| Revision as of 23:08, 18 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 392716138 |
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| Watchedfields = changed |
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| Name = Mitraphylline |
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| verifiedrevid = 424765806 |
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| ImageFile = Mitraphylline.svg |
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| Name = Mitraphylline |
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<!-- | ImageSize = 200px --> |
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| ImageName = Mitraphylline |
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| ImageFile = Mitraphylline.svg |
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| IUPACName = Mitraphylline |
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| ImageName = Mitraphylline |
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| IUPACName = Methyl 19α-methyl-2-oxoformosanan-16-carboxylate |
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| Section1 = {{Chembox Identifiers |
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| SystematicName = Methyl (1′''S'',3''R'',4′a''S'',5′a''S'',10′a''R'')-1′-methyl-2-oxo-1,2,4′a,5′,5′a,7′,8′,10′a-octahydro-1′''H'',10′''H''-spiroindolizine]-4′-carboxylate |
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| CASNo = 509-80-8 |
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|Section1={{Chembox Identifiers |
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| SMILES = |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 509-80-8 |
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| EINECS = 208-106-0 |
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| PubChem = 94160 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 84977 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 1H9SRL2456 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 2135897 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C09227 |
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| SMILES = C12CN3CC4(3C2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21+/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = JMIAZDVHNCCPDM-DAFCLMLCSA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>21</sub>H<sub>24</sub>N<sub>2</sub>O<sub>4</sub> |
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| Formula = C<sub>21</sub>H<sub>24</sub>N<sub>2</sub>O<sub>4</sub> |
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| MolarMass = 368.1736 g/mol |
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| MolarMass = 368.1736 g/mol |
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'''Mitraphylline''', an ] derivative, is an active ] in the leaves of the trees ], commonly known as ]. As a non-narcotic constituent, it also occurs to a significant amount in the bark of '']'', Cat’s Claw, along with a number of ] alkaloids.<ref> H. Stuppner, S. Sturm, and G. Konwalinka, (1992). "HPLC analysis of the main oxindole alkaloids from Uncaria tomentosa". ''Chromatographia'' '''34''' 11-12; 597-604. </ref> Due to its structural similarity to ] and ] from ], effects on mu and Delta opiate receptors as well as NMDA-antagonistic actions have been postulated. |
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'''Mitraphylline''', an ] derivative, is an active ] in the leaves of the tree '']'', commonly known as kratom.<ref>{{cite journal|first1=Vamshi|last1=Manda|first2=Bharathi|last2=Avula|first3=Zulfiqar|last3=Ali|first4=Ikhlas|last4=Khan|title=Evaluation of ''In Vitro'' Absorption, Distribution, Metabolism, and Excretion (ADME) Properties of Mitragynine, 7-Hydroxymitragynine, and Mitraphylline|journal=Planta Medica|date=May 2014|issn=0032-0943|pages=568–576|volume=80|issue=7|doi=10.1055/s-0034-1368444|pmid=24841968|first5=Larry|last5=Walker|first6=Shabana|last6=Khan}}</ref> As a non-narcotic constituent, it also occurs to a significant amount in the bark of '']'' (Cat's Claw) along with a number of ] ]s.<ref>{{cite journal|first1=H.|last1=Stuppner|first2=S.|last2=Sturm|first3=G.|last3=Konwalinka|title=HPLC analysis of the main oxindole alkaloids from ''Uncaria tomentosa''|journal=Chromatographia|date=December 1992|issn=0009-5893|pages=597–600|volume=34|issue=11–12|doi=10.1007/BF02269869|s2cid=95048480 }}</ref> |
