Cyclization of xanthohumol as a strategy for its gas chromatographic analysis

Area of Science:

• Analytical Chemistry
• Natural Product Analysis
• Chromatography

Background:

• Xanthohumol, a prenylated flavonoid from hops, possesses significant bioactive properties.
• Its high boiling point necessitates specialized analytical methods, with liquid chromatography being standard.
• Existing methods for xanthohumol determination face limitations in certain applications.

Purpose of the Study:

• To develop and validate a novel gas chromatography (GC) method for xanthohumol analysis.
• To enable accurate quantification of xanthohumol in various complex matrices.
• To explore a new derivatization pathway for GC analysis of hop compounds.

Main Methods:

• Xanthohumol was converted to its cyclic pyran derivative via intramolecular cyclization.
• Boron trifluoride etherate (BF₃·Et₂O) was employed as the catalyst for derivatization.
• The pyran derivative was analyzed using gas chromatography (GC).

Main Results:

• The developed GC method demonstrated excellent linearity (R² ≥ 0.985), precision (<6%), and accuracy (>95%).
• Low detection limits (<0.13 μg/mL) were achieved for xanthohumol quantification.
• The method was successfully applied to analyze xanthohumol in beer, dietary supplements, hop cones, and plasma.

Conclusions:

• This study presents the first successful GC analysis of xanthohumol via its pyran derivative.
• The developed method offers a sensitive and accurate alternative for xanthohumol determination.
• The procedure is also applicable for the GC analysis of isoxanthohumol in similar matrices.