PTAQUILOSIDE (BioDeep_00000409941)

Main id: BioDeep_00000004037

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


PTAQUILOSIDE

化学式: C20H30O8 (398.194058)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=CC2(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C[C@@H](C)C(=O)[C@@H]2[C@](C)(O)C12CC2
InChI: InChI=1S/C20H30O8/c1-9-6-20(28-17-15(25)14(24)13(23)11(8-21)27-17)7-10(2)19(4-5-19)18(3,26)16(20)12(9)22/h7,9,11,13-17,21,23-26H,4-6,8H2,1-3H3/t9-,11-,13-,14+,15-,16-,17+,18+,20-/m1/s1

描述信息

CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 30
D009676 - Noxae > D002273 - Carcinogens
D009676 - Noxae > D009153 - Mutagens

同义名列表

2 个代谢物同义名

PTAQUILOSIDE; Ptaquiloside



数据库引用编号

31 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

68 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Daniel B García-Jorgensen, Maja Holbak, Hans Christian Bruun Hansen, Per Abrahamsen, Efstathios Diamantopoulos. Modeling the environmental fate of bracken toxin ptaquiloside: Production, release and transport in the rhizosphere. The Science of the total environment. 2024 Apr; 921(?):170658. doi: 10.1016/j.scitotenv.2024.170658. [PMID: 38340825]
  • Laura S Aguirre, Olga G Martínez, Dale R Gardner, Claudio G Barbeito, Juan F Micheloud. Determination of ptaquiloside in ten species of Pteris in northwestern Argentina. Toxicon : official journal of the International Society on Toxinology. 2023 Sep; 233(?):107260. doi: 10.1016/j.toxicon.2023.107260. [PMID: 37619743]
  • János Vetter. The Norsesquiterpene Glycoside Ptaquiloside as a Poisonous, Carcinogenic Component of Certain Ferns. Molecules (Basel, Switzerland). 2022 Oct; 27(19):. doi: 10.3390/molecules27196662. [PMID: 36235199]
  • Vaidotas Kisielius, Mikkel Drejer, Jimmy Kjellerup Dornhoff, Natasa Skrbic Mrkajic, Dan Nybro Lindqvist, Hans Christian Bruun Hansen, Lars Holm Rasmussen. Occurrence and stability of ptesculentoside, caudatoside and ptaquiloside in surface waters. Environmental science. Processes & impacts. 2022 Feb; 24(2):277-289. doi: 10.1039/d1em00364j. [PMID: 35043811]
  • D B García-Jorgensen, H C B Hansen, P Abrahamsen, E Diamantopoulos. A novel model concept for modelling the leaching of natural toxins: results for the case of ptaquiloside. Environmental science. Processes & impacts. 2020 Aug; 22(8):1768-1779. doi: 10.1039/d0em00182a. [PMID: 32716437]
  • Debora da Silva Freitas Ribeiro, Kelly Moura Keller, Benito Soto-Blanco. Ptaquiloside and Pterosin B Levels in Mature Green Fronds and Sprouts of Pteridium arachnoideum. Toxins. 2020 05; 12(5):. doi: 10.3390/toxins12050288. [PMID: 32369939]
  • Rui M Gil da Costa, Tiago Neto, Diogo Estêvão, Magda Moutinho, Ana Félix, Rui Medeiros, Carlos Lopes, Margarida M S M Bastos, Paula A Oliveira. Ptaquiloside from bracken (Pteridium spp.) promotes oral carcinogenesis initiated by HPV16 in transgenic mice. Food & function. 2020 Apr; 11(4):3298-3305. doi: 10.1039/d0fo00207k. [PMID: 32222741]
