Analytical scale supercritical fluid fractionation and identification of single polar lipids from deoiled soybean lecithin

Abstract

The phosphatidylcholine (PC)-enriched fraction from soybean lecithin is of interest due to its critical role in both the pharmaceutical and industrial field. In this work, enhancement of the purity of the PC fraction along with other individual polar lipid fractions was achieved from crude soybean lecithin by using supercritical fluid extraction (SFE) with methanol-modified SC-CO(2). Neutral lipids were first removed from the crude sample using pure CO(2). Then, the effect of CO(2 )pressure, temperature, and modifier percentage on phospholipid (PL) fractionation from deoiled lecithin was compared with and without silica gel mixed with the lecithin. Pure fractions of phosphatidylethanolamine (PE) and PC were obtained by varying the modifier concentration of the extraction fluid at 460 atm and 40 degrees C with silica gel added to the deoiled lecithin. Without silica gel, coextraction of PE and PC was observed. A total of six components were isolated and tentatively identified in the extract of deoiled crude soybean lecithin.

Molecular species determination of oligosaccharides and glycoconjugates in soybean lecithin powders

“…In this fraction, sugar might exist in other trace components that were not detected. Three ceramides containing three different long‐chain bases, 4,8‐sphingadienine (d18:2), 8‐sphingenine (d18:1), and primarily sphinganine (d18:0), acylated to saturated hydroxy‐ and nonhydroxy with fatty acids with 16 and 18 carbon atoms were confirmed as C16:0d18:0, C18:0dC18:2 and C16:0 h dC18:1 by their elution orders and similar data from previous related researches …”

“…and Table , and qualitative fragmentations of glycolipids through their mass spectrometry data by reference of known data in previous literature . As the m z −1 of glycolipids mostly ranged from 500 to 920, the m z −1 of various glycolipids was searched for the analysis of the glycoconjugates …”

“…4(C)), but mass spectra with ammonium ([M + NH 4 ] + ) and sodium ([M + Na] + ) adduct ions of seven molecular species were obtained ( Table 6). By referring to known information in previous lecithin papers, 1,2,39,40 four sterylglucosides containing sitosterol-3 -glucoside, campesteryl-3 -glucoside, stigmasteryl-3 -glucoside, and wileyonlinelibrary.com/jsfa brassicasteryl-3 -glucoside 33 were confirmed to be the dominating compositions in fraction 3. 32,38,41,42 One GluCer 42-45 with hydroxy stearic acid and sphingosine, one glucose ester, and one monogalactosyldiacylglycerol (C18:3/C18:3) were clearly detected in this mass spectrometry analysis system.…”

“…Three ceramides containing three different long-chain bases, 4,8-sphingadienine (d18:2), 8-sphingenine (d18:1), and primarily sphinganine (d18:0), acylated to saturated hydroxy-and nonhydroxy with fatty acids with 16 and 18 carbon atoms were confirmed as C16:0d18:0, C18:0dC18:2 and C16:0 h dC18:1 by their elution orders and similar data from previous related researches. 34,36,37,39,40 Molecular species of fraction 3 No clear separation of fraction 3 appeared in this UPLC-MS ( Fig. 4(C)), but mass spectra with ammonium ([M + NH 4 ] + ) and sodium ([M + Na] + ) adduct ions of seven molecular species were obtained ( Table 6).…”

“…33,35 As the m z −1 of glycolipids mostly ranged from 500 to 920, the m z −1 of various glycolipids was searched for the analysis of the glycoconjugates. 2,39,40 Molecular species of fraction 1 Na + adduct ([M + Na] + ) or NH4 + ([M + NH4] + ) was evident at each peak of the UPLC-ESI-MS. Fourteen major ions (Table 3), corresponding to 14 molecule species (Fig. 4(A)), were discovered in fraction 1.…”