Ye Zhou , Ruyuan Wang , Rui Feng , Bi Wang , Shu Xu , Mei Tian , Wenhao Liang , Jin Chen , Yu Chen , Xu Feng , Li Lin , Jinyue Luo , Jianlan Wang , Fei Liu
{"title":"The synthesis of arylmethylene bisindoles catalyzed by nickel perchlorate as potential antifungal agent against Clarireedia homoeocarpa","authors":"Ye Zhou , Ruyuan Wang , Rui Feng , Bi Wang , Shu Xu , Mei Tian , Wenhao Liang , Jin Chen , Yu Chen , Xu Feng , Li Lin , Jinyue Luo , Jianlan Wang , Fei Liu","doi":"10.1016/j.phytol.2025.102966","DOIUrl":"10.1016/j.phytol.2025.102966","url":null,"abstract":"<div><div>Arylmethylene bisindole alkaloids are predominantly found in cruciferous plants and as metabolites in marine organisms, exhibiting a diverse range of biological activities. In recent years, these alkaloids have been increasingly explored and utilized for controlling plant pathogenic fungi. However, the synthesis and underlying mechanisms, particularly their effectiveness against plant pathogens such as <em>Clarireedia homoeocarpa</em>, still require further investigation. In this study, a series of arylmethylene bisindoles were synthesized with high yield using aromatic aldehydes and indoles catalyzed by NiClO<sub>4</sub>·6H<sub>2</sub>O. These compounds showed spectral antibacterial activity against six major phytopathogenic fungi and <strong>A13</strong> exhibiting the highest antifungal activity against <em>C. homoeocarpa</em> with an EC<sub>50</sub> value of 0.74 mg/L. Furthermore, <em>in vivo</em> antifungal assays were performed to assess the efficacy of the active compounds against <em>C. homoeocarpa</em>. To elucidate the antifungal mechanism of arylmethylene bisindoles, a comprehensive analysis of physiological and biochemical indices, along with transcriptome profiling, was carried out to elucidate. The results demonstrated that <strong>A13</strong> treatment can efficiently disrupt the cell membranes of <em>C. homoeocarpa</em>. Additionally, we identified and screened the candidate genes implicated in cell membrane alterations under <strong>A13</strong> treatments. KEGG pathway analysis revealed that a considerable number of down-regulated DEGs were significantly enriched in metabolic pathways, biosynthesis of secondary metabolic, and ribosome biogenesis in eukaryotes. This research provides valuable insights for the effective management of lawn coin spot disease.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102966"},"PeriodicalIF":1.3,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143865159","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yancho Zarev , Preslav Enchev , Rositsa Mihaylova , Georgi Momekov , Luc Pieters , Hans Michler , Iliana Ionkova
{"title":"Two new neolignans isolated from the endemic species Astracantha aitosensis","authors":"Yancho Zarev , Preslav Enchev , Rositsa Mihaylova , Georgi Momekov , Luc Pieters , Hans Michler , Iliana Ionkova","doi":"10.1016/j.phytol.2025.102961","DOIUrl":"10.1016/j.phytol.2025.102961","url":null,"abstract":"<div><div>Four compounds, a lignan <strong>1</strong>, including two new neolignans <strong>2</strong> and <strong>3</strong>, and one pterocarpan <strong>4</strong>, were isolated from the arial parts of endemic Bulgarian species <em>Astracantha aitosensis (syn. Astragalus aitosensis)</em> (Ivan.) Fabaceae by means of conventional separation methods. The structure of those compounds was elucidated by means of spectroscopic methods, including 1D and 2D NMR, as well as HRESI-MS. Among the isolated compounds is a new neolignan (<strong>2</strong>) named astracandioxin and a new dihydrobenzofuran (<strong>3</strong>) named astracanamide, while for the maackiain-3-<em>O</em>-<em>β</em>-D-glucoside (<strong>4)</strong> this is the first report of isolation from the genus and for syringaresinol-4-<em>O</em>-<em>β</em>-D-glucoside (<strong>1)</strong> first report of isolation from <em>A. aitosensis</em>, respectively. The antiproliferative activity of the isolated compounds was assessed in a panel of human tumor cell lines of different origin.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102961"},"PeriodicalIF":1.3,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143854857","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xiao-Ning Liu , Yue-Tong Zhu , Bo-Tao Lu , Yong-Xian Cheng , Yan-Zhi Wang
