Preparation of highly purified pinolenic acid from pine nut oil using a combination of enzymatic esterification and urea complexation

No, Da Som; Zhao, Ting; Kim, Yangha; Yoon, Mi Ra; Lee, Jeom Sig; Kim, In Hwan

doi:10.1016/j.foodchem.2014.08.074

Cited by 29 publications

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“…Palmitic acid (16:0) and stearic acid (18:0) represent the major SFAs in PNO (Ryan et al, 2006;Zadernowski et al, 2009). Figure 1 shows a gas chromatogram profile of the fatty acids present in the oil of P. sibirica demonstrating the presence and relative abundance of palmitic acid, oleic acid, linoleic acid, and PNLA.The content of PNLA in oil from P. koraiensis has been markedly enriched up to 45% of fatty acids by Lee, Lee, Lee, Kim, and Rhee (2004) and to > 99% of fatty acids by No et al(2015) by controlled enzymatic and chemical treatments of the oil.…”

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confidence: 99%

A review of the potential health benefits of pine nut oil and its characteristic fatty acid pinolenic acid

Xie

Miles

Calder

2016

Journal of Functional Foods

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Pine nuts contain pinolenic acid (PNLA) which represents14-19% of fatty acids present. Here we review research on pine nut oil (PNO) and PNLA from studies performed in vitro, in animal models and in humans. PNLA has anti-inflammatory action and may improve lymphocyte function. PNO and PNLA have favourable effects on appetite control, perhaps by increasing the blood concentrations of key satiety hormones. Less weight gain and fat deposition were observed in mice fed with high fat diets containing PNO. In vitro research demonstrated that PNLA is a potent dual agonist for co-activation of free fatty acid receptor 1 and4, which could enhance glucose-dependent insulin secretion and insulin sensitivity. PNO increased the activity of antioxidant protective enzymes in serum and decreased the concentration of malondialdehyde, an indicator of lipid peroxidation. Thus, PNLA and its parent PNO could be of potential benefit to human health, although this requires further investigation. KEY WORDSPinolenic acid; P. koraiensis; P. sibirica; pine nut oil; health 1.1 INTRODUCTIONPine nuts have a range of culinary uses in many parts of the world. Pine nuts come from the Pinus genus and 29 species have been listed as having edible nuts by the Food and Agriculture Organization of the United Nations (FAO) (FAO, 2015). Pine nuts derived from Pinus koraiensis (Korean pine), P. sibirica (Siberian pine), P. pinea (stone pine) and P. gerardiana (chilgoza pine) are most commonly consumed by humans (Destaillats, Cruz-Hernandez, Giuffrida, and Dionisi, 2010). The nuts are usually 9-12 mm long (Zadernowski, Naczk, and Czaplicki, 2009) and have a high oil content (see section 2). The oil is rich in fatty acids including Δ5-unsaturated polymethylene-interrupted fatty acids (Δ5-UPIFAs), which are characteristic of the seeds of gymnosperms and differ from the structure of other polyunsaturated fatty acids (PUFAs). Pinolenic acid (PNLA; all cis-5, -9, -12-18:3) is the major Δ5-UPIFA in pine nuts and their oil (Wolff and Bayard, 1995). Other Δ5-UPIFAs in pine nut oils (PNO) are sciadonic acid (all cis-5, -11, -14-20:3) and taxoleic acid (all cis-5, -9-18:2) (Destaillats et al., 2010). The potential influence of PNOs and their characteristic fatty acid constituent, PNLA, on physiological and health related outcomes has been assessed in a number of research studies, mainly performed in vitro and in experimental animals. The aim of this review is for the first time to collate, summarize and discuss the research findings with PNO and PNLA. Only research with Korean or Siberian PNO is considered.

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confidence: 99%

A review of the potential health benefits of pine nut oil and its characteristic fatty acid pinolenic acid

Xie

Miles

Calder

2016

Journal of Functional Foods

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“…A method previously used to extract bran oil and prepare MFAEs was used in this study, with slight modifications [18]. Briefly, FMB oil was extracted using tetrane as a solvent.…”

Section: Sub-critical Fluid Extraction (Sfe) Of Bran Oil and Preparation Of Mixed Fatty Acid Ethyl Esters (Mfaes)mentioning

confidence: 99%

“…UC was performed following a previously described procedure with slight modifications [18]. Briefly, the bran oil ethyl ester was mixed with different amounts of ureasaturated 95% aqueous ethanol and fluxed until a homogenous solution was obtained.…”

