Caffeic acid antioxidative activity

An extract from Lactuca indica showed significant free radical scavenging activity, and protected phixl74 supercoiled DNA against strand cleavage and reduced oxidative stress in human promyelocytic leukemia HL-60 cells. On account of protocatechulic acid, methyl p-hydroxybenzoate, caffeic acid, 3,5-dicaffeoylquinic acid, luteolin 7-O-fT glucopyranoside, and quercetin 3-0-(3-g 1 ucopyranoside are the major antioxidative constituents (111). 

There is the often-overlooked group of polyphenols containing the derivatives of hydro-xycinnamic and hydroxybenzoic acids such as caffeic, chlorogenic, and gallic acids (Figure 29.8), which occur in food and exhibit certain antioxidant activity. For example, some caffeic acid esters isolated from propolis from honeybee hives showed antiinflammatory... 

According to the theory of free radical oxidation, antioxidizing activities of chlorogenic acids are stipulated by their participation in reaction with free radicals. Chlorogenic and caffeic acids have high stoichiometric numbers and reactivity with peroxyl radicals as compared with trolox, the water-soluble analogue of tocopherol [48]. Considering... 

Recently, Maruta et al. [112] have found that methanol extracts of roots of burdock show a significant antioxidant activity in an in vitro lipid peroxidation assay, and have isolated five caffeoylquinic acid derivatives (CQAs) from the roots of burdock (Arctium lappa L ), an edible plant in Japan. Antioxidant activities of DCQAs and related compounds have been investigated by measuring the hydroperoxidation of methyl linolate via radical chain reaction. This study indicates that in this particular system caffeic acid and CQAs are more effective than a-tocopherol. These results approximately agree with our findings [38], Additionally, CQAs as the principle antioxidative substance in burdock root have been characterized. 

Despite the abundance of biological data demonstrating antioxidant activities of chlorogenic acids, the controversy whether these compounds are potent antioxidants or pro-oxidants, remains. The pro-oxidant characteristics of chlorogenic and caffeic acids have been suggested in the several papers [44, 52, 117-121],... 

Plant foods contain a variety of PPs that are regarded as active agents and particularly as antioxidants. The chemical structures are quite complex and there are relatively small molecules such as hydrocinnamic acids (caffeic acid and ferulic acid) and also extremely large molecules like the proantho-... 

Cynarine is the main active agent of artichoke extract. It is a cinnamic acid derivative the substitution pattern of its aromatic rings is similar to that of dopamine. Caffeic acid is also regarded as a major active substance. It has not yet been clarified to which constituents the known modes of action are attributable .) increase in choleresis, (2.) inhibition of cholesterol biosynthesis, (3.) hepatoprotection due to antioxidative effects, and (4.) activation of the urea cycle. 

During malaxation, when water is added to olive paste to wash it, tons of waste water (800.000 in Italy only) are produced from the oil industry and discarded. Water soluble compounds are then transfered from olives into waste waters and could be recovered. HPLC analysis of the waste water extract showed the presence of hydroxytyrosol, tyrosol, p-OH benzoic acid, vanillic acid, caffeic acid, oleuropein, verbascoside and other oleuropein derivatives. The extract had powerful antioxidant activity and could represent a cheap source of natural antioxidants to be used to preserve food and cosmetics from fat oxidation and rancidity [51]. 

Rat hepatocytes were treated with Fe-NTA (nitriloacetic acid) [49]. In this model, all the tested compounds, including tyrosol, were able to inhibit lipoperoxidation in the same concentration range 20-100 pM (hydroxytyrosol, caffeic acid and oleuropein). The antioxidant activity of caffeic acid has been already described in erythrocytes, rat isolated... 

