Amarogentin

Amarogentin is a chemical compound found in gentian (Gentiana lutea) or in Swertia chirata.

Amarogentin

Chemical structure of amarogentin

Chemical structure of amarogentin
Names
IUPAC name
(4aS,5R,6S)-5-Ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl β-D-glucopyranoside 2-(3,3′,5-trihydroxy[1,1′-biphenyl]-2-carboxylate)
Systematic IUPAC name
(2S,3R,4S,5S,6R)-2-{[(4aS,5R,6S)-5-Ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,3′,5-trihydroxy[1,1′-biphenyl]-2-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.166.688
PubChem CID
UNII
  • InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1 Y
    Key: DBOVHQOUSDWAPQ-WTONXPSSSA-N Y
  • InChI=1/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1
    Key: DBOVHQOUSDWAPQ-WTONXPSSBG
SMILES
  • O=C/1OCC[C@@H]5C\1=C\O[C@@H](O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4OC(=O)c3c(c2cccc(O)c2)cc(O)cc3O)CO)[C@@H]5\C=C
Properties
C29H30O13
Molar mass 586.546 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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 glycosides 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 TAS2R50. 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 in animal models being an inhibitor of topoisomerase I.

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