Enhancement of Oxidative Stability of Perilla Seed Oil by Blending It with Other Vegetable Oils.

Perilla seed oil is mainly composed of omega-3 fatty acid (α-linolenic acid, ALA). Despite being nutritionally favorable and rich in unsaturated fatty acids, its low oxidative stability limits its application in food. Thus, the present study aimed to formulate a stable oil blend using perilla seed oil with selected vegetable oil of higher stability characteristics and balance the ratio of the fatty acids. Hence, improving the nutritional and functional value of the blended oil. Perilla seed oil was blended with different edible oil (palm olein, coconut oil, and groundnut oil) in ratios of 20:80 and 30:70. All the blended oils were studied for their fatty acid composition, physicochemical properties, oxidative stability, and nutritional quality index. It was found that perilla seed oil blended with saturated oil like palm olein had improved physicochemical properties and oxidative stability (0.5 h to 6.5 h). The fatty acids ratio of perilla and palm olein blends was close to the recommended value given by the World health organization (WHO). The nutritional quality indices (atherogenic index, the thrombogenic index, and hypocholesterolemic: hypercholesterolemic ratio) of blended oil were also improved compared to the individual oils.

Perilla seed oil in combination with nobiletin-rich ponkan powder enhances cognitive function in healthy elderly Japanese individuals: a possible supplement for brain health in the elderly.

Perilla (Perilla frutescens) seed oil (PO), rich in α-linolenic acid (ALA), can improve cognitive function in healthy elderly Japanese people. Here, supplements containing either PO alone or PO with nobiletin-rich air-dried immature ponkan powder were examined for their effects on cognitive function in 49 healthy elderly Japanese individuals. Patients were enrolled in a 12-month randomized, double-blind, parallel-armed study. Randomized participants in the PO group received soft gelatin capsules containing 1.47 mL (0.88 g of ALA) of PO daily, and those in the PO + ponkan powder (POPP) group received soft gelatin capsules containing both 1.47 mL of PO and 1.12 g ponkan powder (2.91 mg of nobiletin) daily. At the end of intervention, the POPP group showed significantly higher cognitive index scores than the PO group. The pro-cognitive effects of POPP treatment were accompanied by increases in ALA and docosahexaenoic acid levels in red blood cell plasma membranes, serum brain-derived neurotropic factor (BDNF) levels, and biological antioxidant potential. We demonstrate that 12-month intervention with POPP enhances serum BDNF and antioxidant potential, and may improve age-related cognitive impairment in healthy elderly people by increasing red blood cell ω-3 fatty acid levels. Clinical Trial Registry, UMIN000040863.

Anti-oxidative and anti-hyperglycemic properties of Agastache foeniculum essential oil and oily fraction in hyperglycemia-stimulated and lipopolysaccharide-stimulated macrophage cells: In vitro and in silico studies.

ETHNOPHARMACOLOGICAL RELEVANCE: Hyperglycemia (HG) and lipopolysaccharide (LPS) often promote superoxide accumulation, which may increase oxidative stress. Reducing superoxide production in hyperglycemia and the inflammatory condition is an emerging way to reduce protein and lipid oxidation and diabetes complication. AIM OF STUDY: To examine the effect of Agastache foeniculum essential oil (AFEO) and oil fraction (AFoil) on HG- and LPS-stimulated oxidative stress, the pathogenicity of AFEO and AFoil on oxidative stress was assessed. METHODS: The stimulatory effects of AFEO and AFoil on the activity and expression of NADH oxide (NOX), catalase (CAT), superoxide dismutase (SOD), and the expression of nuclear respiratory factor 2 (NRF2) and nuclear factor-kappa B (NF-kB) in the stimulated macrophage cell line, J774.A1, was studied. The interaction patterns of AFEO and AFoil components with NOX, SOD, CAT, NRF2, and NF-kB proteins were also deduced using molecular docking. RESULTS: Estragole was the main ingredient in AFEO (97%). Linolenic acid (32.10%), estragole (16.22%), palmitic acid (12.62%), linoleic acid (12.04%), and oleic acid (8.73%) were the major chemical components of the AFoil. NOX activation was stimulated in macrophage cells by HG and LPS. At 20 µg/mL, AFEO and AFoil decreased NOX activity while increased SOD and CAT activities in stimulated macrophages. AFoil with estragole and omega-3 fatty acids was better than AFEO with estragole in anti-hyperglycemic and anti-oxidative activity. According to molecular docking research, estragole, linoleic acid, and linolenic acid bind to different hydrophobic pockets of NOX, SOD, CAT, NFR2, and NF-kB using hydrogen bonds, van der Waals bonds, pi-alkyl, and pi-anion interactions, with different binding energies. CONCLUSION: AFEO and AFoil showed antioxidant and anti-diabetic activity. The mechanisms in lowering oxidative stress markers depended on down-regulating superoxide-producing enzymes and up-regulating superoxide-removing enzymes at gene and protein levels. The AFoil emulsion can be used to reduce the detrimental impacts of hyperglycemia and oxidative stress.

