Caffeoylquinic acids derivatives

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. 

Superoxide dismutase Polyunsaturated fatty acid 1,1 -Diphenyl-2-picrylhydrazyl Low density lipoprotein Phorbol-12-mysri state-13-acetate 12-0-Tetradecanoylphorbol-13-acetate Di-O-caffeoylquinic acids Di-O-caffeoylquinic acid Herpes simplex virus type 1 Human immunodeficiency virus Acquired immunodeficiency syndrome Human immunodeficiency virus type-1 CafFeoylquinic acid derivatives 3-fer/-Butyl-4-hydroxyanisole... 

From simple phenolic derivatives, there are only a few reports concerning antimicrobial activity from the Anthemideae tribe. Examples included four caffeoylquinic acid derivatives, chlorogenic acid. Fig. (42), cynarin. Fig. (43), 3,5-di-O-caffeoylquinic acid and 4,5-di-(9-caffeoylquinic acid isolated from Cynara scolymus [222] and cynaropicrin, Fig. (44) isolated from Moquinia kingii [227]. 

FIGURE 3 Chemical stractures of several caffeoylquinic acids derived from propolis [51]. 

Cynaropicrin, cynarin (1,3-dicaffeoylqui-nic acid), 3-caffeoylquinic acid (chlorogenic acid), and scolymoside are among various active constituents identified so The maximum content of cynarin, the major caffeoylquinic acid derivative in the artichoke heads, is obtained by aqueous ebullition of... 

The ethyl acetate fraction of Art. campestris was purified to give 3,4-dicafeoylquinic acid (10), 3,S-dicafeoyIquinic acid (11) and 4,5-dicaffeoylquinic acid (12), methyl 3,5-dicaffeoylquinate (13) together with monocaffeoylquinic acid isomers and flavonoids. Figure 3 shows the DPPH radical scavenging activity of caffeoylquinic acid derivatives. Monocaffeoylquinic acids showed the activity comparable to a-tocopherol and ascorbic acid. On the other hand,... 

Di-caffeoylquinic acid (70) Cyclic polyolic derivative 1,5-DCQA(70) Antiviral (Anti-HIV HIV/AIDS and hepatitis B) Inhibits HIV-1 integrase Phase l/Il Chinese Academy of Military Medical Sciences 583-585... 

An HPLC method for chlorogenic acids with lactones in six different commercial brands of roasted coffee was developed by Schrader et al. (143). Hydroxycinnamic acid derivatives, including mono- and di-caffeoylquinic acids, corresponding lactones, and feruloylquinic acids were extracted from coffee with methanol at 80°C for 1 h under reflux. An HPLC method using step-gradient elution with 2% aqueous acetic acid (eluent A) and ACN (eluent B) for a 75-min run time was developed. Determination was carried out by HPLC with UV detection at 324 nm, and further confirmation was conducted by HPLC-thermospray (TSP)-MS and HPLC-diode array detection. Elution order for mono-caffeoylquinic acid (CQA) was 3-CQA, 5-CQA, followed by 4-CQA, which was different from the usual elution order of mono-CQA (Fig. 17). These results indicate that it is currently not possible to predict the elution order of different reversed-phase packings due to the different selectivity (143). 

A book on caffeine and related derivatives has been published.12 Effective thin-layer chromatographic7 and combination t.l.c.-counter-current partition13 methods for the analysis of caffeine have been developed. The content of 4-0-caffeoylquinic acids in roots, stems, and leaves of tobacco plants grown in complete and N-deficient nutrient solutions has been quantitatively determined.14... 

Caffeic acid derivatives Caffeic acid (110), Chloro-genic acid (111) its butyl ester, Rosmarinic acid (112), KOP (Caffeic acid oxidised polymer). 3,4,5-Tri-O-caffeoyl-quinic acid, 4,5-Di-O -caffeoylquinic acid, Synapoic acid Many sp. Securidaca longipedunculala HSV HIV Virucidal, Cellular DNA metabolism. Binding of gpl20 to CD4 HIV-RT [16. 73, 74] [75, 76]... 

