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Neochlorogenic acid

CAS# 906-33-2

Neochlorogenic acid

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Chemical structure

Neochlorogenic acid

3D structure

Chemical Properties of Neochlorogenic acid

Cas No. 906-33-2 SDF Download SDF
PubChem ID 5280633 Appearance White powder
Formula C16H18O9 M.Wt 354.3
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Synonyms trans-5-O-Caffeoylquinic acid
Solubility DMSO : 11 mg/mL (31.05 mM; Need ultrasonic and warming)
Chemical Name (1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
SMILES C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
Standard InChIKey CWVRJTMFETXNAD-NXLLHMKUSA-N
Standard InChI InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14+,16-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Neochlorogenic acid

1 Coffea sp. 2 Cynara sp. 3 Euphorbia sp. 4 Ilex sp. 5 Humulus sp. 6 Marsdenia sp. 7 Menyanthes sp. 8 Oenothera sp. 9 Pimpinella sp. 10 Plantago sp. 11 Punica sp. 12 Ricinus sp. 13 Salix sp. 14 Salvia sp. 15 Solidago sp. 16 Sorbus sp. 17 Viburnum sp.

Biological Activity of Neochlorogenic acid

DescriptionNeochlorogenic acid shows antioxidant, antibacterial, antiviral, and antipyretic activities and exerts neuroprotective effects through the inhibition of pro-inflammatory pathways in activated microglia.
Targetsp65 | NF-kB | NOS | COX | p38MAPK | TNF-α
In vitro

High chlorogenic and neochlorogenic acid levels in immature peaches reduce Monilinia laxa infection by interfering with fungal melanin biosynthesis.[Pubmed: 21370882]

J Agric Food Chem. 2011 Apr 13;59(7):3205-13.

Chlorogenic acid (CGA) and its isomer, Neochlorogenic acid (NCGA), were found to be the major phenolic compounds in the flesh and peel of three peach cultivars.
METHODS AND RESULTS:
Their concentrations are especially high in immature fruits (CGA, 151-548 mg/kg; NCGA, 85-380 mg/kg), whose resistance to the brown rot fungus, Monilinia laxa , is very high. The concentrations of these two phenolic compounds decline in maturing fruits (CGA, 77-181 mg/kg; NCGA, 30-82 mg/kg), and this decline is associated with a concomitant increase in susceptibility to brown rot infection. Other phenolic compounds found in the same HPLC chromatograms at 340 nm from each peach extract at varying sampling dates in each of the three peach cultivars were not correlated with the incidence of brown rot and appeared only in some cultivars. The incidence of brown rot for each cultivar at each sampling date was significantly negatively correlated with the NCGA (r > -0.85) and CGA (r > -0.90) contents. At concentrations that are similar to those in peach fruit, CGA does not inhibit spore germination or mycelial growth of M. laxa in culture but markedly inhibits the production of melanin-like pigments in the mycelia of M. laxa in culture (42% melanin reduction).
CONCLUSIONS:
Accordingly, we propose that the high concentrations of CGA and NGA in immature fruits might contribute to their reduced susceptibility or increased resistance to brown rot infection by interfering with fungal melanin production.

Neochlorogenic Acid Inhibits Lipopolysaccharide-Induced Activation and Pro-inflammatory Responses in BV2 Microglial Cells.[Pubmed: 26152332 ]

Neurochem Res. 2015 Sep;40(9):1792-8.

Microglia is the resident innate immune cells that sense pathogens and tissue injury in the central nervous system. Microglia becomes activated in response to injury, infection, and other stimuli that threaten neuronal survival. Microglia activation plays an important role in neurodegenerative diseases. Neochlorogenic acid (NCA) is a natural polyphenolic compound found in dried fruits and other plants. Although previous studies have shown that phenolic acids including NCA have outstanding antioxidant, antibacterial, antiviral, and antipyretic activities, there has not yet been investigated for anti-inflammatory effects.
METHODS AND RESULTS:
Therefore, for the first time we have examined the potential of NCA to inhibit microglial activation and pro-inflammatory responses in the brain. We found that lipopolysaccharide-induced inducible nitric oxide synthase, and cyclooxygenase-2 expression, and nitric oxide formation was suppressed by NCA in a dose-dependent manner in BV2 microglia. NCA also inhibited the production of pro-inflammatory mediators, tumor necrosis factor-α and interleukin-1 beta. Furthermore, phosphorylated nuclear factor-kappa B p65 and p38 mitogen-activated protein kinase activation were blocked by NCA.
CONCLUSIONS:
Taken together, these results suggest that NCA exerts neuroprotective effects through the inhibition of pro-inflammatory pathways in activated microglia.

Protocol of Neochlorogenic acid

Cell Research

Effect of Chlorogenic Acid and Neochlorogenic Acid on Human Colon Cancer Cells.[Reference: WebLink]

UARKive, 2012,5.

