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1.
Food Res Int ; 186: 114355, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38729701

ABSTRACT

In this study, five C18 fatty acids (FA) with different numbers of double bonds and configurations including stearic acid (SA), oleic acid (OA), elaidic acid (EA), linoleic acid (LA), and α-linolenic acid (ALA), were selected to prepare highland barely starch (HBS)-FA complexes to modulate digestibility and elaborate the underlying mechanism. The results showed that HBS-SA had the highest complex index (34.18 %), relative crystallinity (17.62 %) and single helix content (25.78 %). Furthermore, the HBS-C18 FA complexes were formed by EA (C18 FA with monounsaturated bonds) that had the highest R1047/1022 (1.0509) and lowest full width at half-maximum (FWHM, 20.85), suggesting good short-range ordered structure. Moreover, all C18 FAs could form two kinds of V-type complexes with HBS, which can be confirmed by the results of CLSM and DSC measurements, and all of them showed significantly lower digestibility. HBS-EA possessed the highest resistant starch content (20.17 %), while HBS-SA had the highest slowly digestible starch content (26.61 %). In addition, the inhibition of HBS retrogradation by fatty acid addition was further proven, where HBS-SA gel firmness (37.80 g) and aging enthalpy value were the lowest, indicating the most effective. Overall, compounding with fatty acids, especially SA, could be used as a novel way to make functional foods based on HBS.


Subject(s)
Digestion , Fatty Acids , Hordeum , Oleic Acid , Starch , Starch/chemistry , Fatty Acids/analysis , Fatty Acids/chemistry , Hordeum/chemistry , Oleic Acid/chemistry , Stearic Acids/chemistry , Linoleic Acid/chemistry , alpha-Linolenic Acid/chemistry , Oleic Acids
2.
J Oleo Sci ; 73(5): 743-749, 2024.
Article in English | MEDLINE | ID: mdl-38692896

ABSTRACT

Conjugated fatty acids have anticancer effects. Therefore, the establishment of a synthetic method for conjugated fatty acids is important for overcoming cancer. Here, we attempted to synthesize conjugated fatty acids using enzymes extracted from seaweeds containing these fatty acids. Lipids from 12 species of seaweeds from the seas around Japan were analyzed, and Padina arborescens Holmes was found to contain conjugated fatty acids. Then, we synthesized parinaric acid, a conjugated tetraenoic acid, from α-linolenic acid using the enzyme of P. arborescens. This method is expected to have a variety of potential applications for overcoming cancer.


Subject(s)
alpha-Linolenic Acid , alpha-Linolenic Acid/chemistry , Seaweed/chemistry , Fatty Acids, Unsaturated/chemistry , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology
3.
Int J Biol Macromol ; 270(Pt 1): 132154, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38734331

ABSTRACT

Flaxseed oil, rich in α-linolenic acid, plays a crucial role in various physiological processes. However, its stability presents certain challenges. In this study, the natural lignin-carbohydrate complex (LCC) was used to prepare the physical and oxidative stability of flaxseed oil-in-water emulsions. The LCC was characterized by HPLC, GPC, and FT-IR. The stability of emulsions was evaluated by viscosity, modulus, and micro-morphology changes. Then, the oxidation products were monitored by UV-vis spectrophotometer and HPLC. The results revealed that the high internal phase emulsion (HIPE) was successfully prepared with 2.5 wt% LCC at an oil/water ratio of 75/25 (v/v). Small droplet size (13.361 µm) and high viscosity (36,500 mPa·s) were found even after 30-day storage. Steric interactions of the LCC play a crucial role in ensuring stability, intricately linked to the interfacial properties of the emulsion. Meanwhile, the oxidative stability of α-linolenic acid in the encapsulated flaxseed oil was significantly higher than that in the bulk flaxseed oil. The results revealed that the LCC as a suitable emulsifier opens a new window for the storage of functional lipids rich in polyunsaturated fatty acids.


