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Lumichrome and Phenyllactic Acid as Chemical Markers of Thistle (Galactites tomentosa Moench) Honey

Tuberoso, Carlo I.G., Bifulco, Ersilia, Caboni, Pierluigi, Sarais, Giorgia, Cottiglia, Filippo, Floris, Ignazio
Journal of agricultural and food chemistry 2011 v.59 no.1 pp. 364–369
phenyllactic acid, biomarkers, honey, food analysis, food composition, product authenticity, Asteraceae, chemical compounds, provenance, sensory properties
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.