amarogentin
{{chembox
| 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 = {{cascite|correct|CAS}}
| CASNoOther =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5L82GT5I0W
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 451112
| PubChem = 115149
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 103033
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2622
| 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
| 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 = {{stdinchicite|correct|chemspider}}
| 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 = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DBOVHQOUSDWAPQ-WTONXPSSSA-N
| MeSHName =
}}
|Section2={{Chembox Properties
| C=29 | H=30 | O=13
| Appearance =
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|Section3={{Chembox Hazards
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Amarogentin is a chemical compound found in gentian (Gentiana lutea) or in Swertia chirata.{{cite journal | doi = 10.1055/s-2000-8579 | title = Production of Amarogentin in Root Cultures of Swertia chirata | year = 2000 | last1 = Keil* | first1 = Michael | last2 = Härtle | first2 = Birgit | last3 = Guillaume | first3 = Anna | last4 = Psiorz | first4 = Manfred | journal = Planta Medica | volume = 66 | issue = 5 | pages = 452–7 | pmid = 10909267| s2cid = 21149742 }}
Image:Amarogentin gentiopicrin.png{{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[http://www.awl.ch/heilpflanzen/gentiana_lutea/index.htm Heilpflanzen:Gentiana lutea] {{Webarchive|url=https://web.archive.org/web/20090902132313/http://www.awl.ch/heilpflanzen/gentiana_lutea/index.htm |date=2009-09-02 }} (German) and is used as a scientific basis for measuring bitterness. In humans, it activates the bitter taste receptor TAS2R50.{{cite journal | doi = 10.1021/jf9014334 | title = The Human Bitter Taste Receptor hTAS2R50 is Activated by the Two Natural Bitter Terpenoids Andrographolide and Amarogentin | year = 2009 | last1 = Behrens | first1 = Maik | last2 = Brockhoff | first2 = Anne | last3 = Batram | first3 = Claudia | last4 = Kuhn | first4 = Christina | last5 = Appendino | first5 = Giovanni | last6 = Meyerhof | first6 = Wolfgang | journal = Journal of Agricultural and Food Chemistry | volume = 57 | issue = 21 | pages = 9860–6 | pmid = 19817411}} 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.{{cite journal | doi = 10.1002/1099-0690(200104)2001:8<1459::AID-EJOC1459>3.0.CO;2-0 | title = Unexpected Biosynthetic Precursors of Amarogentin − A Retrobiosynthetic13C NMR Study | year = 2001 | last1 = Wang | first1 = Chang-Zeng | last2 = Maier | first2 = Ulrich H. | last3 = Eisenreich | first3 = Wolfgang | last4 = Adam | first4 = Petra | last5 = Obersteiner | first5 = Ingrid | last6 = Keil | first6 = Michael | last7 = Bacher | first7 = Adelbert | last8 = Zenk | first8 = Meinhart H. | journal = European Journal of Organic Chemistry | volume = 2001 | issue = 8 | pages = 1459}}
It also shows an antileishmanial activity in animal models{{cite journal | doi = 10.1093/jac/44.6.791 | title = Evaluation of the in-vivo activity and toxicity of amarogentin, an antileishmanial agent, in both liposomal and niosomal forms | year = 1999 | last1 = Medda | first1 = S. | journal = Journal of Antimicrobial Chemotherapy | volume = 44 | issue = 6 | pages = 791–4 | pmid = 10590280 | last2 = Mukhopadhyay | first2 = S | last3 = Basu | first3 = MK| doi-access = free }} being an inhibitor of topoisomerase I.{{cite journal | doi = 10.1021/np960018g | title = Amarogentin, a Naturally Occurring Secoiridoid Glycoside and a Newly Recognized Inhibitor of Topoisomerase I fromLeishmania donovani | year = 1996 | last1 = Ray | first1 = Sutapa | last2 = Majumder | first2 = Hemanta K. | last3 = Chakravarty | first3 = Ajit K. | last4 = Mukhopadhyay | first4 = Sibabrata | last5 = Gil | first5 = Roberto R. | last6 = Cordell | first6 = Geoffrey A. | journal = Journal of Natural Products | volume = 59 | pages = 27–9 | pmid = 8984149 | issue = 1}}