An oxindole alkaloid with diverse biological activities
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Isorhynchophylline

Item No. 29650

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(αE,1′S,6′R,7′S,8′aS)-6′-ethyl-1,2,2′,3′,6′,7′,8′,8′a-octahydro-α-(methoxymethylene)-2-oxo-spiro[3H-indole-3,1′(5′H)-indolizine]-7′-acetic acid, methyl ester
CAS Number
6859-01-4
Synonyms
  • (+)-Isorhynchophylline
Molecular Formula
C22H28N2O4
Formula Weight
384.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:5): 0.16 mg/mlEthanol: 1 mg/ml
λmax
242 nm
SMILES
O=C(OC)/C([C@@H]1[C@@H](CC)CN2[C@@]([C@@]3(C(C=CC=C4)=C4NC3=O)CC2)([H])C1)=C/OC
InChi Code
InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22-/m0/s1
InChi Key
DAXYUDFNWXHGBE-VKCGGMIFSA-N
Origin
Plant/Uncaria rhynchophylla
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $63

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    10 mg

    $98

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    25 mg

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    50 mg

    $363

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    Product Description

    Isorhynchophylline is an oxindole alkaloid that has been found in Uncaria and has diverse biological activities, including neuroprotective, anticancer, and antihypertensive properties.1,2,3,4 It inhibits decreases in cell viability and increases in intracellular levels of reactive oxygen species (ROS) and malondialdehyde (MDA) induced by amyloid-β (25-35) (Aβ (25-35); Item No. 24155) in PC12 cells in a concentration-dependent manner.1 Isorhynchophylline (30 and 100 μM) attenuates decreases in population spike amplitudes in the CA1 region of a rat hippocampal slice model of ischemia induced by oxygen and D-glucose deprivation.2 It decreases the viability of HepG2, A549, BxPC-3, Caki-1, RPMI-8226, and 786-O cells (IC50s = 130-292 μM).3 In HepG2 cells, isorhynchophylline induces apoptosis, inhibits cell migration in a wound healing assay, and decreases invasion in a Matrigel™ assay. Isorhynchophylline (0.1% in the diet) decreases right ventricular end systolic pressure, hypertrophy, and fibrosis in a rat model of pulmonary arterial hypertension induced by monocrotaline (Item No. 16666).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Xian, Y.-F., Lin, Z.-X., Mao, Q.-Q., et al. Protective effect of isorhynchophylline against β-amyloid-induced neurotoxicity in PC12 cells. Cell Mol. Neurobiol. 32(3), 353-360 (2012).

    2. Kang, T.-H., Murakami, Y., Takayama, H., et al. Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: Putative neurotransmitter receptors involved in their action. Life Sci. 76(3), 331-343 (2004).

    3. Lee, H., Baek, S.H., Lee, J.H., et al. Isorhynchophylline, a potent plant plkaloid, induces apoptotic and anti-metastatic effects in human hepatocellular carcinoma cells through the modulation of diverse cell signaling cascades. Int. J. Mol. Sci. 18(5), E1095 (2017).

    4. Guo, H., Zhang, H., Cui, Y., et al. Isorhynchophylline protects against pulmonary arterial hypertension and suppresses PASMCs proliferation. Biochem. Biophys. Res. Commun. 450(1), 729-734 (2014).