Anthocyanin (cyanidin) pigmentation can be observed in some cultivars, although its nature has not been fully determined. 3 -Caffeoylquinic is the principal phenolic acid derivative, although 4 - and 5 -caffeoylquinic acids are also present. A concentration of 167 mg caffeic acid per kg has been reported in apricots [19]. The presence of the corresponding p-coumaroyl-and feruloyl quinic acid derivatives has also been reported [16], as have p-coumaroylglucose and feruloyl glucose. 

Among the phenolic acid derivatives, 3 -caffeoylquinic is the main compound in both species, although other p-coumaroyl-, caffeoyl-, and feroulyl quinic derivatives have also been reported in minor amounts. 

The main phenolic acid derivative is chlorogenic acid, although 3 -caffeoylquinic and 4 -cafFeoylquinic acids, and p-coumaroyl- and feruloyl-quinic acid derivatives have also been reported [16]. Up to 128mg caffeic acid per kg fresh peaches have been reported [19]. 

Minimal processing of carrots induces phenylalanine ammonia lyase (PAL) activity and phenolics accumulation. In shredded carrots, chlorogenic acid, which is rapidly accumulated, represents 60% of the total phenolics. In addition traces of 3 -caffeoylquinic and 4 -caffeoylquinic acids are biosynthesised, and 3, 4 -dicaffeoylquinic and 3, 5 -dicaffeoyl quinic acids also accumulate [44]. p-Hydroxybenzoic acid derivatives are also biosynthesised but more slowly, and are related to defence against microbial attack (phytoalexin response), the degree and speed of which depends on the cultivar [45],... 

Quinic acid derivatives can be esterified at the carboxylic acid group. It is unclear whether such ester derivatives are actually naturally occurring compounds or whether they are only artifacts of work-up procedures using alcoholic solvents. Nevertheless, we obtained regioisomeric methylesters of caffeoylquinic acid and compared their tandem mass spectra [21]. Again the mass spectra of all four regioisomeric compounds have been different to allow distinguishing between isomers [21]. 

The major phenolic compound in tobacco roots (Figure 1) is chlorogenic acid (CA), correctly termed 3-O-caffeoylquinic acid (3-O-CQA). Only minor to trace amounts of the 4- and 5-O-CQA isomers are found in the roots, but occur in larger quantities in the leaves. Two coumarin derivatives are found in major amounts in root tissue scopoletin (6-methoxy-7-hydroxycoumarin) and its glucoside, scopolin. Both CA and scopolin can reach levels of 1% of the dry weight of the root. Very little scopolin or scopoletin is found in the leaves. 

Phytochemistry Abovegroundparts containphenolcarbonicacids and their derivatives(caffeic,rosemarinic,l-caffeoylquinic, and 5-caffeoylquinic acids), flavonoids (luteolin, apigenin, scutellarein, and anthocyans) and essential oil (containing thymol, carvacrol, a-pinene, camphene, sabinene, n-thymol, isobomeol, boroneol, undecanoic add, and amyl alcohol Plant Resonrces of the USSR 1991 Kolesnikov and Gins 2001 Stahl-Biskup 2002). 

Moreover, green coffee beans contain a number of chlorogenic acids such as derivatives of caffeoylquinic acid, dicaffeoylquinic acid, and feruloylquinic acid [428], whose amount and distribution in the coffee beans depend on the bean type and degree of ripeness. During the roasting process, a significant... 

The main substrates of polyphenol oxidases in apples are hydrox-ycinnamic acid derivatives, especially caffeic add depsides, such as chlorogenic acid, and some groups of flavonoid compounds, such as flavan-3-ols, flavonols, dihydrochalcones and (in red-skinned apple varieties) also anthocyanins. In the flesh of apples, the main phenohcs are chlorogenic (3-caffeoylquinic) add, flavan-3-ol epicatechm, and procyanidin B2 representing condensed tannins. These three compounds represent more than 90% of the phenolic compounds present. The main substrates in apple peel are flavan-3-ols and flavonols (quercetin glycosides) and to a lesser extent derivatives of hydroxydnnamic acids are present (chlorogenic add and some other depsides). 

---