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Ptaquiloside is a norsesquiterpene glucoside produced by bracken ferns (majorly Pteridium aquilinum) during metabolism. It is identified to be the main carcinogen of the ferns and to be responsible for their biological effects, such as haemorrhagic disease and bright blindness in livestock and oesophageal, gastric cancer in humans. Ptaquiloside has unstable chemical structure and acts as a DNA alkylating agent under physiological conditions. It was first isolated and characterized by Yamada and co-workers in 1983.

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  • Ptaquilósido (es)
  • プタキロサイド (ja)
  • Ptaquiloside (en)
  • Ptaquilosídeo (pt)
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  • プタキロサイド (ptaquiloside) とはワラビに含まれている発癌性物質で、、配糖体の一種。IARC発がん性リスク一覧のグループ3に分類される。1983年に名古屋大学のらによって単離された。 シクロプロパン骨格を含むのが特徴。 家畜がワラビを大量に食べて中毒死したのがきっかけで発見された。ヒトが食べる際には、灰汁抜きの際にプタキロサイドはほとんど流出するため、少量なら問題はない。 発癌のメカニズムは、プタキロサイドが加水分解により真性発癌物質である体となり、シクロプロパン環が開裂してカチオンが生成し、核酸塩基に結合してDNA鎖を切断する(特にAAAT部が損傷しやすい)ことによる。 (ja)
  • Ptaquilosídeo é um glucosídeo do grupo dos do tipo , o qual constitui a principal toxina presente em fetos do género Pteridium. Foi isolado pela primeira vez em 1983, ano em que a sua estereo-estrutura foi determinada. (pt)
  • El Ptaquilósido es la principal toxina de Pteridium aquilinum, aislada por primera vez en 1983.​ Su estereoestructura química es un glucósido norsesquiterpeno de tipo , determinada por Yamada y colaboradores.​ La carcinogenicidad de ptaquilósido fue probada en 1984,​​ y se mostró que el ptaquilósido era responsable de los efectos biológicos característicos de helechos, tales como envenenamiento agudo por helecho Pteridium, ceguera brillante en ovejas, mutagenicidad, efectos de clastogenicidad y genotoxicidad.​ (es)
  • Ptaquiloside is a norsesquiterpene glucoside produced by bracken ferns (majorly Pteridium aquilinum) during metabolism. It is identified to be the main carcinogen of the ferns and to be responsible for their biological effects, such as haemorrhagic disease and bright blindness in livestock and oesophageal, gastric cancer in humans. Ptaquiloside has unstable chemical structure and acts as a DNA alkylating agent under physiological conditions. It was first isolated and characterized by Yamada and co-workers in 1983. (en)
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  • Ptaquiloside (en)
name
  • Ptaquiloside (en)
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  • http://commons.wikimedia.org/wiki/Special:FilePath/Croziers,_fronds,_rhizomes_of_bracken_fern.jpg
  • http://commons.wikimedia.org/wiki/Special:FilePath/Mechanism_of_ptaquilodienone_with_deoxytelranucleotide.jpg
  • http://commons.wikimedia.org/wiki/Special:FilePath/Ptaquiloside.svg
  • http://commons.wikimedia.org/wiki/Special:FilePath/Species-specific_syndromes_caused_by_ptaquiloside.jpg
  • http://commons.wikimedia.org/wiki/Special:FilePath/The_mechanism_of_action_of_ptaquiloside.jpg
  • http://commons.wikimedia.org/wiki/Special:FilePath/Total_synthesis_of_(-)-ptaquilosin.jpg
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