Analysis of plant galactolipids by reversed-phase high-performance liquid chromatography/mass spectrometry with accurate mass measurement

Zábranská, Marie; Vrkoslav, Vladimír; Sobotníková, Jana; Cvačka, Josef

doi:10.1016/j.chemphyslip.2012.03.002

Cited by 13 publications

(16 citation statements)

References 35 publications

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“…The m/z 264. reversed-phase chromatography, the retention of lipids depends on the number of carbon atoms and double bonds in acyl chains. Therefore, the retention times of lipids are usually in good agreement with their ECN values calculated as the total CN minus twice the DB, i.e., ECN = CN  2DB (14,16,54,55). This is also the case of 1-O-ENSs, which makes the validation possible (Fig.…”

Section: -O-acylceramides In Vernix Caseosasupporting

confidence: 53%

Nonhydroxylated 1-O-acylceramides in vernix caseosa

Harazim

Vrkoslav

Budêšínský

et al. 2018

Journal of Lipid Research

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This article is available online at http://www.jlr.org lamellar structure composed of ceramides, cholesterol, and FAs. The stratum corneum provides a major barrier to water loss and the permeation of exogenous substances (1,2). The skin begins to form during embryogenesis in the third week of gestation. The initial layer of ectodermal cells undergoes gradual differentiation to create a stratified epithelium. By the end of the fourth week, the skin consists of a basal layer and the periderm, which protects the fetus from amniotic fluid and ensures glucose uptake. An intermediate layer is then formed by the proliferation of keratinocytes from the spinous layer between the basal layer and the periderm. The stratum corneum begins to be shaped in the eighteenth week. The periderm cells are completely replaced by the twenty-third week of gestation. At about the same time, vernix caseosa starts to be produced (3,4).Vernix caseosa is a cheese-like substance that coats the fetal skin from the middle of gestation (5). It protects the fetus from the amniotic fluid, prevents the loss of water and electrolytes, and aids in postbirth adaptation of a newborn's skin. The main components of the vernix caseosa are water, sebum, desquamated epithelial cells, and shed lanugo hair. Chemically, it is a rich mixture of lipids and proteins. Even though it has been studied for many decades, the chemical constituents of vernix caseosa have not been comprehensively characterized yet. The enormous chemical complexity of vernix caseosa lipids has fascinated scientists, but they are still far from completely understanding the biological roles of individual lipid classes. Earlier studies of lipid composition focused on abundant neutral (nonpolar) species (6-16), with significantly less attention Abstract Vernix caseosa, the waxy substance that coats the skin of newborn babies, has an extremely complex lipid composition. We have explored these lipids and identified nonhydroxylated 1-O-acylceramides (1-O-ENSs) as a new class of lipids in vernix caseosa. These ceramides mostlycontain saturated C11-C38 ester-linked (1-O) acyls, saturated C12-C39 amide-linked acyls, and C16-C24 sphingoid bases. Because their fatty acyl chains are frequently branched, numerous molecular species were separable and detectable by HPLC/MS: we found more than 2,300 molecular species, 972 of which were structurally characterized. The most abundant 1-O-ENSs contained straight-chain and branched fatty acyls with 20, 22, 24, or 26 carbons in the 1-O position, 24 or 26 carbons in the N position, and sphingosine. The 1-O-ENSs were isolated using multistep TLC and HPLC and they accounted for 1% of the total lipid extract. The molecular species of 1-O-ENSs were separated on a C18 HPLC column using an acetonitrile/propan-2-ol gradient and detected by APCI-MS, and the structures were elucidated by high-resolution and tandem MS. Medium-polarity 1-O-ENSs likely contribute to the cohesiveness and to the waterproofing and moisturizing properties of vernix caseosa.-Harazim, E., V. Vrko...