{"title":"Carbonyl compounds and glycosides from the fruits of Alpinia oxyphylla as potential renoprotective agents","authors":"Xiao-Ning Liu , Yue-Tong Zhu , Bo-Tao Lu , Yong-Xian Cheng , Yan-Zhi Wang","doi":"10.1016/j.phytol.2025.102965","DOIUrl":"10.1016/j.phytol.2025.102965","url":null,"abstract":"<div><div>The phytochemical investigation of the fruits of <em>Alpinia oxyphylla</em> Miq. led to the isolation and identification of seventeen structurally diverse compounds, including one undescribed carbonyl compound (<strong>1</strong>) and two new glycosides (<strong>6</strong> and <strong>10</strong>) together with fourteen known compounds. Their structures were assigned by spectroscopic and computational methods combined with acid hydrolysis. Nine compounds (<strong>1</strong>, <strong>2</strong>, <strong>6</strong>, <strong>8</strong>, <strong>10</strong>, <strong>11</strong>, <strong>14</strong>, <strong>15</strong> and <strong>17</strong>) displayed inhibitory activities to renal fibrosis in TGF-<em>β</em>1 induced kidney proximal tubular cells, and a dose-effect relationship was observed in compounds <strong>2</strong>, <strong>6</strong> and <strong>10</strong>. The antifibrotic mechanism of compound <strong>10</strong> was related to the inhibition of phosphorylation of Smad2/3.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102965"},"PeriodicalIF":1.3,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143844506","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Wen-Xin Liu , Jun Li , Cheng-Juan Liao , Fu-Wen Yang , Hui-Chun Geng , Min Zhou
{"title":"New thiohydantoin derivatives from the roots of Lepidium meyenii","authors":"Wen-Xin Liu , Jun Li , Cheng-Juan Liao , Fu-Wen Yang , Hui-Chun Geng , Min Zhou","doi":"10.1016/j.phytol.2025.102964","DOIUrl":"10.1016/j.phytol.2025.102964","url":null,"abstract":"<div><div>Three new thiohydantoin derivatives, namely, (4<em>R</em>,6<em>R</em>)-6-hydroxyl macathiohydantoin C (<strong>1</strong>), (4 <em>R</em>,6<em>S</em>)-6-hydroxyl macathiohydantoin C (<strong>2</strong>), and (4<em>S</em>,6<em>S</em>)-6-hydroxyl macathiohydantoin A (<strong>3</strong>), were isolated from the roots of <em>Lepidium meyenii</em>. The structures of these compounds were elucidated by extensive spectroscopic analyses. The absolute configuration of compound <strong>1</strong> was elucidated by electronic circular dichroism and extensive nuclear magnetic resonance chemical shift calculations, followed by DP4 + probability.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102964"},"PeriodicalIF":1.3,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143833898","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Qingsen Shao , Huiyu Li , Mingfeng Li , Wei Yi , Qiugui Zhou , Lijuan Zheng , Meng Wang , Hong-mei Hu , Chao Wen , Yun Tang , Wei Li
{"title":"Isolation and structural elucidation of two novel lignans from the flowers of Gardenia jasminoides with potent α-glucosidase inhibitory activity","authors":"Qingsen Shao , Huiyu Li , Mingfeng Li , Wei Yi , Qiugui Zhou , Lijuan Zheng , Meng Wang , Hong-mei Hu , Chao Wen , Yun Tang , Wei Li","doi":"10.1016/j.phytol.2025.102959","DOIUrl":"10.1016/j.phytol.2025.102959","url":null,"abstract":"<div><div>This research presents the isolation and structural elucidation of two novel lignans, designated as Jasminoside U (<strong>1</strong>) and Jasminoside W (<strong>2</strong>), from the flowers of <em>Gardenia jasminoides</em>. The structures of these compounds were determined using a comprehensive analytical approach that included NMR spectroscopy, HR-ESI-MS, and detailed analysis of ROE correlations and coupling constants. Additionally, the <em>α</em>-glucosidase inhibitory activities of compounds <strong>1</strong> and <strong>2</strong> were evaluated using a standard enzyme assay protocol. The assay results demonstrated that both Jasminoside U (<strong>1</strong>) and Jasminoside W (<strong>2</strong>) possess significant inhibitory effects on <em>α</em>-glucosidase, with IC<sub>50</sub> values determined to be 266 and 323 μmol/L, respectively, indicating their potential as therapeutic agents for the treatment of diabetes and related metabolic disorders.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102959"},"PeriodicalIF":1.3,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143829311","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Zhang Mingyue , Song Yongqi , Chen Xiaohui , Feng Yuxiao , Shi Jiaqi , Li Yonghui , Wang Shoudong , Guo Tao
