Neochlorogenic acid

Names

[ CAS No. ]:
906-33-2

[ Name ]:
Neochlorogenic acid

[Synonym ]:
(1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
3-{[3-(3,4-Dihydroxyphenyl)acryloyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid
3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy] 1,4,5-trihydroxycyclohexanecarboxylic acid
Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4,5-trihydroxy-

Biological Activity

[Description]:

Neochlorogenic acid is a natural polyphenolic compound found in dried fruits and other plants. Neochlorogenic acid inhibits the production of TNF-α and IL-1β. Neochlorogenic acid suppresses iNOS and COX-2 protein expression. Neochlorogenic acid also inhibits phosphorylated NF-κB p65 and p38 MAPK activation.

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Interleukin Related

Signaling Pathways >> Apoptosis >> TNF Receptor

Natural Products >> Phenylpropanoids

Research Areas >> Inflammation/Immunology

[Target]

p65

IL-1β

TNF-α

COX-2

[In Vitro]

Neochlorogenic acid (NCA) shows a reduction of lipopolysaccharide (LPS)-induced NO production by suppressing iNOS and COX-2 protein expression and production of pro-inflammatory cytokines, such as TNF-α and IL-1β, in BV2 microglia cells. In addition, phosphorylated p38 MAPK and NF-κB p65 are also inhibited by Neochlorogenic acid in activated microglia. iNOS and COX-2 levels are increased in LPS-induced BV2 cells, but this increase is significantly inhibited after treatment with 50 and 100 μM Neochlorogenic acid[1].

[Cell Assay]

Mouse BV2 microglial cells are maintained in DMEM, supplemented with 5 % FBS and 1 % antibiotic–antimycotic in a humidified incubator with 5 % CO2 at 37°C. Neochlorogenic acid and Dexamethasone as positive control are dissolved in DMSO to a final concentration of 10 mM for the stock solution. Treatments with LPS and/or Neochlorogenic acid are carried out under serum-free conditions. Effects of Neochlorogenic acid are measured on cell viability in lipopolysaccharide (LPS)-stimulated BV2 microglial cells. The cells are treated with or without LPS (4 μg/ml) and Neochlorogenic acid (10, 50, and 100 μM) for 24 h. Dexamethasone (10 μM) is used for positive control. Cell viability is confirmed by the MTT assay. The medium was removed from the wells, MTT was added, and the samples were then incubated for 3 h at 37°C. The formazan crystals were dissolved by adding DMSO, and the absorbance values were measured at 540 nm using a microplate reader[1].

[References]

[1]. Kim M, et al. Neochlorogenic Acid Inhibits Lipopolysaccharide-Induced Activation and Pro-inflammatory Responses in BV2 Microglial Cells. Neurochem Res. 2015 Sep;40(9):1792-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
665.0±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₆H₁₈O₉

[ Molecular Weight ]:
354.309

[ Flash Point ]:
245.5±25.0 °C

[ Exact Mass ]:
354.095093

[ PSA ]:
164.75000

[ LogP ]:
-0.36

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.690

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xn

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
29182900

Articles

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Food Chem. 173 , 855-63, (2014)

The physicochemical characteristics of four cherry species (Prunus avium, Prunus cerasus, Prunus pseudocerasus and Prunus tomentosa) were evaluated. Inter-species variability was greater than intra-sp...

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J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 986-987 , 69-84, (2015)

Gua-Lou-Gui-Zhi decoction (GLGZD) is a classical formula of traditional Chinese medicine, which has been commonly used to treat dysfunction after stroke, epilepsy and spinal cord injury. In this study...

Optimization of extraction parameters on the isolation of phenolic compounds from sour cherry (Prunus cerasus L.) pomace.

J. Food Sci. Technol. 52(5) , 2851-9, (2015)

There is an increasing interest to bio-components obtained from fruit & vegetable wastes. Anthocyanin is one of the components regained from fruits especially from red ones. Sour cherry is considered ...