Subject(s)
Emulsions , Lignin , Linseed Oil , Oxidation-Reduction , Water , Linseed Oil/chemistry , Emulsions/chemistry , Lignin/chemistry , Water/chemistry , Viscosity , Carbohydrates/chemistry , alpha-Linolenic Acid/chemistry , Particle Size
4.
J Agric Food Chem ; 72(11): 5503-5525, 2024 Mar 20.
Article in English | MEDLINE | ID: mdl-38442367

ABSTRACT

Conjugated linoleic acid (CLA) has been extensively characterized due to its many biological activities and health benefits, but conjugated linolenic acid (CLnA) is still not well understood. However, CLnA has shown to be more effective than CLA as a potential functional food ingredient. Current research has not thoroughly investigated the differences and advantages between CLnA and CLA. This article compares CLnA and CLA based on molecular characteristics, including structural, chemical, and metabolic characteristics. Then, the in vivo research evidence of CLnA on various health benefits is comprehensively reviewed and compared with CLA in terms of effectiveness and mechanism. Furthermore, the potential of CLnA in production technology and product protection is analyzed. In general, CLnA and CLA have similar physicochemical properties of conjugated molecules and share many similarities in regulation effects and pathways of various health benefits as well as in the production methods. However, their specific properties, regulatory capabilities, and unique mechanisms are different. The superior potential of CLnA must be specified according to the practical application patterns of isomers. Future research should focus more on the advantageous characteristics of different isomers, especially the effectiveness and safety in clinical applications in order to truly exert the potential value of CLnA.


Subject(s)
Food Ingredients , Linoleic Acids, Conjugated , alpha-Linolenic Acid/chemistry , Linoleic Acids, Conjugated/chemistry , Isomerism , Functional Food
5.
J Agric Food Chem ; 71(19): 7324-7333, 2023 May 17.
Article in English | MEDLINE | ID: mdl-37130169

ABSTRACT

Modern people generally suffer from α-linolenic acid (ALA) deficiency, since most staple food oils are low in ALA content. Thus, the enhancement of ALA in staple oil crops is of importance. In this study, the FAD2 and FAD3 coding regions from the ALA-king species Perilla frutescens were fused using a newly designed double linker LP4-2A, driven by a seed-specific promoter PNAP, and engineered into a rapeseed elite cultivar ZS10 with canola quality background. The mean ALA content in the seed oil of PNAP:PfFAD2-PfFAD3 (N23) T5 lines was 3.34-fold that of the control (32.08 vs 9.59%), with the best line being up to 37.47%. There are no significant side effects of the engineered constructs on the background traits including oil content. In fatty acid biosynthesis pathways, the expression levels of structural genes as well as regulatory genes were significantly upregulated in N23 lines. On the other hand, the expression levels of genes encoding the positive regulators of flavonoid-proanthocyanidin biosynthesis but negative regulators of oil accumulation were significantly downregulated. Surprisingly, the ALA level in PfFAD2-PfFAD3 transgenic rapeseed lines driven by the constitutive promoter PD35S was not increased or even showed a slight decrease due to the lower level of foreign gene expression and downregulation of the endogenous orthologous genes BnFAD2 and BnFAD3.


Subject(s)
Brassica napus , Brassica rapa , Perilla , Humans , Brassica napus/genetics , Brassica napus/metabolism , alpha-Linolenic Acid/chemistry , Fatty Acid Desaturases/genetics , Fatty Acid Desaturases/metabolism , Brassica rapa/genetics , Brassica rapa/metabolism , Seeds/genetics , Seeds/metabolism , Oils/metabolism
6.
J Oleo Sci ; 71(8): 1135-1144, 2022 Aug 04.
Article in English | MEDLINE | ID: mdl-35793971

ABSTRACT

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.


Subject(s)
Plant Oils , alpha-Linolenic Acid , Fatty Acids/chemistry , Oxidative Stress , Plant Oils/chemistry , alpha-Linolenic Acid/chemistry
7.
Food Funct ; 13(5): 2768-2781, 2022 Mar 07.
Article in English | MEDLINE | ID: mdl-35171190

ABSTRACT

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.


Subject(s)
Antioxidants/pharmacology , Cognition/drug effects , Cognitive Dysfunction/prevention & control , Dietary Supplements , Flavones/pharmacology , Perilla frutescens , alpha-Linolenic Acid/pharmacology , Aged , Aged, 80 and over , Antioxidants/administration & dosage , Antioxidants/chemistry , Double-Blind Method , Fatty Acids, Omega-3/metabolism , Female , Flavones/administration & dosage , Flavones/chemistry , Humans , Male , Plant Oils/administration & dosage , Plant Oils/chemistry , Plant Oils/pharmacology , Treatment Outcome , alpha-Linolenic Acid/administration & dosage , alpha-Linolenic Acid/chemistry
8.
J Ethnopharmacol ; 284: 114814, 2022 Feb 10.
Article in English | MEDLINE | ID: mdl-34775034

ABSTRACT

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.


