Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages

Uwai, Koji; Osanai, Yuu; Imaizumi, Takuma; Kanno, Syu‐ichi; Takeshita, Mitsuhiro; Ishikawa, Masaaki

doi:10.1016/j.bmc.2008.07.006

Cited by 72 publications

(68 citation statements)

References 29 publications

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“…Moreover, caffeic acid derivatives also showed inhibitory effects on LPSinduced NO production in Raw 264.7 cells (Uwai et al, 2008). CAPE is the most extensively studied caffeic acid derivative of propolis, which has been reported as an antiinflammatory compound and also as a potent and specific inhibitor of NF-NB activation and protein kinase B (ANt) phosphorylation in T cells, with no effect on p38 MAP kinase phosphorylation (Wang et al, 2010).…”

Section: Discussionmentioning

confidence: 99%

Propolis and its constituent caffeic acid suppress LPS-stimulated pro-inflammatory response by blocking NF-κB and MAPK activation in macrophages

Búfalo

Ferreira

Costa

et al. 2013

Journal of Ethnopharmacology

156

102

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Propolis and its constituent caffeic acid suppress LPS-stimulated pro-inflammatory response by blocking NF-κB and MAPK activation in macrophages, Journal of Ethnopharmacology, http://dx.doi.org/ 10. 1016/j.jep.2013.06.004 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting galley proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. AbstractEthnopharmacological relevance: Propolis is a bee product with numerous biological and pharmacological properties, such as immunomodulatory and anti-inflammatory activities.It has been used in folk medicine as a healthy drink and in food to improve health and prevent inflammatory diseases. However, little is known about its mechanism of action.Thus, the goal of this study was to verify the antioxidant activity and to explore the antiinflammatory properties of propolis by addressing its intracellular mechanism of action.Caffeic acid was investigated as a possible compound responsible for propolis action. Materials and Methods:The antioxidant properties of propolis and caffeic acid were evaluated by using the 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH) scavenging method. To analyze the anti-inflammatory activity, Raw 264.7 macrophages were treated with different concentrations of propolis or caffeic acid, and nitric oxide (NO) production, a strong pro-inflammatory mediator, was evaluated by the Griess reaction. The concentrations of propolis and caffeic acid that inhibited NO production were evaluated on intracellular signaling pathways triggered during inflammation, namely p38 mitogenactivated protein kinase (MAPK), c-jun NH 2 -terminal kinase (JNK1/2), the transcription nuclear factor (NF)-NB and extracellular signal-regulated kinase (ERK1/2), through Western blot using specific antibodies. A possible effect of propolis on the cytotoxicity of hepatocytes was also evaluated, since this product can be used in human diets.Results: Caffeic acid showed a higher antioxidant activity than propolis extract. Propolis and caffeic acid inhibited NO production in macrophages, at concentrations without cytotoxicity. Furthermore, both propolis and caffeic acid suppressed LPS-induced signaling pathways, namely p38 MAPK, JNK1/2 and NF-NB. ERK1/2 was not affected by propolis extract and caffeic acid. In addition, propolis and caffeic acid did not induce hepatotoxicity at concentrations with strong anti-inflammatory potential. Conclusions:Propolis exerted an antioxidant and anti-inflammatory action and caffeic acid may be involved in its inhibitory effects on NO production and intracellular signaling cascades, suggesting its use as a natural source of safe anti-inflammatory drugs.

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Section: Discussionmentioning

confidence: 99%

Propolis and its constituent caffeic acid suppress LPS-stimulated pro-inflammatory response by blocking NF-κB and MAPK activation in macrophages

Búfalo

Ferreira

Costa

et al. 2013

Journal of Ethnopharmacology

156

102

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“…Several publications have shown that many compounds structurally related to CAPE, preserve in different degree its biological activity, and these compounds are known by properties like antibacterial, anti-inflammatory, immunostimulatory, anti-atherosclerotic, neuroprotective, antiproliferative, antiviral and antioxidative (Chang et al, 2007;Natarajan et al, 1996;Son & Lewis, 2002;Uwai et al, 2008).…”

Section: Fig 2 Qsar Methodology Diagrammentioning

confidence: 99%

“…The inhibitory effect of these derivatives on NO production in RAW264.7 macrophage was dependent on the length and size of the alkyl moiety, and undecyl caffeate was the most potent inhibitor of NO production (Uwai et al, 2008).…”

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confidence: 97%

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Searching for Analogues of the Natural Compound, Caffeic Acid Phenethyl Ester, with Chemprotective Activity

Macías‐Pérez¹,

Beltrán-Ramírez²,

Villa‐Treviño³

2012

A Compendium of Essays on Alternative Therapy

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“…The potential anticancer performance of the esters of caffeic acid present in vegetable extracts has led researchers to synthesize and study cogeners of CfE with a variable length alkyl chain (up to the hexadecyl ester and tridecyl amide) in order to study the effects of their structure on the molecule stability [43] and their quantitative structure-activity relationships (QSAR) [44]. The inhibitory effect of several caffeic ester derivatives on nitric oxide production in murine macrophage cells was found to be dependent on the length and form of the alcoholic alkyl side chain [45].…”

Section: Isolation Of Cfementioning

confidence: 99%

Ethyl caffeate from Verdicchio wine: Chromatographic purification and in vivo evaluation of its antifibrotic activity

Boselli

Bendia

Lecce

et al. 2009

J of Separation Science

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Ethyl caffeate (CfE, caffeic acid ethyl ester) was extracted from dealcoholized Verdicchio, a white wine from Marche (Italy) with ethyl acetate and then purified with semipreparative reversed-phase high-performance liquid chromatography (RP-HPLC) using an ODS2 column (25 cm Â 20 mm id) at an isocratic flow of 5 mL/min (the mobile phase A was formic acid 4.5% in water and the mobile phase B was acetonitrile). The CfE extract administered intraperitoneally at 1 mmol/L in rats previously treated with 10 mg/kg dimethylnitrosamine was able to prevent the dimethylnitrosamine-induced loss in body and liver weight, as well as to reduce the degree of liver injury, as determined by alanine aminotransferase values and necroinflammatory score, after a 1-week treatment. This was associated with a reduced hepatic stellate cells activation (from 16.8 to 8.3% of smooth muscle actin positive parenchyma) and proliferation (from 11.3 to 5.5 cells/mm 2 ). The collagen synthesis was also reduced: the percentage of Sirius Red positive parenchyma decreased from 21.7 to 7.2%. The CfE levels of Verdicchio wine determined with RP-HPLC-DAD were about 14 times the active levels tested in the in vivo test. CfE can be considered as a promising natural compound for future application in chronic liver disease.

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Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages

Cited by 72 publications

References 29 publications

Propolis and its constituent caffeic acid suppress LPS-stimulated pro-inflammatory response by blocking NF-κB and MAPK activation in macrophages

Propolis and its constituent caffeic acid suppress LPS-stimulated pro-inflammatory response by blocking NF-κB and MAPK activation in macrophages

Searching for Analogues of the Natural Compound, Caffeic Acid Phenethyl Ester, with Chemprotective Activity

Ethyl caffeate from Verdicchio wine: Chromatographic purification and in vivo evaluation of its antifibrotic activity

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