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Journal of Oleo Science May 2021The effects of 6,9,12,15-hexadecatetraenoic acid (C16:4n-1, HDTA), an n-1 polyunsaturated fatty acid (FA), on plasma and liver lipid content and distribution in blood...
The effects of 6,9,12,15-hexadecatetraenoic acid (C16:4n-1, HDTA), an n-1 polyunsaturated fatty acid (FA), on plasma and liver lipid content and distribution in blood and tissues were investigated. Mice were fed experimental diets containing 10% HDTA or eicosapentaenoic acid in ethyl ester form based on corn oil for four weeks. Dietary HDTA intake lowered plasma triacylglycerol content without affecting plasma total cholesterol content. HDTA barely accumulated in the epididymal white adipose tissue (eWAT), while C18:4n-1, an HDTA metabolite, was detected in small amounts (< 1% of total FAs) in the plasma, liver, and eWAT.
Topics: Adipose Tissue, White; Animals; Cholesterol; Corn Oil; Eating; Edetic Acid; Eicosapentaenoic Acid; Esters; Fatty Acids; Fatty Acids, Unsaturated; Lipid Metabolism; Liver; Male; Mice, Inbred C57BL; Tissue Distribution; Triglycerides; Mice
PubMed: 33840668
DOI: 10.5650/jos.ess21025 -
Scientific Reports Aug 2017Euphausia pacifica is a good candidate for a resource of marine n-3 PUFA. However, few reports exist of the lipid and fatty acid composition of E. pacifica. To examine...
Euphausia pacifica is a good candidate for a resource of marine n-3 PUFA. However, few reports exist of the lipid and fatty acid composition of E. pacifica. To examine the potential of E. pacifica as a resource of marine n-3 PUFA, we analyzed E. pacifica oil. We extracted lipids from E. pacifica harvested from the Pacific Ocean near Sanriku, Japan. Lipid classes of E. pacifica oil were analyzed by TLC-FID and the fatty acid composition of the oil was analyzed by GC/MS. Free fatty acids and hydroxy-fatty acids were analyzed by LC/QTOFMS. The lipid content of E. pacifica ranged from 1.30% to 3.57%. The ratios of triacylglycerols, phosphatidylcholine, phosphatidylethanolamine and free fatty acids in E. pacifica lipids were 5.3-23.0%, 32.6-53.4%, 8.5-25.4% and 2.5-7.0%, respectively. The content of n-3 PUFA in E. pacifica lipids was 38.6-46.5%. We also showed that E. pacifica contains unusual fatty acids and derivatives: C16-PUFAs (9,12-hexadecadienoic acid, 6,9,12-hexadecatrienoic acid and 6,9,12,15-hexadecatetraenoic acid) and hydroxy-PUFAs (8-HETE and 10-HDoHE). E. pacifica is a good resource of marine n-3 PUFA. Moreover, E. pacifica can provide C16-PUFA and hydroxy-PUFAs.
Topics: Animals; Chromatography, Liquid; Chromatography, Thin Layer; Euphausiacea; Flame Ionization; Japan; Lipids; Mass Spectrometry; Pacific Ocean
PubMed: 28855640
DOI: 10.1038/s41598-017-09637-9 -
Poultry Science Nov 2023Chemical composition, amino acids (AAs), and fatty acid (FAs) profiles, and health and nutrition values of breast muscle of ROSS 308 broiler chickens were studied after...