Subject(s)
Agastache/chemistry , Antioxidants/pharmacology , Hypoglycemic Agents/pharmacology , Oils, Volatile/pharmacology , Plant Oils/pharmacology , Allylbenzene Derivatives/chemistry , Allylbenzene Derivatives/pharmacology , Animals , Anisoles/chemistry , Anisoles/pharmacology , Antioxidants/chemistry , Catalase/genetics , Catalase/metabolism , Cell Line , Cell Survival/drug effects , Gene Expression Regulation/drug effects , Glucose , Hypoglycemic Agents/chemistry , Linoleic Acid/chemistry , Linoleic Acid/pharmacology , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Mice , Models, Molecular , Multienzyme Complexes/chemistry , Multienzyme Complexes/metabolism , NADH, NADPH Oxidoreductases/chemistry , NADH, NADPH Oxidoreductases/metabolism , Oils, Volatile/chemistry , Oxidative Stress , Plant Oils/chemistry , Protein Conformation , Superoxide Dismutase/genetics , Superoxide Dismutase/metabolism , alpha-Linolenic Acid/chemistry , alpha-Linolenic Acid/pharmacology
9.
Molecules ; 26(22)2021 Nov 09.
Article in English | MEDLINE | ID: mdl-34833849

ABSTRACT

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.


Subject(s)
Adenocarcinoma of Lung/metabolism , Anti-Inflammatory Agents , Antioxidants , Cinnamates , Depsides , Fatty Acids, Omega-3 , Lung Neoplasms/metabolism , Perilla/chemistry , alpha-Linolenic Acid , A549 Cells , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Antioxidants/chemistry , Antioxidants/pharmacology , Cinnamates/chemistry , Cinnamates/pharmacology , Depsides/chemistry , Depsides/pharmacology , Fatty Acids, Omega-3/chemistry , Fatty Acids, Omega-3/pharmacology , Humans , Oxidative Stress/drug effects , Plant Oils/chemistry , Plant Oils/pharmacology , alpha-Linolenic Acid/chemistry , alpha-Linolenic Acid/pharmacology , Rosmarinic Acid
10.
J Oleo Sci ; 70(11): 1575-1583, 2021 Nov 03.
Article in English | MEDLINE | ID: mdl-34645745

ABSTRACT

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.


Subject(s)
Chemical Phenomena , Linoleic Acid/analysis , Perilla frutescens/chemistry , Phytosterols/analysis , alpha-Linolenic Acid/analysis , Alcohols/analysis , Antioxidants/analysis , Hydrocarbons/analysis , Isomerism , Liquid-Liquid Extraction/methods , Palmitic Acid/analysis , Plant Oils/chemistry , Plant Oils/isolation & purification , Squalene/analysis , Tocopherols/analysis , Triglycerides/analysis , alpha-Linolenic Acid/chemistry , alpha-Linolenic Acid/isolation & purification
11.
Biochem Biophys Res Commun ; 582: 49-56, 2021 12 10.
Article in English | MEDLINE | ID: mdl-34689105

ABSTRACT

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.


Subject(s)
Fatty Acids, Omega-3/metabolism , Fatty Acids, Omega-6/metabolism , Renal Insufficiency/diet therapy , Reperfusion Injury/diet therapy , Soybean Oil/metabolism , Animals , Arachidonic Acid/metabolism , Blood Urea Nitrogen , Creatinine/blood , Fatty Acids, Omega-3/administration & dosage , Fatty Acids, Omega-6/administration & dosage , Kidney/drug effects , Kidney/metabolism , Kidney/pathology , Lipid Metabolism/drug effects , Male , Phospholipids/metabolism , Plant Oils/chemistry , Rats , Rats, Sprague-Dawley , Renal Insufficiency/metabolism , Renal Insufficiency/pathology , Reperfusion Injury/metabolism , Reperfusion Injury/pathology , Soybean Oil/administration & dosage , Soybean Oil/chemistry , Treatment Failure , alpha-Linolenic Acid/chemistry
12.
J Food Sci ; 86(10): 4393-4404, 2021 Oct.
Article in English | MEDLINE | ID: mdl-34514602

ABSTRACT

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.


