HPLC Analysis of chlorogenic acid lactones in roasted coffee

Bennat, C; Engelhardt, Ulrich H.; Kiehne, Andrea; Wirries, Frank Michael; Maier, Hans Gerhard

doi:10.1007/bf01192945

Cited by 47 publications

(39 citation statements)

References 6 publications

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“…This is accompanied by some hydrolysis releasing cinnamic aids and quinic acid. Later in the roasting quinic acid epimerises and lactonises, and several chlorogenic lactones, including 3-and 4-O-caffeoyl-1,5-quinide (figure 5), also form (Scholz and Maier, 1990;Bennat et al, 1994;Schrader et al, 1996;Farah et al, 2005). The cinnamic acids may be decarboxylated and transformed to a number of simple phenols and range of phenylindans probably via decarboxylation and cyclisation of the vinylcatechol intermediate (Stadler et al, 1996).…”

Section: Discussionmentioning

confidence: 99%

On-line HPLC analysis of the antioxidant activity of phenolic compounds in brewed, paper-filtered coffee

Stalmach

Mullen

Nagai

et al. 2006

Braz. J. Plant Physiol.

102

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Caffeoyl-, feruloyl-and dicaffeoylquinic acids (chlorogenic acids) in infusions from green and medium roasted coffee beans were identified and quantified by reverse phase HPLC with photodiode array and MS 3 detection prior to assessment of the antioxidant activity using an HPLC system with post-column on-line antioxidant detection based on 2,2'-azinobis-3-ethylbenzothiazoline-6-sulphonic acid radical scavenging activity. Caffeoylquinic acids were the most abundant antioxidants and roasting induced isomerisation with a decline in 5-O-caffeoylquinic acid and concomitant increases in the 3-and 4-Oderivatives. This did not affect the level of caffeoylquinic acid-derived antioxidant activity in the roasted coffee. Roasting did, however, result in the appearance of additional unidentified HPLC peaks with antioxidant activity. Because of this and an increase in the antioxidant activity of components that did not elute from the reversed phase HPLC column, the antioxidant capacity of the beverage derived from medium roast beans was double that of the unroasted coffee. The antioxidant activity of coffees that have undergone different degrees of roasting would, therefore, appear to be due to combinations of different components. The effect of roasting on chlorogenic acids in coffee beans is considered, and the possible contribution of Maillard reaction products to the antioxidant capacity of roasted coffees is discussed. Key words: Coffea, ABTS + , chlorogenic acids, hydroxycinnamates, HPLC-MS n .Análise por HPLC "on-line" da atividade antioxidante de compostos fenólicos em café preparado por infusão e filtrado em papel: Ácidos cafeoil-, feruloil-e dicafeoilquínicos (ácidos clorogênicos) em infusões de sementes de café verde e sementes medianamente torradas foram identificados e quantificados por cromatografia líquida de alta eficiência (HPLC) em fase reversa com detecção em fotodiodo e MS 3 , antes da avaliação da atividade antioxidante usando um sistema HPLC com detecção antioxidante "on-line", baseada na eliminação de radicais pelo ácido 2,2'-azinobis-3-etilbenzotiazolina-6-sulfônico. Ácidos cafeoilquínicos foram os mais abundantes antioxidantes e a torração induziu a isomerização, com declínio do ácido 5-O-cafoilquínico e concomitante aumento dos derivados 3-e 4-O-cafeoilquínicos. Isto não afetou o nível da atividade antioxidante derivada de ácidos cafeoilquínicos no café torrado. Torração, no entanto, resultou no aparecimento de picos adicionais nas corridas cromatográficas, com atividade antioxidante. Por causa disto e de um aumento na atividade antioxidante dos componentes que não eluíram da coluna cromatográfica de fase reversa da HPLC, a capacidade antioxidante da bebida preparada de grãos de café medianamente torrados foi o dobro daquela de grãos não torrados, verdes. Portanto, a atividade antioxidante de cafés que tenham sofrido diferentes graus de torração parece ser devido a combinações de diferentes componentes. O efeito da torração sobre os ácidos clorogênicos nas sementes de café é discutido, assim como as ...

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Section: Discussionmentioning

confidence: 99%

On-line HPLC analysis of the antioxidant activity of phenolic compounds in brewed, paper-filtered coffee

Stalmach

Mullen

Nagai

et al. 2006

Braz. J. Plant Physiol.

102

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“…Early in roasting when there is still adequate water content, isomerization (acyl migration) occurs accompanied by some hydrolysis releasing the cinnamic acids and quinic acid. Later in roasting the free quinic acid epimerizes and lactonizes, and several chlorogenic lactones including caffeoyl quinides (Figure 7.62), also form (Scholz and Maier 1990;Bennat et al 1994;Schrader et al 1996;Farah et al 2005). The cinnamic acids may be decarboxylated and transformed to a number of simple phenols and range of phenylindans probably via decarboxylation and cyclization of the vinylcatechol intermediate (Stadler et al 1996).…”

Section: Coffeementioning

confidence: 99%

Secondary Metabolites in Fruits, Vegetables, Beverages and Other Plant‐based Dietary Components

Crozier¹,

Yokota²,

Jaganath³

et al. 2006

Plant Secondary Metabolites

113

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“…Because elimination of a water molecule from the six-membered ring of the quinic acid requires a syn-1,3-diaxial configuration of the hydroxyl and carboxyl groups, only those isomers that lack a cinnamoyl substituent in the 5-position of the quinic acid are able to form a 1,5-quinide. As a result, the most abundant quinides in roasted coffee are 3-caffeoyl-1,5-quinide (3-CQL), 4-caffeoyl-1,5-quinide (4-CQL), each present in less than 0.3% dry weight of the beans (Bennat et al 1994;Schrader et al 1996), and 3,4-dicaffeoyl-1,5-quinide (DICAQ). Because neither DIFEQ nor DICOQ are present in detectable amounts in roasted coffee, they should be regarded as model compounds of their close structural analog, DICAQ.…”

Section: Discussionmentioning

confidence: 99%

“…However, the feruloyl-1,5-quinides constituted 0.48% in the extract (Table 1) and therefore representing only approximately 0.05% in the original instant coffee. The more abundant caffeoyl derivatives 3-CQL and 4-CQL in roasted coffee (Bennat et al 1994;Schrader et al 1996) constituted 2.2% in the extract. A possible explanation why Boublik's study did not recognize the presence of 4-CQL in instant coffee is that they used silica gel for the purification (Wynne et al 1987).…”

Section: Discussionmentioning

confidence: 99%

4-Caffeoyl-1,5-quinide in roasted coffee inhibits [3H]naloxone binding and reverses anti-nociceptive effects of morphine in mice

et al. 2004

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HPLC Analysis of chlorogenic acid lactones in roasted coffee

Cited by 47 publications

References 6 publications

On-line HPLC analysis of the antioxidant activity of phenolic compounds in brewed, paper-filtered coffee

On-line HPLC analysis of the antioxidant activity of phenolic compounds in brewed, paper-filtered coffee

Secondary Metabolites in Fruits, Vegetables, Beverages and Other Plant‐based Dietary Components

4-Caffeoyl-1,5-quinide in roasted coffee inhibits [3H]naloxone binding and reverses anti-nociceptive effects of morphine in mice

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