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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

Quality Level

100

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 Code

11 - Combustible Solids

WGK

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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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
Juan Li et al.
Artificial cells, nanomedicine, and biotechnology, 48(1), 96-106 (2019-12-20)
The diabetic foot ulcer (DFU) may be associated with late healing and septic manifestation, subsequently lead to amputation which is an overpriced incident. Neferine is an alkaloid found lotus. Neferine possesses many physiological functions such as anti-inflammatory, antioxidant, antimicrobial activity
Hui Ding et al.
European journal of pharmacology, 650(1), 163-169 (2010-10-26)
Neferine is a major alkaloid component of "Lian Zi Xin", embryos of the seeds of Nelumbo nucifera Gaertner, Nymphaeaceae. Previous studies have shown that neferine has an inhibitory effect on pulmonary fibrosis through its anti-inflammatory and anti-oxidative activities and inhibition
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
Paramasivan Poornima et al.
Food chemistry, 136(2), 659-667 (2012-11-06)
Evidence has accumulated concerning the medicinal application of Nelumbo nucifera in the treatment of various diseases. Neferine, an alkaloid from N. nucifera was found to exert cytotoxicity on liver cancer cells HepG2 in a dose-dependent manner. We evaluated its anticancer
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