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

  title={4-Caffeoyl-1,5-quinide in roasted coffee inhibits [3H]naloxone binding and reverses anti-nociceptive effects of morphine in mice},
  author={Tomas de Paulis and Patricia A. Commers and Adriana Farah and Jiali Zhao and Michael P. McDonald and Ruggero Galici and Peter R. Martin},
RationaleCinnamoylquinides are formed from the corresponding chlorogenic acids during coffee roasting. Instant coffee has been shown to displace binding of the mu opioid receptor antagonist, [3H]naloxone, but the putative active agent, feruloylquinide, has not been characterized.ObjectivesThe goal was to identify the active agent(s) in coffee by measuring the binding affinity of individual cinnamoyl-1,5-quinides to the human mu opioid receptor, and determine the effects of these compounds on… 

Effect of roasting on the formation of chlorogenic acid lactones in coffee.

The levels of lactones in roasted coffee do not reflect the levels of precursors in green coffee, suggesting that roasting causes isomerization of chlorogenic acids prior to the formation of lactone levels.

A new method for the preparative isolation of chlorogenic acid lactones from coffee and model roasts of 5-caffeoylquinic acid.

An UHPLC method was developed that enabled the separation of the lactones from roasted coffee in significantly shorter time than conventional HPLC.

Investigação de novos ácidos clorogênicos e lactomas em café brasileiro verde e torrado.

Coffee is the most consumed beverage in the world and a significant source of phenolic compounds, particularly chlorogenic acids (CGA). During coffee roasting, some CGA are partially transformed into

Chlorogenic acids and lactones in regular and water-decaffeinated arabica coffees.

Differences in CGA and CGL contents of regular and decaffeinated roasted coffees appear to be relatively small, but they may be enough to affect flavor characteristics as well as the biopharmacological properties of the final beverage, suggesting the need for further study.

Bioavailability and metabolism of chlorogenic acids (acyl-quinic acids) in humans.

There is a critical need for precise urinary biomarkers of consumption of acyl-quinic acids, accounting for variability in individual metabolism and in beverage composition, thus facilitating better translation of urinary metabolite measurements into accurate coffee consumption data to improve the outcomes of future epidemiological and intervention studies.

Contents of key bioactive and detrimental compounds in health performance coffees compared to conventional types of coffees sold in the United States market.

Most health claims on labels related to the amount of bioactive compounds in health performance coffees were unjustified, suggesting the need for improvement in coffee labeling regulation in the U.S. market.

Quantitative analysis of plasma caffeic and ferulic acid equivalents by liquid chromatography tandem mass spectrometry.

  • P. GuyM. Renouf H. Steiling
  • Chemistry, Biology
    Journal of chromatography. B, Analytical technologies in the biomedical and life sciences
  • 2009



Coffee contains potent opiate receptor binding activity

It is reported here that instant coffee powders from a variety of manufacturers compete with tiitiated naloxone for binding to opiate receptors in the rat brain membrane preparations, with no significant difference between normal and decaffeinated coffee.

Determination of Chlorogenic Acids with Lactones in Roasted Coffee

An HPLC method has been developed which allowed the determination of mono- and dicaffeoylquinic acids (CQA and di-CQA), corresponding lactones (CQL) and feruloylquinic acids (FQA) in roasted coffee

Antinociceptive activity of a novel buprenorphine analogue.

HPLC Analysis of chlorogenic acid lactones in roasted coffee

ZusammenfassungEs wird die Identifizierung von 3- und 4-Caffeoyl-γ-chinid (CQL) in Röstkaffee beschrieben. Die Lactone wurden mit Hilfe eines isokratischen RP-HPLC-Systems und Dioden-Array-Detektion

Failure of coffee to inhibit the pharmacodynamic activity of morphine in vivo

Caffeine-containing as well as decaffeinated instant coffee neither inhibited morphine-induced analgesia in mice nor the morphine- induced fall of blood pressure, heart rate and respiratory rate in rats, indicating that coffee does not exhibit opiate-antagonizing activity in the whole organism in vivo.