Molecular Mechanism of Antioxidant and Anti-Inflammatory Effects of Omega-3 Fatty Acids in Perilla Seed Oil and Rosmarinic Acid Rich Fraction Extracted from Perilla Seed Meal on TNF-α Induced A549 Lung Adenocarcinoma Cells.

Industrially, after the removal of oil from perilla seeds (PS) by screw-type compression, the large quantities of residual perilla seed meal (PSM) becomes non-valuable waste. Therefore, to increase the health value and price of PS and PSM, we focused on the biological effects of perilla seed oil (PSO) and rosmarinic acid-rich fraction (RA-RF) extracted from PSM for their role in preventing oxidative stress and inflammation caused by TNF-α exposure in an A549 lung adenocarcinoma culture model. The A549 cells were pretreated with PSO or RA-RF and followed by TNF-α treatment. We found that PSO and RA-RF were not toxic to TNF-α-induced A549 cells. Both extracts significantly decreased the generation of reactive oxygen species (ROS) in this cell line. The mRNA expression levels of IL-1ß, IL-6, IL-8, TNF-α, and COX-2 were significantly decreased by the treatment of PSO and RA-RF. The Western blot indicated that the expression of MnSOD, FOXO1, and NF-κB and phosphorylation of JNK were also significantly diminished by PSO and RA-RF treatment. The results demonstrated that PSO and RA-RF act as antioxidants to scavenge TNF-α induced ROS levels, resulting in decreased the expression of MnSOD, FOXO1, NF-κB and JNK signaling pathway in a human lung cell culture exposed to TNF-α.

Chemical Characterization of Chinese Perilla Seed Oil.

Physicochemical properties and chemical composition of Chinese perilla seed oil has been characterized in this study. The result showed that both the cold press oil and the solvent extracted oil possessed low acid value and peroxide value. The fatty acid composition result showed that the oil has high content of linolenic acid (C18:3) up to 66.4 g/100 g, followed by linoleic acid (C18:2) of 15.3 g/100 g. The total triacylglycerol (TAG) profiles results showed that the oil contained 20 TAGs including 17 regioisomers, including LnLnLn (35.8 g/100 g), LLnLn (20.2 g/100 g), LLLn (17.7 g/100 g) and PLnLn (14.9 g/100 g) (Ln, linolenic acid; L, linoleic acid; P, palmitic acid). With content of only 0.57 g/100 g oil, the unsaponifiable matters were mainly composed of phytosterols, squalene, tocopherol, alcohols and hydrocarbons. The total phytosterols content was 0.39 g/100 g oil, in which ß-sitosterol has high content of 0.31 g/100 g oil.

Dietary intake of n-3 polyunsaturated fatty acids alters the lipid mediator profile of the kidney but does not attenuate renal insufficiency.

