The phallotoxins consist of at least seven compounds, all of which are bicyclic
heptapeptide
Peptides (, ) are short chains of amino acids linked by peptide bonds. Long chains of amino acids are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides.
A ...
s (seven amino acids), isolated from the death cap mushroom ''(
Amanita phalloides
''Amanita phalloides'' (), commonly known as the death cap, is a deadly poisonous basidiomycete fungus, one of many in the genus ''Amanita''. Widely distributed across Europe, but now sprouting in other parts of the world, ''A. phalloides ...
)''. They differ from the closely related
amatoxin Amatoxin is the collective name of a subgroup of at least nine related toxic compounds found in three genera of poisonous mushrooms (''Amanita'', '' Galerina'' and '' Lepiota'') and one species ( Conocybe filaris) of the genus '' Conocybe''. Amatoxi ...
s by being one residue smaller, both in the final product and the precursor protein.
Phalloidin
Phalloidin belongs to a class of toxins called phallotoxins, which are found in the death cap mushroom ''(Amanita phalloides)''. It is a rigid bicyclic heptapeptide that is lethal after a few days when injected into the bloodstream. The major sy ...
had been isolated in 1937 by
Feodor Lynen
Feodor Felix Konrad Lynen (; 6 April 19116 August 1979) was a German biochemist. In 1964 he won the Nobel Prize in Physiology or Medicine together with Konrad Bloch for their discoveries concerning the mechanism and regulation of cholesterol an ...
,
Heinrich Wieland
Heinrich Otto Wieland (; 4 June 1877 – 5 August 1957) was a German chemist. He won the 1927 Nobel Prize in Chemistry for his research into the bile acids.
Career
In 1901 Wieland received his doctorate at the University of Munich while studyin ...
's student and son-in-law, and Ulrich Wieland of the
University of Munich
The Ludwig Maximilian University of Munich (simply University of Munich or LMU; german: Ludwig-Maximilians-Universität München) is a public research university in Munich, Germany. It is Germany's sixth-oldest university in continuous operatio ...
. The remaining six are
prophalloin,
phalloin,
phallisin,
phallacidin,
phallacin and
phallisacin. 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
The blusher is the common name for several closely related species of the genus ''Amanita''. ''A. rubescens'' or the blushing amanita, is found in Europe and eastern North America, and ''A. novinupta'', also known as the new bride blushing aman ...
(''Amanita rubescens'')
have not been confirmed by later researchers
[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.]
Chemical structures
Image:Skeletal formula of phalloidin.svg, Phalloidin
Image:prophalloin.png, Prophalloin
Image:phalloin.png, Phalloin
Image:phallisin.png, Phallisin
Image:phallacidin.png, Phallacidin
Image:phallacin.png, Phallacin
Image:phallisacin.png, Phallisacin
References
{{Poisonous Amanitas
Mycotoxins found in Basidiomycota
Tryptamines
Cyclic peptides