Amarogentin

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title: "Amarogentin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["bitter-compounds", "iridoid-glycosides", "topoisomerase-inhibitors"] topic_path: "general/bitter-compounds" source: "https://en.wikipedia.org/wiki/Amarogentin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 456683340 | Name = | ImageFile = Amarogentin.png | ImageSize = 200px | ImageName = Chemical structure of amarogentin | ImageAlt = Chemical structure of amarogentin | ImageCaption = Chemical structure of amarogentin | ImageFile2 = Amarogentin 3D BS.png | ImageSize2 = 200px | ImageName2 = Chemical structure of amarogentin | ImageAlt2 = Chemical structure of amarogentin | ImageCaption2 = Chemical structure of amarogentin | IUPACName = (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) | SystematicName = (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 | OtherNames = |Section1={{Chembox Identifiers | CASNo = 21018-84-8 | CASNo_Ref = | UNII_Ref = | UNII = 5L82GT5I0W | ChEMBL_Ref = | ChEMBL = 451112 | PubChem = 115149 | ChemSpiderID_Ref = | ChemSpiderID = 103033 | ChEBI_Ref = | ChEBI = 2622 | SMILES = O=C/1OCC[C@@H]5C\1=C\OC@@H[C@@H]5\C=C | 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 | InChIKey = DBOVHQOUSDWAPQ-WTONXPSSBG | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = DBOVHQOUSDWAPQ-WTONXPSSSA-N |Section2={{Chembox Properties | C=29 | H=30 | O=13 |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | GHSPictograms = | GHSSignalWord = | HPhrases = | PPhrases = | GHS_ref =

Amarogentin is a chemical compound found in gentian

::figure[src="https://upload.wikimedia.org/wikipedia/commons/9/9d/Amarogentin_gentiopicrin.png" caption="Amarogentin and gentiopicrin, the bitter glycosides from gentian root]]{{clear left}}"] ::

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.

References

References

  1. GHS: [https://www.sigmaaldrich.com/product/SIAL/phl80178 sigma-aldrich phl80178] "Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008"
  2. [http://www.awl.ch/heilpflanzen/gentiana_lutea/index.htm Heilpflanzen:Gentiana lutea] {{Webarchive. link. (2009-09-02 ('''German'''))
  3. (2009). "The Human Bitter Taste Receptor hTAS2R50 is Activated by the Two Natural Bitter Terpenoids Andrographolide and Amarogentin". Journal of Agricultural and Food Chemistry.
  4. (2001). "Unexpected Biosynthetic Precursors of Amarogentin − A Retrobiosynthetic13C NMR Study". European Journal of Organic Chemistry.
  5. (1999). "Evaluation of the in-vivo activity and toxicity of amarogentin, an antileishmanial agent, in both liposomal and niosomal forms". Journal of Antimicrobial Chemotherapy.
  6. (1996). "Amarogentin, a Naturally Occurring Secoiridoid Glycoside and a Newly Recognized Inhibitor of Topoisomerase I fromLeishmania donovani". Journal of Natural Products.

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bitter-compoundsiridoid-glycosidestopoisomerase-inhibitors