Chung-Wei Fu , Atallah F. Ahmed , Lin Chiang , Shu-Fen Chiou , Hui-Chun Wang , Jyh-Horng Sheu
{"title":"Isolation of a new natural bromopyrrole alkaloid agenakasine, a biosynthetically related metabolite laughine, and norzooanemonin from a marine sponge Agelas nakamurai","authors":"Chung-Wei Fu , Atallah F. Ahmed , Lin Chiang , Shu-Fen Chiou , Hui-Chun Wang , Jyh-Horng Sheu","doi":"10.1016/j.phytol.2025.102975","DOIUrl":"10.1016/j.phytol.2025.102975","url":null,"abstract":"<div><div>Chemical investigation of the secondary metabolites of a Formosan sponge, <em>Agelas nakamurai</em>, has led to the isolation of one undescribed natural bromopyrrole alkaloidal ester, agenakasine (<strong>1</strong>), along with known alkaloids, laughine (<strong>2</strong>) and norzooanemonin (<strong>3</strong>). The structures of these compounds were determined by detailed spectroscopic analysis, including 2D NMR spectroscopy, and literature data comparison. Compound <strong>3</strong> was crystallized as a TFA salt, with the structure confirmed by single-crystal X-ray diffraction analysis. Laughine and norzooanemonin were isolated for the first time from <em>Agelas</em> genus. The biosynthesis pathway of agenakasine and laughine was proposed in this study. Agenakasine demonstrated effective inhibitory activity against <em>Klebsiella pneumoniae</em>.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102975"},"PeriodicalIF":1.3,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143937681","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}
Kate Tolan , Mohammed Ali Selo , Ismael Obaidi , Peter O’Connell , Michael Carty , Shipra Nagar , Anne Marie Healy , Helen Sheridan
{"title":"The effects of upstream processing on the chemical profile and immunomodulating activity of Echinacea purpurea tinctures","authors":"Kate Tolan , Mohammed Ali Selo , Ismael Obaidi , Peter O’Connell , Michael Carty , Shipra Nagar , Anne Marie Healy , Helen Sheridan","doi":"10.1016/j.phytol.2025.102971","DOIUrl":"10.1016/j.phytol.2025.102971","url":null,"abstract":"<div><div><em>Echinacea purpurea</em> (L.) Moench is a medicinal plant that is widely known for its immunomodulating properties. There is a lack of understanding regarding how <em>E. purpurea</em> tinctures should be prepared to ensure the most favourable biological activity. To address this gap, a total of 24 tinctures of <em>E. purpurea</em> were prepared with fresh or dried plant material, that was chopped (>2000 µm) or shredded (500–2000 µm), and that was 2 or 3-years-old at the time of harvest. Tinctures contained herba or radix or a combination of both. The chemical profile of the tinctures was determined using HPLC coupled with a principal component analysis of <sup>1</sup>H NMR data. This analysis revealed that tinctures prepared with dried plant material (n = 8) had significantly higher concentrations of caffeic acid derivatives than tinctures prepared with fresh plant material, with the exception of 4 tinctures. The immunomodulating ability of tincture extracts, at a concentration of 100 µg/mg, was evaluated <em>in vitro</em> using non stimulated and lipopolysaccharide (LPS)-stimulated immortalised bone marrow derived macrophages (iBMDM) and THP-1 cell lines. Tincture extracts containing dried plant material reduced IL-6 production in LPS-stimulated iBMDM and THP-1 cells and increased production of TNF-α in THP-1 cells to a greater extent than tincture extracts prepared with fresh plant material. Despite the absence of caffeic acid derivatives, a number of tincture extracts prepared with fresh and shredded plant material had significant anti-inflammatory activity. The inclusion of herba in the tincture was seen to significantly inhibited IL-6 in both iBMDM and THP-1 cells. This study highlights the importance of selecting appropriate upstream processing methods to ensure the production of quality <em>E. purpurea</em> tinctures.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102971"},"PeriodicalIF":1.3,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143937680","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}
Jian-Bo Liu , Wan-Ying Li , Xue Zhao , Feng-Ying Yang , Lei Fang
{"title":"Corrigendum to \"Peganutonin A, a novel melatonin analogue from the seeds of Peganum harmala\" [Phytochem. Lett. 56 (2023) 78–80]","authors":"Jian-Bo Liu , Wan-Ying Li , Xue Zhao , Feng-Ying Yang , Lei Fang","doi":"10.1016/j.phytol.2025.102978","DOIUrl":"10.1016/j.phytol.2025.102978","url":null,"abstract":"","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102978"},"PeriodicalIF":1.3,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143937683","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}
