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Cyclization of xanthohumol as a strategy for its gas chromatographic analysis.

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Τίτλος: Cyclization of xanthohumol as a strategy for its gas chromatographic analysis.
Συγγραφείς: Typek R; Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie Sklodowska University in Lublin, 20-031 Lublin, Poland., Dybowski MP; Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie Sklodowska University in Lublin, 20-031 Lublin, Poland., Dawidowicz AL; Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie Sklodowska University in Lublin, 20-031 Lublin, Poland. Electronic address: andrzej.dawidowicz@mail.umcs.pl., Holowinski P; Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie Sklodowska University in Lublin, 20-031 Lublin, Poland.
Πηγή: Food chemistry [Food Chem] 2026 Aug 15; Vol. 520, pp. 149882. Date of Electronic Publication: 2026 May 30.
Τύπος έκδοσης: Journal Article; Evaluation Study
Γλώσσα: English
Στοιχεία περιοδικού: Publisher: Elsevier Applied Science Publishers Country of Publication: England NLM ID: 7702639 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-7072 (Electronic) Linking ISSN: 03088146 NLM ISO Abbreviation: Food Chem Subsets: MEDLINE
Imprint Name(s): Publication: Barking : Elsevier Applied Science Publishers
Original Publication: Barking, Eng., Applied Science Publishers.
Ιατρικοί όροι (MeSH): Propiophenones*/chemistry , Flavonoids*/chemistry , Humulus*/chemistry , Plant Extracts*/chemistry, Chromatography, Gas/methods ; Beer/analysis ; Cyclization ; Molecular Structure
Περίληψη: Xanthohumol is a prenylated flavonoid present in female hop inflorescences, attracting scientific interest due to its diverse bioactive properties. Its high boiling point (576.5 °C) renders liquid chromatography the primary analytical technique for its determination in various matrices. This study is the first to demonstrate that xanthohumol can be successfully analyzed by gas chromatography after conversion to its cyclic pyran form via intramolecular addition of the phenolic OH group to the -C=C- bond. Experimental results indicate that BF₃·Et₂O is the most effective catalyst, enabling nearly complete transformation of xanthohumol into its pyran derivative. The developed method was validated, showing excellent linearity (R2 ≥ 0.985), precision (< 6%), accuracy (> 95%), and low detection limits (< 0.13 μg/mL). Its applicability was confirmed through analyses of beer, dietary supplements, hop cones, and plasma samples containing xanthohumol. The described procedure can also be used for GC analysis of isoxanthohumol in the same matrices.
(Copyright © 2026 The Authors. Published by Elsevier Ltd.. All rights reserved.)
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Contributed Indexing: Keywords: Food and plant analysis; Pharmaceutical analysis; Xanthohumol; Xanthohumol GC–MS analysis; Xanthohumol cyclization; iso- xanthohumol
Substance Nomenclature: T4467YT1NT (xanthohumol)
0 (Propiophenones)
0 (Flavonoids)
0 (Plant Extracts)
Entry Date(s): Date Created: 20260601 Date Completed: 20260613 Latest Revision: 20260613
Update Code: 20260613
DOI: 10.1016/j.foodchem.2026.149882
PMID: 42225031
Βάση Δεδομένων: MEDLINE
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  Data: Cyclization of xanthohumol as a strategy for its gas chromatographic analysis.
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  Data: &lt;searchLink fieldCode=&quot;AU&quot; term=&quot;%22Typek+R%22&quot;&gt;Typek R&lt;/searchLink&gt;; Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie Sklodowska University in Lublin, 20-031 Lublin, Poland.&lt;br /&gt;&lt;searchLink fieldCode=&quot;AU&quot; term=&quot;%22Dybowski+MP%22&quot;&gt;Dybowski MP&lt;/searchLink&gt;; Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie Sklodowska University in Lublin, 20-031 Lublin, Poland.&lt;br /&gt;&lt;searchLink fieldCode=&quot;AU&quot; term=&quot;%22Dawidowicz+AL%22&quot;&gt;Dawidowicz AL&lt;/searchLink&gt;; Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie Sklodowska University in Lublin, 20-031 Lublin, Poland. Electronic address: andrzej.dawidowicz@mail.umcs.pl.&lt;br /&gt;&lt;searchLink fieldCode=&quot;AU&quot; term=&quot;%22Holowinski+P%22&quot;&gt;Holowinski P&lt;/searchLink&gt;; Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie Sklodowska University in Lublin, 20-031 Lublin, Poland.
