Caffeic acid derivatives

Fig. 2.77 Compounds 246-249, caffeic-acid derivatives from Echinacea angustifolia. Compounds 250 and 251, sweet principals from Lippia dulcis...

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. 

Rechner, A.R., Spencer, J.P., Kuhnle, G., Hahn, U., and Rice-Evans, C.A., Novel biomarkers of the metabolism of caffeic acid derivatives in vivo, Free Radical Biol Med., 30, 1213, 2001. 

Wollenweber, E. et al., A novel caffeic acid derivative and other constituents of Populus bud excretion and propolis (bee-glue), Z. Naturforsch, 42c, 1030, 1987. 

Bauer R, Foster S. Analysis of alkamides and caffeic acid derivatives from Echinacea simulata and E. paradoxa roots. Planta Med 1991 57 447-449. 

Main actives Caffeic acid derivatives (c.1%) including chlorgenic acid, flavonoids (c.0.5%) and sesquiterpene lactones (up to 4%) - the major component is cyanaropicrin. 

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

Main actives Complex mixture of volatile oils, glycosides of the alcoholic and phenolic volatile components, caffeic acid derivatives, flavonoids and triteipene acids. 

Main actives Iridoids, flavonoids and caffeic acid derivatives. 

Rechner AR, Pannala AS, Rice-Evans CA. 2001. Caffeic acid derivatives in artichoke extract are metabolised to phenolic acids in vivo. Free Radio Res 35 195-202. 

Clifford MN, Wu W, Kirkpatrick J, Kuhnert N. 2007. Profiling the chlorogenic acids and other caffeic acid derivatives of herbal chrysanthemum by LC-MSn. J Agric Food Chem 55 929-936. 

A biomimetic catechol cleavage reaction was carried out on dihydro-caffeic acid derivative 1922 using the iron(III)-catalyzed peracetic acid cleavage process of Pandell.25 This produced the cyclized muconic acid derivative 20 which could be transformed into pyrone 21 by treatment with hydrochloric acid. Bromination followed by azide displacement gave key intermediate 22 which could either be reduced directly to (i)-stizolobic acid 16 or ammonolyzed and then reduced to give ( )-3-(6-carboxy-2-oxo-4-pyridyl)alanine 17 (Scheme 4). 

Bergeron, C., Gafner, S., Batcha, L., and Angerhofer, C. 2002. Stabilization of caffeic acid derivatives in Echinacea purpurea L. glycerin extract. J. Agric. Food Chem. 50, 3967-3970. 

Kim, H., Durance, T., Seaman, C., and Kitts, D. 2000b. Retention of caffeic acid derivatives in dried Echinacea purpurea. J. Agric. Food Chem. 48, 4182-4186. 

Luo, X., Chen, B., Yao, S., and Zeng, J. 2003. Simultaneous analysis of caffeic acid derivatives and alkamides in roots and extracts of Echinacea purpurea by high performance liquid chromatography-photodiode array detection-electrospray mass spectrometry. J. Chromatogr. A 986, 73-81. 

Schieffer, G. 2000. Validated HPLC method for caffeic-acid derivatives and alkylamides of Echinacea solid-dosage forms using a single extraction procedure. J. Am. Nutraceutical Assoc. 3, 67-81. 

Echinacea is one of the best-selling herbal products in the United States (Brevoort, 1998) and is promoted as an immunostimulatory agent (Bauer, 1999a, 2000). The alkamides, caffeic acid derivatives (e.g., cichoric acid), glycoproteins, and polysaccharides are believed to be responsible for Echinacea s observed immunostimulatory activity. Bauer (1997) reported that the variation in alkamide concentrations of Echinacea products was due to a number of factors such as growing season, which part of the plant was utilized in the preparation of the commercial product,... 

Qualitative Evaluation of the Caffeic Acid Derivatives in Echinacea Species Using Micellar Electrokinetic Chromatography (Pietta et al., 1998)... 

T., Ishihara, T., Noguchi, T., Morita, L, and Murota, S.-i., Novel caffeic acid derivatives. Extremely potent inhibitors of 12-lipoxygenase, J. Med. Chem., 34, 1503, 1991. 

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