{"title":"Two new diterpenes isolated from the roots of Grangea maderaspatana","authors":"Jittraporn Tipmala , Natcha Injan , Somkiat Nokbin , Ratchanaporn Chokchaisiri , Surat Laphookhieo , Kittirat Saharat , Narawadee Rujanapun , Rawiwan Charoensup , Thunwadee Limtharakul , Sarot Cheenpracha","doi":"10.1016/j.phytol.2025.102973","DOIUrl":"10.1016/j.phytol.2025.102973","url":null,"abstract":"<div><div>Two new diterpenes, maderaspatins A (<strong>1</strong>) and B (<strong>2</strong>), and four known analogues (<strong>3</strong>–<strong>6</strong>) were isolated from an acetone extract of the roots of <em>Grangea maderaspatana</em> (L.) Poir. Their chemical structures were elucidated by the 1D and 2D NMR spectra, complemented by HR-ESI-MS data. The absolute configurations were determined through comparative analysis of experimental CD and calculated ECD spectra. The <em>in vitro</em> cytotoxic activity of purified compounds against the SW480 cell line were evaluated.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102973"},"PeriodicalIF":1.3,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143937682","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}
Zeynep Kalaycıoğlu , Çisil Alim , Sevgi Kolaylı , F. Bedia Erim
{"title":"Capillary electrophoresis as a green and rapid technique for the quantification of caffeic acid phenethyl ester (CAPE): Correlation between CAPE contents and anti-inflammatory activities of propolis extracts","authors":"Zeynep Kalaycıoğlu , Çisil Alim , Sevgi Kolaylı , F. Bedia Erim","doi":"10.1016/j.phytol.2025.102970","DOIUrl":"10.1016/j.phytol.2025.102970","url":null,"abstract":"<div><div>Caffeic acid phenethyl ester (CAPE) is propolis's most notable bioactive compound. Since CAPE has many pharmacological properties, the bioactivities of propolis can mostly be attributed to its CAPE content. As the administration of propolis extracts to the body for therapeutic purposes increases, reliable determination of the CAPE content of the extracts becomes important. This study developed a green micellar electrokinetic chromatography (MEKC) method to determine the CAPE amount in propolis extracts rapidly. The method was applied for the determination of CAPE amounts in commercial propolis spray samples and two propolis samples collected from beekeepers in Anatolia. Moreover, the anti-inflammatory activities of propolis samples were measured based on the <em>in-vitro</em> inhibitory activity of the tumor necrosis factor-<em>α</em> (TNF-<em>α</em>) enzyme. The correlation between the amount of CAPE and the anti-inflammatory activities of the samples was investigated and found to be 0.90. This high correlation indicates that CAPE has an important role in the anti-inflammatory effect of propolis.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102970"},"PeriodicalIF":1.3,"publicationDate":"2025-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143927812","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}
Mathilda Loinseboh Amahndong , Kevine Johanne Jumeta Dongmo , Christine Claire Waleguele , Billy Toussie Tchegnitegni , Georges Bellier Tabouekeng , Jean Rodolphe Chouna , Céline Nguefeu Nkenfou , Jean Jules Kezetas Bankeu , Bruno Ndjakou Lenta , Norbert Sewald
{"title":"Bidesmosidic triterpenoid saponins and other bioactive constituents from the stem bark of Pittosporum viridiflorum","authors":"Mathilda Loinseboh Amahndong , Kevine Johanne Jumeta Dongmo , Christine Claire Waleguele , Billy Toussie Tchegnitegni , Georges Bellier Tabouekeng , Jean Rodolphe Chouna , Céline Nguefeu Nkenfou , Jean Jules Kezetas Bankeu , Bruno Ndjakou Lenta , Norbert Sewald","doi":"10.1016/j.phytol.2025.102972","DOIUrl":"10.1016/j.phytol.2025.102972","url":null,"abstract":"<div><div>Three previously unreported triterpenoid saponins namely pittosposides A–C (<strong>1</strong>–<strong>3</strong>), were isolated from the stem bark of <em>Pittosporum viridiflorum</em>, alongside nine known compounds <strong>4</strong>−<strong>11</strong>. The structures were elucidated based on spectroscopic data as well as chemical conversions. The extract, fractions, and some isolated compounds were assessed for their antibacterial activity against sixteen multi-resistant bacterial strains. The extract and fractions exhibited good antibacterial activity on at least one of the tested strains. The EtOAc fraction was the most active against almost all the strains (MIC values, 15.6<img>500 μg/mL). 2,6‑Dimethoxybenzoquinone (<strong>7</strong>) was active against almost all the selected bacterial strains with the best activity against <em>E. coli</em> ATCC35218 (MIC = 1.9 μg/mL). In addition, the extract, fractions, and compounds <strong>1</strong>−<strong>4</strong>, <strong>7</strong>, and <strong>11</strong> were assessed for their cytotoxic activity on the normal <em>Vero</em> cell line. Compounds <strong>1</strong>, <strong>2</strong> and <strong>4</strong> were further assessed for their cytotoxic activity on the KB-3–1 cervical carcinoma cell line against which compound <strong>4</strong> displayed moderate cytotoxicity (IC<sub>50</sub> = 23.9 μM). The chemophenetic significance of the isolates was discussed.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"68 ","pages":"Article 102972"},"PeriodicalIF":1.3,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143924621","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}
