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Keywords = d4-pterosin

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21 pages, 1784 KiB  
Article
Toxic Threats from the Fern Pteridium aquilinum: A Multidisciplinary Case Study in Northern Spain
by L. María Sierra, Isabel Feito, Mª Lucía Rodríguez, Ana Velázquez, Alejandra Cué, Jaime San-Juan-Guardado, Marta Martín, Darío López, Alexis E. Peña, Elena Canga, Guillermo Ramos, Juan Majada, José Manuel Alvarez and Helena Fernández
Int. J. Mol. Sci. 2025, 26(15), 7157; https://doi.org/10.3390/ijms26157157 - 24 Jul 2025
Viewed by 191
Abstract
Pteridium aquilinum (bracken fern) poses a global threat to biodiversity and to the health of both animals and humans due to its toxic metabolites and aggressive ecological expansion. In northern Spain, particularly in regions of intensive livestock farming, these risks may be exacerbated, [...] Read more.
Pteridium aquilinum (bracken fern) poses a global threat to biodiversity and to the health of both animals and humans due to its toxic metabolites and aggressive ecological expansion. In northern Spain, particularly in regions of intensive livestock farming, these risks may be exacerbated, calling for urgent assessment and monitoring strategies. In this study, we implemented a multidisciplinary approach to evaluate the toxicological and ecological relevance of P. aquilinum through four key actions: (a) quantification of pterosins A and B in young fronds (croziers) using ultra-high-performance liquid chromatography coupled with tandem mass spectrometry (UHPLC-MS/MS); (b) analysis of in vivo genotoxicity of aqueous extracts using Drosophila melanogaster as a model organism; (c) a large-scale survey of local livestock farmers to assess awareness and perceived impact of bracken; and (d) the development and field application of a drone-based mapping tool to assess the spatial distribution of the species at the regional level. Our results confirm the consistent presence of pterosins A and B in croziers, with concentrations ranging from 0.17 to 2.20 mg/g dry weight for PtrB and 13.39 to 257 µg/g for PtrA. Both metabolite concentrations and genotoxicity levels were found to correlate with latitude and, importantly, with each other. All tested samples exhibited genotoxic activity, with notable differences among them. The farmer survey (n = 212) revealed that only 50% of respondents were aware of the toxic risks posed by bracken, indicating a need for targeted outreach. The drone-assisted mapping approach proved to be a promising tool for identifying bracken-dominated areas and provides a scalable foundation for future ecological monitoring and land management strategies. Altogether, our findings emphasize that P. aquilinum is not merely a local concern but a globally relevant toxic species whose monitoring and control demand coordinated scientific and policy-based efforts. Full article
(This article belongs to the Special Issue The Transcendental World of Plant Toxic Compounds)
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8 pages, 640 KiB  
Article
Four New Pterosins from Pteris cretica and Their Cytotoxic Activities
by Jian Lu, Caiying Peng, Shuang Cheng, Jianqun Liu, Qinge Ma and Jicheng Shu
Molecules 2019, 24(15), 2767; https://doi.org/10.3390/molecules24152767 - 30 Jul 2019
Cited by 16 | Viewed by 3323
Abstract
Phytochemical investigation of the aerial parts of Pteris cretica led to the isolation and elucidation of nine pterosins, including four new pterosins, creticolacton A (1), 13-hydroxy-2(R),3(R)-pterosin L (2), creticoside A (3), and spelosin [...] Read more.
Phytochemical investigation of the aerial parts of Pteris cretica led to the isolation and elucidation of nine pterosins, including four new pterosins, creticolacton A (1), 13-hydroxy-2(R),3(R)-pterosin L (2), creticoside A (3), and spelosin 3-O-β-d-glucopyranoside (4), together with five known pterosins 59. Their structures were identified mainly on the basis of 1D and 2D NMR spectral data, ESI-MS and literature comparisons. Compounds 1 and 3 were new type of petrosins with a six membered ring between C-14 and C-15. The new compounds were tested in vitro for their cytotoxic activities against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Results showed that compounds 1 and 2 exhibited cytotoxic activity against HCT-116 cells with IC50 value of 22.4 μM and 15.8 μM, respectively. Full article
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20 pages, 2704 KiB  
Article
Chemical Constituents Analysis and Antidiabetic Activity Validation of Four Fern Species from Taiwan
by Chen-Yu Chen, Fu-Yu Chiu, Yenshou Lin, Wei-Jan Huang, Po-Shiuan Hsieh and Feng-Lin Hsu
Int. J. Mol. Sci. 2015, 16(2), 2497-2516; https://doi.org/10.3390/ijms16022497 - 22 Jan 2015
Cited by 24 | Viewed by 7339
Abstract
Pterosins are abundant in ferns, and pterosin A was considered a novel activator of adenosine monophosphate-activated protein kinase, which is crucial for regulating blood glucose homeostasis. However, the distribution of pterosins in different species of ferns from various places in Taiwan is currently [...] Read more.
