An alkaloid with diverse biological activities
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Rhyncophylline

Item No. 37946

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(αE,1′R,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
76-66-4
Synonyms
  • NSC 21731
  • Mitrinermine
Molecular Formula
C22H28N2O4
Formula Weight
384.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 30 mg/mlDMF: 1 mg/ml
λmax
244 nm
SMILES
O=C1[C@]2(C3=CC=CC=C3N1)[C@@](C[C@@H]4/C(C(OC)=O)=C\OC)([H])N(C[C@@H]4CC)CC2
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-KAXDATADSA-N
Origin
Plant/Uncaria tomentosa
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

    $103

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    10 mg

    $184

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    Product Description

    Rhyncophylline is an alkaloid that has been found in U. rhyncophylla and has diverse biological activities.1,2,3,4 It inhibits aggregation of isolated rabbit platelets induced by arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607), collagen, or ADP (IC50s = 0.72, 0.74, and 0.67 mmol/L).1 In vivo, rhyncophylline (0.25 mg/kg) decreases the number of sleep-wake cycles and increases total sleep time and rapid eye movement (REM) sleep in rats.2 It reduces infarct volume and reverses sensory-motor and spatial memory defects in a mouse model of stroke induced by middle cerebral artery occlusion (MCAO) when administered at a dose of 40 mg/kg.3 Rhyncophylline (10 and 20 mg/kg) also reduces hippocampal production of reactive oxygen species (ROS) and malondialdehyde (MDA) levels and decreases escape latency in the Morris water maze test in a mouse model of Alzheimer’s disease induced by amyloid-β (1-42) (Aβ42).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, C.X., Jin, R.M., Li, Y.K., et al. Inhibitory effect of rhynchophylline on platelet aggregation and thrombosis. Zhongguo Yao Li Xue Bao 13(2), 126-130 (1992).

    2. Yoo, J.H., Ha, T.-W., Hong, J.T., et al. Rhynchophylline, one of major constituents of Uncariae Ramulus et Uncus enhances oentobarbital-induced sleep behaviors and rapid eye movement sleep in rodents. Nat. Prod. Sci. 22(4), 263 (2016).

    3. Wang, L., Wang, Y., Chen, Y., et al. Rhynchophylline ameliorates cerebral ischemia by improving the synapticvplasticity in a middle cerebral artery occlusion induced stroke model. Eur. J. Pharmacol. 940, 175390 (2023).

    4. Jiang, P., Chen, L., Xu, J., et al. Neuroprotective effects of rhynchophylline against Aβ1-42-induced oxidative stress, neurodegeneration, and memory impairment via Nrf2-ARE activation. Neurochem. Res. 46(9), 2439-2450 (2021).