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Molecules 2016, 21(9), 1157; doi:10.3390/molecules21091157

Identification of Iridoids in Edible Honeysuckle Berries (Lonicera caerulea L. var. kamtschatica Sevast.) by UPLC-ESI-qTOF-MS/MS

1
Department of Fruit and Vegetables and Cereals Technology, Wrocław University of Environmental and Life Science, Chełmońskiego 37, 51-630 Wrocław, Poland
2
Department of Pharmacognosy, Wrocław Medical University, Borowska 211A, 50-556 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 2 August 2016 / Revised: 23 August 2016 / Accepted: 26 August 2016 / Published: 1 September 2016
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Abstract

Iridoid profiles of honeysuckle berry were studied. Compounds were identified by ultra-performance liquid chromatography coupled with electrospray ionization mass spectrometry UPLC-ESI-qTOF-MS/MS in positive and negative ions mode. The MS fragmentation pathways of detected iridoid glycosides were also studied in both modes. In the negative ESI mass spectra, iridoids with a methyl ester or lactone structure have preferentially produced adduct [M + HCOOH − H] ions. However, protonated ions of molecular fragments, which were released by glycosidic bond cleavage and following fragmentation of aglycone rings, were more usable for iridoid structure analysis. In addition, the neutral losses of H2O, CO, CO2, CH3OH, acetylene, ethenone and cyclopropynone have provided data confirming the presence of functional substituents in the aglycone. Among the 13 iridoids, 11 were identified in honeysuckle berries for the first time: pentosides of loganic acid (two isomers), pentosides of loganin (three isomers), pentosyl sweroside, and additionally 7-epi-loganic acid, 7-epi-loganin, sweroside, secologanin, and secoxyloganin. The five pentoside derivatives of loganic acid and loganin have not been previously detected in the analyzed species. Honeysuckle berries are a source of iridoids with different structures, compounds that are rarely present in fruits. View Full-Text
Keywords: iridoids; loganin 7-O-pentoside; epi-isomers; honeysuckle berries; LC-ESI-qTOF-MS/MS; fragmentation pathway iridoids; loganin 7-O-pentoside; epi-isomers; honeysuckle berries; LC-ESI-qTOF-MS/MS; fragmentation pathway
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Kucharska, A.Z.; Fecka, I. Identification of Iridoids in Edible Honeysuckle Berries (Lonicera caerulea L. var. kamtschatica Sevast.) by UPLC-ESI-qTOF-MS/MS. Molecules 2016, 21, 1157.

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