Phenolic acids include the benzoic acids (Ce-Ci), e.g., gallic, vanillic, syringic, protocatechuic, p-hydroxy-benzoic acid, as well as cinnamic acids (C6-C3), e.g., caffeic, p-coumaric, ferulic, sinapic acids, and their dep-sides and derivates, e.g., rosmarinic acid and lithospermic acid (Fig. 1). Phenolic acids and flavonoids in plants may occur in the free form, but they are often glycosylated with various sugars, especially glucose. Phenolic acids may also be present in the esterified as well as bound forms. Free phenolic acids are found especially in herbs and spices and, very often, in compounds responsible for antioxidant activity (benzoic and cinnamic acids and some of their derivatives). The bound forms are more common for the fruits, vegetables, and other plant materials. Therefore, in some cases, it is necessary to combine the analysis of their free and bound forms. 

In products with complex combinations of various types of flavonoids and other phenolic compounds, effort has been made to ascribe the antioxidant activity of the product to different classes of polyphenols. Frankel et al. (1995) studied 20 selected California wines and related the antioxidant activity to the polyphenolic components of the wines, rather than to resveratrol. Antioxidant activity was measured by the ability of the wines to inhibit copper-catalyzed oxidation of human LDL. The correlation coefficient between antioxidant activity and total phenolic components of the wines was r = 0.94. Individual phenolic compounds (gallic acid, catechin, myricetin, quercetin, caffeic acid, rutin, epicatechin, cyanidin, malvidin-3-glucoside) contributed to the antioxidant activity. The correlation coefficient for the compounds ranged from r = 0.92 to r = 0.38 in descending order. 

The antioxidant activities of red and white commercial grape juices have been studied using in vitro inhibition of the copper-catalyzed oxidation of human LDL (Frankel et al., 1998). The correlation between total phenols, expressed as GAE, and relative percent of inhibition of LDL oxidation was r = 0.99. In red Concord grape juices, the antioxidant activity was related to the anthocyanin levels. In the white grape juice, the antioxidant activity was associated with the levels of hydrox-ycinnamates (caffeic acid) and flavanols (catechin). When compared at the same level of total phenolics (10 pM GAE), the antioxidant activities of the grape juices were comparable to the antioxidant activities of red wine (Frankel et al., 1995). Laplaud et al. (1997) found protective action of copper-mediated LDL oxidation in aqueous V. myrtillus extracts. On a molar base, the extracts were more efficient than ascorbic acid and BHT in inhibiting LDL oxidation. 

Erigeron annuus leaf extracts containing caffeic acid as an active compound have antioxidative and neuroprotective effects on neuronal cells. 

In washed human platelets, NDGA inhibited the formation of 12-LOX products as well as the COX product 12-hydroxyheptadecatrienoic acid (12-HHT), with an IC50 of 5 pM, while boswellic acids (mixture of a- and P-isomers) at concentrations up to 400 pM exerted no effect. In addition, in a cell-free system, the non-enzymatic peroxidation of AA by iron (II)-ascorbate was not affected by boswellic acid at concentrations up to 400 pM, whereas NDGA abolished the peroxidation of AA in this test at a concentration of 10 pM. These results suggest that the activity of boswellic acids is selective in the 5-LOX pathway, and the mechanism of inhibition is different from that of the classic antioxidant 5-LOX inhibitors (NDGA, caffeic acid, quercetin) [96]. 

TLC analysis of the antioxidatively acting compounds [48] in the ethanolic extract from Fraxinus ornus bark revealed the presence of additional antioxidative acting compounds. Among them calceolarioside B (23) demonstrated a significant activity. Most probably, caffeic acid (16) and the caffeoyl esters of phenylethanoid glycosides 22, 24-27 also contribute to the antioxidative properties of the extract. 

The antioxidants or quenchers of free radicals are known to minimize skin photoaging and the protective action of sun screens correlates closely to their free radical scavenging activity [49,50]. This prompted us to use the prevention of photodynamic yeast cell damage to comparatively investigate the protective activity of the four hydroxycoumarins esculin, esculetin, fraxin and fraxetin, and a widely used sun screen p-aminobenzoic acid (PABA). We applied the same test to characterize the protective activity of four Fraxinus ornus bark preparations containing these coumarins in different concentrations and to examine the activity of caffeic acid (16), a minor constituent of these preparations [51]. 

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