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Cyanidin-3-O-glucoside chloride

$120

  • Brand : BIOFRON

  • Catalogue Number : AV-H19060

  • Specification : 98%

  • CAS number : 7084-24-4

  • Formula : C21H21ClO11

  • Molecular Weight : 484.84

  • PUBCHEM ID : 197081

  • Volume : 20mg

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Catalogue Number

AV-H19060

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

484.84

Appearance

Palm Red crystalline powder/Yellow powder

Botanical Source

Centaurea cyanus L./Found in many plants and fruits, e.g. cherries, olives, grapes, Allium spp., Cotoneaster spp. and Ilex spp. First Chrysanthemum indicum.

Structure Type

Anthocyanins

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC(=C(C=C1C2=[O+]C3=CC(=CC(=C3C=C2OC4C(C(C(C(O4)CO)O)O)O)O)O)O)O.[Cl-]

Synonyms

β-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1-benzopyrylium-3-yl, chloride (1:1)/2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychromenium-3-yl β-D-glucopyranoside chloride/Cyanidin Chloride 3-Glucoside/cyanidin 3-O-beta-D-glucoside/(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol,chloride/2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-chromeniumyl β-D-glucopyranoside chloride/Kuromanin/Kuromanin chloride/2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-chromeniumyl-β-D-glucopyranosidechlorid/Chlorure de β-D-glucopyranoside de 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-chromeniumyle/2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}chromeniumchlorid/2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}chromenium chloride/Chlorure de 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}chromenium/Cyanidin 3-O-glucoside chloride/Kuromanin (chloride)

IUPAC Name

(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride

Applications

Kuromanin (chloride), extracted from mulberry leaves, has been shown to improve blood glucose concentrations and lipid homeostasis and to reduce obesity.

Density

Solubility

Methanol; Water

Flash Point

Boiling Point

Melting Point

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:7084-24-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31894009

Abstract

Objective To explore the influence of cyanidin-3-O-glucoside (C3G) on the proliferation of colorectal cancer cells and its mechanism. Methods In vitro binding and in vitro kinase assay were used to detect the binding ability of C3G and T-LAK cell-originated protein kinase (TOPK) and its effect on TOPK activity. Soft AGAR test was used to detect the effect of C3G on the clonal ability of colon cancer cells. The cytotoxicity of C3G was determined by MTS assay. E. coli BL21 was used to express GST-histone H3 fusion protein. The effect of C3G on the clonogenesis of colon cancer cells with silenced TOPK was examined by lentivirus infection. The phosphorylation of histone H3 by C3G in HCT116 cells was determined by Western blotting. A mouse model of xenograft was established to study the phosphorylation level of histone H3 by immunohistochemical staining. Results C3G was directly bound to TOPK in vitro and inhibited TOPK activity. C3G inhibited the proliferation and clone formation of colon cancer cells in a concentration-dependent manner. Silencing TOPK decreased the sensitivity of colon cancer cells to C3G. C3G inhibited the phosphorylation of histone H3 downstream of TOPK in a time- and concentration-dependent manner. In addition, C3G inhibited tumor growth in mice with xenograft tumors from colon cancer tissues of a patient. Conclusion C3G can inhibit colorectal cancer growth by targeting TOPK.

Title

[Cyanidin-3-O-glucoside inhibits proliferation of colorectal cancer cells by targeting TOPK].

Author

Wang L1, Liu F2, Liu Y3, Gao H1, Dong M4.

Publish date

2019 Dec

PMID

31879741

Abstract

To study the effects of the anthocyanin single component cyanidin-3-O-glucoside (Cy-3-glu) on the proliferation and migration of mouse melanoma cells and to elucidate the underlying mechanisms, B16-F10 cells were treated with different concentrations of Cy-3-glu. Cell viability was analyzed by a CCK-8 method. Cell migration was determined by the callus scratching technique. Cell cycle was measured by the flow cytometry. The expression levels of genes involved in cell cycle regulation were detected by real-time PCR. Protein expression levels of p-AKT, E-cadherin, N-cadherin and vimentin were analyzed by Western blot. The growth and migration of B16-F10 cells in C57BL/6J mice were monitored by the cryogenically cooled IVIS-imaging system. The results showed that Cy-3-glu significantly inhibited the growth (P < 0.001) and migration (P < 0.01) of B16-F10 cells, and arrested the cell cycle in the S phase. After Cy-3-glu treatment, the expression levels of p-AKT (P < 0.05), N-cadherin and vimentin (P < 0.001) were decreased significantly, and the expression level of E-cadherin was dramatically increased (P < 0.05). The size and weight of tumors and tumor metastasis in mice fed with a diet containing Cy-3-glu were significantly reduced (P < 0.05). In conclusion, Cy-3-glu inhibits proliferation and migration of B16-F10 cells by inhibiting the PI3K/AKT signaling pathway, cell adhesion and migration signals.

Title

[Mechanism of the anthocyanin single component cyanidin-3-O-glucoside inhibiting proliferation and migration of B16-F10 cells].

Author

Wang L1, Cheng P2, Qu CF2, Li XY2.

Publish date

2019 Dec 25

PMID

31743023

Abstract

Protein tyrosine phosphatase 1B (PTP1B) is an important target for type 2 diabetes. PTP1B inhibitors can reduce blood glucose levels by increasing insulin sensitivity. Anthocyanins often play a hypoglycemic effect, but the research about them have mainly focused on glucosidase. At present, the research about protein tyrosine phosphatase 1B (PTP1B) target is less, and the corresponding molecular mechanism is still unclear. Therefore, in this present study, anthocyanins isolated from blueberry were used to study the inhibitory activity on PTP1B. The isolated cyanidin-3-arabinoside (Cya-3-Ara) exhibited a better inhibitory activity with IC50 = 8.91 ± 0.63 μM, which was higher than the positive control (oleanolic acid, IC50 = 13.9 ± 1.01 μM), and the mechanism of PTP1B inhibition was reversible mixed pattern. The structure-activity relationship (SAR) between anthocyanins and PTP1B inhibition was investigated. The enzyme activity inhibition and molecular docking showed that anthocyanins had high selectivity for PTP1B inhibition. Further study showed that Cya-3-Ara could promote glycogen synthesis through ameliorating PTP1B-involved IRS-1/PI3K/Akt/GSK3β pathways. Cya-3-Ara could also be regarded as a synergistic inhibitor (CI ≤ 0.54) of oleanolic acid to obtain a better inhibitory effect on PTP1B. Taken together, our study clearly illustrates the SAR between anthocyanins and PTP1B inhibition and the mechanism of Cya-3-Ara in the insulin signaling pathway.

KEYWORDS

PTP1B; anthocyanins; hypoglycemic effect; molecular docking; synergistic inhibition

Title

Identification of Cyanidin-3-arabinoside Extracted from Blueberry as a Selective Protein Tyrosine Phosphatase 1B Inhibitor.

Author

Tian JL1, Liao XJ2, Wang YH1, Si X1, Shu C1, Gong ES1, Xie X1, Ran XL1, Li B1.

Publish date

2019 Dec 11