  • Vaidotas Kisielius, Dan Nybro Lindqvist, Mikkel Boas Thygesen, Michael Rodamer, Hans Christian Bruun Hansen, Lars Holm Rasmussen. Fast LC-MS quantification of ptesculentoside, caudatoside, ptaquiloside and corresponding pterosins in bracken ferns. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Feb; 1138(?):121966. doi: 10.1016/j.jchromb.2019.121966. [PMID: 31931331]
  • Paulo César Dos Reis Aranha, Lars Holm Rasmussen, Godelind Alma Wolf-Jäckel, Henrik Michael Elvang Jensen, Hans Christian Bruun Hansen, Christian Friis. Fate of ptaquiloside-A bracken fern toxin-In cattle. PloS one. 2019; 14(6):e0218628. doi: 10.1371/journal.pone.0218628. [PMID: 31226154]
  • Sarvesh K Rai, Rinku Sharma, Alka Kumari, Lars H Rasmussen, Rajendra D Patil, Rasbehari Bhar. Survey of ferns and clinico-pathological studies on the field cases of Enzootic bovine haematuria in Himachal Pradesh, a north-western Himalayan state of India. Toxicon : official journal of the International Society on Toxinology. 2017 Nov; 138(?):31-36. doi: 10.1016/j.toxicon.2017.08.010. [PMID: 28803058]
  • Lars Holm Rasmussen, Henrik AErenlund Pedersen. Screening for Ptaquiloside in Ferns: Using Herbarium Specimens for Qualitative Mapping Purposes. Phytochemical analysis : PCA. 2017 Nov; 28(6):575-583. doi: 10.1002/pca.2707. [PMID: 28703460]
  • Juan Francisco Micheloud, Luis Adrián Colque-Caro, Olga Gladys Martinez, Eduardo Juan Gimeno, Debora da Silva Freitas Ribeiro, Benito Soto Blanco. Bovine enzootic haematuria from consumption of Pteris deflexa and Pteris plumula in northwestern Argentina. Toxicon : official journal of the International Society on Toxinology. 2017 Aug; 134(?):26-29. doi: 10.1016/j.toxicon.2017.05.023. [PMID: 28559101]
  • Arata Hidano, Basant Sharma, Karma Rinzin, Narapati Dahal, Kinzang Dukpa, Mark A Stevenson. Revisiting an old disease? Risk factors for bovine enzootic haematuria in the Kingdom of Bhutan. Preventive veterinary medicine. 2017 May; 140(?):10-18. doi: 10.1016/j.prevetmed.2017.02.011. [PMID: 28460742]
  • Eirini Skourti-Stathaki, Frederik Clauson-Kaas, Kristian Koefoed Brandt, Lars Holm Rasmussen, Hans Christian Bruun Hansen. Dissipation of pterosin B in acid soils - Tracking the fate of the bracken fern carcinogen ptaquiloside. Chemosphere. 2016 Dec; 165(?):453-459. doi: 10.1016/j.chemosphere.2016.09.050. [PMID: 27677121]
  • Connie O'Driscoll, Carmel Ramwell, Brendan Harhen, Liam Morrison, Frederik Clauson-Kaas, Hans Christian B Hansen, Graeme Campbell, Jerome Sheahan, Bruce Misstear, Liwen Xiao. Ptaquiloside in Irish Bracken Ferns and Receiving Waters, with Implications for Land Managers. Molecules (Basel, Switzerland). 2016 Apr; 21(5):. doi: 10.3390/molecules21050543. [PMID: 27128893]
  • Alberto Oliveros-Bastidas, María Pía Calcagno-Pissarelli, Marlene Naya, Jorge Luis Ávila-Núñez, Miguel E Alonso-Amelot. Human gastric cancer, Helicobacter pylori and bracken carcinogens: A connecting hypothesis. Medical hypotheses. 2016 Mar; 88(?):91-9. doi: 10.1016/j.mehy.2015.11.007. [PMID: 26632203]
  • Antonella Virgilio, Annamaria Sinisi, Valeria Russo, Salvatore Gerardo, Adriano Santoro, Aldo Galeone, Orazio Taglialatela-Scafati, Franco Roperto. Ptaquiloside, the major carcinogen of bracken fern, in the pooled raw milk of healthy sheep and goats: an underestimated, global concern of food safety. Journal of agricultural and food chemistry. 2015 May; 63(19):4886-92. doi: 10.1021/acs.jafc.5b01937. [PMID: 25932502]