The efficacy of n-3 polyunsaturated fatty acids (PUFAs) in improving outcomes in a renal ischemia-reperfusion injury (IRI) model has previously been reported. However, the underlying mechanisms remain poorly understood and few reports demonstrate how dietary n-3 PUFAs influence the composition of membrane phospholipids in the kidney. Additionally, it has not been elucidated whether perilla oil (PO), which is mainly composed of the n-3 alpha-linolenic acid, mitigates renal IRI. In this study, we investigated the effect of dietary n-3 PUFAs (PO), compared with an n-6 PUFA-rich soybean oil (SO) diet, on IRI-induced renal insufficiency in a rat model. Levels of membrane phospholipids containing n-3 PUFAs were higher in the kidney of PO-rich diet-fed rats than the SO-rich diet-fed rats. Levels of blood urea nitrogen and serum creatinine were significantly higher in the ischemia-reperfusion group than the sham group under both dietary conditions. However, no significant differences were observed in blood urea nitrogen, serum creatinine, or histological damage between PO-rich diet-fed rats and SO-rich diet-fed rats. In the kidney of PO-rich diet-fed rats, levels of arachidonic acid and arachidonic acid-derived pro-inflammatory lipid mediators were lower than SO-rich diet-fed rats. Eicosapentaenoic acid and eicosapentaenoic acid-derived lipid mediators were significantly higher in the kidney of PO-rich than SO-rich diet-fed rats. These results suggest that dietary n-3 PUFAs alter the fatty acid composition of membrane phospholipids and lipid mediators in the kidney; however, this does not attenuate renal insufficiency or histological damage in a renal IRI model.

Effects of ethanol, activated carbon, and activated kaolin on perilla seed oil: Volatile organic compounds, physicochemical characteristics, and fatty acid composition.

Perilla seed oil (PSO) has a special aromatic odor, which is unpleasant to the personal preferences of some consumers. To this end, this article evaluated the differences in volatile organic compounds (VOCs), physicochemical characteristics, and fatty acid composition of PSO treated with ethanol (PSO-EA), activated carbon (PSO-AC), and activated kaolin (PSO-AK). The results showed that in the PSO, PSO-EA, PSO-AC, and PSO-AK samples, the content of linolenic acid, oleic acid, and linoleic acid hardly changed. Among the physicochemical characteristics of the four samples, the color difference between PSO and PSO-EA was greater than the color difference between PSO and PSO-AC, PSO-AK. The three treatment methods had the greatest impact on the PSO peroxide value but had little effect on other indicators. Gas chromatography-ion mobility spectrum results identified 28 known volatiles, of which aldehydes, alkenals, alcohols, ketones, and esters were the main groups. Fingerprint analysis found that PSO had an aromatic odor, which includes 1-hexanol, hexanal, and 2-pentylfuran; the removal effect of ethanol on VOCs in PSO was better than that of activated carbon and activated kaolin. The difference between the four oil samples was found from the strength of the VOCs' signals in a two-dimensional map. From the principal components analysis and the "nearest neighbor" fingerprint analysis, it was found that PSO is generally quite different from PSO-EA, PSO-AC, and PSO-AK, while in the "nearest neighbor" fingerprint analysis, PSO-AC and PSO-AK are similar in general. In short, PSO will have better applications in the food field. PRACTICAL APPLICATION: Treatment of PSO with ethanol, activated carbon, and activated kaolin is conducive to the comprehensive utilization of edible resources. In this work, ethanol, activated carbon, and activated kaolin were used to remove VOCs in PSO, and PSO-EA, PSO-AC, and PSO-AK were obtained. The perilla seed oil after these three treatment methods was tested for VOCs, physicochemical characteristics, and fatty acid composition. They can meet the needs of more consumers without affecting the fatty acid composition in the PSO, and have broad development prospects.

An alternative solution for α-linolenic acid supplements: in vitro digestive properties of silkworm pupae oil in a pH-stat system.

