Hydroxycinnamic acid derivative

Murata, M., Okada, H., Homma, S., Hydroxycinnamic acid derivatives and p coumaryl-(L)-tryptophan, a novel hydroxycinnamic acid derivative from coffee beans, Biosci. Biotechnol. Biochem., 59(10), 1887, 1995. (CA124 54202q)... 

The most common hydroxycinnamic acid derivatives are p-coumaric (4-hydroxy-cinnamic), caffeic (3,4-dyhydroxycinnamic), ferulic (4-hydroxy-3-methoxycinnamic), and sinapic (4-hydroxy-3,5-dimethoxycinnamic) acids, which frequently occur in foods as simple esters with quinic acid or glucose (Mattila and Kumpulainen 2002). 

We assayed a number of other phenolic compounds, including aurones, flavones, flavanones, flavanols, lignans and 5-hydroxycinnamic acid derivatives, but they all displayed little or no activity. The lack of activity of... 

Mosel, H.D. and Herrmann, K., Changes in catechins and hydroxycinnamic acid derivatives during development of apples and pears, J. ScL Food Agric., 25, 251, 1974. 

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). 

For hydroxycinnamic acid derivatives in citrus products, an HPLC method was also applied to determine the hydroxycinnamic acid esters with glucose or aldaric acids in the peel and pulp... 

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). 

B Risch, K Herrmann. Hydroxycinnamic acid derivatives in citrus fruit. Z Lebensm Unters Forsch 187 530-534, 1988. 

JellinekT, Johns RB (1970) The mechanism of photochemical addition of cysteine to uracil and formation of dihydrouracil. Photochem Photobiol 11 349-359 Jiang Y, Lin W-Z, Yao S-D, Lin N-Y, Zhu D-Y (1999a) Pulse radiolytic study of electron transfer reaction for fast repair of the one-electron oxidized radicals of dAMP and dGMP by hydroxycinnamic acid derivatives. Radiat Phys Chem 54 349-353... 

Bengoechea, L. Hernandez, T. Quesada, C. Barolome, B. Estrella, I. Gomez-Cordoves, C. 1995. Strueture of hydroxycinnamic acid derivatives established by high-performance liquid ehromatography with photodiode-array detection. Chromatographia 41 94-98. 

Among the hydroxycinnamic acids, caftaric acid predominates (up to 50% of total hydroxycinnamic acids). Other important substances are the tartaric esters of p-coumaric acid and ferulic acid, and the franx-p-coumaric glucoside (Somers et al. 1987). The concentration levels of hydroxycinnamic acid derivatives in wine depend on many factors like grape variety, growing conditions, climate, etc. It is... 

Jiang Y, Lin W, Yao S, Lin N, Zhu D. (1999) Fast repair of oxidizing OH adducts of DNA by hydroxycinnamic acid derivatives. A pulse radiolytic study. Radiat Phys Chem 54 355-359. 

Lu C, Liu Y. (2002) Interactions of lipoic acid radical cations with vitamins C and E analogue and hydroxycinnamic acid derivatives. Arch Biochem Biophys 406 78-84. 

Murata M., Okada H. and Homma S. (1995) A novel hydroxycinnamic acid derivative of coffee bean. 16th Int. Colloq. Chem. Coffee (Kyoto, 9-14.4.1995) (ASIC, 1995), 199-207. 

Procyanidins are often accompanied by a large number of phenolic compounds like hydroxycinnamic acid derivatives and flavonoids which show a similar chromatographic behavior [66,151,168,235]. Chlorogenic acid, for example, tends to co-elute with procyanidin B2 applying methanol [176,236], acetonitrile [170,181] as well as tetrahydrofuran gradients [237]. To cope with this problem, Lea [236] removed phenolic acids at pH 7.0 at the beginning of a chromatographic run, then he reverted to pH 2.5 and eluted the procyanidins without any interferences. 

Fig. (4). General structures of antioxidant hydroxycinnamic acid derivatives.

In Fig. 6 a characteristic HPLC chromatogram of lemon juice phenolics is shown. The main phenolics in lemon juice are flavanones and C-glucosylflavones. The small peaks at the beginning of the chromatogram correspond to hydroxycinnamic acid derivatives, which are minor constituents in lemon juice. 

In carrots, the principal phenolics are the hydroxycinnamic acid derivatives. Of these, caffeic acid derivatives are the main components (20-100 mg/kg fw. depending on the cultivar), while ferulic acid derivatives are accumulated in intermediate quantities (10-20 mg/kg) and p-coumaric derivatives, 4-hydroxybenzoic acid derivatives and vanillic acid are present in trace amounts [38]. The main compound in carrots is chlorogenic acid, which has been estimated as between 23 and 121 mg/kg f w. depending on the cultivar. However, in carrot tops, this compound can reach 375-400 mg/kg [40], while cryptochlorogenic, neochlorogenic and 5-feruloylquinic acids have also been detected. 

Bell peppers, both green and red, contain low amounts of phenolic acid derivatives p-Coumaric (< 4 mg/kg), caffeic (< 10 mg/kg), ferulic (<15 mg/kg), sinapic (<5 mg/kg) and vanillic (10 mg/kg) acids [77]. Caffeoyl glucose, feruloyl glucose and sinapoyl glucose are the main hydroxycinnamic acid derivatives found, while no quinic acid derivatives have been detected [63]. Feruloyl glucose may accumulate up to 11 mg/kg f.w. and sinapoyl glucose up to 5 mg/kg in some red cultivars. 

Fig. 11 shows a characteristic HPLC chromatogram of spinach flavonoids. Its complexity is due to the large number of compounds that are biosynthesised by the spinach leaves. However, the analysed methanol extract does not contain many hydroxycinnamic acid derivatives (with only one peak at around 10 minutes in the HPLC chromatogram revealing their presence). 

Nardini M, D Aquino M, Tomassi G, Gentili V, Di Felice M, Scaccini C. Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives. Free Rad Biol Med 1995 19 541-52. 

Kikugawa, K. et al.. Reaction of p-hydroxycinnamic acid derivatives with nitrite and its relevance to... 

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