  • Lars Holm Rasmussen, Eric Donnelly, Bjarne W Strobel, Peter E Holm, Hans Christian Bruun Hansen. Land management of bracken needs to account for bracken carcinogens--a case study from Britain. Journal of environmental management. 2015 Mar; 151(?):258-66. doi: 10.1016/j.jenvman.2014.12.052. [PMID: 25577704]
  • Ann M Bode, Zigang Dong. Toxic phytochemicals and their potential risks for human cancer. Cancer prevention research (Philadelphia, Pa.). 2015 Jan; 8(1):1-8. doi: 10.1158/1940-6207.capr-14-0160. [PMID: 25348854]
  • Claudio Zaccone, Ivana Cavoski, Roberta Costi, Giorgia Sarais, Pierluigi Caboni, Andreina Traversa, Teodoro M Miano. Ptaquiloside in Pteridium aquilinum subsp. aquilinum and corresponding soils from the South of Italy: influence of physical and chemical features of soils on its occurrence. The Science of the total environment. 2014 Oct; 496(?):365-372. doi: 10.1016/j.scitotenv.2014.07.046. [PMID: 25089695]
  • Frederik Clauson-Kaas, Pia H Jensen, Ole S Jacobsen, René K Juhler, Hans Christian B Hansen. The naturally occurring carcinogen ptaquiloside is present in groundwater below bracken vegetation. Environmental toxicology and chemistry. 2014 May; 33(5):1030-4. doi: 10.1002/etc.2533. [PMID: 24464773]
  • Rui M Gil da Costa, Paula A Oliveira, Margarida M S M Bastos, Célia C Lopes, Carlos Lopes. Ptaquiloside-induced early-stage urothelial lesions show increased cell proliferation and intact β-catenin and E-cadherin expression. Environmental toxicology. 2014 May; 29(7):763-9. doi: 10.1002/tox.21803. [PMID: 22859263]
  • Paulo César Reis Aranha, Hans Christian Bruun Hansen, Lars Holm Rasmussen, Bjarne W Strobel, Christian Friis. Determination of ptaquiloside and pterosin B derived from bracken (Pteridium aquilinum) in cattle plasma, urine and milk. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Mar; 951-952(?):44-51. doi: 10.1016/j.jchromb.2014.01.022. [PMID: 24508676]
  • Tõnu Püssa. Toxicological issues associated with production and processing of meat. Meat science. 2013 Dec; 95(4):844-53. doi: 10.1016/j.meatsci.2013.04.032. [PMID: 23660174]
  • Yamile C Cáceres-Peña, Marlene Naya, María Pía Calcagno-Pissarelli, Miguel E Alonso-Amelot. Influence of bracken fern (Pteridium caudatum L. Maxon) pre-treatment on extraction yield of illudane glycosides and pterosins. Phytochemical analysis : PCA. 2013 Jul; 24(4):290-5. doi: 10.1002/pca.2409. [PMID: 23168905]
  • Rinku Sharma, Tej K Bhat, Om P Sharma. The environmental and human effects of ptaquiloside-induced enzootic bovine hematuria: a tumorous disease of cattle. Reviews of environmental contamination and toxicology. 2013; 224(?):53-95. doi: 10.1007/978-1-4614-5882-1_3. [PMID: 23232919]
  • Joana Gomes, Ana Magalhães, Valérie Michel, Inês F Amado, Paulo Aranha, Rikke G Ovesen, Hans C B Hansen, Fátima Gärtner, Celso A Reis, Eliette Touati. Pteridium aquilinum and its ptaquiloside toxin induce DNA damage response in gastric epithelial cells, a link with gastric carcinogenesis. Toxicological sciences : an official journal of the Society of Toxicology. 2012 Mar; 126(1):60-71. doi: 10.1093/toxsci/kfr329. [PMID: 22143989]