Subject(s)
Charcoal , Ethanol , Fatty Acids , Kaolin , alpha-Linolenic Acid , Charcoal/chemistry , Ethanol/chemistry , Fatty Acids/adverse effects , Food Handling/standards , Kaolin/chemistry , Plant Oils/chemistry , Volatile Organic Compounds/analysis , alpha-Linolenic Acid/chemistry
13.
Biomolecules ; 11(2)2021 02 03.
Article in English | MEDLINE | ID: mdl-33546462

ABSTRACT

Synechocystis strains are cyanobacteria that can produce useful biomaterials for biofuel and pharmaceutical resources. In this study, the effects of exogenous glucose (5-mM) on cell growth, photosynthetic pigments, metabolites, and lipids in Synechocystis sp. PCC 7338 (referred to as Synechocystis 7338) were investigated. Exogenous glucose increased cell growth on days 9 and 18. The highest production (mg/L) of chlorophyll a (34.66), phycocyanin (84.94), allophycocyanin (34.28), and phycoerythrin (6.90) was observed on day 18 in Synechocystis 7338 culture under 5-mM glucose. Alterations in metabolic and lipidomic profiles under 5-mM glucose were investigated using gas chromatography-mass spectrometry (MS) and nanoelectrospray ionization-MS. The highest production (relative intensity/L) of aspartic acid, glutamic acid, glycerol-3-phosphate, linolenic acid, monogalactosyldiacylglycerol (MGDG) 16:0/18:1, MGDG 16:0/20:2, MGDG 18:1/18:2, neophytadiene, oleic acid, phosphatidylglycerol (PG) 16:0/16:0, and PG 16:0/17:2 was achieved on day 9. The highest production of pyroglutamic acid and sucrose was observed on day 18. We suggest that the addition of exogenous glucose to Synechocystis 7338 culture could be an efficient strategy for improving growth of cells and production of photosynthetic pigments, metabolites, and intact lipid species for industrial applications.


Subject(s)
Lipids/chemistry , Photosynthesis , Synechocystis/metabolism , Aspartic Acid/chemistry , Biocompatible Materials/chemistry , Chlorophyll A/chemistry , Galactolipids/chemistry , Gas Chromatography-Mass Spectrometry , Glucose/chemistry , Glucose/metabolism , Glutamic Acid/chemistry , Glycerophosphates/chemistry , Lipidomics , Metabolomics , Phycocyanin/chemistry , Phycoerythrin/chemistry , Spectrometry, Mass, Electrospray Ionization , alpha-Linolenic Acid/chemistry
14.
Food Funct ; 12(5): 2171-2188, 2021 Mar 07.
Article in English | MEDLINE | ID: mdl-33566044

ABSTRACT

The present study was designed to explore the beneficial mitochondrial effects and anti-oxidative activities of plant sterol ester of α-linolenic acid (PS-ALA) through AMP-activated protein kinase (AMPK) signaling in the treatment of nonalcoholic fatty liver disease (NAFLD) using in vivo and in vitro models. The mitochondrial function was evaluated and the oxidative stress index was measured. The protein expression was analyzed by immunohistochemical, immunofluorescence, and western blotting methods. The results showed that PS-ALA significantly suppressed NAFLD and alleviated steatosis in HepG2 cells induced by oleic acid (OA). In addition, PS-ALA promoted mitochondrial biogenesis, enhanced mitochondrial fatty acid oxidation capacity, improved mitochondrial dynamics, and restored mitochondrial membrane potential. Moreover, PS-ALA reduced reactive oxygen species production both in the liver tissue of HFD-fed mice and OA-loaded HepG2 cells. At the molecular level, PS-ALA accelerated the phosphorylation of AMPK and increased the protein expression of peroxisome proliferator-activated receptor-γ co-activator 1α (PGC-1α) and nuclear NF-E2-related factor 2 (Nrf2). Furthermore, the stimulating effects of PS-ALA on the PGC-1α/Nrf1/Tfam pathway and Nrf2/HO-1 pathway as well as its mitochondrial biogenesis promotion effects and anti-oxidative activities were abrogated by the AMPK inhibitor in OA-treated HepG2 cells. In conclusion, the protective effects of PS-ALA on NAFLD appear to be associated with improving mitochondrial function and oxidative stress via activating AMPK signaling.


