Identification and quantification of flavonoids and phenolic acids in burr parsley (Caucalis platycarpos L.), using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry.

Ana Plazonić,Nikola Kujundzić,Biljana Nigović,Ana Mornar,Franz Bucar,Zeljan Males

doi:10.3390/molecules14072466

Abstract

A sensitive method coupling high-performance liquid chromatography (HPLC) with diode-array detector (DAD) and electrospray ionization mass spectrometry (MS) was optimized for the separation and identification of phenolic acids, flavonoid glycosides and flavonoid aglycones in the extract of burr parsley (Caucalis platycarpos L.). Fragmentation behavior of flavonoid glycosides and phenolic acids were investigated using ion trap mass spectrometry in negative electrospray ionization. The MS, MSn and UV data together with HPLC retention time (TR) of phenolic acids and flavonoids allowed structural characterization of these compounds. Caffeoylquinic acid (CQA) isomers, p-coumaroyl-quinic acids (p-CoQA), feruloylquinic acids (FQA), dicaffeoylquinic acids (diCQA), luteolin-7-O-rutinoside, apigenin-7-O-rutinoside as well as isolated chrysoeriol-7-O-rutinoside have been identified as constituents of C. platycarpos for the first time. An accurate, precise and sensitive LC-DAD method for quantification of four phenolic acids (3-O-caffeoylquinic, caffeic, p-coumaric, o-coumaric acid), four flavonoid glycosides (luteolin-7-O-glucoside, apigenin-7-O-glucoside, quercetin-3-O-galactoside, quercetin-3-O-rhamnoside), and three flavonoid aglycones (luteolin, apigenin, chrysoeriol) in C. platycarpos extract was validated in terms of linearity, limit of detection, limit of quantification, precision and accuracy. 3-O-caffeoylquinic acid was the predominant phenolic acid and luteolin-7-O-glucoside was the predominant flavonoid glycoside.

Highlights

Due to their high frequency and mortality malignant diseases are currently one of the main issues in medicine
Caffeoylquinic acid (CQA) isomers, p-coumaroylquinic acids (p-CoQA), feruloylquinic acids (FQA), dicaffeoylquinic acids, luteolin-7-O-rutinoside, apigenin-7-O-rutinoside as well as isolated chrysoeriol-7-Orutinoside have been identified as constituents of C. platycarpos for the first time
The purpose of this research was to identify phenolic compounds, quantify main flavonoids and phenolic acids and to isolate a flavonoid glycoside that was found to be characteristic for C

Summary

Introduction

Due to their high frequency and mortality malignant diseases are currently one of the main issues in medicine. A lot of attention is given to natural compounds because they can interfere with tumor growth. Burr parsley (Caucalis platycarpos L., Caucalis daucoides L.), an annual plant growing on clayish lime-containing soils in the Mediterranean and Central Europe, has been used in folk medicine for the treatment of certain types of tumor. Water extracts of the aboveground parts of this plant showed a remarkable antitumor activity in rats and mice. It is probable that antitumor activity is a consequence of stimulation of the immunological system of the host. C. platycarpos water extract showed activation of T-lymphocytes and NK cells and stimulated the spleen as a lymphatic organ, to produce antitumor factors [1]. Phenolic compounds, including phenolic acids and flavonoids, and polysaccharides are considered to be the major bioactive compounds in C. platycarpos [2]

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