  • Rui M Gil da Costa, Paula A Oliveira, Manuel Vilanova, Margarida M S M Bastos, Célia C Lopes, Carlos Lopes. Ptaquiloside-induced, B-cell lymphoproliferative and early-stage urothelial lesions in mice. Toxicon : official journal of the International Society on Toxinology. 2011 Nov; 58(6-7):543-9. doi: 10.1016/j.toxicon.2011.08.016. [PMID: 21907228]
  • Mary T Fletcher, Keith G Reichmann, Ian J Brock, Ross A McKenzie, Barry J Blaney. Residue potential of norsesquiterpene glycosides in tissues of cattle fed Austral bracken (Pteridium esculentum). Journal of agricultural and food chemistry. 2011 Aug; 59(15):8518-23. doi: 10.1021/jf201342t. [PMID: 21726089]
  • Mary T Fletcher, Ian J Brock, Keith G Reichmann, Ross A McKenzie, Barry J Blaney. Norsesquiterpene glycosides in bracken ferns (Pteridium esculentum and Pteridium aquilinum subsp. wightianum) from Eastern Australia: reassessed poisoning risk to animals. Journal of agricultural and food chemistry. 2011 May; 59(9):5133-8. doi: 10.1021/jf104267c. [PMID: 21456622]
  • Joshua P Der, Michael S Barker, Norman J Wickett, Claude W dePamphilis, Paul G Wolf. De novo characterization of the gametophyte transcriptome in bracken fern, Pteridium aquilinum. BMC genomics. 2011 Feb; 12(?):99. doi: 10.1186/1471-2164-12-99. [PMID: 21303537]
  • János Vetter. A biological hazard of our age: bracken fern [Pteridium aquilinum (L.) Kuhn]--a review. Acta veterinaria Hungarica. 2009 Mar; 57(1):183-96. doi: 10.1556/avet.57.2009.1.18. [PMID: 19457786]
  • Lynnette R Ferguson, Martin Philpott. Nutrition and mutagenesis. Annual review of nutrition. 2008; 28(?):313-29. doi: 10.1146/annurev.nutr.28.061807.155449. [PMID: 18399774]
  • Lars Holm Rasmussen, Hans Christian Bruun Hansen, Denis Lauren. Sorption, degradation and mobility of ptaquiloside, a carcinogenic Bracken (Pteridium sp.) constituent, in the soil environment. Chemosphere. 2005 Feb; 58(6):823-35. doi: 10.1016/j.chemosphere.2004.08.088. [PMID: 15621196]
  • M B Lioi, R Barbieri, G Borzacchiello, S Dezzi, S Roperto, A Santoro, V Russo, F Roperto. Chromosome aberrations in cattle with chronic enzootic haematuria. Journal of comparative pathology. 2004 Aug; 131(2-3):233-6. doi: 10.1016/j.jcpa.2004.01.011. [PMID: 15276863]
  • Uvidelio F Castillo, Alistair L Wilkins, Denis R Lauren, Barry L Smith, Miguel Alonso-Amelot. Pteroside A2--a new illudane-type sesquiterpene glucoside from pteridium caudatum L. Maxon, and the spectrometric characterization of caudatodienone. Journal of agricultural and food chemistry. 2003 Apr; 51(9):2559-64. doi: 10.1021/jf026238j. [PMID: 12696937]
  • Lars H Rasmussen, Stine Kroghsbo, Jens C Frisvad, Hans Christian B Hansen. Occurrence of the carcinogenic Bracken constituent ptaquiloside in fronds, topsoils and organic soil layers in Denmark. Chemosphere. 2003 Apr; 51(2):117-27. doi: 10.1016/s0045-6535(02)00694-x. [PMID: 12586144]
