Rhynchophylline

• CAT Number: I004827
• CAS Number: 76-66-4
• Molecular Formula: C22H28N2O4
• Molecular Weight: 384.47
• Purity: ≥95%
• Synonyms: methyl (E)-2-[(3R,6’R,7’S,8’aS)-6′-ethyl-2-oxospiro[1H-indole-3,1′-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7′-yl]-3-methoxyprop-2-enoate
• InChI: 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
• InChIKey: DAXYUDFNWXHGBE-KAXDATADSA-N
• SMILES: CCC1CN2CCC3(C2CC1C(=COC)C(=O)OC)C4=CC=CC=C4NC3=O

Rhyncholphylline is an alkaloid compound isolated from Uncaria rhynchophyllum. Rhyncholphylline is an EphA4 inhibitor. It has high biological activity and is widely used in anti-inflammatory, neuroprotective and other research.[1][2][5][6].
Rhyncholphylline (0-30 μM, 48 h) inhibits the NO production, release of proinflammatory cytokines (TNF-α and IL-1β) in LPS-activated N9 microglial cells[1].
Rhyncholphylline (0-30 μM, 48 h) inhibits ERK and p38 MAPK phosphorylation in LPS-treated N9 microglial cells[1].
Rhyncholphylline inhibits ephrin-A1 induced tyrosine phosphorylation in rat cortical neurons[6].
Rhynchophylline (10 and 30 mg/kg, i.p., once daily for 4 days) protects rats from pMCAO surgery induced ischemic brain damage[2].
Rhynchophylline (100 µM, 2 µL, injected bilaterally in the hippocamp) shows neuroprotective effects against Aβ1-42-induced neurotoxicity in rats[5].
Rhynchophylline (50 mg/kg, p.o., daily, 3-4 weeks) inhibits EphA4 activation in the hippocampus of APP/PS1 mice[6].

Reference

[1]. Dan Yuan, et al. Anti-inflammatory effects of rhynchophylline and isorhynchophylline in mouse N9 microglial cells and the molecular mechanism. International Immunopharmacology
Volume 9, Issues 13–14, December 2009, Pages 1549–1554

[2]. Houcai Huang, et al. Neuroprotective Effects of Rhynchophylline Against Ischemic Brain Injury via Regulation of the Akt/mTOR and TLRs Signaling Pathways. Molecules 2014, 19 (8): 11196-11210; doi:10.3390/molecules190811196

[3]. Tai-Hyun Kang, 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 Sciences
Volume 76, Issue 3, 3 December 2004, Pages 331–343

[4]. Kinzo Matsumoto, et al. Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: Behavioural and electrophysiological studies. European Journal of Pharmacology
Volume 517, Issue 3, 11 July 2005, Pages 191–199

[5]. Yang Y, et al. Rhynchophylline suppresses soluble Aβ1-42-induced impairment of spatial cognition function via inhibiting excessive activation of extrasynaptic NR2B-containing NMDA receptors. Neuropharmacology. 2018 Jun;135:100-112.
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[6]. Fu AK, et al. Blockade of EphA4 signaling ameliorates hippocampal synaptic dysfunctions in mouse models of Alzheimer’s disease. Proc Natl Acad Sci U S A. 2014 Jul 8;111(27):9959-64.
 [Content Brief]