Caffeic Acid Derivatives: In Vitro and In Vivo Anti-inflammatory Properties

Abstract

Caffeic acid and some of its derivatives such as caffeic acid phenetyl ester (CAPE) and octyl caffeate are potent antioxidants which present important anti-inflammatory actions. The present study assessed the in vitro and in vivo effects of five caffeic acid derivatives (caffeic acid methyl, ethyl, butyl, octyl and benzyl esters) and compared their actions to those of CAPE. In the model of LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages, the pre-incubation of all derivatives inhibited nitrite accumulation on the supernatant of stimulated cells, with mean IC50 (microM) values of 21.0, 12.0, 8.4, 2.4, 10.7 and 4.80 for methyl, ethyl, butyl, octyl, benzyl and CAPE, respectively. The effects of caffeic acid derivatives seem to be related to the scavenging of NO, as the compounds prevented SNAP-derived nitrite accumulation and decreased iNOS expression. In addition, butyl, octyl and CAPE derivatives significantly inhibited LPS-induced iNOS expression in RAW 264.7 macrophages. Extending the in vitro results, we showed that the pre-treatment of mice with butyl, octyl and CAPE derivatives inhibited carrageenan-induced paw edema and prevented the increase in IL-1beta levels in the mouse paw by 30, 24 and 36%, respectively. Butyl, octyl and CAPE derivatives also prevented carrageenan-induced neutrophil influx in the mouse paw by 28, 49 and 31%, respectively. Present results confirm and extend literature data, showing that caffeic acid derivatives exert in vitro and in vivo anti-inflammatory actions, being their actions mediated, at least in part by the scavenging of NO and their ability to modulate iNOS expression and probably that of other inflammatory mediators.

Labeled extra virgin olive oil as food supplement; phenolic compounds in oils from some autochthonous Croatian olives

“…Because of, for instance, beneficial anticancer effects, Nichenametla et al (2006), antiinflammatory potential, Pragasam et al (2013) potential beneficial effects in treating metabolic disorders, Yoon et al (2013), antibacterial effects, Lou et al (2012) and a possible preventive effect on myocardial infarct size, Roy et al (2013) of p-coumaric acid, or the beneficial effects of caffeic acid, El Seedi et al (2012), Vauzour et al (2010), da Cunha et al (2004, these and other "minor" phenolics should be an inevitable part in the new labeling framework.…”

Synthesis and leishmanicidal activity of cinnamic acid esters: structure–activity relationship

“…Caffeic acid (1), 3,4-dihydroxy cinnamic acid, and its esters derivatives exhibit a broad spectrum of biological activities, including anti-inflammatory (Jayaprakasam et al, 2006;Da Cunha et al, 2004), antimicrobial (Almajano et al, 2007;Noriaki et al, 2005;King et al,1999;Valenta et al, 1998;Bowles et al, 1994) antioxidant (Hung et al, 2005;Noriaki et al, 2005;Kikuzaki et al,. 2002;Son et al, 2002;Rajan et al, 2001) and anticarcinogenic effects (De et.…”

Toxicity of Some Cinnamic Acid Derivatives to Common Bean (Phaseolus vulgaris)

“…The cinnamic acid and its derivatives are well known for their biological and pharmacological properties: antimicrobial, antioxidant, antiinflamatory, antitumoral (Da Cunha et al, 2004;Narasimhan et al, 2004). Some cinnamic acid derivatives represent secondary metabolites in plants and they have been the subject of a great number of chemical, biological, agricultural and medical studies, the most important category being the hydroxy-cinnamic acids (Urquiaga and Leighton, 2000).…”