Mitraphylline

Mitraphylline
Names

IUPAC name Mitraphylline
Identifiers
CAS Number	509-80-8^Y
ChemSpider	84977^N
EC Number	208-106-0
Jmol interactive 3D	Image
PubChem	94160
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^N Key: JMIAZDVHNCCPDM-DAFCLMLCSA-N^N InChI=1/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-DAFCLMLCBC
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).
N verify (what is ^YN ?)
Infobox references

Mitraphylline, an oxindole derivative, is an active alkaloid in the leaves of the tree Mitragyna speciosa, commonly known as kratom. 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.^[1] Due to its structural similarity to mitragynine and 7-hydroxymitragynine from kratom, effects on mu and delta opiate receptors as well as NMDA-antagonistic actions have been postulated.

Current research is focussing 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.^[2]^[3]

References

↑ Stuppner, H.; Sturm, S.; Konwalinka, G. (1992). "HPLC analysis of the main oxindole alkaloids from Uncaria tomentosa". Chromatographia 34 (11–12): 597–600. doi:10.1007/bf02269869.
↑ 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 Medica 76 (2): 133–6. doi:10.1055/s-0029-1186048. PMID 19724995.
↑ Bacher, N.; Tiefenthaler, M.; Sturm, S.; Stuppner, H.; Ausserlechner, M. J.; 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". British Journal of Haematology 132 (5): 615–22. doi:10.1111/j.1365-2141.2005.05907.x. PMID 16445836.

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