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4-Caffeoyl-1,5-quinide in roasted coffee inhibits [3H]naloxone binding and reverses anti-nociceptive effects of morphine in mice.
Psychopharmacology (Berl). 2004 Nov; 176(2):146-53.P

Abstract

RATIONALE

Cinnamoylquinides 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.

OBJECTIVES

The 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 morphine-induced anti-nociceptive behavior in mice.

METHODS

Cinnamoyl-1,5-quinides in extracts of decaffeinated instant coffee were quantified by reverse-phase HPLC comparisons with synthetic samples of 3-coumaroyl-1,5-quinide and 4-coumaroyl-1,5-quinide, 3-caffeoyl-1,5-quinide and 4-caffeoyl-1,5-quinide (4-CQL) 3-feruloyl-1,5-quinide and 4-feruloyl-1,5-quinides and 3,4-dicaffeoyl-1,5-quinide (DICAQ). Affinities of the cinnamoyl-1,5-quinides and decaffeinated instant coffee extract were determined by displacement of [3H]naloxone binding in cultured HEK-MOR cells. Inhibition of the anti-nociceptive activity of morphine (1 mg/kg IP) was determined in C57BL/6J mice using the hot plate test at 52 degrees C.

RESULTS

Extract of decaffeinated instant coffee produced a displacement K(i) of 42+/-16 mg/l, while the K(i) of a synthetic sample of 4-CQL was 4.4+/-0.4 microM. Compounds with a cinnamoyl substituent in the 4-position of the quinide, i.e. 4-CQL, DICAQ, 3,4-diferuloyl-1,5-quinide, and 3,4-dicoumaroyl-1,5-quinide, had affinities for the mu opioid receptor in the low micromolar range. In the hot plate test, coffee extract, containing 0.78% of 4-CQL, reversed the anti-nociceptive effect of morphine at 10 mg/kg IP. Two cinnamoyl-1,5-quinides found in roasted coffee, DICAQ, and 4-CQL, were active at 1 and 0.1 mg/kg IP, respectively.

CONCLUSIONS

These results suggest that the previously reported anti-opioid activity of instant coffee is caused primarily by the presence of 4-CQL, and to lesser extent by other cinnamoyl-1,5-quinides.

Authors+Show Affiliations

de Paulis T
Department of Psychiatry, Vanderbilt Institute for Coffee Studies, Vanderbilt University School of Medicine, MCN AA-2213, Nashville, TN 37232, USA. tomas.depaulis@vanderbilt.edu
Commers P
No affiliation info available
Farah A
No affiliation info available
Zhao J
No affiliation info available
McDonald MP
No affiliation info available
Galici R
No affiliation info available
Martin PR
No affiliation info available

MeSH

Analgesics, OpioidAnimalsBinding, CompetitiveCell LineCoffeeDose-Response Relationship, DrugHumansMiceMice, Inbred C57BLMorphineNaloxonePain MeasurementProtein BindingQuinic AcidReceptors, Opioid, muTritium

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15088081

Citation

de Paulis, Tomas, et al. "4-Caffeoyl-1,5-quinide in Roasted Coffee Inhibits [3H]naloxone Binding and Reverses Anti-nociceptive Effects of Morphine in Mice." Psychopharmacology, vol. 176, no. 2, 2004, pp. 146-53.
de Paulis T, Commers P, Farah A, et al. 4-Caffeoyl-1,5-quinide in roasted coffee inhibits [3H]naloxone binding and reverses anti-nociceptive effects of morphine in mice. Psychopharmacology (Berl). 2004;176(2):146-53.
de Paulis, T., Commers, P., Farah, A., Zhao, J., McDonald, M. P., Galici, R., & Martin, P. R. (2004). 4-Caffeoyl-1,5-quinide in roasted coffee inhibits [3H]naloxone binding and reverses anti-nociceptive effects of morphine in mice. Psychopharmacology, 176(2), 146-53.
de Paulis T, et al. 4-Caffeoyl-1,5-quinide in Roasted Coffee Inhibits [3H]naloxone Binding and Reverses Anti-nociceptive Effects of Morphine in Mice. Psychopharmacology (Berl). 2004;176(2):146-53. PubMed PMID: 15088081.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 4-Caffeoyl-1,5-quinide in roasted coffee inhibits [3H]naloxone binding and reverses anti-nociceptive effects of morphine in mice. AU - de Paulis,Tomas, AU - Commers,Patricia, AU - Farah,Adriana, AU - Zhao,Jiali, AU - McDonald,Michael P, AU - Galici,Ruggero, AU - Martin,Peter R, Y1 - 2004/04/16/ PY - 2003/09/30/received PY - 2004/03/10/accepted PY - 2004/4/17/pubmed PY - 2005/2/18/medline PY - 2004/4/17/entrez SP - 146 EP - 53 JF - Psychopharmacology JO - Psychopharmacology (Berl) VL - 176 IS - 2 N2 - RATIONALE: Cinnamoylquinides 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. OBJECTIVES: The 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 morphine-induced anti-nociceptive behavior in mice. METHODS: Cinnamoyl-1,5-quinides in extracts of decaffeinated instant coffee were quantified by reverse-phase HPLC comparisons with synthetic samples of 3-coumaroyl-1,5-quinide and 4-coumaroyl-1,5-quinide, 3-caffeoyl-1,5-quinide and 4-caffeoyl-1,5-quinide (4-CQL) 3-feruloyl-1,5-quinide and 4-feruloyl-1,5-quinides and 3,4-dicaffeoyl-1,5-quinide (DICAQ). Affinities of the cinnamoyl-1,5-quinides and decaffeinated instant coffee extract were determined by displacement of [3H]naloxone binding in cultured HEK-MOR cells. Inhibition of the anti-nociceptive activity of morphine (1 mg/kg IP) was determined in C57BL/6J mice using the hot plate test at 52 degrees C. RESULTS: Extract of decaffeinated instant coffee produced a displacement K(i) of 42+/-16 mg/l, while the K(i) of a synthetic sample of 4-CQL was 4.4+/-0.4 microM. Compounds with a cinnamoyl substituent in the 4-position of the quinide, i.e. 4-CQL, DICAQ, 3,4-diferuloyl-1,5-quinide, and 3,4-dicoumaroyl-1,5-quinide, had affinities for the mu opioid receptor in the low micromolar range. In the hot plate test, coffee extract, containing 0.78% of 4-CQL, reversed the anti-nociceptive effect of morphine at 10 mg/kg IP. Two cinnamoyl-1,5-quinides found in roasted coffee, DICAQ, and 4-CQL, were active at 1 and 0.1 mg/kg IP, respectively. CONCLUSIONS: These results suggest that the previously reported anti-opioid activity of instant coffee is caused primarily by the presence of 4-CQL, and to lesser extent by other cinnamoyl-1,5-quinides. SN - 0033-3158 UR - https://www.unboundmedicine.com/medline/citation/15088081/4_Caffeoyl_15_quinide_in_roasted_coffee_inhibits_[3H]naloxone_binding_and_reverses_anti_nociceptive_effects_of_morphine_in_mice_ DB - PRIME DP - Unbound Medicine ER -