α-Linolenic acid (ALA) is recognised to have a regulatory effect on cardiovascular diseases. Due to the low bioavailability of linseed oil (LINO), which is the most common ALA supplement, it is necessary to find a replacement for ALA supplements that is more easily accepted by the human body. The content of ALA in silkworm pupae oil (SPO) is 32.60 ± 0.67%, and SPO can be substituted as a dietary lipid to meet the demand of the human body. In the present study, a pH-stat system was used to investigate the release degree of free fatty acids (FFAs) from SPO and construct a first-order kinetic model. Digestion experiments in vitro with different lipids showed that the maximum release FFA levels were SPO > SO (soybean oil) > LO (lard oil) > MSO (mulberry seed oil) > LINO, and the first-order kinetic apparent rate constants were LINO > SPO > LO > SO > MSO. Triacylglycerol (TAG) and fatty acid composition are the decisive factors in determining the level of lipid digestion. Therefore, the maximum level of FFAs released from SPO (84.34 ± 1.37%) was much higher than that of LINO (49.78 ± 0.52%) when the hydrolysis rates were 0.2114 s-1 and 0.2249 s-1, respectively. In addition, the smaller emulsion droplet size (609.24 ± 43.46 nm) and weaker surface charge (-17.93 ± 0.42 mV) also resulted in higher levels of SPO under in vitro digestion conditions. Meanwhile, due to low melting and crystallisation temperature, SPO is quickly absorbed by the human body. Overall, SPO can be used as a new alternative for ALA supplements based on its superior digestive properties.

Effect of nanoemulsion particle size on the bioavailability and bioactivity of perilla oil in rats.

The aim of this study was to investigate the bioavailability and bioactivity of perilla (Perilla frutescens) oil nanoemulsions prepared at different homogenization pressures by measuring the weight, fatty acid profile, and antioxidant and anti-inflammatory properties in rats. The high-pressure homogenization significantly reduced the particle size of perilla oil nanoemulsions and enhanced their stability, and the minimum particle size was 293.87 ± 6.55 nm at 120 MPa. There was an increase in the weight and fatty acid levels in the plasma and liver of test group rats. The highest glutathione (GSH) and the lowest malondialdehyde (MDA) levels of 18.76 ± 10.51 mg GSH/g prot and 20.27 ± 2.46 nmol/mg prot, respectively, were recorded in rats administrated perilla oil nanoemulsions prepared at 120 MPa. However, there was no significant difference in superoxide dismutase activity (SOD) between the groups. The interferon-gamma (IL-γ), interleukin-1 beta (IL-1ß), IL-6 (interleukin-6), and IL-8 (interleukin-8) levels in the test groups were lower than those in the blank and control groups at 8 hr after lipopolysaccharide injection. The IL-1ß, IL-6, and IL-8 levels were 49.52 ± 14.06, 90.13 ± 6.04, and 419.71 ± 32.03 ng/L, respectively, in rats treated with perilla oil nanoemulsions prepared at 120 MPa. Both perilla oil and its nanoemulsions decreased estradiol levels and damaged the ovaries. Overall, our findings show that the test nanoemulsions enhanced the bioavailability of perilla oil, which resulted in enhanced antioxidant and anti-inflammatory responses; thus, we provide a new approach to deliver perilla oil. PRACTICAL APPLICATION: Nanoemulsions can be used to deliver drugs and bioactive compounds, and perilla oil nanoemulsions can be used in healthcare products and beverage industries.

Rapeseed Lecithin Increases Lymphatic Lipid Output and α-Linolenic Acid Bioavailability in Rats.

