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Biotechnology Letters Feb 2022Nervonic acid (cis-15-tetracosenoic acid, 24:1Δ15) is a long chain monounsaturated fatty acid, mainly exists in white matt er of the human brains. It plays an important... (Review)
Review
Nervonic acid (cis-15-tetracosenoic acid, 24:1Δ15) is a long chain monounsaturated fatty acid, mainly exists in white matt er of the human brains. It plays an important role in the development of nervous system and curing neurological diseases. The limited natural sources and high price are considered limiting factors for the extensive application of nervonic acid. Yarrowia lipolytica is a high lipid producing yeast and engineered strain which can produce nervonic acid. The biosynthesis of nervonic acid has yet to be investigated, although the metabolism has been examined for couple of years. Normally, oleic acid is considered the origin of nervonic acid synthesis through fatty acid prolongation, where malonyl-CoA and acyl-CoA are initially concise by 3-ketoacyl-CoA synthase (KCS). To meet the high requirement of industrial production, the optimization of fermentation and bioreactors configurations are necessary tools to be carried out. This review article summarizes the research literature on advancements and recent trends about the production, synthesis and properties of nervonic acid.
Topics: Fatty Acids; Fatty Acids, Monounsaturated; Fermentation; Humans; Yarrowia
PubMed: 35119573
DOI: 10.1007/s10529-022-03231-4 -
The American Journal of Clinical... Feb 2011Breastfeeding is considered an optimal nutritional source of n-6 (omega-6) and n-3 (omega-3) fatty acids (FAs) for the proper visual and cognitive development of newborn...
Genetic variants in the FADS gene cluster are associated with arachidonic acid concentrations of human breast milk at 1.5 and 6 mo postpartum and influence the course of milk dodecanoic, tetracosenoic, and trans-9-octadecenoic acid concentrations over the duration of lactation.
BACKGROUND
Breastfeeding is considered an optimal nutritional source of n-6 (omega-6) and n-3 (omega-3) fatty acids (FAs) for the proper visual and cognitive development of newborn children. In addition to maternal nutrition as an important regulator of FA concentrations, first results exist on an association of breast-milk FAs with single nucleotide polymorphisms (SNPs) in the FADS gene cluster, which encodes the rate-limiting enzymes in the elongation-desaturation pathway of long-chain polyunsaturated fatty acids (LC-PUFAs).
OBJECTIVE
We analyzed the influence of FADS SNPs on breast-milk FA concentrations and their time course during lactation in the Ulm Birth Cohort study, which comprised 772 nursing mothers at 1.5 mo after giving birth, and in a subset of 463 mothers who were still breastfeeding at 6 mo postpartum.
DESIGN
We conducted linear regression analysis of 8 FADS SNPs with FA concentrations at both time points separately and assessed the genotype effect over time in a longitudinal analysis by using a generalized estimating equation regression model.
RESULTS
We observed significant associations of FADS genotypes with arachidonic acid (AA) concentrations and the 20:4n-6/20:3n-6 ratio at both time points but no association of FADS SNPs with the time course of AA concentrations. A longitudinal analysis of FAs other than LC-PUFAs by genotype over time showed associations for dodecanoic acid, cis-15-tetracosenoic acid, and trans-9-octadecenoic acid.
CONCLUSIONS
Maternal FADS genotypes are associated with breast-milk AA concentrations and might therefore influence the supply of this FA for children. Furthermore, our data indicate an interrelation between the LC-PUFA pathway and saturated and monounsaturated FAs.
Topics: Adult; Arachidonic Acid; Fatty Acid Desaturases; Fatty Acids; Fatty Acids, Monounsaturated; Female; Genotype; Humans; Lactation; Lauric Acids; Linear Models; Longitudinal Studies; Milk, Human; Polymorphism, Single Nucleotide; Postpartum Period; Stearic Acids
PubMed: 21147856
DOI: 10.3945/ajcn.110.004515 -
Food Chemistry Dec 2019Nervonic acid (NA) has attracted considerable attention because of its close relationship with brain development. Sources of NA include oil crop seeds, oil-producing... (Review)
Review
Nervonic acid (NA) has attracted considerable attention because of its close relationship with brain development. Sources of NA include oil crop seeds, oil-producing microalgae, and other microorganisms. Transgenic technology has also been applied to improve the sources and production of NA. NA can be separated and purified by urea adduction fractionation, molecular distillation, and crystallization. Studies on NA functionality involved treatments for demyelinating diseases and acquired immunodeficiency syndrome, as well as prediction of mortality due to cardiovascular diseases and chronic kidney disease. This mini review focuses on the sources, production, and biological functions of NA and provides prospective trends in the investigation of NA.
