 2D NMR, HRESIMS, and IR data. Their absolute configurations were confirmed by comparing experimental electronic circular dichroism data with calculated values, coupled with single-crystal X-ray diffraction analysis. Structurally, compounds <strong>1</strong> and <strong>2</strong> are rare cassane diterpenoids featuring a ketone carbonyl group at C-3. Excessive hepatic gluconeogenesis plays an important role in the occurrence and development of type 2 diabetes mellitus. In the present study, compounds <strong>1</strong>, <strong>3</strong>, <strong>4</strong>, <strong>6</strong>, <strong>11</strong>, and <strong>12</strong> exhibited potent inhibitory effects on gluconeogenesis at a concentration of 20 μM in primary mouse hepatocytes, with inhibitory capacities of 68.2 ± 6.8 %, 78.4 ± 3.5 %, 53.8 ± 6.1 %, 94.8 ± 5.5 %, 85.1 ± 4.1 %, and 106.9 ± 2.9 %, respectively. Further studies indicated that these compounds inhibited gluconeogenesis in a dose-dependent manner across a concentration range from 1 to 50 μM. Notably, compounds <strong>6</strong> and <strong>12</strong> exhibited potent inhibitory effects on gluconeogenesis at a concentration of 2 μM, comparable to the effects of 500 μM metformin, suggesting their potential for ameliorating hyperglycemia.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"240 ","pages":"Article 114628"},"PeriodicalIF":3.2,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144713494","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":"Discovery of rearranged eudesmane-type sesquiterpenes from Artemisia tournefortiana","authors":"Guziliayi Kuerban ,&nbsp;Ablajan Turak ,&nbsp;Nannan Xu ,&nbsp;Dan Tang ,&nbsp;Deng Zang ,&nbsp;Xiayidan Abulimiti ,&nbsp;Jiangyu Zhao ,&nbsp;Haji Akber Aisa","doi":"10.1016/j.phytochem.2025.114627","DOIUrl":"10.1016/j.phytochem.2025.114627","url":null,"abstract":"<div><div>Six undescribed sesquiterpenes artetourneforin F–K (<strong>1</strong>–<strong>6</strong>), along with six known compounds (<strong>7</strong>–<strong>12</strong>), were isolated from <em>Artemisia tournefortiana</em>. Their structures were established by 1D and 2D NMR spectroscopic data, HRESIMS, ECD, and quantum chemical calculations. Artetourneforin F–K (<strong>1</strong>–<strong>6</strong>) represented a rare 4,5-<em>seco</em> undescribed skeleton in natural sesquiterpenes, and a plausible biosynthetic pathway was proposed. The X-ray crystal structures of compounds <strong>7</strong> and <strong>8</strong> were reported for the first time. Compound <strong>9</strong> showed extremely significant anti-inflammatory and cytotoxicity activity against HeLa cell lines with IC₅₀ values of 0.87 ± 0.05 μM and 4.02 ± 0.15 μM, respectively. In the anti-vitiligo activity test, compounds <strong>8</strong> and <strong>10</strong> demonstrated activity in promoting melanogenesis in B16F10 cells. Compound <strong>8</strong> exhibited significant cytotoxicity against the HT29 and MCF7 cell lines, with IC₅₀ values of 6.40 ± 0.41 and 10.18 ± 0.49 μM, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"240 ","pages":"Article 114627"},"PeriodicalIF":3.4,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144718320","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":"Phytochemical profiling of Bai traditional food: Eight previously undescribed meroterpenoids derivatives with cytotoxic potential from the flowers of Rhododendron pachypodum","authors":"Ying Wang ,&nbsp;Jie Luan ,&nbsp;Ji-Ai Wang ,&nbsp;Xiu Chen ,&nbsp;Fu-Cai Ren ,&nbsp;Bing Chen ,&nbsp;Jing Jia ,&nbsp;Gao-Hong Zhang ,&nbsp;Yong Li ,&nbsp;Jiang-Bo He","doi":"10.1016/j.phytochem.2025.114623","DOIUrl":"10.1016/j.phytochem.2025.114623","url":null,"abstract":"<div><div>The flowers of <em>Rhododendron pachypodum</em> (Ericaceae), a traditional edible vegetable of the Bai ethnic group in Yunnan Province, China, are widely used both as food and medicine. A systematic phytochemical survey was conducted to fill the knowledge gap regarding its bioactive constituents. Fourteen meroterpenoids, including eight previously undescribed meroterpenoid compounds, rubiginosin I–J (<strong>1</strong>–<strong>2</strong>), (±)-rubiginosin K (<strong>3</strong>), (±)-rubiginosin L (<strong>4</strong>), (±)-rubiginosin N (<strong>5</strong>), and six known analogues (<strong>6</strong>–<strong>11</strong>), were structurally elucidated using a combination of spectroscopic techniques (1D/2D NMR, HRESIMS, UV, IR). The absolute configurations were unambiguously established by X-ray crystallography and ECD calculations. ‌Selected compounds were assessed for their cytotoxicity, <em>α</em>-glucosidase inhibition, and DPPH radical scavenging activities. Compound <strong>6</strong> demonstrated cytotoxic effects against‌ HepG2 and HeLa cell lines, with IC₅₀ values of 40.56 μM and 57.43 μM, respectively. Compound <strong>7</strong> exhibited a slight cytotoxic activity against A549 cell lines, with an inhibition rate of 60 %, while compound <strong>8</strong> demonstrated mild activity against both A549 and MDA-MB-468 cells, with inhibition rates of 70 % and 65 %, respectively, at a concentration of 100 μM. In the α-glucosidase inhibition assay, compounds <strong>2</strong>–<strong>11</strong> showed weak activity at 100 μg/mL. Similarly, in the DPPH assay, these compounds exhibited poor free radical scavenging activity at 100 μg/mL. This study not only expands the chemical diversity of meroterpenoids in <em>Rhododendron pachypodum</em>, but also provides the first evidence of their cytotoxic potential, although structural optimization is required to enhance bioactivity.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"240 ","pages":"Article 114623"},"PeriodicalIF":3.2,"publicationDate":"2025-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144659884","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}