Purification of docosahexaenoic acid from tuna oil by a two‐step enzymatic method: Hydrolysis and selective esterification

Shimada, Yuji; Maruyama, Kazuaki; Sugihara, Akio; Moriyama, Shigeru; Tominaga, Yoshio

doi:10.1007/s11746-997-0251-5

Cited by 67 publications

(45 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…6), especially when it was increased by 5-fold (from reaction IV to reaction V). This result was obviously expected [11,[23][24][25][26], since the rate limiting component in the enzymatic reactions with high concentrations of substrates is the amount of enzyme. The trend observed in the total omega 3 PUFA content was somewhat different (Fig.…”

Section: Effect Of Enzyme Loadmentioning

confidence: 64%

Upgrading of Farmed Salmon Oil Through Lipase-Catalyzed Hydrolysis

Kahveci¹,

Falkeborg²,

Gregersen³

et al. 2010

TOBIOTJ

View full text Add to dashboard Cite

Upgrading of farmed salmon oil obtained from by-products was carried out by lipase-catalyzed hydrolysis to increase omega 3 polyunsaturated fatty acids (PUFA) content. The lipases tested were from Penicillium camembertii (PC), Rhizomucor javanicus (RJ), Rhizopus niveus (RN), Rhizopus delemar (RD), Burkholderia cepacia (BC), Rhizopus oryzae (RO), Candida rugosa (CR) and Rhizomucor miehei (RM). The lipases from PC, RJ and RN had lower hydrolysis degrees (HDs) compared to the rest of the lipases. The lipase from CR had the highest HD after 24 h (91.89%). Moreover, CR lipase was the most effective one in concentrating omega 3 PUFA. The final value was increased from 13.77% to 27.81% (wt%). The changes in omega 3 PUFA content were significantly different among the lipases although the HD values were similar at the end of the reactions, which was believed to be caused by the substrate specificities of the lipases. The investigation of the relationship between HD and hydrolysis resistant value (HRV) for eicosapentaenoic acid (EPA, 20:5), docosahexaenoic acid (DHA, 22:6) and oleic acid (OA, 18:1) revealed that the fatty acid (FA) selectivity of the lipases were significantly different. CR lipase had the highest preference for hydrolyzing OA selectively over EPA and DHA. The reaction conditions, i.e. presence of surfactants, sonication, buffer-to-oil ratio, enzyme load, did not affect the selectivity. Investigation of the reaction conditions revealed that it was possible to obtain ~2.15-fold of the original omega 3 PUFA content by hydrolysis of salmon oil in the presence of CR lipase (4%, based on oil weight) with a bufferto-oil ratio of 2:1 (v/v) at 37 o C for 4 h.

show abstract

Section: Effect Of Enzyme Loadmentioning

confidence: 64%

Upgrading of Farmed Salmon Oil Through Lipase-Catalyzed Hydrolysis

Kahveci¹,

Falkeborg²,

Gregersen³

et al. 2010

TOBIOTJ

View full text Add to dashboard Cite

show abstract

“…Strong discrimination was offered by CRL and RJL with the former lipase providing the highest DHA concentration level of 22.5% in excellent recovery (94%) at 63% conversion. Tuna oil hydrolysis by CRL has previously been demonstrated to afford DHA concentration levels up to 50% [10][11][12]14]. Moderate discrimination between EPA and DHA was also offered by CLL and ROL.…”

Section: Lipase Fatty Acid Selectivitymentioning

confidence: 99%

“…There are numerous reports in the literature describing the application of commercially available lipases to concentrate EPA and DHA from marine oils in various types of hydrolysis, esterification and transesterification reactions [8][9][10][11][12][13][14]. They reveal that the commercially available lipases discriminate against n-3 PUFA, and that lipases that display any significant activity toward n-3 fatty acids usually prefer EPA to DHA as substrate.…”

Section: Introductionmentioning

confidence: 99%

Lipase selectivity toward fatty acids commonly found in fish oil

Halldórsson

Kristinsson

Haraldsson

2004

Euro J Lipid Sci & Tech

View full text Add to dashboard Cite

The main objective of this study was to compare the fatty acid selectivity of numerous commercially available lipases toward the most ubiquitous fatty acids present in fish oils in form of their corresponding ethyl esters. Special interest was taken in their ability to separate the n‐3 long‐chain polyunsaturated fatty acids (PUFA), mainly eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), from the more saturated fatty acids as well as exploiting the putative discrimination between these highly valuable n‐3 PUFA. Hydrolysis of sardine oil ethyl esters in a Tris buffer solution by 12 microbial lipases is described. The results reveal that all of the lipases strongly discriminate against the n‐3 PUFA and prefer the more saturated fatty acids as substrates. Most of the lipases discriminate between EPA and DHA in favor of EPA, however, 2 bacterial lipases from Pseudomonas were observed to prefer DHA to EPA. Digestive lipolytic enzymes isolated from salmon and rainbow trout intestines displayed reversed fatty acid selectivity when their fish oil triacylglycerol hydrolysis was studied. Thus, the n‐3 PUFA including EPA and DHA were observed to be hydrolyzed at a considerably higher rate than the more saturated fatty acids.

