Purification of Stearidonic Acid from Modified Soybean Oil by Argentation Silica Gel Column Chromatography

Abstract

The objective of this study was to purify stearidonic acid (SDA, 18:4 x-3) from modified soybean oil containing a mixture of over 20 fatty acids (23% SDA). Interest in obtaining purified fractions of SDA arises from reported health benefits associated with polyunsaturated fatty acids (PUFA), such as cardiovascular disease prevention. In addition, SDA may also provide improved stability characteristics since its unsaturation index is less than longer PUFA, such as eicosapentaenoic acid (EPA, 20:5 x-3). First, a chemical ethanolysis of modified soybean oil was performed to transform the triacylglycerols into fatty acid ethyl esters (FAEE). Then, the FAEE were fractionated and SDA-EE was purified by argentation silica gel (10% AgNO 3 ) open column chromatography, which allows selectivity based on degree of unsaturation. Different FAEE sample loads and mobile phases were explored until the best purification of SDA-EE was achieved. The solvents used were hexane and hexane:acetone mixtures (99 and 95%). Under the optimal conditions, a fraction with high SDA-EE purity (96%) was obtained with 77% yield. Besides, it was possible to obtain another fraction enriched in a-linolenic acid-EE (37% purity and 68% yield) and c-linolenic acid-EE (22% purity and 61% yield). A scaled-up process resulted in 840 mg of final product composed of 97% SDA-EE with 71% yield.

Increasing Stearidonic Acid (SDA) in Modified Soybean Oil by Lipase‐Mediated Acidolysis

“…The fatty acid profiles and positional distribution of MSO, LTC-TAG and LTC-FFA, were comparable to that previously reported for MSO [9,13], LTC-TAG [11] and LTC-FFA [10], and are shown in Table 1. For MSO, SDA (25.0%) was the major fatty acid (FA), and this was followed by linoleic (23.7%), oleic (14.5%), palmitic (12.7%), a-linolenic (ALA) and c-linolenic (GLA) acids (10.8, 7.4%, respectively).…”

“…Guil-Guerrero et al [8] obtained SDA methyl ester of 83.2% purity by argentation silica gel column chromatography from Shortfin Mako liver oil (I. oxyrinchus). This technique has been also used by Kleiner-Shuhler et al [9] to obtain FAEE with SDA purity of 97% in a scaled-up process. In addition, Vazquez and Akoh [10,11] have purified SDA enriched FFA and TAG from modified soybean oil by low temperature crystallization.…”

Lipase‐Catalyzed Concentration of Stearidonic Acid in Modified Soybean Oil by Partial Hydrolysis

“…Guil-Guerrero et al [8] obtained SDA methyl ester of 83.2 % purity by argentation silica gel column chromatography from Shortfin Mako liver oil (I. oxyrinchus). This technique was also used in a scaled-up process by Kleiner-Shuhler et al [9] to obtain FAEE with SDA purity of 97 % from modified soybean oil (MSO). Vazquez and Akoh have purified SDA enriched FFA and TAG by low temperature crystallization of MSO [10,11].…”

Advances in Silver Ion Chromatography for the Analysis of Fatty Acids and Triacylglycerols—2001 to 2011

“…46 Silica gel columns loaded with silver ions were used for the isolation of γ-linolenic acid (18:3 ω-6) as methyl ester from microalgae lipids 47 and stearidonic acid (18:4 ω-3) as ethyl ester from modified soybean oil. 48 Several studies [49][50][51] employed silver ion TLC/densitometry for the separation and quantification of configurationally isomeric FA with 0 to 3 double bonds (as methyl or isopropyl esters). The procedure was applied for a rapid assessment of the authenticity of milk fats, 49,51 margarines and frying fats (Fig.…”