Topics: Fatty Acids, Monounsaturated; Microalgae; Plant Oils
PubMed: 31382110
DOI: 10.1016/j.foodchem.2019.125286 -
Biochemistry Apr 1990The synthesis and thermotropic properties of 1,2-di-(9Z)-9-tetracosenoylphosphatidylcholine [delta 9-PC(24:1,24:1), 1], 1,2-di-(5Z)-5-tetracosenoylphosphatidylcholine...
The synthesis and thermotropic properties of 1,2-di-(9Z)-9-tetracosenoylphosphatidylcholine [delta 9-PC(24:1,24:1), 1], 1,2-di-(5Z)-5-tetracosenoylphosphatidylcholine [delta 5-PC(24:1,24:1), 2], and 1,2-di-(15Z)-15- tetracosenoylphosphatidylcholine [delta 15-PC(24:1,24:1), 3] are reported. Liposomes prepared from these phospholipids differ from those of the natural sponge phospholipids, 1,2-di-(5Z,9Z)-5,9-hexacosadienoylphosphatidylcholine (4a) and the corresponding ethanolamine (4b), both of which virtually exclude cholesterol from their bilayers. The behavior of 1 and 2 is similar to that of 1,2-di-(6Z,9Z)-6,9-hexacosadienoylphosphatidylcholine (5), which exhibits a partial molecular interaction with cholesterol. In the case of 3, cholesterol appears to interact with the saturated acyl chain regions of this phospholipid in a manner similar to that of its interaction with DPPC acyl chains. This study delineates the effect of the double-bond location in long fatty acyl chains of phospholipids on their interactions with cholesterol.
Topics: Calorimetry, Differential Scanning; Cell Membrane; Cholesterol; Fatty Acids, Monounsaturated; Indicators and Reagents; Lipid Bilayers; Liposomes; Magnetic Resonance Spectroscopy; Models, Biological; Phosphatidylcholines; Phospholipids; Structure-Activity Relationship
PubMed: 2354147
DOI: 10.1021/bi00466a007 -
Vavilovskii Zhurnal Genetiki I Selektsii Nov 2022Perilla frutescens is mainly cultivated as an oilseed crop. Perilla seeds contain 40-53 % of oil, 28 % of protein. The growing season is 100-150 days. In Russia, perilla...
Perilla frutescens is mainly cultivated as an oilseed crop. Perilla seeds contain 40-53 % of oil, 28 % of protein. The growing season is 100-150 days. In Russia, perilla is grown in the Far East, where the yield is 0.8-1.2 t/ha. Perilla of different geographical origin has its own special, sharply different features that characterize two geographical groups: Japanese and Korean-Chinese. These groups differ from each other in the length of the growing season, the height of plants, the color of the stem, the surface and the size of the leaves, the shape of the bush, the shape and size of the inflorescences, the size of the cups, the size and color of the seeds. P. frutescens contains a large number of polyphenolic compounds that are biologically active components. The purpose of this research was a metabolomic study of extracts from leaves of P. frutescens obtained from the collection of Federal Research Center the N.I. Vavilov All-Russian Institute of Plant Genetic Resources, grown on the fields of the Far East Experiment Station - Branch of Federal Research Center (Primorsky Krai, Russia). To identify target analytes in extracts, HPLC was used in combination with an ion trap. Preliminary results showed the presence of 23 biologically active compounds corresponding to P. frutescens. In addition to the reported metabolites, a number of metabolites were newly annotated in P. frutescens. There were hydroxycoumarin Umbelliferone; triterpene Squalene; omega-3 fatty acid Stearidonic [Moroctic] acid; higher-molecular-weight carboxylic acid: Tetracosenoic acid and Salvianic acid C; lignan Syringaresinol and cyclobutane lignan Sagerinic acid, etc. A wide range of biologically active compounds opens up rich opportunities for the creation of new drugs and dietary supplements based on extracts of perilla of the family Lamiaceae, subfamily Lamioideae, tribe Satureji and subtribe Perillinae.