Subject(s)
AMP-Activated Protein Kinases/metabolism , Esters/therapeutic use , Non-alcoholic Fatty Liver Disease/drug therapy , Oxidative Stress/drug effects , Phytosterols/therapeutic use , alpha-Linolenic Acid/chemistry , Animals , Diet, High-Fat , Enzyme Activation/drug effects , Esters/chemistry , Hep G2 Cells , Humans , Liver/chemistry , Male , Mice , Mice, Inbred C57BL , Mitochondria, Liver/drug effects , Mitochondria, Liver/physiology , Mitochondria, Liver/ultrastructure , Non-alcoholic Fatty Liver Disease/etiology , Non-alcoholic Fatty Liver Disease/physiopathology , Phosphorylation , Phytosterols/chemistry , Reactive Oxygen Species/analysis , Signal Transduction/drug effects
15.
Food Funct ; 12(6): 2428-2441, 2021 Mar 21.
Article in English | MEDLINE | ID: mdl-33624675

ABSTRACT

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.


Subject(s)
Bombyx/chemistry , Digestion/physiology , Models, Biological , Pupa/chemistry , alpha-Linolenic Acid , Animals , Dietary Supplements , Fatty Acids/metabolism , Humans , Hydrogen-Ion Concentration , Particle Size , Plant Oils , Triglycerides/metabolism , alpha-Linolenic Acid/analysis , alpha-Linolenic Acid/chemistry , alpha-Linolenic Acid/metabolism
16.
Bioprocess Biosyst Eng ; 44(3): 627-634, 2021 Mar.
Article in English | MEDLINE | ID: mdl-33159545

ABSTRACT

In this study, α-linolenic acid-enriched diacylglycerols (ALA-DAGs) were prepared via a two-step enzymatic way by combi-lipase using silkworm pupae oils as substrates. Firstly, several factors including temperature, mass ratio of water to oil, pH and enzyme loading were optimized for the hydrolysis of silkworm pupae oil. The maximum fatty acid content (96.51%) was obtained under the conditions: temperature 40 °C, water/oil 3:2 (w/w), pH 7, lipase TL100L loading 400 U/g, lipase PCL loading 30 U/g. Then, ALA was enriched by urea inclusion, with an increased ALA content of 82.50% being obtained. Secondly, the ALA-enriched silkworm pupae DAG oil (SPDO) was prepared by lipase PCL-catalyzed esterification reaction. After molecular distillation, the final SPDO product contained contents of DAGs (97.01%) and ALA (82.50%). This two-step enzymatic way for production of ALA-DAGs was successfully applied in a 100-fold scale-up reaction. Overall, our study provides a promising way for the preparation of ALA-DAGs.


Subject(s)
Bombyx/chemistry , Diglycerides , Lipase/chemistry , Oils/chemistry , Pupa/chemistry , alpha-Linolenic Acid/chemistry , Animals , Diglycerides/chemical synthesis , Diglycerides/chemistry
17.
J Food Sci ; 86(1): 206-214, 2021 Jan.
Article in English | MEDLINE | ID: mdl-33295031

ABSTRACT

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.


Subject(s)
Perilla frutescens/chemistry , alpha-Linolenic Acid/pharmacology , Animals , Anti-Inflammatory Agents , Antioxidants/pharmacology , Biological Availability , Cytokines/genetics , Cytokines/metabolism , Emulsions , Estradiol/metabolism , Fatty Acids , Female , Gene Expression Regulation/drug effects , Male , Nanostructures/chemistry , Ovary/drug effects , Particle Size , Plant Oils/chemistry , Plant Oils/pharmacokinetics , Plant Oils/pharmacology , Plant Oils/toxicity , Rats , alpha-Linolenic Acid/chemistry , alpha-Linolenic Acid/pharmacokinetics , alpha-Linolenic Acid/toxicity
18.
Food Chem ; 343: 128475, 2021 May 01.
Article in English | MEDLINE | ID: mdl-33168257

ABSTRACT

To solve the stability and oxidation issues of alpha-linolenic acid (ALA), this study focused on developing ALA nanoemulsion system (ALA-NE, oil-in-water) and evaluating the effect of environmental conditions on physical stability and the effect of antioxidants on oxidative stability. The physicochemical properties of nanoemulsions were measured at different conditions, including particle diameter, zeta potential, retention rate and peroxidation value (POV). The particle diameter increased significantly and the retention rate decreased after 25 days storage under the conditions of high temperature and metal ions. However, the influence of ionic strength, pH and light was insignificant. As an antioxidant, Vitamin E was more effective at retarding lipid oxidation of nanoemulsions than that of vitamin C. These results provided reference information in preparing effective and stable ALA-NE systems and enlarging the application fields.