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Section: -O-acylceramides In Vernix Caseosasupporting

confidence: 53%

Nonhydroxylated 1-O-acylceramides in vernix caseosa

Harazim

Vrkoslav

Budêšínský

et al. 2018

Journal of Lipid Research

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“…Such behavior indicates the validity of the ECN concept assuming the same effect of a double bond as that of the shortening of the chain by two methylene groups. The ECN concept is valid for reversed-phase separations of many lipid classes including triacylglycerols, wax esters, fatty acid methyl esters or glyceroglycolipids [45][46][47] and used as an independent criterion for the validation of the structures assigned from LC/MS data.…”

Section: Analysis Of 12-dde From Vernix Caseosamentioning

confidence: 99%

Analysis of 1,2-diol diesters in vernix caseosa by high-performance liquid chromatography – atmospheric pressure chemical ionization mass spectrometry

Šubčíková

Hoskovec

Vrkoslav

et al. 2015

Journal of Chromatography A

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“…Broad separation techniques are employed to isolate intact lipids from the crude lipid plant or algal extract, for instance, TLC [11][12][13] and SPE [14][15][16]. However, reverse HPLC is the most preferred [15,[17][18][19][20][21][22][23][24]. For better separation of the particular lipid species, a combination of the methods mentioned above is also occasionally applied [15,16,24].…”

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“…However, reverse HPLC is the most preferred [15,[17][18][19][20][21][22][23][24]. For better separation of the particular lipid species, a combination of the methods mentioned above is also occasionally applied [15,16,24]. Analytical methods utilized for a lipidome analysis should provide information concerning lipid classes, lipid species, localization of the fatty acyl chain in the glycerol backbone [12], and the localization of particular double bonds in fatty acid (FA).…”

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“…The detection of particular lipids is provided by means of light chemistry: UV detector [15], IR detector [23], diode array detector [21], and evaporative light scattering detector [25]. Structure elucidation is then completed by NMR spectroscopy [11,14,21,22] and/or by means of MS/MS with different ionization techniques including matrixassisted laser desorption [22], fast atom bombardment [26], atmospheric-pressure chemical ionization (APCI) [16], but mostly by ESI [12,16,17,[19][20][21]23,24,27]. Fragmentation of MGDG and DGDG sodium adducts provides information about the sn-position of particular FA [17,21,22,24,28].…”

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Separation and identification of lipids in the photosynthetic cousins of Apicomplexa Chromera velia and Vitrella brassicaformis

Tomčala

Kyselová

Schneedorferová

et al. 2017

J of Separation Science

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The alveolate algae Chromera velia and Vitrella brassicaformis (chromerids) are the closest known phototrophic relatives to apicomplexan parasites. Apicomplexans are responsible for fatal diseases of humans and animals and severe economic losses. Availability of the genome sequences of chromerids together with easy and rapid culturing of C. velia makes this alga a suitable model for investigating elementary biochemical principals potentially important for the apicomplexan pathogenicity. Such knowledge allows us to better understand processes during the evolutionary transition from a phototrophy to the parasitism in Apicomplexa. We explored lipidomes of both algae using high-performance liquid chromatography with mass spectrometry or gas chromatography with flame ionization detection. A single high-performance liquid chromatography with mass spectrometry analysis in both ionization modes was sufficient for the separation and semi-quantification of lipids in chromerid algae. We detected more than 250 analytes belonging to five structural lipid classes, two lipid classes of precursors and intermediates, and triacylglycerols as storage lipids. Identification of suggested structures was confirmed by high-resolution mass spectrometry with an Orbitrap mass analyzer. An outstandingly high accumulation of storage triacylglycerols was found in both species. All the investigated aspects make C. velia a prospective organism for further applications in biotechnology.

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Analysis of plant galactolipids by reversed-phase high-performance liquid chromatography/mass spectrometry with accurate mass measurement

Cited by 13 publications

References 35 publications

Nonhydroxylated 1-O-acylceramides in vernix caseosa

Nonhydroxylated 1-O-acylceramides in vernix caseosa

Analysis of 1,2-diol diesters in vernix caseosa by high-performance liquid chromatography – atmospheric pressure chemical ionization mass spectrometry

Separation and identification of lipids in the photosynthetic cousins of Apicomplexa Chromera velia and Vitrella brassicaformis

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