BACKGROUND: Soybean lecithin, a plant-based emulsifier widely used in food, is capable of modulating postprandial lipid metabolism. With arising concerns of sustainability, alternative sources of vegetal lecithin are urgently needed, and their metabolic effects must be characterized. OBJECTIVES: We evaluated the impact of increasing doses of rapeseed lecithin (RL), rich in essential α-linolenic acid (ALA), on postprandial lipid metabolism and ALA bioavailability in lymph-cannulated rats. METHODS: Male Wistar rats (8 weeks old) undergoing a mesenteric lymph duct cannulation were intragastrically administered 1 g of an oil mixture containing 4% ALA and 0, 1, 3, 10, or 30% RL (5 groups). Lymph fractions were collected for 6 h. Lymph lipids and chylomicrons (CMs) were characterized. The expression of genes implicated in intestinal lipid metabolism was determined in the duodenum at 6 h. Data was analyzed using either sigmoidal or linear mixed-effects models, or one-way ANOVA, where appropriate. RESULTS: RL dose-dependently increased the lymphatic recovery (AUC) of total lipids (1100 µg/mL·h per additional RL%; P = 0.010) and ALA (50 µg/mL·h per additional RL%; P = 0.0076). RL induced a faster appearance of ALA in lymph, as evidenced by the exponential decrease of the rate of appearance of ALA with RL (R2 = 0.26; P = 0.0064). Although the number of CMs was unaffected by RL, CM diameter was increased in the 30%-RL group, compared to the control group (0% RL), by 86% at 3-4 h (P = 0.065) and by 81% at 4-6 h (P = 0.0002) following administration. This increase was positively correlated with the duodenal mRNA expression of microsomal triglyceride transfer protein (Mttp; ρ= 0.63; P = 0.0052). The expression of Mttp and secretion-associated, ras-related GTPase 1 gene homolog B (Sar1b, CM secretion), carnitine palmitoyltransferase IA (Cpt1a) and acyl-coenzyme A oxidase 1 (Acox1, beta-oxidation), and fatty acid desaturase 2 (Fads2, bioconversion of ALA into long-chain n-3 PUFAs) were, respectively, 49%, 29%, 74%, 48%, and 55% higher in the 30%-RL group vs. the control group (P < 0.05). CONCLUSIONS: In rats, RL enhanced lymphatic lipid output, as well as the rate of appearance of ALA, which may promote its subsequent bioavailability and metabolic fate.

Intake of Alpha-Linolenic Acid-Rich Perilla frutescens Leaf Powder Decreases Home Blood Pressure and Serum Oxidized Low-Density Lipoprotein in Japanese Adults.

Oxidized low-density lipoprotein (Ox-LDL) is known to be highly atherogenic. Thus, decreasing the blood levels of Ox-LDL through dietary means is an important approach to reduce cardiovascular events in high-risk individuals. In this randomized placebo-controlled human interventional trial, we aimed to evaluate whether Perilla frutescens leaf powder (PLP) ameliorates Ox-LDL and home blood pressure, along with its biological antioxidant potential. Healthy Japanese volunteers aged 30-60 years (n = 60) were randomized to PLP and placebo groups. The PLP group consumed PLP dried using a microwave under reduced pressure, and the placebo group consumed pectin fiber daily for 6 months. Home blood pressure, serum biochemical parameters, and fatty acid profiles of erythrocyte plasma membranes were analyzed. Plasma Ox-LDL levels significantly decreased in the PLP group but not in the placebo group. Mean changes in the biological antioxidant potential and alpha-linolenic acid levels in the erythrocyte plasma membrane were significantly increased in the PLP group than in the placebo group. In subjects with prehypertension (systolic blood pressure [SBP] ³ 120 mmHg), the mean reduction in morning or nocturnal SBP was significantly greater in the PLP group than in the placebo group. Thus, PLP intake may be an effective intervention to prevent cardiovascular diseases.

Flaxseed for Health and Disease: Review of Clinical Trials.

BACKGROUND: Flaxseed (Linum usitatissimum) is an oil-based seed that contains high amounts of alpha-linolenic acid, linoleic acid, lignans, fiber and many other bioactive components which is suggested for a healthier life. Nowadays, flaxseed is known as a remarkable functional food with different health benefits for humans and protects against cardiovascular disease, diabetes, dyslipidemia, obesity and altogether metabolic syndrome. METHODS: To review the bioactive components of flaxseed and their potential health effects, PubMed and Scopus were searched from commencement to July 2019. Keywords including: "flaxseed", "Linum usitatissimum", "metabolic syndrome", "obesity", "inflammation", "insulin resistance", "diabetes", "hyperlipidemia" and "menopause" were searched in the databases with varying combinations. CONCLUSION: Consumption of flaxseed in different forms has valuable effects and protects against cardiovascular disease, hypertension, diabetes, dyslipidemia, inflammation and some other complications. Flaxseed can serve as a promising candidate for the management of metabolic syndrome to control blood lipid levels, fasting blood sugar, insulin resistance, body weight, waist circumference, body mass and blood pressure.

Lipase catalysis of α-linolenic acid-rich medium- and long-chain triacylglycerols from perilla oil and medium-chain triacylglycerols with reduced by-products.