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  Data: &lt;searchLink fieldCode=&quot;JN&quot; term=&quot;%227702639%22&quot;&gt;Food chemistry&lt;/searchLink&gt; [Food Chem] 2026 Aug 15; Vol. 520, pp. 149882. &lt;i&gt;Date of Electronic Publication: &lt;/i&gt;2026 May 30.
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  Data: &lt;searchLink fieldCode=&quot;MM&quot; term=&quot;%22Propiophenones%22&quot;&gt;Propiophenones*&lt;/searchLink&gt;/&lt;searchLink fieldCode=&quot;MM&quot; term=&quot;%22Propiophenones+chemistry%22&quot;&gt;chemistry&lt;/searchLink&gt; &lt;br /&gt;&lt;searchLink fieldCode=&quot;MM&quot; term=&quot;%22Flavonoids%22&quot;&gt;Flavonoids*&lt;/searchLink&gt;/&lt;searchLink fieldCode=&quot;MM&quot; term=&quot;%22Flavonoids+chemistry%22&quot;&gt;chemistry&lt;/searchLink&gt; &lt;br /&gt;&lt;searchLink fieldCode=&quot;MM&quot; term=&quot;%22Humulus%22&quot;&gt;Humulus*&lt;/searchLink&gt;/&lt;searchLink fieldCode=&quot;MM&quot; term=&quot;%22Humulus+chemistry%22&quot;&gt;chemistry&lt;/searchLink&gt; &lt;br /&gt;&lt;searchLink fieldCode=&quot;MM&quot; term=&quot;%22Plant+Extracts%22&quot;&gt;Plant Extracts*&lt;/searchLink&gt;/&lt;searchLink fieldCode=&quot;MM&quot; term=&quot;%22Plant+Extracts+chemistry%22&quot;&gt;chemistry&lt;/searchLink&gt;&lt;br /&gt;&lt;searchLink fieldCode=&quot;MH&quot; term=&quot;%22Chromatography%2C+Gas%22&quot;&gt;Chromatography, Gas&lt;/searchLink&gt;/&lt;searchLink fieldCode=&quot;MH&quot; term=&quot;%22Chromatography%2C+Gas+methods%22&quot;&gt;methods&lt;/searchLink&gt; ; &lt;searchLink fieldCode=&quot;MH&quot; term=&quot;%22Beer%22&quot;&gt;Beer&lt;/searchLink&gt;/&lt;searchLink fieldCode=&quot;MH&quot; term=&quot;%22Beer+analysis%22&quot;&gt;analysis&lt;/searchLink&gt; ; &lt;searchLink fieldCode=&quot;MH&quot; term=&quot;%22Cyclization%22&quot;&gt;Cyclization&lt;/searchLink&gt; ; &lt;searchLink fieldCode=&quot;MH&quot; term=&quot;%22Molecular+Structure%22&quot;&gt;Molecular Structure&lt;/searchLink&gt;
– Name: Abstract
  Label: Abstract
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  Data: Xanthohumol is a prenylated flavonoid present in female hop inflorescences, attracting scientific interest due to its diverse bioactive properties. Its high boiling point (576.5&#160;&#176;C) renders liquid chromatography the primary analytical technique for its determination in various matrices. This study is the first to demonstrate that xanthohumol can be successfully analyzed by gas chromatography after conversion to its cyclic pyran form via intramolecular addition of the phenolic OH group to the -C=C- bond. Experimental results indicate that BF₃&#183;Et₂O is the most effective catalyst, enabling nearly complete transformation of xanthohumol into its pyran derivative. The developed method was validated, showing excellent linearity (R&lt;superscript&gt;2&lt;/superscript&gt;&#160;≥&#160;0.985), precision (&amp;lt; 6%), accuracy (&gt; 95%), and low detection limits (&amp;lt; 0.13&#160;μg/mL). Its applicability was confirmed through analyses of beer, dietary supplements, hop cones, and plasma samples containing xanthohumol. The described procedure can also be used for GC analysis of isoxanthohumol in the same matrices.&lt;br /&gt; (Copyright &#169; 2026 The Authors. Published by Elsevier Ltd.. All rights reserved.)
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  Data: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
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  Label: Substance Nomenclature
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  Data: T4467YT1NT (xanthohumol)&lt;br /&gt;0 (Propiophenones)&lt;br /&gt;0 (Flavonoids)&lt;br /&gt;0 (Plant Extracts)
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      – SubjectFull: Beer analysis
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      – SubjectFull: Cyclization
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