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SML3257

Sigma-Aldrich

Demethyleneberberine

≥98% (HPLC)

Synonym(s):

5,​6-​Dihydro-​2,​3-​dihydroxy-​9,​10-​dimethoxy-dibenzo[a,​g]​quinolizinium, 7,8,13,13a-Tetradehydro-2,3-dihydroxy-9,10-dimethoxy-berbinium, Demethylene-berberine

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About This Item

Empirical Formula (Hill Notation):
C19H18NO4
CAS Number:
25459-91-0
Molecular Weight:
324.35
UNSPSC Code:
12352210
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

, White to very dark grey

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

InChI

1S/C19H17NO4/c1-23-18-4-3-11-7-15-13-9-17(22)16(21)8-12(13)5-6-20(15)10-14(11)19(18)24-2/h3-4,7-10,22H,5-6H2,1-2H3/p+1

InChI key

HVTCKKMWZDDWOY-UHFFFAOYSA-O

Biochem/physiol Actions

Demethyleneberberine, a berberine metabolite, is a mitochondria-targeted antioxidant isolated from Cortex Phellodendri chinensis that exhibits multiple pharmacological activities including anti-microbial, anti-inflammatory, anti-diarrhea and anti-cancer. Demethyleneberberine alleviates ethanol-dependent oxidative stress by suppression of cytochrome CYP2E1 (P450 2E1), hypoxia inducible factor α (HIF-1α) and inducible nitric oxide synthase (iNOS). It appears that demethyleneberberine attenuates non-alcoholic fatty liver disease (NAFLD) through activation of AMPK.

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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Yi-Ting Zhang et al.
Acta pharmacologica Sinica, 40(1), 133-142 (2018-11-18)
Berberine, berberrubine, thalifendine, demethyleneberberine, jatrorrhizine, and columbamine are six natural protoberberine alkaloid (PA) compounds that display extensive pharmacological properties and share the same protoberberine molecular skeleton with only slight substitution differences. The oral delivery of most PAs is hindered by
Xiaoyan Qiang et al.
Biochemical and biophysical research communications, 472(4), 603-609 (2016-03-13)
Non-alcoholic fatty liver disease (NAFLD) has reached an epidemic level globally, which is recognized to form non-alcoholic steatohepatitis (NASH) by the "two-hit" model, including oxidative stress and inflammation. AMP-activated protein kinase (AMPK) has long been regarded as a key regulator
Pengcheng Zhang et al.
The Journal of pharmacology and experimental therapeutics, 352(1), 139-147 (2014-11-02)
Excessive alcohol consumption induces oxidative stress and lipid accumulation in the liver. Mitochondria have long been recognized as the key target for alcoholic liver disease (ALD). Recently, the artificial mitochondria-targeted antioxidant MitoQ has been used to treat ALD effectively in

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