BACKGROUND: Medium- and long- chain triacylglycerols (MLCTs) are functional structural lipids that can provide the human body with essential fatty acids and a faster energy supply. This study aimed to prepare MLCTs rich in α-linolenic by enzymatic interesterification of perilla oil and medium-chain triacylglycerols (MCTs), catalyzed by Lipozyme RM IM, Lipozyme TL IM, Lipozyme 435, and Novozyme 435 respectively. RESULTS: The effects of lipase loading, concentration of MCTs, reaction temperature, and reaction time on the yield of MLCTs were investigated. It was found that the reaction achieved more than a 70% yield of MLCTs in triacylglycerols under the conditions of 400 g kg-1 MCTs and 60 g kg-1 lipase loading after equilibrium. A novel two-stage deodorization was also applied to purify the interesterification products. The triacylglycerols reach over 97% purity in the products with significant removal (P < 0.05) of the free fatty acids, and the trans fatty acids were strictly controlled at below 1%. There was more than 40% α-linolenic in the purified products, with long-chain fatty acids mostly occupying the desired sn-2 position in acylglycerols, which are more active in hydrolysis. CONCLUSION: A series of novel α-linolenic acid-rich medium- and long-chain triacylglycerols was prepared. Under appropriate reaction conditions, the yield of MLCTs in triacylglycerols was above 70%. A novel two-stage deodorization can be used to promote the elimination of free fatty acids and limit the generation of trans fatty acids. © 2020 Society of Chemical Industry.

Influence of refining processes on the bioactive composition, in vitro antioxidant capacity, and their correlation of perilla seed oil.

The effect of chemical refining process on the bioactive composition, in vitro antioxidant capacity, and their correlation of perilla seed oil (PSO) were investigated. In this paper, seven samples corresponding to each step of the refining process (degumming, neutralization, bleaching, deodorization, winterization, crude, and refined oils) were studied. The results showed that phenolic compounds and tocopherols were removed from PSO to a degree of 19.4% and 5.4%, respectively. In addition, the carotenoid content of PSO decreased during the refining process. The main carotenoid of PSO was found to be lutein, and the compound was lost completely during the bleaching step of the refining process. In this paper, we analyzed the variation of carotenoid content in PSO during the refining process for the first time. Neutralization affected the contents of phytosterols the most, followed by the effects of degumming and bleaching. The demonstrated results of Pearson product-moment correlation indicated that total tocopherols were significantly correlated with the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and oxygen radical absorption capacity (ORAC) values, whereas carotenoids were significantly correlated with the DPPH value. However, phenolic compounds and phytosterols have no significant difference with DPPH, 2,2'-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt, ORAC, and ferric reducing antioxidant power values. The collected information can be applied to seeking out optimum factors needed to suffice the fundamental requirements for PSO production and minimize micronutrient losses to enhance its market value. PRACTICAL APPLICATION: The present study aimed to determine influence of chemical refining in the bioactive composition of perilla seed oil (PSO) as well as its antioxidant capacity in vitro. Moreover, we also intend to find the correlation between them. Results indicated that this study supplies a good reference for the industrial parameters of the refining process to minimize micronutrient losses and further obtain high-quality PSO products for consumers.

Therapeutic Effects of Cold-Pressed Perilla Oil Mainly Consisting of Linolenic acid, Oleic Acid and Linoleic Acid on UV-Induced Photoaging in NHDF Cells and SKH-1 Hairless Mice.