show abstract

“…For a long time, these molecules were shown to be of great importance in the prevention of a number of diseases such as inflammation, hypotriglyceridemic effect, allergies, diabetes or coronary heart disease [3][4][5][6]. Up until now, enzymatic methods for concentration of n-3 fatty acids have been used and several lipases have been studied and optimised in a number of reactions (hydrolysis, esterification, transesterification) [7][8][9][10][11][12]. Membrane filtration has proven valuable for the deacidification and degumming of oil, and is also a promising means for the separation and concentration of oils and fats [13][14][15][16][17][18].…”

mentioning

confidence: 99%

Conjugated linoleic acid (CLA) isomers in heat-treated vegetable oils

Juanéda

Cordier

Grégoire

et al. 2001

OCL

View full text Add to dashboard Cite

Summary :The aim of this study was to quantify the conjugated linoleic acids (CLA) isomers present in frying oils and to elucidate their structures. For this purpose, used frying oils were collected in restaurants by the Laboratoire Interrégional de la Répression des Fraudes. Three samples of sunflower oils, one of peanut oil and one of rapeseed oil containing different levels of total polar compounds were analys-ed. The samples were converted to methyl esters using sodium methoxide and the CLA content was determinated by a combination of gas chromatography analysis on a 100m CP Sil88 column and of silver-ion-high pressure liquid chromatography. The identification of the CLA isomers was carried out by gas chromatography coupled with mass spectrometry of the 4-methyl-1,2,4-triazoline-3,5-dione adducts. The amount of polar compounds in the frying oils ranged from 30 to 53%. The quantities of CLA from 0.4 to 0.5%. The 9,11 and 10,12-18:2 were the major CLA isomers. Among them, the di-trans isomers represent about 50% of the total CLA.Keywords : CLA, sunflower, rapeseed , peanut, heat treatment, frying.Résumé : Le but de ce travail est de rechercher la présence d'isomères conjugués de l'acide linoléique (ALC) dans des huiles collectées en restauration par le Laboratoire interrégional de la répression des fraudes, et de déterminer les structures de ces composés. Trois huiles de tournesol, une huile d'arachide et une de colza ont été choisies pour leur teneur élevée en composés polaires (supérieure à 25 %). Les acides gras des huiles ont été méthylés par du méthanolate de sodium selon la méthode de Glass. Le pourcentage d'ALC a été déterminé par chromatographie en phase gazeuse sur colonne CP Sil88 de 100m. La teneur des différents isomères conjugués a été déterminée par chromatographie en phase gazeuse et par chromatographie liquide haute performence sur colonnes imprégnées au nitrate d'argent. L'identification des ALC a été réalisée par chromatographie en phase gazeuse couplée au spectre de masse des dérivés 4-méthyl-1,2,4-triazoline-3,5-dione. Les huiles contiennent de 30 à 53 % de composés polaires. La teneur en ALC est comprise entre 0,4 et 0,5 %. Les 18:2 delta9,11 et 10,12 sont les isomères majoritaires. Les isomères géométriques di-trans représentent environ 50 % des isomères conjugués de l'acide linoléique. Mots ARTICLEFish oils are an important source of polyunsaturated fatty acids (PUFA) and are now widely used in health and nutrition [1][2]. For a long time, these molecules were shown to be of great importance in the prevention of a number of diseases such as inflammation, hypotriglyceridemic effect, allergies, diabetes or coronary heart disease [3][4][5][6]. Up until now, enzymatic methods for concentration of n-3 fatty acids have been used and several lipases have been studied and optimised in a number of reactions (hydrolysis, esterification, transesterification) [7][8][9][10][11][12]. Membrane filtration has proven valuable for the deacidification and degumming of oil, and is also a promising means fo...

show abstract

Purification of docosahexaenoic acid from tuna oil by a two‐step enzymatic method: Hydrolysis and selective esterification

Cited by 67 publications

References 16 publications

Upgrading of Farmed Salmon Oil Through Lipase-Catalyzed Hydrolysis

Upgrading of Farmed Salmon Oil Through Lipase-Catalyzed Hydrolysis

Lipase selectivity toward fatty acids commonly found in fish oil

Conjugated linoleic acid (CLA) isomers in heat-treated vegetable oils

Contact Info

Product

Resources

About