Synonym: (-)-Neferine; 4′′-O-Methylliensinine; 4-[[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]-2-[[(1R)-1,2,3,4-tetrahydro-6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-7-isoquinolinyl]oxy]-phenol; Methylliensinine; Neferin
CAS Number: 2292-16-2
Empirical Formula (Hill Notation): C38H44N2O6
Molecular Weight: 624.77
MDL Number: MFCD22416529
Linear Formula: C38H44N2O6
Product Type: Chemical
| assay |
≥98% (HPLC) |
| color |
white to beige |
| form |
powder |
| InChI |
1S/C38H44N2O6/c1-39-15-14-27-21-36(44-5)38(23-30(27)31(39)17-24-7-10-28(42-3)11-8-24)46-34-19-25(9-12-33(34)41)18-32-29-22-37(45-6)35(43-4)20-26(29)13-16-40(32)2/h7-12,19-23,31-32,41H,13-18H2,1-6H3/t31-,32+/m1/s1 |
| InChI key |
MIBATSHDJRIUJK-ZWXJPIIXSA-N |
| optical activity |
[α]/D -34 to -44° (c=0 3. CHCl3) |
| Quality Level |
100  |
| SMILES string |
COc1ccc(C[C@H]2N(C)CCc3cc(OC)c(Oc4cc(C[C@@H]5N(C)CCc6cc(OC)c(OC)cc56)ccc4O)cc23)cc1 |
| solubility |
DMSO: >15 mg/mL |
| storage condition |
desiccated |
| |
protect from light |
| storage temp. |
2-8°C |
| Application: |
Neferine has been used to study its effect in autophagy signalling. |
| Biochem/physiol Actions: |
Neferine is a bis-benzylisoquinoline alkaloid isolated from the green seed embryos Nelumbo Nucifera Gaertn (Lotus) that displays multiple pharmacological activities including anti-tumor, antidepressant-like and antiarrhythmic actions. Recent studies shown that neferine potently inhibits proliferation of human osteosarcoma cells while is low-toxic on non-neoplastic human osteoblast cells. Apparently in U2OS cells, neferine stabilizes p21 through the activation of p38 MAPK, which leads to G1 cell cycle arrest. Also, neferine inhibits Ang II-induced HUVSMC proliferation by upregulation of HO-1. |
| Features and Benefits: |
This compound is featured on the MAPKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here . |
| Packaging: |
5, 25 mg in glass bottle |
| RIDADR |
NONH for all modes of transport |
| WGK Germany |
WGK 3 |
| Flash Point(F) |
Not applicable |
| Flash Point(C) |
Not applicable |
| Purity |
≥98% (HPLC) |
| Storage Temp. |
2-8°C |
| UNSPSC |
12352200 |
