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Phallotoxin

From Wikipedia, the free encyclopedia
Group of chemical compounds

Thephallotoxins consist of at least seven compounds, all of which are bicyclicheptapeptides (seven amino acids), isolated from the death cap mushroom(Amanita phalloides). They differ from the closely relatedamatoxins by being one residue smaller, both in the final product and the precursor protein.[1]

Phalloidin had been isolated in 1937 byFeodor Lynen,Heinrich Wieland's student and son-in-law, and Ulrich Wieland of theUniversity of Munich.[2][3] The remaining six areprophalloin,phalloin,phallisin,phallacidin,phallacin andphallisacin. Though highly toxic to liver cells, phallotoxins have since been found to have little contribution to the death cap's toxicity because they are not absorbed through the gut. Reports of phalloidin in the edible (and sought after)Blusher (Amanita rubescens)[4] have not been confirmed by later researchers[5]

Chemical structures

[edit]
  • Phalloidin
    Phalloidin
  • Prophalloin
    Prophalloin
  • Phalloin
    Phalloin
  • Phallisin
    Phallisin
  • Phallacidin
    Phallacidin
  • Phallacin
    Phallacin
  • Phallisacin
    Phallisacin

References

[edit]
  1. ^Walton, Jonathan D.; Hallen-Adams, Heather E.; Luo, Hong (2010)."Ribosomal biosynthesis of the cyclic peptide toxins of Amanita mushrooms".Biopolymers.94 (5):659–664.doi:10.1002/bip.21416.PMC 4001729.PMID 20564017.
  2. ^Theodor Wieland (1987). "50 Jahre Phalloidin".Naturwissenschaften.74 (8):367–373.Bibcode:1987NW.....74..367W.doi:10.1007/BF00405464.PMID 3309681.
  3. ^Feodor Lynen, Ulrich Wieland (1938). "Über die Giftstoffe des Knollenblätterpilzes".Justus Liebig's Annalen der Chemie.533 (1):93–117.doi:10.1002/jlac.19385330105.
  4. ^Litten, W. (March 1975). "The most poisonous mushrooms".Scientific American.232 (3):90–101.Bibcode:1975SciAm.232c..90L.doi:10.1038/scientificamerican0375-90.PMID 1114308.
  5. ^Hallen HE, Adams GC, Eicker A (2002) Amatoxins and phallotoxins in indigenous and introduced South African Amanita species. South African Journal of Botany 68:322-326.
PoisonousAmanita mushrooms
Subgenus
Amanita
Amanita
Species
Compounds
Subgenus
Amanitina
Phalloideae
Species
Destroying angels
Other members
Compounds
Amatoxins
Phallotoxins
Virotoxins
Other compounds
Roanokenses
Species
Compounds
Validae
Species
Compounds
Subgenus
Lepidella
Lepidella
(=Saproamanita)
Species
Compounds
  • unknown toxin
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Exotoxin
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Endotoxin
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Fish:
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Reptile/
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  • note: some toxins are produced by lower species and pass through intermediate species
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