Chemical composition, amino acids (AAs), and fatty acid (FAs) profiles, and health and nutrition values of breast muscle of ROSS 308 broiler chickens were studied after being slaughtered at 28, 35, 42, and 49 d of age (n = 126 males and 126 females/slaughter age). The slaughter age significantly affected some AAs levels including glutamic acid, valine, isoleucine, histidine, and leucine, and some FAs level including capric acid, tetradecanoic acid, eicosanoic acid, total saturated fatty acids, 9-pentadecenoic acid, hexadecatetraenoic acid, α-linolenic acid, stearidonic acid, linoleic acid, dihomo-γ-linolenic acid, arachidonic acid, adrenic acid, omega 6, sum polyunsaturated fatty acids (Ʃ PUFAs), and unsaturation index. Subsequently, the slaughter age significantly affected some health indexes including the n-6/n-3 ratio, thrombogenic index, hypocholesterolemic/hypercholesterolemic ratio, and health-promoting index. Valine, leucine, isoleucine, histidine, and glutamic acid levels increased with increasing slaughter age until 35 d of age and then decreased with increasing slaughter age until 49 d of age. Moreover, the health indices of fatty acids were best at slaughter age of 35 d, followed by 49 d, and the lowest health-promoting indices were at 42 d, followed by 28 d. The sex did not affect (P ˃ 0.05) all the evaluating parameters including chemical composition, amino acid and fatty acid profiles, and related health indices. There was no significant interaction effect between sex and slaughter age in all evaluating parameters except in stearidonic acid level. In conclusion, amino acids and fatty acids profiles and health and nutritional values of male and female ROSS 308 broiler chicken breast muscle can be affected by slaughter age. The study provides valuable insights into the nutritional value of meat, including its composition, amino acid, and fatty acid profiles, and associated health indices, for both male and female fast-growing ROSS 308 broiler chickens, as the slaughter age increases.
Topics: Animals; Male; Female; Chickens; Amino Acids; Histidine; Leucine; Isoleucine; Fatty Acids; Muscles; Meat; Nutritive Value; Valine; Glutamates; Animal Feed
PubMed: 37748245
DOI: 10.1016/j.psj.2023.103085 -
Journal of Oleo Science 2013Biosurfactants are surface-active compounds produced by microorganisms. Mannosylerythritol lipids (MEL) are promising biosurfactants produced by Ustilaginomycetes, and...
Biosurfactants are surface-active compounds produced by microorganisms. Mannosylerythritol lipids (MEL) are promising biosurfactants produced by Ustilaginomycetes, and their physicochemical and biochemical properties differ depending on the chemical structure of their hydrophilic and/or hydrophobic moieties. To further develop MEL derivatives and expand their potential applications, we focused our attention on the use of cuttlefish oil, which contains polyunsaturated fatty acids (e.g., docosahexaenoic acid, C₂₂:₆, and eicosapentaenoic acid, C₂₀:₅, as the sole carbon source. Among the microorganisms capable of producing MEL, only nine strains were able to produce them from cuttlefish oil. On gas chromatography-mass spectrometry (GC/MS) analysis, we observed that Pseudozyma churashimaensis OK96 was particularly suitable for the production of MEL-A, a MEL containing hexadecatetraenoic acid (C₁₆:₄) (23.6% of the total unsaturated fatty acids and 7.7% of the total fatty acids). The observed critical micelle concentration (CMC) and surface tension at CMC of the new MEL-A were 5.7×10⁻⁶ M and 29.5 mN/m, respectively, while those of MEL-A produced from soybean oil were 2.7×10⁻⁶ M and 27.7 mN/m, respectively. With polarized optical and confocal laser scanning microscopies, the self-assembling properties of MEL-A were found to be different from those of conventional MEL. Furthermore, based on the DPPH radical-scavenging assay, the anti-oxidative activity of MEL-A was found to be 2.1-fold higher than that of MEL-A produced from soybean oil. Thus, the newly identified MEL-A is attractive as a new functional material with excellent surface-active and antioxidative properties.
Topics: Animals; Decapodiformes; Fatty Acids, Unsaturated; Glycolipids; Oils; Ustilaginales
PubMed: 23648407
DOI: 10.5650/jos.62.319 -
Bioscience, Biotechnology, and... Nov 2000Stearidonic acid (18:4(n-3)) and hexadecatetraenoic acid (16:4(n-3)) are included in some edible marine algae such as Undaria pinnatifida and Ulva pertusa with...
Stearidonic acid (18:4(n-3)) and hexadecatetraenoic acid (16:4(n-3)) are included in some edible marine algae such as Undaria pinnatifida and Ulva pertusa with relatively high compositions (up to 40%) of total fatty acids. In order to prepare 16:4(n-3) and 18:4(n-3) enriched fatty acid concentrates, we screened for a suitable lipase which concentrates these acids by the removal of other fatty acids in the selective esterification reaction reported by Shimada et al. (Shimada et al. (1997), J. Am. Oil Chem. Soc., 74, 1465-1470). In combination with the lipase reaction and reversed-phase medium pressure liquid chromatography, we purified 18:4(n-3) and 16:4(n-3) to more than 95% purity.
