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Lumichrome and phenyllactic acid as chemical markers of thistle (Galactites tomentosa Moench) honey

Tuberoso, Carlo I. G. and Bifulco, Ersilia and Caboni, Pierluigi and Sarais, Giorgia and Cottiglia, Filippo and Floris, Ignazio (2010) Lumichrome and phenyllactic acid as chemical markers of thistle (Galactites tomentosa Moench) honey. Journal of Agricultural and Food Chemistry, Vol. 59 (1), p. 364-369. eISSN 1520-5118. Article.

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DOI: 10.1021/jf1039074

Abstract

HPLC-DAD-MS/MS chromatograms of thistle (Galactites tomentosa Moench) unifloral honeys, previously selected by sensory evaluation and melissopalynological analysis, showed high levels of two compounds. One was characterized as phenyllactic acid, a common acid found in honeys, but the other compound was very unusual for honeys. This compound was extracted from honey with ethyl acetate and purified by SPE using C18, SiOH, and NH2 phases. Its structure was elucidated on the basis of extensive 1D and 2D NMR experiments as well as HPLC-MS/MS and Q-TOF analysis, and it was identified as lumichrome (7,8-dimethylalloxazine). Lumichrome is known to be the main product of degradation obtained in acid medium from riboflavin (vitamin B2), and this is the first report of the presence of lumichrome in honeys. Analysis of the G. tomentosa raw honey and flowers extracts confirmed the floral origin of this compound. The average amount of lumichrome in thistle honey was 29.4 ± 14.9 mg/kg, while phenyllactic acid was 418.6 ± 168.9 mg/kg. Lumichrome, along with the unusual high level of phenyllactic acid, could be used as a marker for the botanical classification of unifloral thistle (G. tomentosa) honey.

Item Type:Article
ID Code:5782
Status:Published
Refereed:Yes
Uncontrolled Keywords:Lumichrome, Galactites tomentosa Moench, honey, botanical characterization, HPLC-DAD, HPLC-MS/MS, Q-TOF, NMR
Subjects:Area 07 - Scienze agrarie e veterinarie > AGR/11 Entomologia generale e applicata
Divisions:001 Università di Sassari > 01 Dipartimenti > Protezione delle piante
Publisher:American Chemical Society
eISSN:1520-5118
Deposited On:10 May 2011 18:13

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