Pterosins are abundant in ferns, and pterosin A was considered a novel activator of adenosine monophosphate-activated protein kinase, which is crucial for regulating blood glucose homeostasis. However, the distribution of pterosins in different species of ferns from various places in Taiwan is currently unclear. To address this question, the distribution of pterosins, glucose-uptake efficiency, and protective effects of pterosin A on β-cells were examined. Our results showed that three novel compounds, 13-chloro-spelosin 3-O-β-d-glucopyranoside (1), (3R)-Pterosin D 3-O-β-d-(3'-p-coumaroyl)-glucopyranoside (2), and (2R,3R)-Pterosin L 3-O-β-d-(3'-p-coumaroyl)-glucopyranoside (3), were isolated for the first time from four fern species (Ceratopteris thalictroides, Hypolepis punctata, Nephrolepis multiflora, and Pteridium revolutum) along with 27 known compounds. We also examined the distribution of these pterosin compounds in the mentioned fern species (except N. multiflora). Although all pterosin analogs exhibited the same effects in glucose uptake assays, pterosin A prevented cell death and reduced reactive oxygen species (ROS) production. This paper is the first report to provide new insights into the distribution of pterosins in ferns from Taiwan. The potential anti-diabetic activity of these novel phytocompounds warrants further functional studies. Full article
(This article belongs to the Section Biochemistry)
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9 pages, 908 KiB  
Article
Cytotoxic Illudalane Sesquiterpenes from the Wood-Decay Fungus Granulobasidium vellereum (Ellis & Cragin) Jülich
by Christina L. Nord, Audrius Menkis and Anders Broberg
Molecules 2014, 19(9), 14195-14203; https://doi.org/10.3390/molecules190914195 - 9 Sep 2014
Cited by 22 | Viewed by 10609
Abstract
Seven illudalane sesquiterpenes were obtained from the wood decomposing fungus Granulobasidium vellereum: granuloinden A, granuloinden B and dihydrogranuloinden, along with the previously known compounds radulactone, pterosin M, echinolactone A and D. Granuloinden B showed potent cytotoxic activity against the Huh7 and MT4 [...] Read more.
Seven illudalane sesquiterpenes were obtained from the wood decomposing fungus Granulobasidium vellereum: granuloinden A, granuloinden B and dihydrogranuloinden, along with the previously known compounds radulactone, pterosin M, echinolactone A and D. Granuloinden B showed potent cytotoxic activity against the Huh7 and MT4 tumor cell lines (CC50 values of 6.7 and 0.15 µM, respectively), whereas granuloinden A and dihydrogranuloinden had no or moderate activity. Full article
(This article belongs to the Section Natural Products Chemistry)
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8 pages, 218 KiB  
Article
A New Facile Synthesis of D4-Pterosin B and D4-Bromopterosin, Deuterated Analogues of Ptaquiloside
by Mohamed Attya, Monica Nardi, Antonio Tagarelli and Giovanni Sindona
Molecules 2012, 17(5), 5795-5802; https://doi.org/10.3390/molecules17055795 - 16 May 2012
Cited by 9 | Viewed by 5969
Abstract
Ptaquiloside (Pta) is a potent carcinogen present in bracken fern and in soil matrices, that can potentially leach to the aquatic environment. More recently its presence in the milk of different farm animals has been reported. Pterosin B (Ptb) and bromopterosin (BrPt) represent [...] Read more.
Ptaquiloside (Pta) is a potent carcinogen present in bracken fern and in soil matrices, that can potentially leach to the aquatic environment. More recently its presence in the milk of different farm animals has been reported. Pterosin B (Ptb) and bromopterosin (BrPt) represent the most convenient analogues in the detection of ptaquiloside by mass spectrometry. Pterosin sesquiterpenes are also involved in many patented biomedical protocols. In this work we introduce a new and convenient approach to the synthesis in three steps and more than 80% yield of d4-pterosin B (d4-Ptb) and d4-bromopterosin (d4-BrPt), useful as internal standards in the quantification of ptaquiloside. Full article
(This article belongs to the Special Issue Challenges in Synthetic Chemistry)
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12 pages, 96 KiB  
Article
New Benzoyl Glucosides and Cytotoxic Pterosin Sesquiterpenes from Pteris ensiformis Burm.
by Yung-Husan Chen, Fang-Rong Chang, Mei-Chin Lu, Pei-Wen Hsieh, Ming-Jiuan Wu, Ying-Chi Du and Yang-Chang Wu
Molecules 2008, 13(2), 255-266; https://doi.org/10.3390/molecules13020255 - 5 Feb 2008
Cited by 59 | Viewed by 14785
Abstract
Three new compounds: 2R,3R-pterosin L 3-O-β-D-glucopyranoside (1), β-Dxylopyranosyl(1→2)-7-O-benzoyl-β-D-glucopyranoside (2) and 4-O-benzoyl-β-D-xylopyranosyl(1→2)-7-O-benzoyl-β-D-glucopyranoside (3), together with nine knowncompounds, were isolated from the ethyl acetate extract of Pteris ensiformis. 5-[2-Hydroxyethylidene]-2(5H)-furanone (4), which had been synthesized, was isolated fromnatural sources for the first time. The structures of [...] Read more.
Three new compounds: 2R,3R-pterosin L 3-O-β-D-glucopyranoside (1), β-Dxylopyranosyl(1→2)-7-O-benzoyl-β-D-glucopyranoside (2) and 4-O-benzoyl-β-D-xylopyranosyl(1→2)-7-O-benzoyl-β-D-glucopyranoside (3), together with nine knowncompounds, were isolated from the ethyl acetate extract of Pteris ensiformis. 5-[2-Hydroxyethylidene]-2(5H)-furanone (4), which had been synthesized, was isolated fromnatural sources for the first time. The structures of all isolated compounds were determinedon the basis of mass and spectroscopic evidence. Compound 1 and pterosin B (5) showcytotoxicity against HL 60 cells (human leukemia) with the IC50 values of 3.7 and 8.7μg/mL, respectively. Full article
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