Amarogentin

Title: Amarogentin
CAS Registry Number: 21018-84-8
CAS Name: [4aS-(4aa,5b,6a)]-3,3¢,5-Trihydroxy[1,1¢-biphenyl]-2-carboxylic acid 2-ester with 5-ethenyl-6-(b-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one
Additional Names: sweroside-2¢-(3¢¢,5¢¢,3¢¢¢-trihydroxydiphenyl)-2¢¢-carboxylic acid ester
Molecular Formula: C29H30O13
Molecular Weight: 586.54
Percent Composition: C 59.38%, H 5.16%, O 35.46%
Literature References: Strongly bitter glucoside. Isoln from Swertia chirata Buch-Ham., Gentianaceae: Korte, Ber. 88, 704 (1955); 89, 2404 (1956); from Swertia japonica Makino: Inouye et al., Chem. Pharm. Bull. 18, 1856 (1970). Occurrence in gentianaceous plants: Inouye, Nakamura, J. Pharm. Soc. Jpn. 91, 755 (1971), C.A. 75, 95431b (1971). Structure: eidem, Tetrahedron Lett. 1968, 4919; eidem, Tetrahedron 27, 1951 (1971).
Properties: Colorless needles, mp 229-230° (monohydrate). [a]D20 -116.6° (methanol). uv max: 230, 266, 306 nm (log e 4.46, 4.07, 3.68). Slightly sol in benzene, water; freely sol in acetone, anhydr dioxane, tetrahydrofuran, methanol, ethanol. Practically insol in petr ether, ether, cyclohexane, CHCl3.
Melting point: mp 229-230° (monohydrate)
Optical Rotation: [a]D20 -116.6° (methanol)
Absorption maximum: uv max: 230, 266, 306 nm (log e 4.46, 4.07, 3.68)
Amarolide Amber Amberlite? Amberlyst 15? Ambrisentan

Amarogentin
Chemical structure of amarogentin
Chemical structure of amarogentin
Identifiers
CAS number 21018-84-8 N=
PubChem 115149
ChemSpider 103033 YesY
ChEBI CHEBI:2622 YesY
ChEMBL CHEMBL451112 YesY
Jmol-3D images Image 1
Properties
Molecular formula C29H30O13
Molar mass 586.54 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Amarogentin is a chemical compound found in gentian (Gentiana lutea) or in Swertia chirata.[1]

Amarogentin and gentiopicrin, the bitter glycosides from gentian root

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[2] and is used as a scientific basis for measuring bitterness. In humans, it activates the bitter taste receptor hTAS2R50.[3] 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.[4]

It also shows an antileishmanial activity[5] being an inhibitor of topoisomerase I.[6]