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Merck
CN

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

Key Documents

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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

Related Categories

Application

Neferine has been used to study its effect in autophagy signalling.

Biochem/physiol Actions

Neferine inhibits proliferation of human osteosarcoma cells by stabilization of p21 through p38 MAPK-mediated activation; antidepressant-like and antiarrhythmic.
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000396758
0000396758
0000173885
0000173886
0000173886

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Hyun Ah Jung et al.
Life sciences, 87(13-14), 420-430 (2010-08-26)
the multifunctional potential of neferine derived from the embryo of Nelumbo nucifera seeds for the age-related neurodegenerative disorders, in vivo anti-amnesic activities and in vitro cholinesterases (ChEs)- and β-site APP cleaving enzyme 1 (BACE1)-inhibitory activities, as well as anti-inflammatory and
Shuaizeng Yin et al.
Journal of biochemical and molecular toxicology, 34(2), e22429-e22429 (2019-12-21)
Alzheimer's disease (AD) is an age-associated neurodegenerative disease, which is developed by oxidative stress and acetylcholine contraction in the synaptic cleft of the neurons. This leads to dementia, memory loss, and decrease in learning ability and orientation. In this research
Seonghee Jung et al.
Experimental & molecular medicine, 52(6), 921-930 (2020-06-28)
Autophagy is an intracellular catabolic pathway in which cellular constituents are engulfed by autophagosomes and degraded upon autophagosome fusion with lysosomes. Autophagy serves as a major cytoprotective process by maintaining cellular homeostasis and recycling cytoplasmic contents. However, emerging evidence suggests
Yumi Sugimoto et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 15(12), 1117-1124 (2008-11-18)
The effects of embryos of the seeds of Nelumbo nucifera on the central nervous system were studied in mice. MeOH extracts of embryos of Nelumbo nucifera seeds significantly inhibited locomotor activity in mice. The MeOH extract was successively partitioned between
Libo Zhao et al.
European journal of pharmacology, 627(1-3), 304-312 (2009-11-17)
In this study, we evaluated the potential anti-fibrotic property of neferine, a bisbenzylisoquinline alkaloid extracted from the seed embryo of Nelumbo mucifera Gaertn. Intratracheal bleomycin administration resulted in pulmonary fibrosis 14 and 21 days posttreatment, as evidenced by increased hydroxyproline
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