Chlorogenic derivatives

N.A. Lycopus virginicus L. Phenolic acids, caffeic derivatives, chlorogenic derivatives, ellagic acids." Treat overactive thyroid gland, an astringent to reduce the production of mucus. 

Simple phenolic compounds include (1) the phenylpropanoids, trans-cinnamic acid, p-coumaric acid and their derivatives (2) the phenylpropanoid lactones called coumarins (Fig. 3.4) and (3) benzoic acid derivatives in which two carbons have been cleaved from the three carbon side chain (Fig. 3.2). More complex molecules are elaborated by additions to these basic carbon skeletons. For example, the addition of quinic acid to caffeic acid produces chlorogenic acid, which accumulates in cut lettuce and contributes to tissue browning (Fig. 3.5). 

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... 

Fig. 2.56. HPLC chromatogram of (a) Golden peel and (b) Golden pulp extracts at 280 nm. Peaks 1 = procyanidin B3 2 = procyanidin Bl 3 = ( + )-catechin 4 = procyanin B2 5 = chlorogenic acid 6 = ( — )-epicatechin 7 = caffeic acid 8 = phloretin derivative 9 = phloridzin 10 = rutin 11, 12 and 13 = flavonol glucosides. Reprinted with permission from A. Escarpa et al. [160].

The major pharmacological constituents of tea are the purine alkaloids caffeine (2.9-4.2%), theobromine (0.15-0.2%), and theophylline (0.02-0.04%). Also present are triterpene saponins (including barringtogenol C and Rl-barringenol), catechins (theaflavine, theaflavin acid, thearubigine), and caffeic acid derivatives (chlorogenic acid and theogallin). A cup of brewed tea contains approximately 20-100 mg of caffeine... 

Mate contains both caffeine (0.4-2.4%) and theobromine (0.3-0.5%). Also found are triterpene saponins and the caffeic acid derivatives—chlorogenic acid, neochlorogenic acid, and cryptochlorogenic acid. Flavonoids in mate are rutin, isoquercetin, and kaemferol glycosides. A nitrile glycoside, menisdaurin, is also present, which is noncyanogenic. 

Tisza, S., Molnar-Perl, I., Friedman, M., Sass, P. (1996). Simultaneous capillary GC of acids and sugars as their silyl(oxime) derivatives Quantitation of chlorogenic acid, raffinose, and pectin substances. J. High Resolut. Chromatogr, 19, 54-58. 

Several simple non-volatile phenylpropanoids are known to be allelochemics. Among these are -coumaric acid, ci and trans-caffeic acid (17), chlorogenic acid, and a caffeyl derivative of an aldaric acid (97). 

The ubiquitous plant compound chlorogenic acid (isolated from green coffee beans) is formed by transesterification with the glycoside cinnamoyl-glucose.187 Coumaroyl-CoA is converted into monomeric and dimeric amides with agmatine, which provides barley plants with resistance to mildew.188 Similar compounds with various polyamines and derived from p-coumaric, caffeic, ferulic, or sinapic acid appear to... 

Set detector at 280 nm for catechins (flavan-3-ols), naringin, and benzoic acid derivatives 320 nm for chlorogenic acid, resveratrol, and hydroxycinnamic acids 370 nm for flavones and flavonols and 520 nm for anthocyanins and anthocyanidins (see Table 11.3.1). 

The phenolic composition of apple consists of cinnamic acids, flavonols, dihydrochalcones, and flavan-3-ols (50,56). In the apple fruit processing industry, hydroxycinnamic acid derivatives and flavan-3-ols are important due to their contribution to the astringency, haze, and browning in apple juice and cider. Chlorogenic acid represents the major hydroxycinnamic acid derivative. The flavan-3-ols (catechins) are present in the monomeric form as well as in oligomeric and polymeric forms (procyanidins) in apple and apple products (56). 

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). 

Main actives Diteipene bitter components including marrubiin (c.1%), caffeic acid derivatives including chlorogenic acid, flavonoids and a trace of volatile oil. 

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