Topics: Chlorophyta; Chromatography, Gas; Chromatography, Liquid; Fatty Acids, Nonesterified; Fatty Acids, Omega-3; Fatty Acids, Unsaturated; Lipase; Phaeophyceae
PubMed: 11193415
DOI: 10.1271/bbb.64.2454 -
The Journal of Biological Chemistry Jun 1995The pathway for the peroxisomal beta-oxidation of arachidonic acid (5,8,11,14-20:4) was elucidated by comparing its metabolism with 4,7,10-hexadecatrienoic acid...
Double bond removal from odd-numbered carbons during peroxisomal beta-oxidation of arachidonic acid requires both 2,4-dienoyl-CoA reductase and delta 3,5,delta 2,4-dienoyl-CoA isomerase.
The pathway for the peroxisomal beta-oxidation of arachidonic acid (5,8,11,14-20:4) was elucidated by comparing its metabolism with 4,7,10-hexadecatrienoic acid (4,7,10-16:3) and 5,8-tetradecadienoic acid (5,8-14:2) which are formed, respectively, after two and three cycles of arachidonic acid degradation. When [1-14C]4,7,10-16:3 was incubated with peroxisomes in the presence of NAD+ and NADPH, it resulted in a time-dependent increase in the production of acid-soluble radioactivity which was accompanied by the synthesis of 2-trans-4,7,10-hexadecatetraenoic acid and two 3,5,7,10-hexadecatetraenoic acid isomers. The formation of conjugated trienoic acids suggests that peroxisomes contain delta 3,5,delta 2,4-dienoyl-CoA isomerase with the ability to convert 2-trans-4,7,10-hexadecatetraenoic acid to 3,5,7,10-hexadecatetraenoic acid. When 1-14C-labeled 6,9,12-octadecatrienoic acid or 7,10,13,16-docosatetraenoic acid was incubated without nucleotides, the 3-hydroxy metabolites accumulated, since further degradation requires NAD(+)-dependent 3-hydroxyacyl-CoA dehydrogenase. When [1-14C]5,8,11,14-20:4 was incubated under identical conditions, no polar metabolite was detected, but 2-trans-4,8,11,14-eicosapentaenoic acid accumulated. When NADPH was added to incubations, 3-hydroxy-8,11,14-eicosatrienoic, 2-trans-4,8,11,14-eicosapentaenoic, 2-trans-8,11,14-eicosatetraenoic, and 8,11,14-eicosatrienoic acids were produced. Analogous compounds were formed from [1-14C]5,8-14:2. Our results show that the removal of double bonds from odd-numbered carbons in arachidonic acid thus requires both NADPH-dependent 2,4-dienoyl-CoA reductase and delta 3,5,delta 2,4-dienoyl-CoA isomerase. One complete cycle of 5,8-14:2 and 5,8,11,14-20:4 beta-oxidation yields, respectively, 6-dodecenoic and 6,9,12-octadecatrienoic acids.
Topics: Animals; Arachidonic Acid; Carbon-Carbon Double Bond Isomerases; Fatty Acid Desaturases; Isomerases; Male; Microbodies; NADP; Oxidation-Reduction; Oxidoreductases Acting on CH-CH Group Donors; Rats; Rats, Sprague-Dawley
PubMed: 7775433
DOI: 10.1074/jbc.270.23.13771 -
Journal of Lipid Research May 1998Human skin fibroblasts can convert arachidonic acid to 14- and 16-carbon polyunsaturated fatty acid products by peroxisomal beta-oxidation. The purpose of this study was...
