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Keywords = Pterosin B

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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 230
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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14 pages, 2566 KiB  
Article
Novel Therapeutic Effects of Pterosin B on Ang II-Induced Cardiomyocyte Hypertrophy
by Chang Youn Lee, Han Ki Park, Bok-Sim Lee, Seongtae Jeong, Sung-Ae Hyun, Jung-Won Choi, Sang Woo Kim, Seahyoung Lee, Soyeon Lim and Ki-Chul Hwang
Molecules 2020, 25(22), 5279; https://doi.org/10.3390/molecules25225279 - 12 Nov 2020
Cited by 17 | Viewed by 4292
Abstract
Pathological cardiac hypertrophy is characterized by an abnormal increase in cardiac muscle mass in the left ventricle, resulting in cardiac dysfunction. Although various therapeutic approaches are being continuously developed for heart failure, several studies have suggested natural compounds as novel potential strategies. Considering [...] Read more.
Pathological cardiac hypertrophy is characterized by an abnormal increase in cardiac muscle mass in the left ventricle, resulting in cardiac dysfunction. Although various therapeutic approaches are being continuously developed for heart failure, several studies have suggested natural compounds as novel potential strategies. Considering relevant compounds, we investigated a new role for Pterosin B for which the potential life-affecting biological and therapeutic effects on cardiomyocyte hypertrophy are not fully known. Thus, we investigated whether Pterosin B can regulate cardiomyocyte hypertrophy induced by angiotensin II (Ang II) using H9c2 cells. The antihypertrophic effect of Pterosin B was evaluated, and the results showed that it reduced hypertrophy-related gene expression, cell size, and protein synthesis. In addition, upon Ang II stimulation, Pterosin B attenuated the activation and expression of major receptors, Ang II type 1 receptor and a receptor for advanced glycation end products, by inhibiting the phosphorylation of PKC-ERK-NF-κB pathway signaling molecules. In addition, Pterosin B showed the ability to reduce excessive intracellular reactive oxygen species, critical mediators for cardiac hypertrophy upon Ang II exposure, by regulating the expression levels of NAD(P)H oxidase 2/4. Our results demonstrate the protective role of Pterosin B in cardiomyocyte hypertrophy, suggesting it is a potential therapeutic candidate. Full article
(This article belongs to the Collection Bioactive Compounds)
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15 pages, 1781 KiB  
Article
A Novel Method for Determination of the Natural Toxin Ptaquiloside in Ground and Drinking Water
by Natasa Skrbic, Ann-Katrin Pedersen, Sarah C. B. Christensen, Hans Christian Bruun Hansen and Lars Holm Rasmussen
Water 2020, 12(10), 2852; https://doi.org/10.3390/w12102852 - 13 Oct 2020
Cited by 11 | Viewed by 4736
Abstract
Ptaquiloside (PTA) is a carcinogenic compound naturally occurring in bracken ferns (Pteridium aquilinum). It is highly water soluble and prone to leaching from topsoil to surface and groundwaters. Due to possible human exposure via drinking water, PTA is considered as an [...] Read more.
Ptaquiloside (PTA) is a carcinogenic compound naturally occurring in bracken ferns (Pteridium aquilinum). It is highly water soluble and prone to leaching from topsoil to surface and groundwaters. Due to possible human exposure via drinking water, PTA is considered as an emerging contaminant. We present a sensitive and robust method for analysis of PTA and its degradation product pterosin B (PtB) in groundwater. The method comprises two steps: sample preservation at the field site followed by sample pre-concentration in the laboratory. The preservation step was developed by applying a Plackett–Burman experimental design testing the following variables: water type, pH, filtering, bottle type, storage temperature, transportation conditions and test time. The best sample preservation was obtained by using amber glass bottles, unfiltered solutions buffered at pH 6, transported without ice, stored at 4 °C and analysed within 48 h. The recovery was 94% to 100%. The sample purification step had a pre-concentration factor of 250, and the recovery percentages of the entire method were 85 ± 2 (PTA) and 91 ± 3 (PtB). The limits of detection (LOD) of the full method were 0.001 µg L−1 and 0.0001 µg L−1 for PTA and PtB, respectively. The method enables sensitive monitoring of PTA and PtB in groundwater. Carcinogenic PTA was detected in one groundwater well (0.35 µg L−1). Full article
(This article belongs to the Special Issue Emerging Contaminants (ECs) in Water)
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8 pages, 528 KiB  
Article
Ptaquiloside and Pterosin B Levels in Mature Green Fronds and Sprouts of Pteridium arachnoideum
by Debora da Silva Freitas Ribeiro, Kelly Moura Keller and Benito Soto-Blanco
Toxins 2020, 12(5), 288; https://doi.org/10.3390/toxins12050288 - 1 May 2020
Cited by 13 | Viewed by 2954
Abstract
Pteridium arachnoideum, a fern of the Pteridium aquilinum species complex found in South America, is responsible for several different syndromes of poisoning. Cases of bovine enzootic hematuria and upper alimentary squamous cell carcinoma are both frequent occurrences in Brazil, whereas only bovine [...] Read more.
Pteridium arachnoideum, a fern of the Pteridium aquilinum species complex found in South America, is responsible for several different syndromes of poisoning. Cases of bovine enzootic hematuria and upper alimentary squamous cell carcinoma are both frequent occurrences in Brazil, whereas only bovine enzootic hematuria is noted with any frequency around the world. The reason for the high frequency of upper alimentary squamous cell carcinoma in Brazil is not currently known. One possible explanation may be the higher levels of ptaquiloside and pterosin B in Brazilian Pteridium than those present in the plant in other countries. However, these levels have not yet been determined in P. arachnoideum. Thus, the present study aimed to measure and compare ptaquiloside and pterosin B levels in mature green fronds and sprouts of P. arachnoideum collected from different locations in Brazil. Samples of P. arachnoideum were collected from the states of Minas Gerais and Rio Grande do Sul. A total of 28 mature leaf samples and 23 sprout samples were used. The mean concentrations of ptaquiloside and pterosin B present in the mature green fronds of P. arachnoideum ranged from 2.49 to 2.75 mg/g and 0.68 to 0.88 mg/g, respectively; in P. arachnoideum sprouts, mean concentrations of ptaquiloside and pterosin B ranged from 12.47 to 18.81 mg/g, and 4.03 to 10.42 mg/g for ptaquiloside and pterosin B, respectively. Thus, ptaquiloside and pterosin B levels in P. arachnoideum samples collected in Brazil were higher in sprouts than in mature green fronds, as observed in other countries. However, there was no variation in ptaquiloside levels among plants collected from different cities in Brazil. The high frequency of upper alimentary squamous cell carcinoma in Brazilian cattle may not be attributed to greater levels of ptaquiloside and pterosin B in P. arachnoideum than in other Pteridium species in other countries. Full article
(This article belongs to the Special Issue Plant Toxins Affecting Animal Health and Production)
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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 10612
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 5972
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 14789
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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