Caffeoyl acid

Marita, J. M. Ralph, J. Hatheld, R. D. Guo, D. Chen, F. Dixon, R. A. Structural and compositional modihcations in lignin of transgenic alfalfa down-regulated in caffeic acid 3-O-methyltransferase and caffeoyl coenzyme A 3-O-methyltransferase. 

The treatment and environment of green coffee beans affects the concentrations of both caffeoyl- and feruloyl quinic acids,52 and several decomposition products have been recognized. Some of these products, in this case from steam-treated green coffee beans, are given in Figure 5.53... 

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... 

Crossing the boundaries of phenolic compounds and amino acids in coffee, caffeoyl tryptophan, and p-coumaiyl-(L)-tryptophan have both been identified recently in green Robusta coffee beans.51 A... 

Scarpati, M. L. and Guiso, M., Caffeoyl-quinic acid from coffee and mate, Ann Chim (Rome) 53, 1315, 1963. 

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. 

Caffeoyl-quinic acid, 3-5-di-O Sd Al04 Caffeoyl-quinic acid, 4 Sd " ° °... 

Butyric acid, N, caffeoyl-4-amino Pl T so Butyric acid, N, N-caffeoyl-4-amino Bd Butyric acid An " " ... 

NT350 Balint, R., G. Cooper, M. Staebell, and P.Filner. N-Caffeoyl-4-amino-N-butyric acid, a new flower-specific metabolite in cultured tobacco cells and tobacco plants. J Biol Chem 1987 262(23) 11026-11031. 

Notes pg, pelargonidin cy, cyanidin dp, delphinidin pn, peonidin pt, petunidin mv, malvidin all, allopyranose ara, a-arabinopyranose gal, galactopyranose glc, glucopyranose glu, glucuronic acid rha, rhamnopyranose xyl, xylopyranose ac, acetyl benz, benzoyl caf, caffeoyl cin, cinnamoyl cou,/>-coumaroyl fer, feruloyl gall, galloyl mal, malonyl sinap, sinapoyl ND, not detected. 

Cheynier, V. and Ricardo Da Silva, J.M., Oxidation of grape procyanidins in model solutions containing tra 5-caffeoyl tartaric acid and grape polyphenoloxidase. J. Agric. Food Chem. 39, 1047, 1991. 

Salgues, M., Cheynier, V., and Gunata, Z., Oxidation of grape juice 2-5-glutathionyl caffeoyl tartaric acid by Botrytis cinerea laccase and characterization of a new substance 2,5 di-5-glutathionyl caffeoyl tartaric acid. J. Food Sci. 5, 1191, 1986. 

The three most widely used species of Echinacea are Echinacea purpurea, E pallida, and E angustifolia. The chemical constituents include flavonoids, lipophilic constituents (eg, alkamides, polyacetylenes), water-soluble polysaccharides, and water-soluble caffeoyl conjugates (eg, echinacoside, chicoric acid, caffeic acid). Within any marketed echinacea formulation, the relative amounts of these components are dependent upon the species used, the method of manufacture, and the plant parts used. Epurpurea has been the most widely studied in clinical trials. Although the active constituents of echinacea are not completely known, chicoric acid from E purpurea and echinacoside from E pallida and E angustifolia, as well as alkamides and polysaccharides, are most often noted as having immune-modulating properties. Most commercial formulations, however, are not standardized for any particular constituent. 

For white wines (85), a similar HPLC condition to that of Betes-Saura et al. (79) was employed with a Nucleosil C)8 column (250 X 4.0-mm ID, 5 /zm) with binary gradient using eluent (A) acidified water (pH 2.65) and eluent (B) 20% A with 80% acetonitrile applied for hydroxy-cinnamate derivatives esters (caffeoyl tartaric, p-coumaroyl tartaric, and feruloyl tartaric acid esters) and free hydroxycinnamic acids (caffeic, ferulic, and p-coumaric acids). 

Figure 3-4. The general phenylpropanoid pathway. The enzymes involved in this pathway are (a) phenylalanine ammonia lyase (PAL E.C. 4.3.1.5), (b) cinnamic acid 4-hydroxylase (C4H E.C. 1.14.13.11), and (J) 4-coumaric acid CoA ligase (4CL E.C. 6.2.1.12). (a) depicts tyrosine ammonia lyase activity in PAL of graminaceous species. The grey structures in the box represent an older version of the phenylpropanoid pathway in which the ring substitution reactions were thought to occur at the level of the hydroxycinnamic acids and/or hydroxycinnamoyl esters. The enzymes involved in these conversions are (c) coumarate 3-hydroxylase (C3H E.C. 1.14.14.1), (d) caffeate O-methyltransferase (COMT EC 2.1.1.68), (e) ferulate 5-hydroxylase (F5H EC 1.14.13), and (g) caffeoyl-CoA O-methyltransferase (CCoA-OMT EC 2.1.1.104). These enzymes are discussed in more detail in Section 10.

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. 

---