{"title":"Synthesis and cytotoxicity evaluation of tyrosine-3 or tyrosine-6 fluorinated analogues of RA-VII, an antitumor bicyclic hexapeptide from Rubia cordifolia","authors":"Yukio Hitotsuyanagi, Ken Morita, Tatsuro Anzai, Tomoyo Hasuda, Niro Inaba, Koichi Takeya","doi":"10.1016/j.phytol.2025.102967","DOIUrl":"10.1016/j.phytol.2025.102967","url":null,"abstract":"<div><div>An RA-VII analogue with a fluorine atom introduced to the Tyr-3 ε position was synthesized from cycloisodityrosine, obtained through the chemical degradation of RA-VII, and fluorotetrapeptide. Additionally, an analogue with a fluorine atom at the Tyr-6 εa position was prepared via a substitution reaction involving the amino group of an amino-RA-VII derivative using a fluoride species. Compared with RA-VII, the Tyr-3 fluorinated analogue exhibited 300 times lower cytotoxicity toward the HL-60 cell line and 370 times lower cytotoxicity toward the HCT-116 cell line. In contrast, the Tyr-6 fluorinated analogue was 3.3 times and 1.1 times less cytotoxic toward these cell lines than RA-VII. These results indicate that substituting a fluorine atom for the aryl proton at the Tyr-3 ε position markedly reduces the cytotoxic activity. In contrast, the impact of such substitution at the Tyr-6 εa position is minimal.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102967"},"PeriodicalIF":1.3,"publicationDate":"2025-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143908239","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}
Mohamed A. Tammam , Leto-Aikaterini Tziveleka , Carlos M. Duarte , Efstathia Ioannou , Vassilios Roussis
{"title":"Sesquiterpenes from the Saudi Arabian Red Sea sponge Lamellodysidea herbacea","authors":"Mohamed A. Tammam , Leto-Aikaterini Tziveleka , Carlos M. Duarte , Efstathia Ioannou , Vassilios Roussis","doi":"10.1016/j.phytol.2025.102969","DOIUrl":"10.1016/j.phytol.2025.102969","url":null,"abstract":"<div><div>Eleven sesquiterpenes (<strong>1</strong>–<strong>11</strong>), with the majority of them decorated with either a furan or a γ-lactone moiety in their carbocycle, were isolated from an organic extract of the marine sponge <em>Lamellodysidea herbacea</em> collected from the coral reefs in the vicinity of Thuwal in Saudi Arabia. Two of the isolated metabolites (<strong>1</strong> and <strong>2</strong>) are not previously described, whereas the linear furanosesquiterpene <strong>11</strong> is reported for the first time from a natural source. The structures and the relative configurations of the isolated metabolites have been determined through extensive analysis of their NMR and MS data. Compounds <strong>1</strong>–<strong>11</strong> were evaluated for their antibacterial and antioxidant activity but did not display any noteworthy activity.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102969"},"PeriodicalIF":1.3,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143891134","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}
Ernest Guiller S. Pineda, Jacquelyn E. Peran, Jeremiah D. Batucan, Zildjian G. Acyatan, Shalice R. Susana-Guevarra, Lilibeth A. Salvador-Reyes
{"title":"Characterization of a new lyso-ornithine lipid from the shipworm symbiont Teredinibacter turnerae","authors":"Ernest Guiller S. Pineda, Jacquelyn E. Peran, Jeremiah D. Batucan, Zildjian G. Acyatan, Shalice R. Susana-Guevarra, Lilibeth A. Salvador-Reyes","doi":"10.1016/j.phytol.2025.102960","DOIUrl":"10.1016/j.phytol.2025.102960","url":null,"abstract":"<div><div><em>Teredinibacter turnerae</em> dedicates a significant portion of its genome to secondary metabolite biosynthesis. In this study, we purified the new lyso-ornithine lipid <em>N</em>-3-hydroxyoleoyl ornithine (<strong>1</strong>) from <em>T. turnerae</em> strains 4401H.S.1B.02-A and 4409 W.S.0 A.02-C. This compound is characterized by a monohydroxylated C18:1 fatty acid attached to an ornithine head group through an amide bond. <em>N</em>-3-hydroxyoleoyl ornithine demonstrated weak antimicrobial activity against planktonic <em>Staphylococcus epidermidis</em> (% inhibition = 53.5 ± 11.8 % at 256 µg/mL (620 µM)) and weak cytotoxicity against HK-2 normal human kidney cells (IC<sub>50</sub> = 11 µM) and HCT116 human colorectal carcinoma (% cell viability = 47.6 ± 8.0 % at 100 µM). The antimicrobial and cytotoxic activities of <strong>1</strong> are, in part, facilitated by its membrane-disrupting activity. <em>N</em>-3-hydroxyoleoyl ornithine (<strong>1</strong>) caused an indirect and irreversible amplification of Ca<sup>2</sup><sup>+</sup> uptake in dorsal root ganglion (DRG) neurons that are insensitive to either menthol or capsaicin at 10 µg/mL (24 µM). Time course studies further revealed that the production of <strong>1</strong> in <em>T. turnerae</em> 4409 W.S.0 A.02-C is negatively regulated by phosphate control, possibly via a Pho-dependent regulation of <em>olsB</em> expression.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"67 ","pages":"Article 102960"},"PeriodicalIF":1.3,"publicationDate":"2025-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143879217","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}
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}