Positive physiological benefits of several plant oils on the UV-induced photoaging have been reported in some cell lines and model mice, but perilla oil collected from the seeds of Perilla frutescens L. has not been investigated in this context. To study the therapeutic effects of cold-pressed perilla oil (CPO) on UV-induced photoaging in vitro and in vivo, UV-induced cellular damage and cutaneous photoaging were assessed in normal human dermal fibroblasts (NHDFs) and HR-1 hairless mice. CPO contained five major fatty acids including linolenic acid (64.11%), oleic acid (16.34%), linoleic acid (11.87%), palmitic acid (5.06%), and stearic acid (2.48%). UV-induced reductions in NHDF cell viability, ROS production, SOD activity, and G2/M cell cycle arrest were remarkably improved in UV + CPO treated NHDF cells as compared with UV + Vehicle treated controls. Also, UV-induced increases in MMP-1 protein and galactosidase levels were remarkably suppressed by CPO. In UV-radiated hairless mice, topical application of CPO inhibited an increase in wrinkle formation, transepidermal water loss (TEWL), erythema value, hydration and melanin index on dorsal skin of UVB-irradiated hairless mice. CPO was observed to similarly suppress UV-induced increases in epidermal thickness, mast cell numbers, and galactosidase and MMP-3 mRNA levels. These results suggest CPO has therapeutic potential in terms of protecting against skin photoaging by regulating skin morphology, histopathology and oxidative status.

Synthesis and application of novel silver magnetic amino silicone adhesive particles for preparation of high purity α-linolenic acid from tree peony seed oil under applied magnetic field.

Silver magnetic amino silicone adhesive (Fe3O4@SiO2@NH2@Ag) particles were prepared for the purification of α-linolenic acid from tree peony seed oil under applied magnetic field. First, Fe3O4@SiO2@NH2@Ag particles were prepared and physicochemically characterized, including XRD, TG, FTIR, SEM, magnetic hysteresis curves and elemental analysis. The static process for the purification of α-linolenic acid using Fe3O4@SiO2@NH2@Ag particles was investigated, including adsorption curve, desorption curve, elution solvent composition and adsorption isotherm. The result indicated that 0-1-4% acetone-n-hexane elution solvent was selected for the gradient elution process, 2 h and 60 min were the time required to reach adsorption and desorption equilibrium, 20 °C was selected as the adsorption temperature, Langmuir model was suitable to fit and explain the equilibrium data, and the adsorption process was spontaneous and exothermic. Under applied magnetic field, the dynamic process for the purification of α-linolenic acid using Fe3O4@SiO2@NH2@Ag particles was investigated, and the optimum conditions were 20:1 µL/g loading amount, 0.5 mL/min flow rate and 51.73 Oe magnetic field intensity. After purification, the purity and recovery ratio of α-linolenic acid were calculated to be 94% and 74%, respectively. Furthermore, the recycled Fe3O4@SiO2@NH2@Ag particles still achieved better purification result. Therefore, the developed method shows a good application prospect in the field of separation and purification of α-linolenic acid.

Comparison of Furans Formation and Volatile Aldehydes Profiles of Four Different Vegetable Oils During Thermal Oxidation.

The evolution of volatile aldehydes and the conversion of oxygenated ityß-unsaturated aldehydes (OαßUAs) into furans were compared in four vegetable oils (soybean oil, olive oil [OVO], peanut oil [PO], and perilla oil [PAO]) thermally oxidized at temperatures of 150, 180, and 210 °C for 10 hr/day over a 3-day period. Results showed that 2 alkyl furans and 23 volatile aldehydes including 4 toxic OdßUAs were detected by GC-MS. The original fatty acid compositions of the oils played a key role in the type and concentration of those volatile compounds. 4-Hydroxy-2-hexenal (HHE) and ethyl furan were only detected in PAO with a high content of linolenic acid, while the greatest level of pentyl furan was detected in PO with abundant linoleic acid. Greater amounts of 4-hydroxy-(E)-2-nonenal (HNE) and 4-oxo-(E)-2-nonenal (ONE) were formed in the OVO with abundant oleic acid. The close relativity of HHE and ethyl furan was also demonstrated. With principal component analysis, these vegetable oils could be discriminated based on their fatty acids and volatile compounds. The loading plot confirmed that HHE and ethyl furan were derived from the linolenic acid oxidation and degradation. PRACTICAL APPLICATION: The chemometric results showed that the formation of the volatile components during heating in different vegetable oils has close correlation with the original fatty acids composition of vegetable oils. Our research has also confirmed the presence of toxic OɑßUAs in oils after heating. Considering that they are proven to generate lots of degenerative diseases, further studies are needed to establish the risk level of using certain oils in frying and seek effective methods to inhibit their formation.

