Liquid chromatography separation of α- and γ-linolenic acid positional isomers with a stationary phase based on covalently immobilized cellulose tris(3,5-dichlorophenylcarbamate)

Ianni, Federica; Blasi, Francesca; Giusepponi, Danilo; Coletti, Alice; Galli, Francesco; Chankvetadze, Bezhan; Galarini, Roberta; Sardella, Roccaldo

doi:10.1016/j.chroma.2019.460461

Cited by 22 publications

(7 citation statements)

References 42 publications

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“…The experimental data shown in Figure 8 indicate structure 7A should be dominant in hempseed oil. This observation corresponds to the results described in the literature [31,35]. The TAG with gamma-linolenic acid composition should be much lower than the TAG with alpha-linolenic acid composition in hemp seed oil.…”

Section: [M + Nh4]supporting

confidence: 91%

“…However, isomers with double bond position variations are still possible. Common structural isomers such as alpha-linolenic acid (ALA) and gamma-linolenic acid (GLA) fatty acid chains are shown in Figure 7 based on literature reports [31,35]. Furthermore, for the parent ion of 894.7525 with a retention time of 31.87 min, the fragmental ratio of 599.5014 and 595.4655 Daltons is 2:1.…”

Section: Structural Identification Of Chemical Marker For Hemp Seed Oilmentioning

confidence: 95%

Section: [M + Nhmentioning

confidence: 99%

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HPLC Method for Separation of Cannabidiol Hemp Seed Oil with Skin Lipids and Tandem HRMS Technology for Characterization of a Chemical Marker

et al. 2021

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Cannabidiol (CBD) hemp seed oil is a commercial raw material with antioxidant and anti-inflammatory benefits that has been formulated into body wash and skin care products. The biggest analytical challenge is how to simultaneously quantify CBD and hemp seed oil as they deposited on the skin surface. CBD is easily separated and quantified from skin surface extracts via a HPLC-mass spectrometry methodology. However, the structural skeleton of triacylglycerides (TAGs) in hemp seed oil is same as those from the skin surface sebum. The strong hydrophobicity with subtle structural difference challenges their separation. In this project, a new reverse phase HPLC-high resolution mass spectrometry methodology was developed with a strong mobile phase normal propanol. The separated hemp seed oil TAGs in the chromatogram were identified and characterized using data-dependent acquisition (DDA) technology. Based on the daughter ion characterization, the separated peak with an ammonium adduct at 890.7226 [M + NH4]+ was confirmed as the parent ion of glycerol with three omega-3 fatty acid chains. This is the first time TAG structure with direct HPLC-tandem mass spectrometry technology has been elucidated without a hydrolysis reaction. The confirmed TAG structure with an ammonium adduct at 890.7226 ± 0.0020 can be used as a representative chemical marker for the hemp seed oil quantification.

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Section: [M + Nh4]supporting

confidence: 91%

Section: Structural Identification Of Chemical Marker For Hemp Seed Oilmentioning

confidence: 95%

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HPLC Method for Separation of Cannabidiol Hemp Seed Oil with Skin Lipids and Tandem HRMS Technology for Characterization of a Chemical Marker

et al. 2021

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“…Regarding the food sector, a method for separation of α - and γ -linolenic acid positional isomers ( Supplementary Materials Figure S6 )—which was a major challenge in previous methods—by liquid chromatography with Lux ® i-Cellulose-5 (250 × 4.6 mm, i.d., 5 μm silica gel, Table 1 ), has been developed by Ianni et al [ 30 ]. They applied a reversed-mode mobile phase (acetonitrile/10 mM aqueous ammonium acetate, 60:40, v:v ), pH 6.0, 25 °C, and a 0.5 mL/min flow rate as the optimal conditions for the separation of the two isomers, with the highest selectivity and resolution being α = 1.10 and R S = 1.21, respectively.…”

Section: Cellulose-based Cspsmentioning

confidence: 99%

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

Bui

Rosenau

2021

Molecules

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Polysaccharides, oligosaccharides, and their derivatives, particularly of amylose, cellulose, chitosan, and β-cyclodextrin, are well-known chiral selectors (CSs) of chiral stationary phases (CSPs) in chromatography, because they can separate a wide range of enantiomers. Typically, such CSPs are prepared by physically coating, or chemically immobilizing the polysaccharide and β-cyclodextrin derivatives onto inert silica gel carriers as chromatographic support. Over the past few years, new chiral selectors have been introduced, and progressive methods to prepare CSPs have been exploited. Also, chiral recognition mechanisms, which play a crucial role in the investigation of chiral separations, have been better elucidated. Further insights into the broad functional performance of commercially available chiral column materials and/or the respective newly developed chiral phase materials on enantiomeric separation (ES) have been gained. This review summarizes the recent developments in CSs, CSP preparation, chiral recognition mechanisms, and enantiomeric separation methods, based on polysaccharides and β-cyclodextrins as CSs, with a focus on the years 2019–2020 of this rapidly developing field.

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“…Thus, a multitude of noncovalent interactions can potentially occur into the groove but, actually, only some of them act to recognize the enantiomers of a given chiral analyte, depending on its particular structure, size and shape which is the sum of geometry and electronic distribution. In this regard, it is worth mentioning that noncovalent interactions operating in this class of polymers can be also ex ploited to discriminate non-enantiomeric compounds which are difficult to separate with conventional achiral materials [41][42][43]. In addition, polysaccharide-based CSPs have been successfully used for preparative enantioseparation due to their high loading capacity which increases the productivity of the separation process [44].…”

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

Noncovalent interactions in high-performance liquid chromatography enantioseparations on polysaccharide-based chiral selectors

Peluso

Mamane

Dallocchio

et al. 2020

Journal of Chromatography A

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HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

show abstract

Liquid chromatography separation of α- and γ-linolenic acid positional isomers with a stationary phase based on covalently immobilized cellulose tris(3,5-dichlorophenylcarbamate)

Cited by 22 publications

References 42 publications

HPLC Method for Separation of Cannabidiol Hemp Seed Oil with Skin Lipids and Tandem HRMS Technology for Characterization of a Chemical Marker

HPLC Method for Separation of Cannabidiol Hemp Seed Oil with Skin Lipids and Tandem HRMS Technology for Characterization of a Chemical Marker

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

Noncovalent interactions in high-performance liquid chromatography enantioseparations on polysaccharide-based chiral selectors

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