Structural elucidation of the ellagitannin with a molecular weight of 2038 isolated from strawberry fruit (Fragaria ananassa Duch.) and named fragariin A

Elżbieta Karlińska; Łukasz Pecio; Jakub Macierzyński; Anna Stochmal; Monika Kosmala

doi:10.1016/j.foodchem.2019.05.191

Structural elucidation of the ellagitannin with a molecular weight of 2038 isolated from strawberry fruit (Fragaria ananassa Duch.) and named fragariin A

Food Chem. 2019 Oct 30:296:109-115. doi: 10.1016/j.foodchem.2019.05.191. Epub 2019 May 29.

Authors

Elżbieta Karlińska¹, Łukasz Pecio², Jakub Macierzyński³, Anna Stochmal⁴, Monika Kosmala⁵

Affiliations

¹ Institute of Food Technology and Analysis, Lodz University of Technology, Stefanowskiego 4/10, 90-924 Łódź, Poland. Electronic address: elzbieta.karlinska@p.lodz.pl.
² Institute of Soil Science and Plant Cultivation, State Research Institute, Department of Biochemistry and Crop Quality, Czartoryskich 8, 24-100 Puławy, Poland. Electronic address: l.pecio@iung.pulawy.pl.
³ Research Institute of Horticulture, Konstytucji 3 Maja 1/3, 96-100 Skierniewice, Poland. Electronic address: jakub.macierzynski@inhort.pl.
⁴ Institute of Soil Science and Plant Cultivation, State Research Institute, Department of Biochemistry and Crop Quality, Czartoryskich 8, 24-100 Puławy, Poland. Electronic address: asf@iung.pulawy.pl.
⁵ Institute of Food Technology and Analysis, Lodz University of Technology, Stefanowskiego 4/10, 90-924 Łódź, Poland. Electronic address: monika.kosmala@p.lodz.pl.

PMID: 31202294
DOI: 10.1016/j.foodchem.2019.05.191

Abstract

The structure of the ellagitannin (ET) with a molecular weight (MW) of 2038 isolated from strawberry fruit was elucidated on the basis of mass spectrometry data and nuclear magnetic resonance studies, with the newly determined compound being named fragariin A. Similarly to the main strawberry ET, agrimoniin (MW 1870), fragariin A was shown to contain a bis-HHDP-glucose moiety (MW 784). It exhibited the same three fragmentation ions with m/z 1567, 1265 and 633, arising from the detachment of consecutive hexahydroxydiphenoyl (HHDP) units from the structure with MW 1870. Based on spectroscopic studies, it was found that, in the tested ET (MW 2038), a free gallic acid is connected by a DOG-type bond to the 4,6-HHDP unit of the second glucose moiety of agrimoniin.

Keywords: Agrimoniin; Ellagitannins; Fragariin A; Molecular weight; NMR; Strawberry.

MeSH terms

Chromatography, High Pressure Liquid
Fragaria / chemistry*
Fragaria / metabolism
Fruit / chemistry
Fruit / metabolism
Hydrolyzable Tannins / chemistry*
Hydrolyzable Tannins / isolation & purification
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Conformation
Molecular Weight
Plant Extracts / chemistry

Substances

Hydrolyzable Tannins
Plant Extracts
ellagitannin