page_title: Ptaquiloside
section_title: General mechanism
hierarchical_section_title: Ptaquiloside / Mechanism of action / General mechanism
caption_attribution_description: English: The mechanism of action of ptaquiloside under acidic and weakly alkaline conditions.
context_page_description: Ptaquiloside is a norsesquiterpene glucoside produced by bracken ferns 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.
  The pure form ptaquiloside is a colorless amorphous compound. It is readily soluble in water and fairly soluble in ethyl acetate. Except in the plants, ptaquiloside has been detected in the milk and meat of affected livestock, as well as in the underground water and dry soil around bracken fern vegetation. The prevalence of ptaquiloside in daily sources along with its carcinogenic effects make it an increasing biological hazard in modern days.
context_section_description: In acidic conditions, ptaquiloside gradually undergoes aromatization with the elimination of D-glucose to afford ptaquilosin, and finally pterosin B. Under weakly alkaline conditions, ptaquiloside and its aglycone ptaquilosin are converted into an unstable conjugated dienone intermediate. This ptaquilodienone is the activated form of ptaquiloside and is regarded as the ultimate carcinogen of bracken ferns. Due to the constitution of a cyclopropyl carbinol system, ptaquilodienone is a strong electrophile and acts as a powerful alkylating agent that reacts directly with biological nucleophiles including amino acids, nucleosides, and nucleotides under weakly acidic conditions at room temperature (as shown in the scheme below).
caption: The mechanism of action of ptaquiloside
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