mitraphylline
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424765806
| Name = Mitraphylline
| ImageFile = Mitraphylline.svg
| ImageName = Mitraphylline
| IUPACName = Methyl 19α-methyl-2-oxoformosanan-16-carboxylate
| SystematicName = Methyl (1′S,3R,4′aS,5′aS,10′aR)-1′-methyl-2-oxo-1,2,4′a,5′,5′a,7′,8′,10′a-octahydro-1′H,10′H-spiro[indole-3,6′-pyrano[3,4-f]indolizine]-4′-carboxylate
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 509-80-8
| EINECS = 208-106-0
| PubChem = 94160
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 84977
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 1H9SRL2456
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2135897
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C09227
| SMILES = C[C@H]1[C@H]2CN3CC[C@]4([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = JMIAZDVHNCCPDM-DAFCLMLCSA-N
}}
|Section2={{Chembox Properties
| Formula = C21H24N2O4
| MolarMass = 368.1736 g/mol
| Density =
| MeltingPt =
| BoilingPt =
}}
}}
Mitraphylline, an oxindole derivative, is an active alkaloid in the leaves of the tree Mitragyna speciosa, commonly known as kratom.{{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}} As a non-narcotic constituent, it also occurs to a significant amount in the bark of Uncaria tomentosa (Cat's Claw) along with a number of isomeric alkaloids.{{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 }}
Current research is focusing on antiproliferative and cytotoxic effects and its in vivo efficacy to induce apoptosis in human breast cancer, sarcoma, as well as lymphoblastic leukemia cell lines.{{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}}{{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}}{{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}}{{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}}{{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}}{{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}}