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Open AccessArticle

Identification of Ubiquinones in Honey: A New View on Their Potential Contribution to Honey’s Antioxidant State

1
Department Drug Discovery and Development, Bee-Biomedicals Inc., St. Catharines, ON L2S 3A1, Canada
2
Department of Biochemistry, McMaster University, Hamilton, ON L8S 4L8, Canada
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(12), 3067; https://doi.org/10.3390/molecules23123067
Received: 12 November 2018 / Revised: 21 November 2018 / Accepted: 21 November 2018 / Published: 23 November 2018
(This article belongs to the Special Issue Biological Activities of Honeybee Products)
Honey is composed of macromolecules arranged into multicomponent colloidal particles dispersed in a supersaturated sugar solution. The core part of colloidal particles in honey is made up of high-molecular weight protein-polyphenol complexes. We designed a multi-step extraction process to gain better insight into the phenolic compounds strongly bound to proteins in honey. Honeys were sequentially extracted by solvents of reduced polarities and the extraction process was monitored by LC-ESI-MS/MS. Unexpectedly, the results revealed ubiquinone-like compounds that partitioned to both, soluble supernatants and protein-bound insoluble residues from which they were released after the pronase-digestion of proteins. The accurate mass measurement and MS/MS fragmentation patterns using UPHLC-MS/MS coupled to quadrupole orbitrap confirmed their identification as ubiquinones. Distribution of ubiquinone-bound proteins was further investigated by the fractionation of honey protein-polyphenol complexes by size-exclusion chromatography followed by LC-ESI-MS analysis. Mass spectra revealed the presence of ubiquinones (UQs) in fractions of high polyphenol to protein ratio. The dominant mass peaks observed in these fractions were identified as UQ-3, UQ-5, and UQ-7. Since the quinone group of UQs is involved in redox reaction, we discuss the possibility that UQs may contribute to the antioxidant/proxidant activity of these complexes. View Full-Text
Keywords: ubiquinone; honey; LC-ESI-MS; UPHLC-ESI-MS/MS; protein-polyphenol complexes ubiquinone; honey; LC-ESI-MS; UPHLC-ESI-MS/MS; protein-polyphenol complexes
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Brudzynski, K.; Maldonado-Alvarez, L. Identification of Ubiquinones in Honey: A New View on Their Potential Contribution to Honey’s Antioxidant State. Molecules 2018, 23, 3067.

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