ChemicalBook Product Catalog Biochemical Engineering Saccharides Monosaccharide Cynaroside

Cynaroside

Product NameCynaroside
CAS5373-11-5
MFC21H20O11
MW448.38
EINECS226-365-8
MOL File5373-11-5.mol

Chemical Properties

Melting point	256～258℃
storage temp.	Sealed in dry,2-8°C
solubility	DMSO (Slightly), Methanol (Slightly)
Boiling point	838.1±65.0 °C(Predicted)
Density	1.713±0.06 g/cm3(Predicted)
pka	6.10±0.40(Predicted)
form	Solid
color	Yellow to Very Dark Yellow
Stability	Hygroscopic
Major Application	metabolomics vitamins, nutraceuticals, and natural products
InChIKey	PEFNSGRTCBGNAN-QNDFHXLGSA-N
SMILES	C1(C2=CC=C(O)C(O)=C2)OC2=C(C(O)=CC(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)=C2)C(=O)C=1 \|&1:17,18,20,22,24,r\|
LogP	-0.090 (est)
CAS DataBase Reference	5373-11-5(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Safety Statements	24/25
WGK Germany	3
RTECS	DJ3009400
HS Code	29389090
Storage Class	11 - Combustible Solids

Usage And Synthesis

Effects

Luteolin has a strong bactericidal effect on the respiratory tract, and it is the main active ingredient in the treatment of bronchitis in Qinglan, a unique medicinal material in Xinjiang. Lowers the role of cholesterol in atherosclerosis and enhances capillary relaxation.

Description

Luteolin-7-O-glucoside is a flavonoid that has been found in many Chinese herbs with diverse biological activities. It reduces lactate dehydrogenase (LDH) and caspase-3 activities and production of reactive oxygen species (ROS) and increases cell viability and 14-3-3η protein levels in H9C2 cardiomyocytes after anoxia/reoxygenation injury. Luteoloside blocks 3C protease activity (IC₅₀ = 0.36 mM) and reduces the cytopathic effect of enterovirus 71 in rhabdomyosarcoma cells (EC₅₀ = 0.43 mM). It inhibits the growth of hepatocellular carcinoma (HCC) cells in vitro via reduction in ROS accumulation, caspase-1 activity, and expression of the NLRP3 inflammasome and reduces the number of lung metastases in an SMMC-7721 HCC mouse xenograft model when administered at a dose of 2 mg/kg. Luteoloside also reduces acanthosis and expression of epidermal differentiation markers in a mouse model of psoriasis induced by imiquimod .

Chemical Properties

Off-white powder

Uses

Luteolin 7-Glucoside is a strong antioxidant ant radical scavenger. Used in cancer prevention.

Definition

ChEBI: A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.

in vivo

Cynaroside (i.p.; 5mg/kg) reduces binding of PKM2 to hypoxia-inducible factor-1α (HIF-1α) by abolishing translocation of PKM2 to the nucleus and promoting PKM2 tetramer formation, as well as suppressing phosphorylation of PKM2 at Y105^[2].

Animal Model:	Mice model of sepsis^[2]
Dosage:	5mg/kg
Administration:	Cynaroside (i.p.; 5mg/kg)
Result:	Inhibited PKM2 dimer formation in liver of septic mice.

References

[1] ZHANTU LIU. Luteoloside attenuates anoxia/reoxygenation-induced cardiomyocytes injury via mitochondrial pathway mediated by 14-3-3η protein.[J]. Phytotherapy Research, 2018, 32 6: 1126-1134. DOI: 10.1002/ptr.6053
[2] ZEYU CAO. Luteoloside Acts as 3C Protease Inhibitor of Enterovirus 71 In Vitro.[J]. PLoS ONE, 2016, 11 1: e0148693. DOI: 10.1371/journal.pone.0148693
[3] SHAO-HUA FAN. Luteoloside suppresses proliferation and metastasis of hepatocellular carcinoma cells by inhibition of NLRP3 inflammasome.[J]. PLoS ONE, 2014: e89961. DOI: 10.1371/journal.pone.0089961
[4] R PALOMBO. Luteolin-7-glucoside inhibits IL-22/STAT3 pathway, reducing proliferation, acanthosis, and inflammation in keratinocytes and in mouse psoriatic model[J]. Cell Death & Disease, 2016, 7 8: e2344-e2344. DOI: 10.1038/cddis.2016.201

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