Acyl migration evaluation in monoacylglycerols from Echium plantagineum seed oil and Marinol

Cervera, Miguel Ángel Rincón; Venegas, Elena; Ramos‐Bueno, Rebeca P.; García, Ignacio; Guil‐Guerrero, José Luis

doi:10.1016/j.jbiosc.2012.11.023

Cited by 12 publications

(4 citation statements)

References 16 publications

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“…Extracted seed oils were fractionated by thin‐layer chromatography (TLC) to separate lipid classes according to a previous work (Rincón‐Cervera et al, ). Each oil (15 mg) was dissolved in 0.2 mL diethyl ether and then applied into a previously activated (105 °C, 60 min) silica gel plate (20 × 20 cm) (SIL G‐25 from Macherey‐Nagel GmbH, Düren, Germany).…”

Section: Methodsmentioning

confidence: 99%

Fatty Acid Profile and Bioactive Compound Extraction in Purple Viper's Bugloss Seed Oil Extracted with Green Solvents

Rincón‐Cervera

Galleguillos‐Fernández

González‐Barriga

et al. 2020

J Americ Oil Chem Soc

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Oil extraction from seeds of purple viper's bugloss (Echium plantagineum) was carried out using different solvents (chloroform:methanol, n‐hexane, ethanol, 2‐propanol and ethyl acetate) at room temperature and also using Randall extraction. Extraction yields were calculated and oils were analyzed in terms of fatty acid profiles and distribution among lipid classes, total polyphenol content, oxygen radical absorbance capacity (ORAC) and phytosterol content. No considerable differences were found on fatty acid profiles and distribution in oils regardless of the solvent and temperature used for the extraction. However, ethanol combined with Randall extraction (85 °C for 1 hour) offered the best results in terms of total polyphenol content (20.9 mg GAE/100 g oil), ORAC (468.0 μmol TE/100 g oil), and phytosterol amount (437.2 mg identified phytosterols/100 g oil) among all assayed extraction methods. A higher extraction temperature led to significantly higher concentrations of bioactive compounds and ORAC values in the oil when ethanol or 2‐propanol were used as extracting solvent, but that was not the case using n‐hexane except for the concentrations of β‐sitosterol and stigmasterol, which were significantly higher using Randall extraction than room temperature extraction with n‐hexane. Ethanol is classified as a “green solvent,” and it could be considered a suitable option to produce oil from E. plantagineum seeds with a higher antioxidant capacity and bioactive compound concentration than the current commercial oil, which is usually extracted with n‐hexane.

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Section: Methodsmentioning

confidence: 99%

Fatty Acid Profile and Bioactive Compound Extraction in Purple Viper's Bugloss Seed Oil Extracted with Green Solvents

Rincón‐Cervera

Galleguillos‐Fernández

González‐Barriga

et al. 2020

J Americ Oil Chem Soc

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“…Resulting upper phase was isolated in a separatory funnel, dried over anhydrous sodium sulfate and kept in a nitrogen atmosphere at −20 °C until further processing. Efficiency of hydrolysis and ethanolysis was checked by thin layer chromatography (TLC): aliquots of both FFA and EE were spotted on TLC silica plates (Sil G‐25, Macherey Nagel, Germany), developed in a mobile phase of n‐hexane:diethyl ether:acetic acid 70:30:1 (v/v/v) and revealed under a iodine nitrogen stream . No bands other of those of FFA and EE, respectively were found, meaning that TAG in the original oils were efficiently subjected to hydrolysis or ethanolysis.…”

Section: Methodsmentioning

confidence: 99%

Concentration of Gamma‐Linolenic and Stearidonic Acids as Free Fatty Acids and Ethyl Esters from Viper's Bugloss Seed Oil by Urea Complexation