{"title":"Isopimarane diterpene glycosides of endophytic fungus Xylaria sp. ZY-13","authors":"Zhang Mingyue , Song Yongqi , Chen Xiaohui , Feng Yuxiao , Shi Jiaqi , Li Yonghui , Wang Shoudong , Guo Tao","doi":"10.1016/j.phytol.2025.102963","DOIUrl":"10.1016/j.phytol.2025.102963","url":null,"abstract":"<div><div>Two previously undescribed isopimarane diterpene glycosides, namely xylarisides A (<strong>1</strong>) and B (<strong>2</strong>), along with five known analogues (<strong>3 −7</strong>), were characterized from the fermentation products of the fungus <em>Xylaria</em> sp. ZY-13, isolated from the medicinal plant <em>Cephalotaxus fortunei</em> Hook. The structural characterization and absolute stereochemistry of two previously unreported compounds were identified utilizing comprehensive modern spectroscopic approaches, electronic circular dichroism analyses, and acid hydrolysis of sugar. Additionally, we assessed the <em>in vitro</em> anti-inflammatory effects of all compounds, and only <strong>7</strong> showed weak inhibitory activities.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102963"},"PeriodicalIF":1.3,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143826386","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Li-Ping Feng , Zhan-Guo Li , Qian Ding , Chun Luo , Xue-Ping Lu , Xiao-Hui Li
{"title":"Bioactive homoisoflavonoids from the fibrous roots of Ophiopogon japonicus","authors":"Li-Ping Feng , Zhan-Guo Li , Qian Ding , Chun Luo , Xue-Ping Lu , Xiao-Hui Li","doi":"10.1016/j.phytol.2025.102962","DOIUrl":"10.1016/j.phytol.2025.102962","url":null,"abstract":"<div><div>Phytochemical exploration of the fibrous roots of <em>Ophiopogon japonicus</em> culminated in the identification of two novel homoisoflavonoids, designated as 5-<em>O</em>-methylophiopogonone C (<strong>1</strong>) and (3<em>S</em>)-7,2’-dihydroxy - 3’,4’-methylenedioxyhomoisoflavan (<strong>2</strong>). Leveraging an array of advanced spectroscopic methodologies, inclusive of nuclear magnetic resonance (NMR), infrared spectroscopy (IR), ultraviolet spectroscopy (UV), and high - resolution electrospray ionization mass spectrometry (HRESIMS), the structures of two isolated compounds were meticulously elucidated. Subsequently, their tyrosine kinase inhibitory activities were evaluated.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102962"},"PeriodicalIF":1.3,"publicationDate":"2025-04-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143824003","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yu-hao Zhang , Deng-yi Du , Ruo-fei Bai , Cong-wei Zhou , Zi-jian Zhao , Shan-shan Yang
{"title":"A new β-caryophyllene type sesquiterpenoid pentoside with nine known compounds from the aerial parts of Biebersteinia heterostemon as a α-glucosidase inhibitor in vitro","authors":"Yu-hao Zhang , Deng-yi Du , Ruo-fei Bai , Cong-wei Zhou , Zi-jian Zhao , Shan-shan Yang","doi":"10.1016/j.phytol.2025.102956","DOIUrl":"10.1016/j.phytol.2025.102956","url":null,"abstract":"<div><div>To elucidate the chemical basis of the hypoglycemic activity of <em>Biebersteinia heterostemon</em> Maxim, a Tibetan folk medicinal herb, a new <em>β</em>-caryophyllene type sesquiterpenoid pentoside (<strong>1</strong>) and nine known compounds (<strong>2</strong>–<strong>10</strong>) were isolated from its aerial part, and their structures were identified by the use of UV, NMR and HR-MS analyses. Significantly, the compound <strong>1</strong> was isolated from this plant for the first time in the form of a pentaglycoside. The results of <em>α</em>-glucosidase inhibitory activity assays indicated that the compound <strong>1</strong>, ethyl acetate fraction, compound <strong>2</strong> and remaining aqueous fraction exhibited weak inhibitory activity, with IC<sub>50</sub> values of 2.46, 3.59, 4.87 and 5.03 mg/mL, respectively, all of which were weaker inhibitory activity than that of the positive control, acarbose (IC<sub>50</sub> = 0.78 mg/mL). Among the tested samples, compound <strong>1</strong> displayed the most promising inhibitory activity, with an inhibition rate of 70.90 ± 6.07 % at a concentration of 5.0 mg/mL. In contrast, among the other isolated compounds, especially the flavonoid compounds (<strong>5–10</strong>), some showed low inhibitory activities, while others showed no inhibitory activity at all.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102956"},"PeriodicalIF":1.3,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143821003","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