Preparative and scaled-up separation of high-purity α-linolenic acid from perilla seed oil by conventional and pH-zone refining counter current chromatography.

α-Linolenic acid is an essential omega-3 fatty acid needed for human health. However, the isolation of high-purity α-linolenic acid from plant resources is challenging. The preparative separation methods of α-linolenic acid by both conventional and pH-zone refining counter current chromatography were firstly established in this work. The successful separation of α-linolenic acid by conventional counter current chromatography was achieved by the optimized solvent system n-heptane/methanol/ water/acetic acid (10:9:1:0.04, v/v), producing 466 mg of 98.98% α-linolenic acid from 900 mg free fatty acid sample prepared from perilla seed oil with linoleic acid and oleic acid as by-products. The scaled-up separation in 45× is efficient without loss of resolution and extension of separation time. The separation of α-linolenic acid by pH-zone refining counter current chromatography was also satisfactory by the solvent system n-hexane/methanol/water (10:5:5, v/v) and the optimized concentration of trifluoroacetic acid 30 mM and NH4 OH 10 mM. The separation can be scaled up in 180× producing 9676.7 mg of 92.79% α-linolenic acid from 18 000 mg free fatty acid sample. pH-zone refining counter current chromatography exhibits a great advantage over conventional counter current chromatography with 20× sample loading capacity on the same column.

Thermal stability and bioavailability of inclusion complexes of perilla oil with γ-cyclodextrin.

Perilla oil is abundant in α-linolenic acid, which is metabolized to long-chain n-3 fatty acids. This study aimed to determine thermal stability and bioavailability of perilla oil that was powdered by inclusion complexation with γ-cyclodextrin. Fatty acid analysis revealed that the relative abundance of α-linolenic and linoleic acids in the complexes was not affected by heating at 40 °C for six days but decreased after heating at 60 °C for three days. No adverse events occurred in rats fed with an experimental diet containing the complexes for two weeks. Plasma α-linolenic and eicosapentaenoic acids in rats fed with diets containing complexes and liquid perilla oil were equally high, indicating the preserved bioavailability of perilla oil in the complexes. Plasma arachidonic acid decreased only in rats fed with a diet containing the complexes. Results suggest that the complexes have potential as a useful source of α-linolenic acid to increase plasma n-3 fatty acids.

Fatty acid composition and quality properties of chicken sausage formulated with pre-emulsified perilla-canola oil as an animal fat replacer.

The potential use of an oil in water (o/w) emulsion made from perilla and canola oil in chicken sausage as an animal fat replacer was assessed. The (o/w) emulsion was made from 50% (wt/wt) perilla-canola oil mixture in a 30:70 ratio, 3.20% (wt/wt) polyglycerol polyricinoleate, 4.48% (wt/wt) soy protein isolate, 14% (wt/wt) inulin, and 28.32% (wt/wt) water. The sausages were manufactured with 60% (wt/wt) ground chicken breast, 20% (wt/wt) fat (beef tallow as a control), and 20% (wt/wt) ice water. Full replacement of animal fat with a perilla-canola oil (o/w) emulsion reduced the fat content and estimated calories but increased the moisture, protein, ash, and carbohydrate content. The proportion of α-linolenic acid (C18:3n3) was increased when animal fat was replaced with either a perilla-canola oil mixture or pre-emulsified perilla-canola oil, resulting in a lower n6 to n3 polyunsaturated fatty acid ratio than the control. The perilla-canola oil (o/w) emulsion improved emulsion stability and minimized cooking loss during sausage manufacturing. Higher L* value (lightness) and whiteness were observed in the sausages formulated with the perilla-canola oil mixture, followed by the pre-emulsified perilla-canola oil and the control. The perilla-canola oil (o/w) emulsion also increased the hardness but maintained an acceptable appearance, flavor, and overall impression similar to the control. The shelf life could be extended by vacuum packing and storing the cooked sausages formulated with a perilla-canola oil (o/w) emulsion for 30 D at 2 ± 1°C. Pre-emulsified perilla-canola oil could be used to replace animal fat in reduced-fat chicken sausage manufacture.