ptaquiloside
Sign in to saveAlso known as (2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,7a-dihydro-2H-indene-6,1'-cyclopropane]-1-one
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 an 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.
Wikidata facts
- Mass
- 398.19406792
Show 5 more facts
- isomeric SMILES
- C[C@@H]1C[C@]2(C=C(C3(CC3)[C@@]([C@H]2C1=O)(C)O)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
- chemical formula
- C₂₀H₃₀O₈
- found in taxon
- Pteridium caudatum
- canonical SMILES
- O=C1C(C)CC2(OC3OC(CO)C(O)C(O)C3O)C=C(C)C4(CC4)C(O)(C)C12
- Commons category
- Ptaquiloside
Sources (2)
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Encyclopedic overview
15 sectionsContents
- Sources
- In plants and food chains
- Ways of ptaquiloside exposure
- Mechanism of action
- General mechanism
- Under physiological conditions
- Syndromes
- Ruminants
- Non-ruminants
- Human populations
- Control and detection
- Synthesis
- Biosynthesis
- Total synthesis
- References
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 an 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.
Excerpted from Wikipedia’s “ptaquiloside” article, available under the CC BY-SA 4.0 licence.