Human skin fibroblasts can convert arachidonic acid to 14- and 16-carbon polyunsaturated fatty acid products by peroxisomal beta-oxidation. The purpose of this study was to determine whether similar products are formed from eicosapentaenoic acid (EPA) and whether EPA and arachidonic acid compete for utilization by this oxidative pathway. Three radiolabeled metabolites with shorter retention times than EPA on reverse-phase high-performance liquid chromatography accumulated in the medium during incubation of fibroblasts with [5,6,8,9,11,12,14,15,17,18-3H] EPA ([3H]EPA). These metabolites, which were not formed from [1-14C]EPA and were not detected in the cells, were identified as tetradecatrienoic acid (14:3n-3), hexadecatetraenoic acid (16:4n-3), and octadecatetraenoic acid (18:4n-3). The most abundant product under all of the conditions tested was 16:4n-3. [3H]EPA was converted to 16:4n-3 and 14:3n-3 by fibroblasts deficient in mitochondrial long-chain acyl CoA dehydrogenase, but not by Zellweger syndrome or acyl CoA oxidase mutants that are deficient in peroxisomal beta-oxidation. Competition studies indicated that 16:4n-3 formation from 5 microM [3H]EPA was reduced by 60% when 10 microM arachidonic acid was added, but the conversion of [3H]arachidonic acid to its chain-shortened products was not decreased by the addition of 10 microM EPA. These findings demonstrate that as in the case of arachidonic acid, chain-shortened polyunsaturated fatty acid products accumulate when EPA undergoes peroxisomal beta-oxidation. While EPA does not reduce arachidonic acid utilization by this pathway, it is possible that some biological actions of EPA may be mediated by the formation of the corresponding EPA products, 16:4n-3 and 14:3n-3.
Topics: Arachidonic Acid; Cells, Cultured; Chromatography, High Pressure Liquid; Eicosapentaenoic Acid; Fatty Acids, Omega-3; Fibroblasts; Humans; Hydrogen; Methylation; Microbodies; Oxidation-Reduction; Skin
PubMed: 9610764
DOI: No ID Found -
Polish Journal of Microbiology 2019Biofouling is a phenomenon that describes the fouling organisms attached to man-made surfaces immersed in water over a period of time. It has emerged as a chronic...
Biofouling is a phenomenon that describes the fouling organisms attached to man-made surfaces immersed in water over a period of time. It has emerged as a chronic problem to the oceanic industries, especially the shipping and aquaculture fields. The metal-containing coatings that have been used for many years to prevent and destroy biofouling are damaging to the ocean and many organisms. Therefore, this calls for the critical need of natural product-based antifoulants as a substitute for its toxic counterparts. In this study, the antibacterial and antibiofilm activities of the bioactive compounds of sp. IBRL PD4.8 have been investigated against selected fouling bacteria. The crude extract has shown strong antibacterial activity against five fouling bacteria, with inhibition zones ranging from 9.8 to 13.7 mm and minimal inhibitory concentrations of 0.13 to 8.0 mg/ml. Meanwhile, the antibiofilm study has indicated that the extract has attenuated the initial and pre-formed biofilms of FB3 by 45.37 ± 4.88% and 29.85 ± 2.56%, respectively. Moreover, micrographs from light and scanning electron microscope have revealed extensive structural damages on the treated biofilms. The active fraction was fractionated with chromatographic methods and liquid chromatography-mass spectroscopy analyses has further disclosed the presence of a polyunsaturated fatty acid 4,7,10,13-hexadecatetraenoic acid (CHO). Therefore, this compound was suggested as a potential bioactive compound contributing to the antibacterial property. In conclusion, sp. IBRL PD4.8 is a promising source as a natural antifouling agent that can suppress the growth of five fouling bacteria and biofilms of FB3. Biofouling is a phenomenon that describes the fouling organisms attached to man-made surfaces immersed in water over a period of time. It has emerged as a chronic problem to the oceanic industries, especially the shipping and aquaculture fields. The metal-containing coatings that have been used for many years to prevent and destroy biofouling are damaging to the ocean and many organisms. Therefore, this calls for the critical need of natural product-based antifoulants as a substitute for its toxic counterparts. In this study, the antibacterial and antibiofilm activities of the bioactive compounds of sp. IBRL PD4.8 have been investigated against selected fouling bacteria. The crude extract has shown strong antibacterial activity against five fouling bacteria, with inhibition zones ranging from 9.8 to 13.7 mm and minimal inhibitory concentrations of 0.13 to 8.0 mg/ml. Meanwhile, the antibiofilm study has indicated that the extract has attenuated the initial and pre-formed biofilms of FB3 by 45.37 ± 4.88% and 29.85 ± 2.56%, respectively. Moreover, micrographs from light and scanning electron microscope have revealed extensive structural damages on the treated biofilms. The active fraction was fractionated with chromatographic methods and liquid chromatography-mass spectroscopy analyses has further disclosed the presence of a polyunsaturated fatty acid 4,7,10,13-hexadecatetraenoic acid (CHO). Therefore, this compound was suggested as a potential bioactive compound contributing to the antibacterial property. In conclusion, sp. IBRL PD4.8 is a promising source as a natural antifouling agent that can suppress the growth of five fouling bacteria and biofilms of FB3.