Subject(s)
Emulsions/chemistry , alpha-Linolenic Acid/chemistry , Antioxidants/chemistry , Ascorbic Acid/chemistry , Food Storage , Hydrogen-Ion Concentration , Light , Nanostructures/chemistry , Oxidation-Reduction , Particle Size , Polysorbates , Solubility , Temperature , Vitamin E/chemistry , Water/chemistry
19.
J Appl Microbiol ; 130(6): 1893-1901, 2021 Jun.
Article in English | MEDLINE | ID: mdl-33034112

ABSTRACT

AIMS: The aim of this study was to determine the effects of unsaturated fatty acids on clinical plasmids. METHODS AND RESULTS: Two unsaturated fatty acids, linoleic acid (LA) and α-linolenic acid (ALA) at final concentration 0, 0·03, 0·3 and 3 mmol l-1 , respectively, were used to assess the effects on conjugative transfer of a mcr-1-harbouring plasmid pCSZ4 (IncX4) in conjugation experiment. The inhibitory mechanisms were analysed by molecular docking and the gene expression of virB11 was quantitated by qRT-PCR. Target plasmid diversity was carried out by TrwD/VirB11 homology protein sequence prediction analysis. Our results showed that LA and ALA inhibit plasmid pCSZ4 transfer by binding to the amino acid residues (Phe124 and Thr125) of VirB11 with dose-dependent effects. The expression levels of virB11 gene were also significantly inhibited by LA and ALA treatment. Protein homology analysis revealed a wide distribution of TrwD/VirB11-like genes among over 37 classes of plasmids originated from both Gram-negative and Gram-positive bacteria. CONCLUSIONS: This study demonstrates representing a diversity of plasmids that may be potentially inhibited by unsaturated fatty acids. SIGNIFICANCE AND IMPACT OF THE STUDY: Our work reported here provides additional support for application of curbing the spread of multiple plasmids by unsaturated fatty acids.


Subject(s)
Escherichia coli/genetics , Gene Transfer, Horizontal/drug effects , Linoleic Acid/pharmacology , alpha-Linolenic Acid/pharmacology , Adenosine Triphosphatases/chemistry , Adenosine Triphosphatases/genetics , Colistin/pharmacology , Conjugation, Genetic , Drug Resistance, Bacterial , Escherichia coli/classification , Escherichia coli Proteins/chemistry , Escherichia coli Proteins/genetics , Gene Expression/drug effects , Linoleic Acid/chemistry , Linoleic Acid/metabolism , Molecular Docking Simulation , Plasmids/genetics , alpha-Linolenic Acid/chemistry , alpha-Linolenic Acid/metabolism
20.
Int J Biol Macromol ; 166: 687-693, 2021 Jan 01.
Article in English | MEDLINE | ID: mdl-33130263

ABSTRACT

Alzheimer's disease is characterized by important patho-proteins, which being composed of Amyloid-ß plaques and intracellular neurofibrillary tangles of Tau. Intrinsically disordered protein tau has several interacting partners, which are necessary for its normal functioning. Tau has been shown to interact with various proteins, nucleic acid, and lipids. α-Linolenic acid (ALA) a plant-based omega-3 fatty acid has been studied for its role as neuroprotective and beneficial fatty acid in the brain. In this study, we are focusing on the ability of ALA to induce spontaneous assembly in tau protein. ALA inhibited the Tau aggregation as indicated by reduced ThS fluorescence kinetics, which indicates no aggregation of Tau. Similarly, SDS-PAGE analysis supported that ALA exposure inhibited the aggregation as no higher-order tau species were observed. Along with its ability to impede the aggregation of Tau, ALA also maintains a native random coiled structure, which was estimated by CD spectroscopy. Finally, TEM analysis showed that the formation of Tau fibrils was found to be discouraged by ALA. Hence, conclusion of the study suggested that ALA profoundly inhibited aggregation of Tau and maintained it's the random-coil structure.


Subject(s)
Protein Multimerization/drug effects , alpha-Linolenic Acid/pharmacology , tau Proteins/chemistry , Humans , Protein Conformation , Protein Unfolding/drug effects , alpha-Linolenic Acid/chemistry , tau Proteins/metabolism
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