Simultaneous extraction of phosphatidylcholine and phosphatidylethanolamine from soybean lecithin

Abstract

A high composition of phosphatidylcholine (PC) and phosphatidylethanolamine (PE) was simultaneously extracted from soybean lecithin by using a mixed solvent consisting of ethanol and chloroform. The addition of chloroform in ethanol improved the total extraction yield to give high a composition of PC and PE. Thus, the best extraction yield (52%) of PC and PE was achieved at an ethanol/chloroform ratio of 6/4 (v/v). Molecular dynamics calculations of the amorphous cell bearing PC, PE, and solvent molecules were performed in order to understand the distribution of PC and PE molecules in specific solvent conditions. The extraction yield was also sensitive to extraction temperature, time and liquid to solid ratio. The extracted PC and PE mixture was successfully purified by flash chromatography using chloroform/methanol (8/2 v/v) as eluting solvent. The purified yields of PE and PC from lecithin extract were 16 and 35%, respectively. The structure of the extracted products was characterized by thin-layer chromatography and 1 H, 13 C, 31 P NMR, FTIR and UV/vis spectroscopies, and elemental analysis. The purity of PE and PC was higher than 95%.Practical applications: Lecithin composed of phosphoric acid, choline, fatty acids, glycerol, glycolipids, triglycerides, and phospholipids is widely used in human food, animal feed, pharmaceuticals, paints, and other industrial applications. Lecithin can easily be extracted chemically using various solvents in order to obtain pure components. Due to the importance of phospholipids there have been a number of reports on the extraction of PC from lecithin; however, there have been few reports on the extraction of PE or the simultaneous extraction of PC and PE. Thus the simultaneous extraction of PC (35%) and PE (16%) from soybean lecithin by using a mixed solvent consisting of ethanol and chloroform can be a good example to obtain such components in high yields. The protocol employed here is quite straightforward so that pure PC and PE can be obtained economically and may attract interest on mixed solvent systems for the simultaneous extraction of lecithin components.

Egg Yolk Phosphatidylethanolamine: Extraction Optimization, Antioxidative Activity, and Molecular Structure Profiling

“…The similar results for soybean lecithin have been reported by John et al. () in which ethanol and chloroform mixture was a combination to achieve PE extraction. The total amount of extract of PE increased as the increased amount of chloroform till the composition of chloroform reaching 40%.…”

“…The fractionation of phospholipids by extraction with various solvents may be affected by several factors (solvent ratio, solvent volume, and extraction temperature) and the interactions between them (Cabezas, Diehl, & Tomás, ; John, Park, Lee, Suh, & Kim, ). Differing solubilities of phospholipid classes in organic solvents, principally caused by different polarities, make the separation feasible.…”

“…John et al. () found that PE molecules could form hydrogen bonds between themselves and with ethanol molecules. Therefore, ethanol concentration might be a significant factor in the extraction of PE.…”

Simultaneous texturization and extraction of phospholipids from liquid egg yolk using renewable solvents

“…A most recent publication on extracting PL from soybean lecithin also used ethanol at elevated temperatures . However, the carcinogenic and environmentally unsafe co‐solvent chloroform was used along with ethanol.…”

Phospholipid End‐Capped Acid‐Degradable Polyurethane Micelles for Intracellular Delivery of Cancer Therapeutics

“…In this work, keeping the current problems of polymeric nanomedicines, including their non‐degradability, low encapsulation, and non‐viability to clinical therapeutics, in mind we report on a simple and commercially tangible approach for the synthesis of PL end‐capped poly(urea acetal)s for use as a drug carrier. These hybrid materials were synthesized via condensation of 3,9‐bis(3‐aminopropyl)‐2,4,8,10‐tetraoxaspiro[5.5]‐undecane (ATU) and isophorone diisocyanate (IPDI) and end capping with phospholipids, such as soybean lecithin‐based l ‐α‐phosphatidylethanolamine (SPE) extracted from soybean lecithin and 1,2‐bis(10,12‐tricosadiynoyl)‐ sn ‐glycero‐3‐phosphoethanol‐amine (DCPE). The acid‐degradable nature of the material was confirmed by nuclear magnetic resonance (NMR) spectroscopy and dynamic light scattering (DLS).…”