An oxindole alkaloid with diverse biological activities
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Isomer(s)
25528Mitraphylline
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Isopteropodine

Item No. 40237

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
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
5171-37-9
Synonyms
  • Uncarine E
Molecular Formula
C21H24N2O4
Formula Weight
368.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Soluble
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-PFDNRQJHSA-N
Origin
Plant/Uncaria rhynchophylla （Miq.） Miq. ex Havil
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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    25 mg

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    Cayman Chemical
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    Product Description

    Isopteropodine is an oxindole alkaloid that has been found in U. tomentosa and has diverse biological activities.1,2,3,4 It induces activation of the pregnane X receptor (PXR) in a reporter assay using DPX2 cells expressing the human receptor (EC50 = 0.7656 µM).1 Isopteropodine is a positive modulator of M1 muscarinic acetylcholine receptors (mAChRs) and the serotonin (5-HT) receptor subtype 5-HT2 (EC50s = 9.92 and 14.5 µM for the rat receptors, respectively).2 It is active against S. aureus and B. subtilis (MICs = 408 and 679 µM, respectively).3 Isopteropodine (100 µM) inhibits the proliferation of CCRF CEM C7H2 lymphoblastic leukemia cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lei, S., Lu, J., Cheng, A., et al. Identification of PXR activators from Uncaria rhynchophylla (Gou Teng) and Uncaria tomentosa (cat’s claw). Drug Metab. Dispos. 51(5), 629-636 (2023).

    2. Kang, T.H., Matsumoto, K., Tohda, M., et al. Pteropodine and isopteropodine positively modulate the function of rat muscarinic M1 and 5-HT2 receptors expressed in Xenopus oocyte. Eur. J. Pharmacol. 444(1-2), 39-45 (2002).

    3. García, R., Cayunao, C., Bocic, R., et al. Antimicrobial activity of isopteropodine. Z. Naturforsch. C. J. Biosci. 60(5-6), 385-388 (2005).

    4. 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).