An alkaloid with anticancer activity
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Isomitraphylline

Item No. 39452

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1′S,3S,4′aS,5′aS,10′aR)-1,2,5′,5′a,7′,8′,10′,10′a-octahydro-1′-methyl-2-oxo-spiro[3H-indole-3,6′(4′aH)-[1H]pyrano[3,4-f]indolizine]-4′-carboxylic acid, methyl ester
CAS Number
4963-01-3
Synonyms
  • Ajmalicine Oxindole A
Molecular Formula
C21H24N2O4
Formula Weight
368.4
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly soluble: 0.1-1 mg/mlChloroform: Sparingly soluble: 1-10 mg/ml
SMILES
O=C(C1=CO[C@H]([C@]2(CN3CC[C@@]4([C@](C[C@@]21[H])3[H])C(C=CC=C5)=C5NC4=O)[H])C)OC
InChi Code
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
InChi Key
JMIAZDVHNCCPDM-NWQITLLVSA-N
Origin
Plant/Mitragyna ciliata
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    10 mg

    $546

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    Cayman Chemical
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    Product Description

    Isomitraphylline is an alkaloid that has been found in U. tomentosa and has anticancer activity.1,2 It is an antagonist of ecdysteroid receptors in a reporter assay using Drosophila BII cells (EC50 = 160 µM).1 Isomitraphylline (50 or 100 µM) reduces the proliferation of, and induces apoptosis in, CCRF CEM C7H2 lymphoblastic leukemia cells.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dinan, L., Bourne, P.C., Meng, Y., et al. Assessment of natural products in the Drosophila melanogaster BII cell bioassay for ecdysteroid agonist and antagonist activities. Cell. Mol. Life Sci. 58(2), 321-342 (2001).

    2. Bacher, N., Tienfenthaler, M., Sturm, S., et al. 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 (2006).