Investigations into the Phenolic Constituents of Dog's Mercury (<i>Mercurialis perennis</i> L.) by LC‐MS/MS and GC‐MS analyses

Lorenz, Peter; Conrad, Jürgen; Bertrams, Julia; Berger, Melanie; Duckstein, Sarina M.; Meyer, Ulrich; Stintzing, Florian C.

doi:10.1002/pca.1325

Cited by 41 publications

(31 citation statements)

References 29 publications

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“…The system was equipped with slightly polar-fused silica capillary column coated with a 5 % phenyl-containing polydimethylsiloxane stationary phase (30 m×0.25 mm, d f = 0.25 μm HP-5ms; Agilent J&W Columns, Santa Clara, CA, USA). The temperature program was as follows: isothermal hold at 100°C (2 min) and constant raise to 320°C (4°C/min) with a final hold time of 10 min [18]. Transfer line and ion source were set to 250 and 230°C, respectively.…”

Section: Gc-ms Analysesmentioning

confidence: 99%

“…The combined ethyl acetate phase was dried over 1.0 g sodium sulphate, filtered and evaporated to dryness at 30°C in vacuo. Toluene (2×5.0 mL) was used to remove acetic acid [18].…”

Section: Alkaline and Enzymatic Hydrolysis Experimentsmentioning

confidence: 99%

“…Alkaline hydrolysis was performed following a modified procedure according to Lorenz et al [18]. The analytes were re-dissolved in 3.5 mL ddH 2 O and 1.0 mL of 1 M aqueous sodium hydroxide solution, flushed with nitrogen and continuously agitated at 200 rpm for 24 h at room temperature.…”

Section: Alkaline and Enzymatic Hydrolysis Experimentsmentioning

confidence: 99%

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Studies into the phenolic patterns of different tissues of pineapple (Ananas comosus [L.] Merr.) infructescence by HPLC-DAD-ESI-MS n and GC-MS analysis

et al. 2015

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In a comprehensive study, more than 60 phenolic compounds were detected in methanolic extracts from different tissues of pineapple infructescence by high-performance liquid chromatography with diode array detection and electrospray ionisation multiple-stage mass spectrometry (HPLC-DAD-ESI-MS (n) ) as well as by gas chromatography-mass spectrometry (GC-MS). The analytical workflow combining both methods revealed numerous compounds assigned for the first time as pineapple constituents by their mass fragmentations. Pineapple crown tissue was characterised by depsides of p-coumaric and ferulic acid. In contrast, major phenolic compounds in pineapple pulp extracts were assigned to diverse S-p-coumaryl, S-coniferyl and S-sinapyl derivatives of glutathione, N-L-γ-glutamyl-L-cysteine and L-cysteine, which were also identified in the peel. The latter was additionally characterised by elevated concentrations of p-coumaric, ferulic and caffeic acid depsides and glycerides, respectively. Two peel-specific cyanidin hexosides were found. Elevated concentrations of isomeric N,N'-diferuloylspermidines may be a useful tool for the detection of fraudulent peel usage for pineapple juice production. Mass fragmentation pathways of characteristic pineapple constituents are proposed, and their putative biological functions are discussed.

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Section: Gc-ms Analysesmentioning

confidence: 99%

“…The combined ethyl acetate phase was dried over 1.0 g sodium sulphate, filtered and evaporated to dryness at 30°C in vacuo. Toluene (2×5.0 mL) was used to remove acetic acid [18].…”

Section: Alkaline and Enzymatic Hydrolysis Experimentsmentioning

confidence: 99%

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Studies into the phenolic patterns of different tissues of pineapple (Ananas comosus [L.] Merr.) infructescence by HPLC-DAD-ESI-MS n and GC-MS analysis

et al. 2015

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“…In accordance with Clifford et al (2005), the negative ion MS 2 and MS 3 fragmentation patterns of compounds 1-3 allowed their identification as 3-, 5-, and 4-O-CQA (IUPAC numbering system), while compounds 5, 9-11 and 13 were assigned as isomers of DCQA (Table 1). Peaks 4, 6-8, 12 and 14-16 showed a cleavage of two to four caffeoyl [M -H-162] -moieties resulting in m/z 209 fragment (Table 1), indicating the presence of glucaric acid or galactaric acid, the so-called aldaric acids (Ruiz et al 2013;Lorentz et al 2012). However, up to now, only the presence of hydroxycinnamic acid glucarates has been reported (Maas et al 2009;Lorentz et al 2012;Ruiz et al 2014).…”

