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In the chemical industry, dicoumarol is extracted from the plant to produce rodenticides.
Administration of vitamin K is therefore the antidote for dicoumarol toxicity.
Identified in 1940, dicoumarol became the prototype of the 4-hydroxycoumarin derivative anticoagulant drug class.
It contains dicoumarol that is an anticoagulant.
They confirmed their results by synthesizing dicoumarol and proving in 1940 that it was identical to the naturally occurring agent.
Through degradation experiments they established that the anticoagulant was 3,3'-methylenebis-(4-hydroxycoumarin), which they later named dicoumarol.
Dicoumarol appears in spoiled sweet clover silages and is considered to be a fermentation product and mycotoxin.
Although coumarin itself has no anticoagulant properties, it is transformed into the natural anticoagulant dicoumarol by a number of species of fungi.
Warfarin is a synthetic derivative of dicoumarol, a 4-hydroxycoumarin-derived mycotoxin anticoagulant originally discovered in spoiled sweet clover-based animal feeds.
Dicoumarol does affect coagulation, and was discovered in mouldy wet sweet-clover hay, as the cause of a naturally occurring bleeding disease in cattle.
This occurs as the result of the production of 4-hydroxycoumarin, then further (in the presence of naturally occurring formaldehyde) into the actual anticoagulant dicoumarol, a fermentation product and mycotoxin.
Fungal attack of the damaged and dying clover stalks explained the presence of the anticoagulant only in spoiled clover silages; dicoumarol is considered to be a fermentation product and mycotoxin.
Coumarin, in turn, is converted by fungi (including Penicillium, Aspergillus, Fusarium, and Mucor) into a poisonous anticoagulant, called dicoumarol, that may be found in moldly or spoiled sweet-clover.
Although 4-hydroxycoumarin itself is not an anticoagulant, it is an important fungal metabolite from the precursor coumarin (also not an anticoagulant), and its production leads to further fermentative production of the natural anticoagulant dicoumarol.
However, coumarins themselves do not influence clotting or warfarin-like action, but must first be metabolized by various fungi into compounds such as 4-hydroxycoumarin, then further (in the presence of naturally occurring formaldehyde) into dicoumarol, in order to have any anticoagulant properties.
It is a derivative of coumarin, a bitter tasting but sweet-smelling substance made by plants that does not itself affect coagulation, but which is (classically) transformed in mouldy feeds or silages by a number of species of fungi, into active dicoumarol.