Chlorogenic coffee

Numerous organic acids iu coffee iuclude acids of metaboHc origin, eg, acetic lactic, citric, malic, and oxaUc free quiuic acid [77-95-2], and various chlorogenic acid (CGA) isomers that appear to be species specific. 

Amounts of chlorogenic acids found in roasted coffee are given in... 

More recently, a series of 11 chlorogenic acids has been recognized in green Robusta coffee beans.51... 

Chlorogenic acid lactones are produced in roasted coffee and range from 1.5 to 3.5 g/kg in commercial roasted coffee samples. Two lactones that have been identified in roasted coffee are 3-caffeoyl- and 4-caffeoyl-quinic acid-y-lactone.60... 

Deshpande, S. N., Aguilar, A. A., Effects of roasting temperatures and gamma-irradiation on the content of chlorogenic acid, caffeic acid and soluble carbohydrates of coffee, Int. J. Appl. Radiat. Isot., 26, 656, 1975. (CA84 57527r)... 

Bennat, C., Engelhardt, U. H., Kiehne, A., Wirries, F. M., Maier, H. G., HPLC analysis of chlorogenic acid lactones in roasted coffee, Z. Lebensm.-Unters. Forsch., 199(1), 17, 1994. (CA121 178291a)... 

Melo, M., Amorim, H. V., Chemistry of Brazilian green coffee and the quality of the beverage. VI, The uv and visible spectral analysis and chlorogenic acids content in TCA soluble buffer extracts, Turrialba, 25, 243, 1975. (CA84 57533q)... 

Rees, D. I., Theaker, P. D., High pressure liquid chromatography of chlorogenic acid isomers in coffee, Coll. Sc 1. Int. Cafe, 8, 79, 1977. (CA92 196458x)... 

Belyaya, K. J., Clifford, M. N., Individual chlorogenic acids and caffeine contents in commercial grades of wet and dry processed Indian green robusta coffee, J. Food Sc 1. Technol, 32(2),104, 1995. (CA123 197159w)... 

Clifford MN, Knight S, Surucu B and Kuhnert N. 2006a. Characterization by LC-MS(n) of four new classes of chlorogenic acids in green coffee beans dimethoxycinnamoylquinic acids, diferuloylquinic acids, caffeoyl-dimethoxycinnamoylquinic acids, and feruloyl-dimethoxycinnamoylquinic acids. J Agric Food Chem 54(6) 1957-1969. 

Guerrero G, Suarez M and Moreno G. 2001. Chlorogenic acids as a potential criterion in coffee genotype selections. J Agric Food Chem 49(5) 2454-2458. 

Saldana MDA. 1997. Extraction of caffeine, trigonelline and chlorogenic acid from Brazilian coffee beans using supercritical CO2 MSc. Thesis, UNICAMP, Campinas, Brazil. 

Anti-adhesive effect. Green and roasted coffee, used in a treatment mixture and as a pretreatment on beads, inhibited the Strep tococcus mutans sucrose-independent adsorption to saliva-coated hydroxyapatite beads. The inhibition of Salmonelb mutans adsorption indicated that coffee-active molecules may adsorb to a host surface, preventing the tooth receptor from interacting with any bacterial adhesions. Among the known tested coffee components, trigonelline and nicotinic and chlorogenic acids are very... 

Trugo, L. C., C. A. B. de Maria, and C. C. Werneck. Simultaneous determination of total chlorogenic acid and caffeine in coffee by high performance gel filtration chromatography. Food Chem 1991 42(1) 81-87. 

Changes in the content of chlorogenic CA138 acids in row coffee beans during accelerated aging. Zesz Nauk Akad Ekon Poznaniu Ser 1981 1(88) 94-97. 

Hydroxybenzoic acids are comparatively minor, but widespread components of the diet. The hydroxycinnamic acids, especially the chlorogenic acids of coffee, are a major contributor to the total dietary intake of PPT. ... 

Johnston, K.L., Clifford, M.N., and Morgan, L.M., Coffee acutely modifies gastrointestinal hormone secretion and glucose tolerance in humans glycemic effects of chlorogenic acid and caffeine. Am. J. Clin. Nutr., 78, 728, 2003. 

Monteiro, M., Farah, A., Perrone, D., Trugo, L. C., Donangelo, C. (2007). Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans. J. Nutr, 137, 2196-2201. 

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... 

The term chlorogenic acid was introduced in 1846 [1] to describe a coffee bean component that was later characterized as 5-0-caffeoylquinic acid [2], which is an ester of caffeic acid with quinic acid. Such esters are known as depsides, and the term chlorogenic acids is now often used to refer to the range of depsides that have been found in plants and it is in this sense that this term will be employed throughout this paper. 

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). 

Fig. 17 HPLC separation of chlorogenic acids from roasted coffee. (From Ref. 143.) 1-15 = hydroxy-cinnamic acids 7, 8 = coumaroylquinic acids 16 = caffeoyltryptophan.

K Schrader, A Kiehne, UH Engelhardt, HG Maier. Determination of chlorogenic acids with lactones in roasted coffee. J Sci Food Agric 71 392-398, 1996. 

Green coffee beans (Coffea arabica) are one of the richest dietary sources of chlorogenic acids. 5-O-Caffeoylquinic acid is the dominant chlorogenic acid accounting for 50% of the total. This is followed by 3-0- and 4-O-caffeoyl-quinic acid, the three analogous feruloylquinic acids and 3,4-0-, 3,5-0- and 4,5-O-dicaffeoylquinic acids (Fig. 1.32) [Clifford, 1999]. Levels decline ca. 80% during the roasting of coffee beans, but sizable amounts with substantial antioxidant activity are still found in the typical cup of coffee. 

O-Dicaffeoylquinic acid Figure 1.32 Main chlorogenic acids in green coffee beans. 

---