Prune consumption has been associated with a decreased risk of colon cancer, yet there has been confusion as to which chemical component(s) of the prune are responsible for its anticarcinogenic properties. Previous studies have evaluated chlorogenic acid as a chemotherapeutic agent, however only a limited amount of studies have investigated Neochlorogenic acid, the predominant phenolic compound found in the prune. The purpose of this study was to determine the effects that chlorogenic acid and Neochlorogenic acid have as anticarcinogenics on the human adenocarcinoma, Caco-2 cell line.
METHODS AND RESULTS:
The anti-colon cancer effects or chlorogenic acid and Neochlorogenic acid were analyzed by experiments that measured cell proliferation and morphology in culture of Caco-2 cells. Treatment of cells with chlorogenic acid and Neochlorogenic acid significantly reduced cell proliferation at concentrations of 150-500μmol at 24, 48, and 72 hours by 63.7-96.0% and 69.7-94.2%, respectively (p<0.05). At the majority of sample times and concentrations, chlorogenic acid and Neochlorogenic acid did not significantly differ in percent reduction of viable cells (p<0.05). The cell morphology of treated cells changed, as the surface of cells became more rough, uneven, and irregularly-shaped as the concentration of the treatment increased, compared to the untreated Caco-2 cell.
CONCLUSIONS:
These findings of significant cell proliferation inhibition suggest that both chlorogenic acid and Neochlorogenic acid could be colon cancer suppressive components of the prune.

Neochlorogenic acid Dilution Calculator

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Neochlorogenic acid Molarity Calculator

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Preparing Stock Solutions of Neochlorogenic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8225 mL 14.1123 mL 28.2247 mL 56.4493 mL 70.5617 mL
5 mM 0.5645 mL 2.8225 mL 5.6449 mL 11.2899 mL 14.1123 mL
10 mM 0.2822 mL 1.4112 mL 2.8225 mL 5.6449 mL 7.0562 mL
50 mM 0.0564 mL 0.2822 mL 0.5645 mL 1.129 mL 1.4112 mL
100 mM 0.0282 mL 0.1411 mL 0.2822 mL 0.5645 mL 0.7056 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Neochlorogenic acid

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.

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].

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.

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References on Neochlorogenic acid

Neochlorogenic Acid Inhibits Lipopolysaccharide-Induced Activation and Pro-inflammatory Responses in BV2 Microglial Cells.[Pubmed:26152332]

Neurochem Res. 2015 Sep;40(9):1792-8.

Microglia is the resident innate immune cells that sense pathogens and tissue injury in the central nervous system. Microglia becomes activated in response to injury, infection, and other stimuli that threaten neuronal survival. Microglia activation plays an important role in neurodegenerative diseases. Neochlorogenic acid (NCA) is a natural polyphenolic compound found in dried fruits and other plants. Although previous studies have shown that phenolic acids including NCA have outstanding antioxidant, antibacterial, antiviral, and antipyretic activities, there has not yet been investigated for anti-inflammatory effects. Therefore, for the first time we have examined the potential of NCA to inhibit microglial activation and pro-inflammatory responses in the brain. We found that lipopolysaccharide-induced inducible nitric oxide synthase, and cyclooxygenase-2 expression, and nitric oxide formation was suppressed by NCA in a dose-dependent manner in BV2 microglia. NCA also inhibited the production of pro-inflammatory mediators, tumor necrosis factor-alpha and interleukin-1 beta. Furthermore, phosphorylated nuclear factor-kappa B p65 and p38 mitogen-activated protein kinase activation were blocked by NCA. Taken together, these results suggest that NCA exerts neuroprotective effects through the inhibition of pro-inflammatory pathways in activated microglia.

High chlorogenic and neochlorogenic acid levels in immature peaches reduce Monilinia laxa infection by interfering with fungal melanin biosynthesis.[Pubmed:21370882]

J Agric Food Chem. 2011 Apr 13;59(7):3205-13.

Chlorogenic acid (CGA) and its isomer, Neochlorogenic acid (NCGA), were found to be the major phenolic compounds in the flesh and peel of three peach cultivars. Their concentrations are especially high in immature fruits (CGA, 151-548 mg/kg; NCGA, 85-380 mg/kg), whose resistance to the brown rot fungus, Monilinia laxa , is very high. The concentrations of these two phenolic compounds decline in maturing fruits (CGA, 77-181 mg/kg; NCGA, 30-82 mg/kg), and this decline is associated with a concomitant increase in susceptibility to brown rot infection. Other phenolic compounds found in the same HPLC chromatograms at 340 nm from each peach extract at varying sampling dates in each of the three peach cultivars were not correlated with the incidence of brown rot and appeared only in some cultivars. The incidence of brown rot for each cultivar at each sampling date was significantly negatively correlated with the NCGA (r > -0.85) and CGA (r > -0.90) contents. At concentrations that are similar to those in peach fruit, CGA does not inhibit spore germination or mycelial growth of M. laxa in culture but markedly inhibits the production of melanin-like pigments in the mycelia of M. laxa in culture (42% melanin reduction). Accordingly, we propose that the high concentrations of CGA and NGA in immature fruits might contribute to their reduced susceptibility or increased resistance to brown rot infection by interfering with fungal melanin production.

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.

Keywords:

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