Mitraphylline

Mitraphylline
Names
	IUPAC name Methyl (1'S,3R,4'aS,5'aS,10'aR)-2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate
Identifiers
CAS Number	509-80-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2135897 ;
ChemSpider	84977 ;
ECHA InfoCard	100.007.370
EC Number	208-106-0;
KEGG	C09227 ;
PubChem CID	94160;
UNII	1H9SRL2456 ;
CompTox Dashboard (EPA)	DTXSID50198926 ;
	InChI InChI=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 Key: JMIAZDVHNCCPDM-DAFCLMLCSA-N ;
	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;
Properties
Chemical formula	C21H24N2O4
Molar mass	368.1736 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Mitraphylline, an oxindole derivative, is an active alkaloid in the leaves of the tree Mitragyna speciosa, commonly known as kratom.[1] 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.[2]

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 leukaemia cell lines.[3][4][5][6][7]

References

Manda, Vamshi; Avula, Bharathi; Ali, Zulfiqar; Khan, Ikhlas; Walker, Larry; Khan, Shabana (May 2014). "Evaluation of In Vitro Absorption, Distribution, Metabolism, and Excretion (ADME) Properties of Mitragynine, 7-Hydroxymitragynine, and Mitraphylline". Planta Medica. 80 (7): 568–576. doi:10.1055/s-0034-1368444. ISSN 0032-0943. PMID 24841968.
Stuppner, H.; Sturm, S.; Konwalinka, G. (December 1992). "HPLC analysis of the main oxindole alkaloids from Uncaria tomentosa". Chromatographia. 34 (11–12): 597–600. doi:10.1007/BF02269869. ISSN 0009-5893.
García Giménez, Dolores; Prado, Elena García; Rodríguez, Teresa Sáenz; Arche, Angeles Fernández; Puerta, Rocío De la (February 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 Medica. 76 (2): 133–136. doi:10.1055/s-0029-1186048. ISSN 0032-0943. PMID 19724995.
Bacher, Nicole; Tiefenthaler, Martin; Sturm, Sonja; Stuppner, Hermann; Ausserlechner, Michael J.; Kofler, Reinhard; Konwalinka, Günther (March 2006). "Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells". British Journal of Haematology. 132 (5): 615–622. doi:10.1111/j.1365-2141.2005.05907.x. ISSN 1365-2141. PMID 16445836.
Rojas-Duran, R.; González-Aspajo, G.; Ruiz-Martel, C.; Bourdy, G.; Doroteo-Ortega, V. H.; Alban-Castillo, J.; Robert, G.; Auberger, P.; Deharo, E. (11 October 2012). "Anti-inflammatory activity of Mitraphylline isolated from Uncaria tomentosa bark". Journal of Ethnopharmacology. 143 (3): 801–804. doi:10.1016/j.jep.2012.07.015. PMID 22846434.
Zhang, Qian; Zhao, Jiao Jiao; Xu, Jian; Feng, Feng; Qu, Wei (15 September 2015). "Medicinal uses, phytochemistry and pharmacology of the genus Uncaria". Journal of Ethnopharmacology. 173: 48–80. doi:10.1016/j.jep.2015.06.011. PMID 26091967.
Montserrat-de la Paz, S.; de la Puerta, R.; Fernandez-Arche, A.; Quilez, A. M.; Muriana, F. J. G.; Garcia-Gimenez, M. D.; Bermudez, B. (21 July 2015). "Pharmacological effects of mitraphylline from Uncaria tomentosa in primary human monocytes: Skew toward M2 macrophages". Journal of Ethnopharmacology. 170: 128–135. doi:10.1016/j.jep.2015.05.002. hdl:10261/124399. PMID 25975515.

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[1] Manda, Vamshi; Avula, Bharathi; Ali, Zulfiqar; Khan, Ikhlas; Walker, Larry; Khan, Shabana (May 2014). "Evaluation of In Vitro Absorption, Distribution, Metabolism, and Excretion (ADME) Properties of Mitragynine, 7-Hydroxymitragynine, and Mitraphylline". Planta Medica. 80 (7): 568–576. doi:10.1055/s-0034-1368444. ISSN 0032-0943. PMID 24841968.

[2] Stuppner, H.; Sturm, S.; Konwalinka, G. (December 1992). "HPLC analysis of the main oxindole alkaloids from Uncaria tomentosa". Chromatographia. 34 (11–12): 597–600. doi:10.1007/BF02269869. ISSN 0009-5893.

[3] García Giménez, Dolores; Prado, Elena García; Rodríguez, Teresa Sáenz; Arche, Angeles Fernández; Puerta, Rocío De la (February 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 Medica. 76 (2): 133–136. doi:10.1055/s-0029-1186048. ISSN 0032-0943. PMID 19724995.

[4] Bacher, Nicole; Tiefenthaler, Martin; Sturm, Sonja; Stuppner, Hermann; Ausserlechner, Michael J.; Kofler, Reinhard; Konwalinka, Günther (March 2006). "Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells". British Journal of Haematology. 132 (5): 615–622. doi:10.1111/j.1365-2141.2005.05907.x. ISSN 1365-2141. PMID 16445836.

[5] Rojas-Duran, R.; González-Aspajo, G.; Ruiz-Martel, C.; Bourdy, G.; Doroteo-Ortega, V. H.; Alban-Castillo, J.; Robert, G.; Auberger, P.; Deharo, E. (11 October 2012). "Anti-inflammatory activity of Mitraphylline isolated from Uncaria tomentosa bark". Journal of Ethnopharmacology. 143 (3): 801–804. doi:10.1016/j.jep.2012.07.015. PMID 22846434.

[6] Zhang, Qian; Zhao, Jiao Jiao; Xu, Jian; Feng, Feng; Qu, Wei (15 September 2015). "Medicinal uses, phytochemistry and pharmacology of the genus Uncaria". Journal of Ethnopharmacology. 173: 48–80. doi:10.1016/j.jep.2015.06.011. PMID 26091967.

[7] Montserrat-de la Paz, S.; de la Puerta, R.; Fernandez-Arche, A.; Quilez, A. M.; Muriana, F. J. G.; Garcia-Gimenez, M. D.; Bermudez, B. (21 July 2015). "Pharmacological effects of mitraphylline from Uncaria tomentosa in primary human monocytes: Skew toward M2 macrophages". Journal of Ethnopharmacology. 170: 128–135. doi:10.1016/j.jep.2015.05.002. hdl:10261/124399. PMID 25975515.