Amarogentin is a chemical compound found in gentian (''

Gentiana lutea ''Gentiana lutea'', the great yellow gentian, is a species of gentian native to the mountains of central and southern Europe. Growth ''Gentiana lutea'' is an herbaceous perennial plant, growing to tall, with broad lanceolate to elliptic leave ...

'') or in ''

Swertia chirata ''Swertia'' is a genus in the gentian family containing plants sometimes referred to as the felworts. Some species bear very showy purple and blue flowers. Many members of this genus have medicinal and cultural purposes. Plants of genus '' Fras ...

''. 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

secoiridoid Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, mo ...

glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...

s amarogentin and gentiopicrin. The former is one of the most

bitter Bitter may refer to: Common uses * Resentment, negative emotion or attitude, similar to being jaded, cynical or otherwise negatively affected by experience * Bitter (taste), one of the five basic tastes Books * '' Bitter (novel)'', a 2022 nove ...

natural compounds known and is used as a scientific basis for measuring bitterness. In humans, it activates the bitter

taste receptor A taste receptor or tastant is a type of cellular receptor which facilitates the sensation of taste. When food or other substances enter the mouth, molecules interact with saliva and are bound to taste receptors in the oral cavity and other loc ...

TAS2R50 Taste receptor type 2 member 50 is a protein that in humans is encoded by the ''TAS2R50'' gene. Function TAS2R50 belongs to the large TAS2R receptor family. TAS2Rs are expressed on the surface of taste receptor cells and mediate the perception ...

. The biphenylcarboxylic acid moiety is biosynthesized by a

polyketide Polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone (or reduced forms of a ketone) and methylene groups: (-CO-CH2-). First studied in the early 20th century, discovery, biosynth ...

-type pathway, with three units of acetyl-CoA and one unit of 3-hydroxybenzoyl-CoA, this being formed from an early

shikimate pathway The shikimate pathway (shikimic acid pathway) is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for the biosynthesis of folates and aromatic amino acids (tryptophan, phenylalanine, and tyrosine) ...

intermediate and not via cinnamic or benzoic acid. It also shows an antileishmanial activity in

animal model An animal model (short for animal disease model) is a living, non-human, often genetic-engineered animal used during the research and investigation of human disease, for the purpose of better understanding the disease process without the risk of ha ...

s being an inhibitor of topoisomerase I.

References

{{reflist, 2 Bitter compounds Iridoid glycosides Topoisomerase inhibitors