Rincón‐Cervera

Galleguillos‐Fernández

González‐Barriga

et al. 2018

Euro J Lipid Sci & Tech

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In this work, gamma‐linolenic acid (GLA) and stearidonic acid (SDA) are successfully concentrated as free fatty acids (FFA) and ethyl esters (EE) using the urea complexation method at room temperature and two sources of these fatty acids: commercial Echium plantagineum seed oil as well as extracted oil from this species which is grown in Chile. Concentration factors (% fatty acid in the concentrate/% fatty acid in the original oil) for both fatty acids are found to be between 2.35 and 2.65, although they are more efficiently concentrated as FFA than as EE using both commercial and extracted oils. This is the first work which reports the use of Echium plantagineum seed oil from Chilean origin to produce GLA and SDA concentrates as FFA and EE, with similar results that those obtained with commercial Echium oil. Practical Applications: The interest for GLA and SDA as functional ingredients is increasing in the last few years because of their beneficial effects for human health and their plant origin, as they are mainly provided by seed oils from some Boraginaceae species. In this work, GLA and SDA are selectively concentrated from the rest of fatty acids contained in Echium seed oil by the urea method at room temperature, which is a cheap, safe, and easily scalable process. These concentrates, especially as FFA because of their nutritional characteristics versus EE, may become high added‐value ingredients to be incorporated to functional oils or even substrates for the enzymatic synthesis of structured lipids providing GLA and SDA with a higher bioefficiency than currently available oils. Operational scheme developed in this work which consists of: 1) derivatization of Echium plantagineum oil from two origins (extracted from Chilean seeds and commercial oil) to free fatty acids (FFA) and ethyl esters (EE) and 2) processing of FFA and EE by urea at room temperature to concentrate GLA and SDA.

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“…Other authors reported the synthesis of 2‐MAG from echium oil using pancreatic lipase, achieving a 2‐MAG yield of 79.1% (percentage expressed as maximum theoretical yield, 33% of total reaction products) (Rincón Cervera et al, 2013). However, the production of 2‐MAG using pancreatic lipase is not recommended if the reaction products are to be used later in the synthesis of structured lipids as water rests could favor the hydrolytic activity of lipases, carrying out the opposite reaction.…”

Section: Resultsmentioning

confidence: 99%

Integrated Green and Enzymatic Process to Produce Omega‐3 Acylglycerols from Echium plantagineum Using Immobilized Lipases

Castejón

Señoráns

2020

J Americ Oil Chem Soc

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This work presents an original approach to develop an integrated process to improve the nutritional characteristics of natural oils, starting with the extraction from raw material by ecofriendly methods, followed by the production of novel acylglycerols using immobilized lipases. Specifically, 2‐monoacylglycerols (2‐MAG) enriched in omega‐3 stearidonic acid (SDA) were synthesized by selective ethanolysis of extracted Echium plantagineum oil using the lipase from Thermomyces lanuginosus (TLL). Different reaction conditions were investigated to minimize acyl migration and to ensure the purity of final products. The biocatalyst produced in our laboratory by the immobilization of TLL on Sepabeads C‐18 reached the maximum theoretical amount of 2‐MAG (33%) in only 2 hour at mild reaction conditions (25 °C), achieving a product enriched in omega‐3 SDA (up to 25%). Moreover, the produced biocatalyst exhibited higher stability than commercial lipases. The average activity after five cycles was 71%, allowing several reutilization cycles and developing a feasible enzymatic process. Finally, 2‐MAG were used as starting material to synthesize structured triacyclglycerols (STAG) through transesterification with caprylic acid ethyl esters using the lipase from Rhizomucor miehei (RML) in solvent‐free systems. The use of molecular sieves in combination with RML immobilized on Sepabeads C‐18 was demonstrated to be an extraordinarily fast strategy to produce pure STAG (100% in 1 hour), four times higher than the activity showed by commercial biocatalyst. Thus, the enzymatic processes developed in this study open a range of possibilities to synthesize omega‐3 acylglycerols with improved characteristics, proving the usefulness of immobilized lipases to produce novel lipids.

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Acyl migration evaluation in monoacylglycerols from Echium plantagineum seed oil and Marinol

Cited by 12 publications

References 16 publications

Fatty Acid Profile and Bioactive Compound Extraction in Purple Viper's Bugloss Seed Oil Extracted with Green Solvents

Fatty Acid Profile and Bioactive Compound Extraction in Purple Viper's Bugloss Seed Oil Extracted with Green Solvents

Concentration of Gamma‐Linolenic and Stearidonic Acids as Free Fatty Acids and Ethyl Esters from Viper's Bugloss Seed Oil by Urea Complexation

Integrated Green and Enzymatic Process to Produce Omega‐3 Acylglycerols from Echium plantagineum Using Immobilized Lipases

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