A novel strategy for target profiling analysis of bioactive phenylethanoid glycosides in Plantago medicinal plants using ultra‐performance liquid chromatography coupled with tandem quadrupole mass spectrometry

Abstract

Phenylethanoid glycosides are a group of phenolic compounds with diverse biological activities such as hypotensive, diuretic, and hypoglycemic effects. In this study, a target profiling analysis approach using ultra-performance liquid chromatography coupled with tandem quadrupole mass spectrometry (MS) was established on the basis of parent ion scanning for m/z 161, the characteristic product ion for phenylethanoid glycosides. It was successfully employed to discriminate the chemical composition of phenylethanoid glycosides between Plantaginis Herba and Plantaginis Semen, two medicinal parts of Plantago plants, which are widely used as herbal medicine in China. Totally, 34 phenylethanoid glycosides were characterized and tentatively identified by their retention times, MS, and tandem quadrupole MS (MS/MS) data. Combined with chemometrics analysis of principal component analysis and orthogonal projection to latent structural discriminate analysis, eight of them, especially acteoside and plantamajoside, were picked out and contributed to the chemical distinction between Plantaginis Herba and Plantaginis Semen, which might be responsible for the differences in diuretic and hypotensive effects between the two medicinal parts. This new approach for target profiling provides not only a novel idea for specific analysis of active chemical constituents in the same type, but also a promising and reference method for quality evaluation of traditional Chinese medicines.

Plantamajoside — A current review

“…Other lesser used techniques for detection of plantamajoside are capillary electrophoresis (CE) (Gonda et al, 2013), ultraperformance liquid chromatography (UPLC)-MS/MS (Qi et al, 2012), ultra-performance liquid chromatography (UPLC)-UV (Zhou et al, 2013), high performance centrifugal partition chromatography (HPCPC)-electrospray ionization multi stage tandem mass spectrometry (ESI-MS) the negative ion mode (Li et al, 2008), (HPCPC)-HPLC (Li et al, 2009), spectrophotometry (Murai et al, 2009a), NMR spectroscopy (Rønsted et al, 2000) and liquid chromatography (LC)-combined with mass spectroscopy (MS)/MS .…”

“…With respect to the chemical structure and bioactivity of the of the polyphenolic glycoside compounds, Qi et al (2012) suggested that the difference between verbascoside containing a glucose and a rhamnose, and plantamajoside with two glucose moieties were likely to account for the differences in diuretic or hypotensive effects of extracts of plant drugs as Plantaginis Herba and Plantaginis Semen. In contrast to the antiproliferative activity, the sugar groups may have a certain influence on hypotensive effects (Mølgaard, 1992;Qi et al, 2012).…”

Plantago asiatica L. 车前 (Cheqian, Asiatic Plantain)

“…Acteoside (1), plantamajoside (2), isoacteoside (3), isoplantamajoside (4), desrhamnosylverbascoside, rehmannioside and many others are representative phenylethanoid glycosides isolated from Cheqian [4,5]. Some of them are shown in Fig.…”

Effects of N source concentration and NH 4 + /NO 3 − ratio on phenylethanoid glycoside pattern in tissue cultures of Plantago lanceolata L.: A metabolomics driven full-factorial experiment with LC–ESI–MS 3

“…Putative identification was carried out using detailed study of the fragmentation patterns of the two authentic standards plantamajoside and acteoside, application to the similar PGs, and consulting the scientific literature. Fragmentation patterns of most PGs also present in these samples are described in , Petreska et al, 2011and Qi et al, 2012and Shi et al (2013. For practical reasons and to show the "taxonomy" of the detected molecules and fragments, the abbreviations of the PG subunits (glucose (Glc), caffeic acid (CA), hydroxytyrosol (HT), etc.)…”

“…Chief fragmentation patterns of PGs were evaluated on basis of , Petreska et al, 2011and Qi et al, 2012and Shi et al (2013. Frequently found fragments and neutral loss values were interpreted by literature review and comparison with chief fragmentation routes of our standards (acteoside and plantamajoside).…”