High‐Resolution NMR Spectroscopy: An Alternative Fast Tool for Qualitative and Quantitative Analysis of Diacylglycerol (DAG) Oil

Hatzakis, Emmanuel; Agiomyrgianaki, Alexia; Kostidis, Sarantos; Dais, Photis

doi:10.1007/s11746-011-1848-2

Cited by 75 publications

(69 citation statements)

References 38 publications

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“…According to our results, the resonance of the C-2 H atom was situated at weaker field. This disagreed with data reported earlier for DAG from olives and vegetable oils [16,17]. …”

contrasting

confidence: 99%

Structure and Biological Activity of Several Classes of Compounds from the Brown Alga Sargassum pallidum

et al. 2013

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Sargassum pallidum (Phaeophyceae) is broadly distributed in the Yellow Sea and the Sea of Japan, on the southeastern shores of Sakhalin Island, and on the southern islands of the Kuril archipelago. Algae of the genus Sargassum, including S. pallidum, produce chemical compounds of various structures such as polysaccharides (in particular, sulfated fucan), plastoquinones, chromanols, chromenes, sterols, and lipids [1][2][3][4] and are used in Eastern medicine because they exhibit antitumor, antioxidant, antiviral, and antimicrobial activities [4][5][6][7][8]. Lipids, e.g., monogalactosyldiacylglycerols from S. thunbergii exhibited antifungal activity against Candida albicans [9]; from S. fulvellum, fibrinolytic activity [10]. A sulfoglycerolipid from S. wightii showed antibacterial activity [11].During a study of the lipid composition of S. pallidum at various stages of the life cycle and at various times of the year, we detected substances that were not previously found in this alga, the contents of which were rather noticeable and had a distinct seasonal nature, in addition to the lipids typical for algae of the genus Sargassum [12]. These substances were isolated in order to study their structural properties. Lipid extracts from freshly collected specimens were obtained and separated into pure components according to the method described earlier by us [13]. The substances were purified over additional columns. The elutions were monitored by TLC on silica gel plates (Silica gel 60 F254 , Merck, Germany) using the previously described solvent systems [13,14].The neutral lipids (NL) contained according to TLC and lipid standards the usual lipids triacylglycerols (TAG) and free sterols in addition to significant quantities of free fatty acids (FFAs) and two compounds were detected. These were compound 1 that was located significantly below the FFAs and compound 2 that had an R f value slightly greater than that of the TAG. Work up of the chromatogram with H 2 SO 4 (10%) and ashing of it at 180°C gave a lilac color. We detected compound 3 in the glyceroglycolipids. It gave a positive reaction with anthrone reagent and was located on the chromatogram between monogalactosyl-and digalactosyldiacylglycerols. Compound 4 gave a positive reaction with Dragendorff's reagent and had an R f value on the chromatograms using the solvent systems for a lipid betaine [14] that was analogous to the R f value of a standard isolated by us by preparative TLC from the alga S. miyabe, in which this compound and diacylglycerohydroxymethyltrimethylalanine (DGTA) were identified [15].In our opinion, compounds 1 and 3 and FFAs are normal metabolic products of the alga and not artifacts formed during the extraction process.The structures of the compounds were identified by PMR, 13 C NMR, and 2D spectra and comparison of them with the literature. The compounds were identified as 1,2-diacyl-3-hydroxy-sn-glycerol (1, 1,2-DAG), di-(2-ethylhexyl)-phthalate (2, DEHP), 1-O-acyl-3-O-(E-D-galactopyranosyl)-sn-glycerol (3, monogalactosylmonoacylglycero...

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“…According to our results, the resonance of the C-2 H atom was situated at weaker field. This disagreed with data reported earlier for DAG from olives and vegetable oils [16,17]. …”

contrasting

confidence: 99%

Structure and Biological Activity of Several Classes of Compounds from the Brown Alga Sargassum pallidum

et al. 2013

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“…They allow a better assignment than the one-dimensional spectra, improving the characterization of food lipid samples [143,149]. However, the main difficulty derived from the application of these tools is the high time required for the acquisition.…”

Section: Magnetic Resonancementioning

confidence: 99%

A review of analytical methods measuring lipid oxidation status in foods: a challenging task

Barriuso

Astiasarán

Ansorena

2012

Eur Food Res Technol

276

220

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Lipid oxidation analysis in food samples is a relevant topic since compounds generated in the process are related to undesirable sensory and biological effects. As the process is complex and depends on the type of lipid substrate, oxidation agents and environmental factors, proper measurement of lipid oxidation remains a challenging task. A great variety of methodologies have been developed and implemented so far, both for determining primary oxidation products and secondary oxidation products. Most common methods and classical procedures are described, including peroxide value, TBARS analysis and chromatography. Some other methodologies such as chemiluminescence, fluorescence emission, Raman spectroscopy, infrared spectroscopy or magnetic resonance, provide interesting and promising results, so attention must be paid to these alternative techniques in the area of food lipid oxidation analysis.

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“…, Hatzakis et al. ). Most likely, the DAG from S. pallidum and F. evanescens are usual components of those algae, and their presence in algae is associated with biosynthesis and the degradation of glycolipids and phospholipids (Ohlrogge and Browse , Sato and Wada ).…”

Section: Discussionmentioning

confidence: 99%

Examination of the structures of several glycerolipids from marine macroalgae by NMR and GC‐MS

Logvinov

Gerasimenko

Esipov

et al. 2015

Journal of Phycology

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Several classes of glycerolipids were isolated from the total lipids of the algae Saccharina cichorioides, Eualaria fistulosa, Fucus evanescens, Sargassum pallidum, Silvetia babingtonii (Ochrophyta, Phaeophyceae), Tichocarpus crinitus, and Neorhodomela larix (Rhodophyta, Florideophyceae). The structures of these lipids were examined by nuclear magnetic resonance (NMR) spectroscopy, including 1D ((1) H and (13) C) and 2D (COSY, HSQC and HMBC) experiments. All of the investigated algae included common galactolipids and sulfonoglycolipids as the major glycolipids. Minor glycolipids isolated from S. cichorioides, T. crinitus, and N. laris were identified as lyso-galactolipids with a polar group consisted of the galactose. Comparison of the (1) H NMR data of minor nonpolar lipids isolated from the extracts of the brown algae S. pallidum and F. evanescens with the (1) H NMR data of other lipids allowed them to be identified as diacylglycerols. The structures of betaine lipids isolated from brown algae were confirmed by NMR for the first time. The fatty acid compositions of the isolated lipids were determined by gas chromatography-mass spectrometry.

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High‐Resolution NMR Spectroscopy: An Alternative Fast Tool for Qualitative and Quantitative Analysis of Diacylglycerol (DAG) Oil

Cited by 75 publications

References 38 publications

Structure and Biological Activity of Several Classes of Compounds from the Brown Alga Sargassum pallidum

Structure and Biological Activity of Several Classes of Compounds from the Brown Alga Sargassum pallidum

A review of analytical methods measuring lipid oxidation status in foods: a challenging task

Examination of the structures of several glycerolipids from marine macroalgae by NMR and GC‐MS

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