  • Lars Holm Rasmussen, Lasse Sander Jensen, Hans Christian Bruun Hansen. Distribution of the carcinogenic terpene ptaquiloside in bracken fronds, rhizomes (Pteridium aquilinum), and litter in Denmark. Journal of chemical ecology. 2003 Mar; 29(3):771-8. doi: 10.1023/a:1022885006742. [PMID: 12757333]
  • K A Kumar, M Kataria, R Somvanshi, S Kumar, M Saini. Characterization of toxin from cheilanthes fern and its effect on lymphocyte proliferation and DNA fragmentation. Indian journal of experimental biology. 2001 Oct; 39(10):1065-7. doi: ". [PMID: 11883517]
  • E Marrero, C Bulnes, L M Sánchez, I Palenzuela, R Stuart, F Jacobs, J Romero. Pteridium aquilinum (bracken fern) toxicity in cattle in the humid Chaco of Tarija, Bolivia. Veterinary and human toxicology. 2001 Jun; 43(3):156-8. doi: NULL. [PMID: 11383656]
  • R N Freitas, P J O'Connor, A S Prakash, M Shahin, A C Povey. Bracken (Pteridium aquilinum)-induced DNA adducts in mouse tissues are different from the adduct induced by the activated form of the Bracken carcinogen ptaquiloside. Biochemical and biophysical research communications. 2001 Feb; 281(2):589-94. doi: 10.1006/bbrc.2001.4388. [PMID: 11181088]
  • M E Alonso-Amelot, M Avendaño. Possible association between gastric cancer and bracken fern in Venezuela: an epidemiologic study. International journal of cancer. 2001 Jan; 91(2):252-9. doi: 10.1002/1097-0215(20010115)91:2<252::aid-ijc1028>3.0.co;2-o. [PMID: 11146454]
  • D M Potter, M S Baird. Carcinogenic effects of ptaquiloside in bracken fern and related compounds. British journal of cancer. 2000 Oct; 83(7):914-20. doi: 10.1054/bjoc.2000.1368. [PMID: 10970694]
  • S Gounalan, R Somvanshi, M Kataria, G S Bisht, B L Smith, D R Lauren. Effect of bracken (Pteridium a quilinum) and dryopteris (Dryopteris juxtaposita) fern toxicity in laboratory rabbits. Indian journal of experimental biology. 1999 Oct; 37(10):980-5. doi: NULL. [PMID: 10783757]
  • M Shahin, B L Smith, A S Prakash. Bracken carcinogens in the human diet. Mutation research. 1999 Jul; 443(1-2):69-79. doi: 10.1016/s1383-5742(99)00011-3. [PMID: 10415432]
  • U F Castillo, M Ojika, M Alonso-Amelot, Y Sakagami. Ptaquiloside Z, a new toxic unstable sesquiterpene glucoside from the neotropical bracken fern Pteridium aquilinum var. caudatum. Bioorganic & medicinal chemistry. 1998 Nov; 6(11):2229-33. doi: 10.1016/s0968-0896(98)00168-0. [PMID: 9881114]
  • M Shahin, M R Moore, S Worrall, B L Smith, A A Seawright, A S Prakash. H-ras activation is an early event in the ptaquiloside-induced carcinogenesis: comparison of acute and chronic toxicity in rats. Biochemical and biophysical research communications. 1998 Sep; 250(2):491-7. doi: 10.1006/bbrc.1998.9341. [PMID: 9753659]
  • M E Alonso-Amelot. The link between bracken fern and stomach cancer: milk. Nutrition (Burbank, Los Angeles County, Calif.). 1997 Jul; 13(7-8):694-6. doi: 10.1016/s0899-9007(97)83017-1. [PMID: 9263265]
  • A J Ngomuo, R S Jones. Cytotoxicity studies of quercetin, shikimate, cyclohexanecarboxylate and ptaquiloside. Veterinary and human toxicology. 1996 Feb; 38(1):14-8. doi: NULL. [PMID: 8825742]
