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SML0349

Sigma-Aldrich

Neferine

≥98% (HPLC)

Synonym(s):

(-)-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

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About This Item

Empirical Formula (Hill Notation):
C38H44N2O6
CAS Number:
2292-16-2
Molecular Weight:
624.77
MDL number:
MFCD22416529
UNSPSC Code:
12352200
PubChem Substance ID:
329825352
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -34 to -44° (c=0 3. CHCl3)

storage condition

desiccated
protect from light

color

white to beige

solubility

DMSO: >15 mg/mL

storage temp.

2-8°C

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

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

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Shao Liu et al.
Journal of separation science, 32(14), 2476-2481 (2009-06-27)
A preparative high-speed counter-current chromatography method for separation and purification of liensinine, isoliensinine and neferine from seed embryo of Nelumbo nucifera GAERTN was successfully established by using n-hexane-ethyl acetate-methanol-water (5:8:4:5, v/v, containing 0.5% NH(4)OH) as the two-phase solvent system. From
Yumi Sugimoto et al.
European journal of pharmacology, 634(1-3), 62-67 (2010-02-24)
The effects of neferine, an alkaloid of Nelumbo nucifera Gaertner embryos, on immobility in the forced swimming test, which is used to evaluate antidepressants, were investigated in mice. The administration of neferine from 25 to 100 mg/kg i.p. elicited anti-immobility
Yang Pan et al.
Journal of ethnopharmacology, 124(1), 98-102 (2009-06-17)
Neferine was isolated from green seed embryo of Nelumbo nucifera Gaertn which has been used as an anti-obesity agent in traditional Chinese herbal medicine. This study was conducted to investigate the effects of neferine on enhancing insulin sensitivity in insulin
Neferine, is not inducer but blocker for macroautophagic flux targeting on lysosome malfunction
Xu T, et al.
Biochemical and biophysical research communications, 495(1), 1516-1521 (2018)
Sadik Altan Ozal et al.
Cutaneous and ocular toxicology, 39(2), 97-105 (2020-02-18)
Purpose: Proliferative vitreoretinopathy (PVR) occurs in approximately 5-10% of patients after retinal detachment surgery. Neferine is a bis-benzylisoquinoline alkaloid found in the green seed embryos (Nelumbo nucifera) of the lotus flower and has various properties, such as being antithrombotic, antioxidant
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