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Current research is focusing on ] and ] effects and its '']'' efficacy to induce ] in human ], ], as well as lymphoblastic leukemia cell lines.<ref>{{cite journal|first1=Dolores|last1=García Giménez|first2=Elena García|last2=Prado|first3=Teresa Sáenz|last3=Rodríguez|first4=Angeles Fernández|last4=Arche|title=Cytotoxic Effect of the Pentacyclic Oxindole Alkaloid Mitraphylline Isolated from ''Uncaria tomentosa'' Bark on Human Ewing's Sarcoma and Breast Cancer Cell Lines|journal=Planta Medica|date=February 2010|issn=0032-0943|pages=133–136|volume=76|issue=2|doi=10.1055/s-0029-1186048|pmid=19724995|first5=Rocío De la|last5=Puerta|hdl=11441/38905 |hdl-access=free}}</ref><ref>{{cite journal|first1=Nicole|last1=Bacher|first2=Martin|last2=Tiefenthaler|first3=Sonja|last3=Sturm|first4=Hermann|last4=Stuppner|title=Oxindole alkaloids from ''Uncaria tomentosa'' induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells|journal=British Journal of Haematology|date=March 2006|issn=1365-2141|pages=615–622|volume=132|issue=5|doi=10.1111/j.1365-2141.2005.05907.x|pmid=16445836|first5=Michael J.|last5=Ausserlechner|first6=Reinhard|last6=Kofler|first7=Günther|last7=Konwalinka|doi-access=free}}</ref><ref>{{Cite web |title=Formosanan-16-carboxylic acid, 19-methyl-2-oxo-, methyl ester, (19α)- |url=http://krakenkratom.com |access-date=2023-04-15 |website=webbook.nist.gov |language=en}}</ref><ref>{{cite journal|first1=R.|last1=Rojas-Duran|first2=G.|last2=González-Aspajo|first3=C.|last3=Ruiz-Martel|first4=G.|last4=Bourdy|title=Anti-inflammatory activity of Mitraphylline isolated from ''Uncaria tomentosa'' bark|journal=Journal of Ethnopharmacology|date=11 October 2012|pages=801–804|volume=143|issue=3|doi=10.1016/j.jep.2012.07.015|pmid=22846434|first5=V. H.|last5=Doroteo-Ortega|first6=J.|last6=Alban-Castillo|first7=G.|last7=Robert|first8=P.|last8=Auberger|first9=E.|last9=Deharo}}</ref><ref>{{cite journal|first1=Qian|last1=Zhang|first2=Jiao Jiao|last2=Zhao|first3=Jian|last3=Xu|first4=Feng|last4=Feng|title=Medicinal uses, phytochemistry and pharmacology of the genus ''Uncaria''|journal=Journal of Ethnopharmacology|date=15 September 2015|pages=48–80|volume=173|doi=10.1016/j.jep.2015.06.011|pmid=26091967|first5=Wei|last5=Qu}}</ref><ref>{{cite journal|first1=S.|last1=Montserrat-de la Paz|first2=R.|last2=de la Puerta|first3=A.|last3=Fernandez-Arche|first4=A. M.|last4=Quilez|title=Pharmacological effects of mitraphylline from ''Uncaria tomentosa'' in primary human monocytes: Skew toward M2 macrophages|journal=Journal of Ethnopharmacology|date=21 July 2015|pages=128–135|volume=170|doi=10.1016/j.jep.2015.05.002|pmid=25975515|first5=F. J. G.|last5=Muriana|first6=M. D.|last6=Garcia-Gimenez|first7=B.|last7=Bermudez|hdl=10261/124399|hdl-access=free}}</ref> |
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Current research is focussing on ] and ] effects and its in-vivo efficacy to induce ] in human ], ] as well as lymphoblastic leukaemia cell lines. <ref> García Giménez D, García Prado E, Sáenz Rodríguez T, Fernández Arche A, De la Puerta R. (2010). “Cytotoxic effect of the pentacyclic oxindole alkaloid mitraphylline isolated from Uncaria tomentosa bark on human Ewing's sarcoma and breast cancer cell lines”. ''Planta Med'' '''76''' (2): 133-136. PMID 19724995 </ref> <ref> Bacher N, Tiefenthaler M, Sturm S, Stuppner H, Ausserlechner MJ, Kofler R, Konwalinka G. (2006). “Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells“. ''Br. J. Haematol''. : '''132''' (5): 615-622. PMID 16445836 </ref> |
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==See also== |
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==References== |
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== References == |
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