Section: Ela Enrichment By Ucmentioning

confidence: 99%

Purification of Ethyl Linoleate from Foxtail Millet (Setaria italica) Bran Oil via Urea Complexation and Molecular Distillation

Huang

Yana

Hou

2021

Foods

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Foxtail millet (Setaria italica) bran oil is rich in linoleic acid, which accounts for more than 60% of its lipids. Ethyl linoleate (ELA) is a commercially valuable compound with many positive health effects. Here, we optimized two ELA processing steps, urea complexation (UC) and molecular distillation (MD), using single-factor and response surface analyses. We aimed to obtain a highly concentrated ELA at levels that are permitted by current regulations. We identified the optimal conditions as follows: 95% ethanol-to-urea ratio = 15:1 (w/w), urea-to-fatty acid ratio = 2.5:1 (w/w), crystallization time = 15 h, and crystallization temperature = −6 °C. Under these optimal UC conditions, ELA concentration reached 45.06%. The optimal MD purification conditions were established as follows: distillation temperature = 145 °C and vacuum pressure = 1.0–5.0 × 10−2 mbar. Under these conditions, ELA purity increased to 60.45%. Together, UC and MD were effective in improving the total concentration of ELA in the final product. This work shows the best conditions for separating and purifying ELA from foxtail millet bran oil by UC and MD.

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“…However, owing to the use of urea, further procedures, including acidification and extraction, are required to recover PLA from the filtrate. Alternatively, PLA concentrates can be prepared enzymatically from pine nut oil or FFA mixtures from the oil 6,8 . These enzymatic reactions involve the use of lipases that have positional specificity or selectivity toward specific FA.…”

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confidence: 99%

“…The Candida antarctica lipase B-catalyzed ethanolysis of pine nut oil, in which most PLA found in the oil is esterified at the sn-3 position, is a possible approach to prepare PLA concentrates because the lipase has specificity toward FA in the sn-3 position of triacylglycerols TAG in the presence of ethanol 6,7 . No et al 8 used a Candida rugosa lipase, which has specificity toward unsaturated FA USFA with a double bond at the Δ9 carbon, including oleic 18:1n-9 and linoleic acids 18:2n-6 , to prepare PLA concentrates by esterification of FFA mixtures obtained from pine nut oil. The lipase-catalyzed reaction leads to the elimination of 18:2n-6 and 18:1n-9, which are the two principal FA in the FFA mix-tures from the oil, thereby enriching PLA.…”

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Preparation of Pinolenic Acid Concentrates from Pine Nut Oil Fatty Acids by Solvent Fractionation

Chung

Kim

2018

J. Oleo Sci.

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INTRODUCTION Pinolenic acid PLA; c5,c9,c12-18:3 is a polyunsaturated fatty acid PUFA with a polymethylene-interrupted double bond at the Δ5 carbon. PLA is exclusively found in the oils of the edible nuts of pines, such as Siberian pine nut Pinus sibirica; PLA content, 19 wt and Korean pine nut P. koraiensis; PLA content, 14 wt 1. PLA intake is effective for reducing body weight because PLA provides an appetite-suppression effect derived from the increased secretion of gut satiety hormones, such as cholecystokinin-8 and glucagon-like peptide-1 in humans 1 3. Recently, interest in methods for preparing PLA concentrates has increased owing to the health benefits of PLA. PLA concentrates can be prepared using physical methods 4, 5 , enzymatic reactions 6, 7 , or both 8. Urea crystallization is the most common physical method for preparaing PLA concentrates 4, 5, 8. Using urea crystallization, PLA concentrates can be prepared from free fatty acid FFA mixtures obtained from pine nut oil because fatty acids FA that are more saturated than PLA form crystals with

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Preparation of highly purified pinolenic acid from pine nut oil using a combination of enzymatic esterification and urea complexation

Cited by 29 publications

References 37 publications

A review of the potential health benefits of pine nut oil and its characteristic fatty acid pinolenic acid

A review of the potential health benefits of pine nut oil and its characteristic fatty acid pinolenic acid

Purification of Ethyl Linoleate from Foxtail Millet (Setaria italica) Bran Oil via Urea Complexation and Molecular Distillation

Preparation of Pinolenic Acid Concentrates from Pine Nut Oil Fatty Acids by Solvent Fractionation

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