Amarogentin
Encyclopedia
Amarogentin is a chemical compound found in gentian (Gentiana lutea
) or in Swertia chirata.
Gentian root has a long history of use as a herbal bitter in the treatment of digestive disorders and is an ingredient of many proprietary medicines. The bitter principles of gentian root are seco-iridoid
glycoside
s amarogentin and gentiopicrin. The former is one of the most bitter natural compounds known and is used as a scientific basis for measuring bitterness. In humans, it activates the bitter taste receptor
hTAS2R50. The biphenylcarboxylic acid moiety is biosynthesized by a polyketide
-type pathway, with three units of acetyl-CoA
and one unit of 3-hydroxybenzoyl-CoA, this being formed from an early shikimate pathway intermediate and not via cinnamic or benzoic acid.
It also shows an antileishmanial activity being an inhibitor of topoisomerase I.
Gentiana lutea
Gentiana lutea is a species of gentian native to the mountains of central and southern Europe. Other names include 'Yellow Gentian', 'Bitter Root', 'Bitterwort', 'Centiyane', and 'Genciana'.-Growth:...
) or in Swertia chirata.
Gentian root has a long history of use as a herbal bitter in the treatment of digestive disorders and is an ingredient of many proprietary medicines. The bitter principles of gentian root are seco-iridoid
Iridoid
Iridoids are a class of secondary metabolites found in a wide variety of plants and in some animals. They are monoterpenes biosynthesized from isoprene and they are often intermediates in the biosynthesis of alkaloids. Chemically, the iridoids usually consist of a cyclopentane ring fused to a...
glycoside
Glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to a non-carbohydrate moiety, usually a small organic molecule. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme...
s amarogentin and gentiopicrin. The former is one of the most bitter natural compounds known and is used as a scientific basis for measuring bitterness. In humans, it activates the bitter taste receptor
Taste receptor
A Taste receptor is a type of receptor which facilitates the sensation of taste.Examples include TAS2R16 and TAS2R38.They are divided into two families:* Type 1, sweet, first characterized in 2001: –...
hTAS2R50. The biphenylcarboxylic acid moiety is biosynthesized by a polyketide
Polyketide
Polyketides are secondary metabolites from bacteria, fungi, plants, and animals. Polyketides are usually biosynthesized through the decarboxylative condensation of malonyl-CoA derived extender units in a similar process to fatty acid synthesis...
-type pathway, with three units of acetyl-CoA
Acetyl-CoA
Acetyl coenzyme A or acetyl-CoA is an important molecule in metabolism, used in many biochemical reactions. Its main function is to convey the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production. In chemical structure, acetyl-CoA is the thioester...
and one unit of 3-hydroxybenzoyl-CoA, this being formed from an early shikimate pathway intermediate and not via cinnamic or benzoic acid.
It also shows an antileishmanial activity being an inhibitor of topoisomerase I.