Delphinidin-3-O-glucoside chloride

Names

[ Name ]:
Delphinidin-3-O-glucoside chloride

[Synonym ]:
myrtillin-a
delphinidin-3-glucoside
5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3-chromeniumyl β-D-glucopyranoside chloride
Chlorure de 5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}-2-(3,4,5-trihydroxyphényl)chroménium
Chlorure de β-D-glucopyranoside de 5,7-dihydroxy-2-(3,4,5-trihydroxyphényl)-3-chroméniumyle
5,7-Dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromenium chloride
β-D-Glucopyranoside, 5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1-benzopyrylium-3-yl, chloride (1:1)
5,7-Dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromeniumchlorid
5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3-chromeniumyl-β-D-glucopyranosidechlorid
5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenium-3-yl β-D-glucopyranoside chloride

Biological Activity

[Description]:

Delphinidin 3-glucoside chloride (Delphinidin 3-O-glucoside chloride) is an active anthocyanin found in bilberry extract. Delphinidin 3-glucoside chloride induces a pro-apoptotic effect in B cell chronic lymphocytic leukaemia (B CLL)[1]. Delphinidin 3-glucoside chloride exerts phytoestrogen activity by binding to ERβ, with an IC50 of 9.7 μM[2]. Delphinidin-3-O-glucoside chloride inhibits EGFR with an IC50 of 2.37 µM[3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> JAK/STAT Signaling >> EGFR

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> EGFR

[Target]

IC50: 2.37 µM (EGFR)[3]

[References]

[1]. Mahmoud Alhosin, et al. Bilberry extract (Antho 50) selectively induces redox-sensitive caspase 3-related apoptosis in chronic lymphocytic leukemia cells by targeting the Bcl-2/Bad pathway. Sci Rep. 2015 Mar 11;5:8996.

[2]. Naoki Nanashima, et al. Phytoestrogenic Activity of Blackcurrant Anthocyanins Is Partially Mediated through Estrogen Receptor Beta. Molecules. 2017 Dec 29;23(1):74.

[3]. Candice Mazewski, et al. Comparison of the effect of chemical composition of anthocyanin-rich plant extracts on colon cancer cell proliferation and their potential mechanism of action using in vitro, in silico, and biochemical assays. Food Chem. 2018 Mar 1;242:378-388.

Chemical & Physical Properties

[ Molecular Formula ]:
C₂₁H₂₁ClO₁₂

[ Molecular Weight ]:
500.837

[ Exact Mass ]:
500.072144

[ PSA ]:
213.67000

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DK1275000

CHEMICAL NAME :: 1-Benzopyrylium, 5,7-dihydroxy-3-(beta-D-glucopyranosyloxy)-2-(3,4,5-t rihydroxyphenyl)-, chloride

CAS REGISTRY NUMBER :: 6906-38-3

LAST UPDATED :: 199603

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C21-H21-O12.Cl

MOLECULAR WEIGHT :: 500.87

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1850 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4229439

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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