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Coumarin, found in plants like tonka beans and cinnamon, has several derivatives with anti-inflammatory and anticoagulant properties. Bishydroxycoumarin, a natural or synthetic derivative, was first discovered in sweet clover and later used as an oral anticoagulant. Warfarin, a popular synthetic drug, was originally used as a rodenticide. Coumarin derivatives can be toxic in high quantities but can be counteracted with Vitamin K. Umbelliferone, a natural derivative, has antioxidant properties and is used in medicine as an adjunct to sunscreen and for the synthesis of anticancer drugs.
Coumarin derivatives are widely used in pharmaceutical and commercial applications due to their health properties. A compound found naturally in plants such as tonka beans, cinnamon, sweet clover, and vanilla grass, coumarin has several chemical derivatives that can be found naturally or synthesized in a laboratory. These include the natural umbelliferone, as well as the synthetic drugs warfarin and bishydroxycoumarin. Coumarin derivatives have been shown to possess anti-inflammatory and anticoagulant properties, but they can also be toxic in high quantities and are sometimes used as rodenticides.
While coumarin itself does not function as an anticoagulant, a substance that prevents blood from clotting, it can be chemically modified through natural or man-made processes to do so. The coumarin molecule is modified through the addition of certain chemical groups in a substance called 4-hydroxycoumarin, which can in turn be transformed into drugs with anticoagulant properties. There are several forms of 4-hydroxycoumarins.
4-Hydroxycoumarin known as bishydroxycoumarin, or dicoumarol, can be formed by natural or artificial methods. When sweet clover interacts with fungi and becomes moldy, it undergoes a chemical change that causes the coumarin in the plant to turn into bishydroxycoumarin. The anticoagulant properties of coumarin derivatives such as dicoumarol were first discovered in 1939 from evidence that cattle in North America that had been fed sweet clover suffered from hemorrhaging or bleeding. Bishydroxycoumarin was later produced synthetically for use as an oral anticoagulant.
Warfarin, a dicoumarol derivative, is a popular synthetic drug used to prevent blood clots in cases where clot formation could cut off the blood supply to a major organ such as the heart or brain. Prior to its development as an anticoagulant, this drug was commonly used as a rodenticide. Warfarin and other coumarin derivatives work as pesticides causing uncontrolled bleeding in the target animal.
The anticoagulant activity of coumarin derivatives can be toxic to humans if these compounds are ingested in excessive amounts. Vitamin K is a well-known antidote in cases where excessive ingestion has occurred. This is because substances such as dicoumarol work by inhibiting the action of Vitamin K in the production of prothrombin, an essential compound in the blood clotting process. With the addition of Vitamin K, the anticoagulant action of dicumarol can be counteracted.
Umbelliferone, unlike warfarin and other synthetic compounds, occurs naturally in some fruits. It too has medicinal properties, including antioxidant activity. In other words, it can help prevent oxidation, a chemical reaction that can lead to cell destruction. Umbelliferone is useful in medicine as an adjunct to sunscreen and as a starting point for the synthesis of anticancer drugs.
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