Section: Resultsmentioning

confidence: 96%

“…Peaks 4, 6-8, 12 and 14-16 showed a cleavage of two to four caffeoyl [M -H-162] -moieties resulting in m/z 209 fragment (Table 1), indicating the presence of glucaric acid or galactaric acid, the so-called aldaric acids (Ruiz et al 2013;Lorentz et al 2012). However, up to now, only the presence of hydroxycinnamic acid glucarates has been reported (Maas et al 2009;Lorentz et al 2012;Ruiz et al 2014). The presence of this rare type of compounds was not reported in Inula sp.…”

Section: Resultsmentioning

confidence: 96%

Hydroxycinnamates from elecampane (Inula helenium L.) callus culture

2016

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Hydroalcoholic extract from Inula helenium callus tissue showed remarkable reducing capacity. An HPLC/DAD analysis revealed the presence of numerous hydroxycinnamic acid derivatives, including chlorogenic acid (5-O-CQA, 0.1 % dry weight) and 3,5-dicaffeoylquinic acid (3,5-DCQA, 0.3 % dry weight), which were among major constituents of the examined extract. Application of a hyphenated chromatographic method-UHPLC/DAD/MS n -allowed identification of sixteen compounds, derivatives of caffeic acid. Apart from the compounds commonly found in Inula sp., the plant material contained eight conjugates of caffeic acid with aldaric acid. The aldarates constituted over 50 % of the hydroxycinnamate fraction in the examined tissue. This is the first report on the occurrence of the caffeoylaldaric acids in Inula sp. and in a plant tissue culture.

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An Approach to the Chemotaxonomic Differentiation of Two European Dog's Mercury Species: Mercurialis annua L. and M. perennis L.

Lorenz

Duckstein

Conrad

et al. 2012

Chemistry & Biodiversity

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Mercurialis annua and M. perennis are medicinal plants used in complementary medicine. In the present work, analytical methods to allow a chemotaxonomic differentiation of M. annua and M. perennis by means of chemical marker compounds were established. In addition to previously published compounds, the exclusive presence of pyridine-3-carbonitrile and nicotinamide in CH(2) Cl(2) extracts obtained from the herbal parts of M. annua was demonstrated by GC/MS. Notably, pyridine-3-carbonitrile was identified for the first time as a natural product. Further chromatographic separation of the CH(2) Cl(2) extracts via polyamide yielded a MeOH fraction exhibiting a broad spectrum of side-chain saturated n-alkylresorcinols. While the n-alkylresorcinol pattern was similar for both plant species, some specific differences were observed for particular n-alkylresorcinol homologs. Finally, the investigation of H(2) O extracts by LC/MS/MS revealed the presence of depside constituents. Whereas, in M. perennis, a mixture of mercurialis acid (=(2R)-[(E)-caffeoyl]-2-oxoglutarate) and phaselic acid (=(E)-caffeoyl-2-malate) could be detected, in M. annua solely phaselic acid was found. By comparison with synthesized enantiomerically pure (2R)- and (2S)-phaselic acids, the configuration of the depside could be determined as (2S) in M. annua and as (2R) in M. perennis.

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Investigations into the Phenolic Constituents of Dog's Mercury (Mercurialis perennis L.) by LC‐MS/MS and GC‐MS analyses

Abstract: The present investigation constitutes the first comprehensive report on the hydrophilic constituents of the rarely studied plant Mercurialis and thus completes the phytochemical knowledge on M. perennis.

Cited by 41 publications

References 29 publications

Studies into the phenolic patterns of different tissues of pineapple (Ananas comosus [L.] Merr.) infructescence by HPLC-DAD-ESI-MS n and GC-MS analysis

Studies into the phenolic patterns of different tissues of pineapple (Ananas comosus [L.] Merr.) infructescence by HPLC-DAD-ESI-MS n and GC-MS analysis

Hydroxycinnamates from elecampane (Inula helenium L.) callus culture

An Approach to the Chemotaxonomic Differentiation of Two European Dog's Mercury Species: Mercurialis annua L. and M. perennis L.

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