Phenylethanoid and Iridoid Glycosides in the New Zealand Snow Hebes (Veronica, Plantaginaceae)

Taskova, Rilka M.; Kokubun, Tetsuo; Ryan, Ken G.; Garnock‐Jones, P. J.; Jensen, Søren Rosendal

doi:10.1248/cpb.58.703

Cited by 27 publications

(15 citation statements)

References 35 publications

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“…Numerous studies on the identification of secondary metabolites in Veronica species have already been published, being iridoid glucosides, phenylethanoid and flavonoid glycosides mainly reported (Taskova et al, 2010;Harput et al, 2011). In addition to the chemotaxonomic and phytochemical importance of the genus, Veronica species have become prominent due to their traditional uses and biological activities.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial activity of Veronica montana L. extract and of protocatechuic acid incorporated in a food system

Stojković

Živković

Sokóvić

et al. 2013

Food and Chemical Toxicology

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This study was designed to evaluate the antibacterial activity of the Veronica montana L. water extract and its main phenolic compound, protocatechuic acid. The antibacterial activity was determined by microdilution assay against six strains of Gram-positive and Gram-negative bacteria. Listeria monocytogenes was the most sensitive of the tested bacterial species.Antibacterial preserving properties of protocatechuic acid were also evaluated after its incorporation in cream cheese, using L. monocytogenes as commonly cheese contaminant. The compound successfully inhibited L. monocytogenes development in cream cheese, at room temperature and in refrigerator (25 °C and 4 °C, respectively), after 3 days of inoculation.Sensory evaluation was carried out in order to validate the mentioned food system. A possible mode of action of the tested compound towards bacterial cells was assessed and appears to be direct lysis of pathogenic cytoplasmic membrane. Prediction of pharmacokinetic properties was also performed using computational analyzes. The obtained results can serve as an important platform for the development of effective natural preservatives.

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Section: Introductionmentioning

confidence: 99%

Antibacterial activity of Veronica montana L. extract and of protocatechuic acid incorporated in a food system

Stojković

Živković

Sokóvić

et al. 2013

Food and Chemical Toxicology

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“…A part of the BuOH extract was passed through a porous‐polymer polystyrene resin ( Diaion HP‐20 ) column, and the fraction eluting with 50% MeOH was subjected to silica gel column chromatography (CC) to afford three new phenylethanoid glycosides, 1 – 3 , in addition to five known compounds. The known glycosides were identified as purpureaside B , 3′′′′‐ O ‐methylmaxoside , purpureaside E , maxoside , and chionoside F , by comparison of their spectroscopic data with literature values.…”

Section: Resultsmentioning

confidence: 99%

Phenylethanoid Glycosides from the Roots ofDigitalis ciliataTrautv.

et al. 2016

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Three new phenylethanoid glycosides, named digicilisides A – C (1 – 3, resp.), have been isolated from the roots of Digitalis ciliata, along with five known phenylethanoid glycosides. The structures of 1 – 3 were identified as 2‐(4‐hydroxy‐3‐methoxyphenyl)ethyl β‐d‐glucopyranosyl‐(1→3)‐[α‐l‐rhamnopyranosyl‐(1→6)]‐4‐O‐[(E)‐feruloyl]‐β‐d‐glucopyranoside (1), 2‐(3,4‐dihydroxyphenyl)ethyl α‐l‐arabinopyranosyl‐(1→2)‐[β‐d‐glucopyranosyl‐(1→3)]‐[α‐l‐rhamnopyranosyl‐(1→6)]‐4‐O‐[(E)‐feruloyl]‐β‐d‐glucopyranoside (2), and 2‐(3,4‐dihydroxyphenyl)ethyl β‐d‐glucopyranosyl‐(1→3)‐{6‐O‐[(E)‐feruloyl]‐β‐d‐glucopyranosyl‐(1→6)}‐4‐O‐[(E)‐caffeoyl]‐β‐d‐glucopyranoside (3).

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“…The negative ion mode ESI mass spectra for Sg-10 and -13 indicated the presence of the same [M-H]ion at m/z 667.2233 (C 31 H 39 O 16 , 667.2238, -0.75 ppm), consistent with the constitutional isomers of scroside B and hemiphroside A. [3,5,9,20] As shown in Table 2…”

Section: Identification Ofmentioning

confidence: 99%

Screening of glycoside isomers in P. scrophulariiflora using ionic liquid‐based ultrasonic‐assisted extraction and ultra‐performance liquid chromatography/electrospray ionization quadrupole time‐of‐flight tandem mass spectrometry

Cao

Qiao

Wang

et al. 2012

Rapid Comm Mass Spectrometry

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A powerful ionic liquid-based ultrasonic-assisted extraction (ILUAE) method combined with ultra-performance liquid chromatography coupled to electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC/ESI-QTOFMS(n) ) was employed in the rapid simultaneous screening of iridoid glycosides, phenylethanoid glycosides, and cucurbitacin glycosides from P. scrophulariiflora. The ILUAE procedure was optimized over several ultrasonic parameters, including the ultrasonic power, concentration of the ionic liquid, and solid-liquid ratio. A comparison with conventional heat-reflux extraction and regular UAE demonstrated that the optimized approach yielded a high extraction efficiency (Picroside I, 2.84%; Picroside II, 3.57%; 6-O-E-feruloyl catalpol, 2.20%) within a short extraction time of 30 min. Negative ion mode ESI-QTOFMS(2) analysis of the fragmentation reactions of the [M-H](-) ions was conducted to characterize the diagnostic ions related to the glycosyl moieties, aglycone units, and the type and substituted position of the ester groups. Interestingly, the positional isomers of the iridoid glycosides could be easily discriminated based on the characteristic ions. A total of 15 glycosides, including three groups of iridoid glycoside isomers and two groups of phenylethanoid glycoside isomers, were conveniently identified within 13.5 min. Moreover, 6'-O-vanilloyl catalpol was identified in P. scrophulariiflora for the first time. The method developed here was further validated by measuring the recovery, correlation coefficient (R(2) ), and reproducibility (RSD, n = 5) of three iridoid glycosides: 89.60%-109.02%, 0.9991-0.9998, and 0.93%-1.44%, respectively. This study demonstrated the capabilities of ILUAE combined with UPLC/ESI-QTOFMS(n) for the rapid screening of glycosides in P. scrophulariiflora. This method offers an approach to similar studies on other natural plants.

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Phenylethanoid and Iridoid Glycosides in the New Zealand Snow Hebes (Veronica, Plantaginaceae)

Cited by 27 publications

References 35 publications

Antibacterial activity of Veronica montana L. extract and of protocatechuic acid incorporated in a food system

Antibacterial activity of Veronica montana L. extract and of protocatechuic acid incorporated in a food system

Phenylethanoid Glycosides from the Roots ofDigitalis ciliataTrautv.

Screening of glycoside isomers in P. scrophulariiflora using ionic liquid‐based ultrasonic‐assisted extraction and ultra‐performance liquid chromatography/electrospray ionization quadrupole time‐of‐flight tandem mass spectrometry

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