Planta Med 2007; 73(15): 1592-1595
DOI: 10.1055/s-2007-993740
Natural Product Chemistry
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Kynurenic Acid in Honey from Arboreal Plants: MS and NMR Evidence

Giangiacomo Beretta1 , Enrico Caneva2 , Roberto Maffei Facino1
  • 1Istituto di Chimica Farmaceutica e Tossicologica ”Pietro Pratesi”, Faculty of Pharmacy, University of Milan, Milan, Italy
  • 2Ciga - Centro Interdipartimentale Grandi Apparecchiature, University of Milan, Italy
Further Information

Publication History

Received: September 11, 2007 Revised: October 6, 2007

Accepted: October 16, 2007

Publication Date:
12 November 2007 (online)

Abstract

KYNA, a Trp metabolite, shows neuroprotective activity against excitotoxic amino acids by antagonizing the NMDA receptor (glycine, glutamate). Here we report the identification of KYNA by a combination of ESI-MS/MS and 1D- and 2D-NMR analyses in honey varieties of arboreal origin. KYNA are absent in single-flower honeys from herbal flowers. These different distribution patterns might possibly involve an indirect plant defence mechanism against fungal pathogens and herbivorous parasites, ever-present on wild trees. The presence of KYNA in honey may explain its pain-relieving effects reported in the literature. The substance, acting in concert with honey flavonoids (COX-2 inhibitors), by antagonizing the NMDA receptor may contribute to the antinociceptive effect of honey. Moreover, kynureninates, owing to their antimicrobial properties, can favour the successful outcome of wounds and burns.

Abbreviations

CID:collision-induced decomposition

COSY:correlation spectroscopy

COX-2:cyclo-oxygenase-2

DMSO:dimethyl sulfoxide

ESI-MS:electrospray ionisation mass spectrometry

HETCOR:hetero-correlation

HMBC:heteronuclear multiple bond correlation

HMQC:heteronuclear multiple quantum correlation

IL:interleukin

KYNA:kynurenic acid

NMDA:N-methyl-d-aspartic acid

QUIN:quinoline

RP-SPE:reverse-phase solid phase extraction

Trp: tryptophan

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Dr. Giangiacomo Beretta

Istituto di Chimica Farmaceutica e Tossicologica

Faculty of Pharmacy

University of Milan

Viale Abruzzi 42

20131 Milan

Italy

Phone: +39-(02)-503-17519

Fax: +39-(02)-503-17565

Email: giangiacomo.beretta@unimi.it