Misplaced Pages

Amarogentin: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively
Page 1
Page 2
← Previous editContent deleted Content addedVisualWikitext
Revision as of 14:29, 21 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').← Previous edit Latest revision as of 03:20, 22 January 2024 edit undoEejit43Bot (talk | contribs)Bots9,175 editsm →See also: Fix improperly capitalized section headers, general fixesTag: AWB 
(28 intermediate revisions by 22 users not shown)
Line 1: Line 1:
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 455187292
| Watchedfields = changed
⚫ | verifiedrevid = 456683340
| Name = | Name =
| ImageFile = Amarogentin.png | ImageFile = Amarogentin.png
Line 6: Line 8:
| ImageName = Chemical structure of amarogentin | ImageName = Chemical structure of amarogentin
| ImageAlt = Chemical structure of amarogentin | ImageAlt = Chemical structure of amarogentin
<!-- | ImageCaption = Chemical structure of --> | ImageCaption = Chemical structure of amarogentin
| ImageFile2 = Amarogentin 3D BS.png
⚫ | IUPACName = <nowiki>pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]2,4-dihydroxy-6-(3-ydroxyphenyl)benzoate</nowiki>
| ImageSize2 = 200px
| ImageName2 = Chemical structure of amarogentin
| ImageAlt2 = Chemical structure of amarogentin
| ImageCaption2 = Chemical structure of amarogentin
| IUPACName = (4a''S'',5''R'',6''S'')-5-Ethenyl-1-oxo-4,4a,5,6-tetrahydro-1''H'',3''H''-pyranopyran-6-yl β-<small>D</small>-glucopyranoside 2-(3,3′,5-trihydroxy-2-carboxylate)
⚫ | SystematicName = (2''S'',3''R'',4''S'',5''S'',6''R'')-2-{pyran-6-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,3′,5-trihydroxy-2-carboxylate
| OtherNames = <!-- <br> --> | OtherNames = <!-- <br> -->
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = <!-- blanked - oldvalue: 21018-84-8 --> | CASNo = 21018-84-8
| CASNo_Ref = | CASNo_Ref = {{cascite|correct|CAS}}
| CASOther = | CASNoOther =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5L82GT5I0W
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 451112 | ChEMBL = 451112
| PubChem = 115149 | PubChem = 115149
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 103033 | ChemSpiderID = 103033
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2622 | ChEBI = 2622
| SMILES = O=C/1OCC5C\1=C\O(O4O((O)(O)4OC(=O)c3c(c2cccc(O)c2)cc(O)cc3O)CO)5\C=C | SMILES = O=C/1OCC5C\1=C\O(O4O((O)(O)4OC(=O)c3c(c2cccc(O)c2)cc(O)cc3O)CO)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 | 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 | InChIKey = DBOVHQOUSDWAPQ-WTONXPSSBG
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DBOVHQOUSDWAPQ-WTONXPSSSA-N | StdInChIKey = DBOVHQOUSDWAPQ-WTONXPSSSA-N
| MeSHName = | MeSHName =
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>29</sub>H<sub>30</sub>O<sub>13</sub> | C=29 | H=30 | O=13
| MolarMass = 586.54 g/mol
| ExactMass = 586.168641 u
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = <!-- °C --> | MeltingPt =
| BoilingPt = <!-- °C --> | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| GHSPictograms =
| RPhrases = <!-- {{R10}}, {{R23}}, {{R34}}, {{R50}} etc. -->
| GHSSignalWord =
| SPhrases = <!-- {{S1/2}}, {{S9}}, {{S16}}, {{S26}}, {{S36/37/39}}, {{S45}}, {{S61}} etc. -->
| HPhrases = {{HPhrases|}}
| PPhrases = {{PPhrases|}}
| GHS_ref = <ref>GHS: "Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008"</ref>
}} }}
}} }}
⚫ '''Amarogentin''' is a chemical compound found in gentian ('']'') or in '']''.<ref>Production of amarogentin in root cultures of Swertia chirata. Keil M, Härtle B, Guillaume A and Psiorz M, Planta Med. 2000 Jun;66(5), pages 452-457, {{PMID|10909267}}, {{doi|10.1055/s-2000-8579}}</ref>


⚫ '''Amarogentin''' is a chemical compound found in gentian ('']'') or in '']''.<ref>{{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 }}</ref>
⚫ ]
⚫ 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 seco-] ]s amarogentin and ]. The former is one of the most ] natural compounds known<ref> ('''German''')</ref> and is used as a scientific basis for measuring bitterness. In humans, it activates the bitter ] ].<ref>The human bitter taste receptor hTAS2R50 is activated by the two natural bitter terpenoids andrographolide and amarogentin. Behrens M, Brockhoff A, Batram C, Kuhn C, Appendino G and Meyerhof W, J Agric Food Chem. 2009 Nov 11, 57(21), pages 9860-9866, {{doi|10.1021/jf9014334}}</ref> The biphenylcarboxylic acid moiety is biosynthesized by a ]-type pathway, with three units of ] and one unit of ], this being formed from an early ] intermediate and not via cinnamic or benzoic acid.<ref>Unexpected Biosynthetic Precursors of Amarogentin − A Retrobiosynthetic <sup>13</sup>C NMR Study. Chang-Zeng Wang, Ulrich H. Maier, Wolfgang Eisenreich, Petra Adam, Ingrid Obersteiner, Michael Keil, Adelbert Bacher and Meinhart H. Zenk, European Journal of Organic Chemistry, Volume 2001, Issue 8, pages 1459–1465, April 2001, {{doi|10.1002/1099-0690(200104)2001:8<1459::AID-EJOC1459>3.0.CO;2-0}}</ref>


⚫ ]{{clear left}}
It also shows an ] activity<ref>Evaluation of the in-vivo activity and toxicity of amarogentin, an antileishmanial agent, in both liposomal and niosomal forms. Swapna Medda, Sibabrata Mukhopadhyay and Mukul Kumar Basu, J. Antimicrob. Chemother., (1999) 44 (6), pages 791-794, {{doi|10.1093/jac/44.6.791}}</ref> being an ].<ref>Amarogentin, a Naturally Occurring Secoiridoid Glycoside and a Newly Recognized Inhibitor of Topoisomerase I from Leishmania donovani. Sutapa Ray, Hemanta K. Majumder, Ajit K. Chakravarty, and Sibabrata Mukhopadhyay, J. Nat. Prod., 1996, 59 (1), pages 27–29, {{doi|10.1021/np960018g}}</ref>

⚫ 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 ] ]s amarogentin and ]. The former is one of the most ] natural compounds known<ref> {{Webarchive|url=https://web.archive.org/web/20090902132313/http://www.awl.ch/heilpflanzen/gentiana_lutea/index.htm |date=2009-09-02 }} ('''German''')</ref> and is used as a scientific basis for measuring bitterness. In humans, it activates the bitter ] ].<ref>{{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}}</ref> The biphenylcarboxylic acid moiety is biosynthesized by a ]-type pathway, with three units of ] and one unit of ], this being formed from an early ] intermediate and not via cinnamic or benzoic acid.<ref>{{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}}</ref>

It also shows an ] activity in ]s<ref>{{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 }}</ref> being an ].<ref>{{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}}</ref>

==See also==
* ]


==References== ==References==
{{reflist}} {{reflist|2}}


] ]
] ]
] ]

{{natural-phenol-stub}}