Amarogentine

A bitter substance that is found in gentian root and centaury and is responsible for the bitterness in these drugs. Several bitter substance receptors with which humans perceive amarogentin have been identified, including TAS2R1 and TAS2R50.

Chemically, it is a trihydroxydiphenlycarboxylic acid ester of sweroside. The substance is poorly soluble in water, well soluble in ethanol and acetone.

Amarogentin has antiproliferative, immunomodulatory effects. In mast cells amarogentine inhibits the substance-P induced production of TNF-alpha. In keratinocyte cultures the substance reduces the expression of IL-8 and MMP-1.

Various studies indicate that amarogentin is the bitterest natural substance known to date. The substance is contained in larger quantities in the Ayurvedic medicinal plant Maha-tita (king of bitters), which is used in South Asia for infections.

1. Behrens M et al (2009) The human bitter taste receptor hTAS2R50 is activated by the two natural bitter terpenoids andrographolides and amarogentin. J Agric Food Chem 57:9860-9866.
2. Huang C et al (2016) Amarogentin Induces Apoptosis of Liver CancerCells via Upregulation of p53 and Downregulation of Human Telomerase ReverseTranscriptase in Mice. Technol Cancer Res Treat pii: 1533034616657976.
3. Wölfle U et al (2015) Amarogentin Displays Immunomodulatory Effects in Human Mast Cells and Keratinocytes. Mediators Inflamm doi: 10.1155/2015/630128.
4. Zhao JG et al (2016) Amarogentin secoiridoid inhibits in vivo cancer cell growth in xenograft mice model and induces apoptosis in human gastric cancer cells (SNU-16) through G2/M cell cycle arrest and PI3K/Akt signalling pathway. J BUON 21:609-617.