K.A. Toledo-González , C.A. Riley-Saldaña , R. Salas-Lizana , I. De-la-Cruz-Chacón , A.R. González-Esquinca
{"title":"Alkaloid induction by the interaction between Annona purpurea Moc. & Sessé ex Dunal Curvularia lunata (Wakker) Boedijn and Rhizopus stolonifer Ehrenb. (Ex Fr.) Lind.","authors":"K.A. Toledo-González , C.A. Riley-Saldaña , R. Salas-Lizana , I. De-la-Cruz-Chacón , A.R. González-Esquinca","doi":"10.1016/j.phytol.2025.102958","DOIUrl":"10.1016/j.phytol.2025.102958","url":null,"abstract":"<div><div><em>Annona purpurea</em> is a species of the Annonaceae family that biosynthesizes more than 50 alkaloids, most of them with benzylisoquinoline structure. Some alkaloids perform defense functions and can be grouped from the ecological perspective as constitutive and induced metabolites. Induced metabolites are expressed in response to changes in abiotic or biotic conditions that trigger plant stress. Few studies have been conducted on alkaloid production as a function of biotic stress. In this work, the response of the alkaloid metabolism of <em>A. purpurea</em> seedlings to infection with fungi <em>Curvularia lunata</em> and <em>Rhizopus stolonifer</em> was analyzed. To determine the alkaloid profile, methanolic extracts were obtained from leaves, stems and roots of control and infected seedlings, which were analyzed by Gas Chromatography coupled to Mass Spectrometry. Chemical diversity was determined by the presence and organ-specific abundance and by means of the adapted ecological indices of Margalef, Shannon and Simpson. In addition, Principal Component Analysis (PCA), PERMANOVA and paired PERMANOVA were performed. Induced responses with <em>C. lunata</em> and especially with <em>R. stolonifer</em> were found. Results indicate that seedlings have an arsenal of available alkaloids, some of which respond according to the infecting phytopathogen.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102958"},"PeriodicalIF":1.3,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143791145","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Wen-Ying Zhou , Xiao-Xiao Zheng , Yang-Mei Ou , Yang-Lin Ou , Hong-Yu Jang , Yu-Xin Peng , Yi-Yi Wang , Bi-Qing Zhao , Li Li
{"title":"Three new sesquiterpenes with cytotoxic activity from Croton tiglium","authors":"Wen-Ying Zhou , Xiao-Xiao Zheng , Yang-Mei Ou , Yang-Lin Ou , Hong-Yu Jang , Yu-Xin Peng , Yi-Yi Wang , Bi-Qing Zhao , Li Li","doi":"10.1016/j.phytol.2025.102957","DOIUrl":"10.1016/j.phytol.2025.102957","url":null,"abstract":"<div><div>Sesquiterpenes are a class of natural products known for their diverse structures and biological activities. In this study, three new sesquiterpenes, crotiglimins A (<strong>1</strong>), B (<strong>2</strong>) and C (<strong>3</strong>) were isolated from the leaves of <em>Croton tiglium</em> collected in Yibin County of Sichuan Province, People’s Republic of China. The structures of all isolated compounds were determined on the basis of extensive spectroscopic analyses, as well as by comparison with literature reports. Compounds <strong>1–3</strong> were examined for their cytotoxic activities against the HepG2 cells, and IC<sub>50</sub> values of <strong>1</strong>, <strong>2</strong>, and <strong>3</strong> are 20.67, 10.13, and 9.65 <em>μ</em>M, respectively. Therefore, compounds 1–3 have the value of further research and may be serve as potential anti-liver cancer agent in the future.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102957"},"PeriodicalIF":1.3,"publicationDate":"2025-04-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143785687","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}