Topics: Anti-Bacterial Agents; Biofilms; Biofouling; Disk Diffusion Antimicrobial Tests; Fatty Acids, Unsaturated; Microscopy, Electron, Scanning; Pseudoalteromonas; Vibrio alginolyticus
PubMed: 31050250
DOI: 10.21307/pjm-2019-003 -
Journal of Lipid Research Nov 1966The lipid of Euglena gracilis, dark-grown in a complete medium, contained 2% galactose. The lipid of Euglena gracilis, light-grown in either a complete or an inorganic...
The lipid of Euglena gracilis, dark-grown in a complete medium, contained 2% galactose. The lipid of Euglena gracilis, light-grown in either a complete or an inorganic medium, contained 13-14% galactose. Pure monogalactosyl and digalactosyl diglyceride fractions, isolated by column plus thin-layer chromatography, contained 50% of the lipid-bound galactose of dark-grown cells, and 80% of that of light-grown cells. Molar ratios of monogalactosyl to digalactosyl compounds ranged from 2 to 3. The results show that galactosyl diglycerides, stored in large amount in light-grown cells, persist in small amount in the dark-grown cells. Fatty acids in both the monogalactosyl and the digalactosyl diglycerides were mainly of the 16- and 18-carbon varieties, with high proportions of trienes. The monogalactosyl diglycerides were rich in hexadecatetraenoic acid. Strictly photobiotic cells had twice as much hexadecadienoic and hexadecatetraenoic acids in their monogalactosyl diglycerides, and three times as much hexadecadienoic and octadecadienoic acids in their digalactosyl diglycerides as did illuminated cells grown in a complete medium. Dark-grown (obligate) heterotrophs contained galactosyl diglycerides with high percentages of monoenes. Great compositional variations in the galactosyl diglycerides are thus induced by light and also by nonlipid exogenous metabolites.
Topics: Chromatography; Chromatography, Thin Layer; Euglena; Fatty Acids; Galactose; Glycerides; Light; Phosphorus; Spectrophotometry
PubMed: 5971568
DOI: No ID Found -
Journal of Lipid Research Jun 2004Geranylgeranoic acid (GGA; all-trans 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenoic acid) has been shown to induce apoptosis in a human hepatoma-derived cell line,...
Geranylgeranoic acid (GGA; all-trans 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenoic acid) has been shown to induce apoptosis in a human hepatoma-derived cell line, HuH-7. We aimed not only to confirm the apoptogenic properties of GGA and its derivatives, but also to search for natural GGA in medicinal herbs. GGA induced apoptosis in human hepatoma-derived cell lines, HuH-7, PLC/PRF-5, and mouse transformed hepatocyte-derived cell line, MLE-10, in a dose- and time-dependent manner, but failed to induce cell death in human hepatoblastoma-derived HepG-2 and mouse primary hepatocytes in the same condition. Besides GGA, 4,5-didehydro GGA, 14,15-dihydro GGA, and 2,3-dihydro GGA were also active to induce cell death in HuH-7 cells, while 4,5-didehydro-10,11, 14,15-tetrahydro GGA, 4,5,8,9-tetrahydro GGA, farnesoic acid, and geranylgeraniol were inert. By using liquid chromatography/mass spectrometry, we found natural GGA as a negative ion of m/z 303.4 in a Chinese herb, Schisandra chinensis, and Schisandra GGA was identified by derivatization with both mild methylation and catalytic hydrogenation. Some other GGAs hydrogenated in the different degrees, including phytanic acid (perhydro GGA), were also found in S. chinensis. GGA and phytanic acid were detected in 24 out of 25 herbs tested. The present study is the first report of natural GGA in medicinal herbs.
Topics: Animals; Cell Death; Cells, Cultured; Chromatography, Liquid; Diterpenes; Gas Chromatography-Mass Spectrometry; Humans; Liver Neoplasms; Male; Mice; Molecular Structure; Phytotherapy; Plant Extracts; Plants, Medicinal
PubMed: 15060084
DOI: 10.1194/jlr.M300502-JLR200