Coumarins
Synonym(s)
DefinitionThis section has been translated automatically.
The term "coumarins" refers to a group of naturally occurring derivatives of coumarinum, also known as coumarin, a colorless, burning-tasting substance that exudes a sweet, spicy, hay-like odor. The derivatives of coumarin are present as methoxy or hydroxy compounds. As plant constituents, they are usually present in the cell as glycosidic compounds (meliolotoside). If the cell is damaged or under enzymatic influence, the aglycas are split off, whereby the typical aromatic odor(woodruff, hay) develops.
OccurrenceThis section has been translated automatically.
Coumarin is the parent compound of more than 3000 natural derivatives. They are widely distributed in the plant world, for example Apiaceae, Fabaceae, Rutaceae, Solanaceae, Asteraceae. Furthermore in essential oils, such as cinnamon or peppermint oil. Derivatives of coumarinum such as phenprocoumon or dicumarol act as competitive inhibitors of the enzyme gamma-glutamylcarboxylase. They inhibit the synthesis of the prothrombin complex and thus have an anticoagulant effect (see coumarins systemic).
7-Hydroxycoumarin (Umbelliferon) is by far the most common natural coumarin derivative.
Furanocoumarins are tricyclic ring systems. 7,6 Furanocoumarins are called psoralenes and are of great medical importance (seePUVA).
Note(s)This section has been translated automatically.
Coumarin was first isolated in 1813 by A. Vogel from the seeds of the tonka tree (cumarú in Spanish), a tree native to Guyana (Coumaruona odorata). The fruits have a coumarin content of around 2 to 3%.
LiteratureThis section has been translated automatically.
- Abraham, K (2007) Cinnamon and coumarin: a clarification from a scientific and regulatory point of view. Dtsch. Lebensmittel-Rundschau 10: 480-487.
- Beamand J A. (1998) Lack of effect of coumarin on unscheduled DNA synthesis in precision-cut human liver slices. Food Chem. Toxicol. 36:647-653.
- BGA (1994) Liver toxic effects of coumarins. Drug information of the BGA Pharm In. 56; IV/92.
- Booth NL et al (2004) Confusion regarding anticoagulant coumarins in dietary supplements. Clin. Pharmacol. Ther. 76:511-516.
- Lake BG et al (1996) Use of precision-cut liver slices to evaluate species differences in 2-actylaminofluorene induced unscheduled DNA synthesis. Tox. Appl. Pharm. 138:231-241.
- Ritschel W.A. et al. (1979) First -pass effect of coumarin. Int. J. Clin. Pharmacol. Biopharm. 17:9-103.
- Vassallo JD et al (2004) Metabolic detoxication determines species differences in coumarin induced hapototoxixity. Toxicological Science 80: 249-257