  • M Yoshida, T Saito. Non-urotoxic induction of hemorrhagic cystitis by braxin C, a bracken toxin, in guinea pigs. The Journal of toxicological sciences. 1994 May; 19(2):55-9. doi: 10.2131/jts.19.2_55. [PMID: 8072040]
  • B L Smith, A A Seawright, J C Ng, A T Hertle, J A Thomson, P D Bostock. Concentration of ptaquiloside, a major carcinogen in bracken fern (Pteridium spp.), from eastern Australia and from a cultivated worldwide collection held in Sydney, Australia. Natural toxins. 1994; 2(6):347-53. doi: ". [PMID: 7704447]
  • I Hirono, M Ito, S Yagyu, M Haga, K Wakamatsu, T Kishikawa, O Nishikawa, K Yamada, M Ojika, H Kigoshi. Reproduction of progressive retinal degeneration (bright blindness) in sheep by administration of ptaquiloside contained in bracken. The Journal of veterinary medical science. 1993 Dec; 55(6):979-83. doi: 10.1292/jvms.55.979. [PMID: 8117827]
  • T Sato, H Inaba, K Kawai, H Furukawa, I Hirono, T Miyazawa. Low-level chemiluminescence from Drosophila melanogaster fed with chemical mutagens polycyclic aromatic hydrocarbon quinones and a carcinogenic bracken fern. Mutation research. 1991 Nov; 251(1):91-7. doi: 10.1016/0027-5107(91)90218-d. [PMID: 1944380]
  • M Asano, C Ohkubo, A Sasaki, I Hirono, K Yamada, H Niwa, M Ojika. Acute microcirculatory changes induced by intravenous administration to rabbits of ptaquiloside, a bracken carcinogen. Journal of ethnopharmacology. 1989 Nov; 27(1-2):213-20. doi: 10.1016/0378-8741(89)90092-5. [PMID: 2615421]
  • B L Smith, P P Embling, D R Lauren, M P Agnew, A D Ross, P L Greentree. Carcinogen in rock fern (Chielanthes sieberi) from New Zealand and Australia. Australian veterinary journal. 1989 Jul; 66(7):230-1. doi: 10.1111/j.1751-0813.1989.tb09822.x. [PMID: 2775071]
  • M Matoba, E Saito, K Saito, K Koyama, S Natori, T Matsushima, M Takimoto. Assay of ptaquiloside, the carcinogenic principle of bracken, Pteridium aquilinum, by mutagenicity testing in Salmonella typhimurium. Mutagenesis. 1987 Nov; 2(6):419-23. doi: 10.1093/mutage/2.6.419. [PMID: 3328033]
  • I Hirono. Carcinogenicity of plant constituents: pyrrolizidine alkaloids, flavonoids, bracken fern. Progress in clinical and biological research. 1986; 206(?):45-53. doi: ". [PMID: 3952097]
  • W D Zhang. [Studies on the carcinogenicity of bracken fern (Pteridium aquilinum)]. Zhonghua yi xue za zhi. 1985 Jul; 65(7):435-8. doi: ". [PMID: 3938333]
  • M Ojika, H Kigoshi, H Kuyama, H Niwa, K Yamada. Studies on Pteridium aquilinum var. latiusculum, IV. Isolation of three p-hydroxystyrene glycosides and an efficient method for the isolation of ptaquiloside, an unstable bracken carcinogen. Journal of natural products. 1985 Jul; 48(4):634-7. doi: 10.1021/np50040a019. [PMID: 4045476]
  • R Schoental. Bracken toxicity and soil mycotoxins. The Veterinary record. 1984 Nov; 115(19):500. doi: 10.1136/vr.115.19.500. [PMID: 6516185]
  • I Hirono, Y Kono, K Takahashi, K Yamada, H Niwa, M Ojika, H Kigoshi, K Niiyama, Y Uosaki. Reproduction of acute bracken poisoning in a calf with ptaquiloside, a bracken constituent. The Veterinary record. 1984 Oct; 115(15):375-8. doi: 10.1136/vr.115.15.375. [PMID: 6506412]