PubMed: 36532628
DOI: 10.18699/VJGB-22-78 -
Journal of Lipids 2016The oil contents and fatty acid (FA) compositions of ten new and one wild Camellia oleifera varieties were investigated. Oil contents in camellia seeds from new C....
The oil contents and fatty acid (FA) compositions of ten new and one wild Camellia oleifera varieties were investigated. Oil contents in camellia seeds from new C. oleifera varied with cultivars from 41.92% to 53.30% and were affected by cultivation place. Average oil content (47.83%) of dry seeds from all ten new cultivars was almost the same as that of wild common C. oleifera seeds (47.06%). New C. oleifera cultivars contained similar FA compositions which included palmitic acid (C16:0, PA), palmitoleic acid (C16:1), stearic acid (C18:0, SA), oleic acid (C18:1, OA), linoleic acid (C18:2, LA), linolenic acid (C18:3), eicosenoic acid (C20:1), and tetracosenoic acid (C24:1). Predominant FAs in mature seeds were OA (75.78%~81.39%), LA (4.85%~10.79%), PA (7.68%~10.01%), and SA (1.46%~2.97%) and OA had the least coefficient of variation among different new cultivars. Average ratio of single FA of ten artificial C. oleifera cultivars was consistent with that of wild common C. oleifera. All cultivars contained the same ratios of saturated FA (SFA) and unsaturated FA (USFA). Oil contents and FA profiles of new cultivars were not significantly affected by breeding and selection.
PubMed: 26942012
DOI: 10.1155/2016/3982486 -
Plant Diversity Feb 2021Nervonic acid (NA, cis-15-tetracosenoic acid) is a very long-chain monounsaturated fatty acid that has been shown to be a core component of nerve fibers and nerve cells....
Nervonic acid (NA, cis-15-tetracosenoic acid) is a very long-chain monounsaturated fatty acid that has been shown to be a core component of nerve fibers and nerve cells. It can be used to treat and prevent many neurological diseases. At present, commercially available NA is mainly derived from seeds, which contain about 5%-6% NA in their seed oil. The aim of this study were to identify and analyze NA-containing species that could be used as NA resource plants. For this purpose, 46 species seeds were collected in China and in some or all of the seed oils from these species 15 fatty acids were detected, including linoleic acid, oleic acid (C18:1, C18:1), erucic acid, palmitic acid, NA, linolenic acid (C18:3, C18:3), eicosenoic acid (C20:1, C20:1), stearic acid, behenic acid, tetracosanoic acid, arachidic acid, and docosadienoic acid. Nervonic acid was detected in all samples, but the content was highly variable among species. NA content over 9% was detected in eleven species, of which had the highest levels (13.90%). The seed oil content, seed weight, and fatty acid profiles varied among species, but the comprehensive evaluation value (W) showed that could be a new potential NA resources plant. The results also showed that NA was significantly negatively correlated with palmitic acid, oleic acid, and eicosenoic acid, but positively correlated with eicosadienoic acid, behenic acid, erucic acid, and tetracosanoic acid, which indicate the probable pathway for NA biosynthesis in plants. This study has identified species that may serve as NA resources and will help guide subsequent species breeding programs.
PubMed: 33778229
DOI: 10.1016/j.pld.2020.10.003 -
Journal of Oleo Science 2014A high-nervonic acid (cis-15-tetracosenoic acid, C24:1, n-9)-producing filamentous fungus of the Mortierella species was discovered among soil filamentous fungi. The...
A high-nervonic acid (cis-15-tetracosenoic acid, C24:1, n-9)-producing filamentous fungus of the Mortierella species was discovered among soil filamentous fungi. The filamentous fungal strain -RD000969- was isolated from soil collected in Kanagawa Prefecture (Japan) and was found to accumulate nervonic acid at a rate of 6.94% of the total cellular fatty acids. The base sequences of 28S rDNA D1/D2 and ITS 5.8S rDNA showed 100% homology with Mortierella capitata CBS 293.96. In addition to nervonic acid, strain RD000969 produced a large amount of long-chain monounsaturated fatty acids (C20:1, 12.22%; C22:1, 4.07%; C26:1, 5.91%) and a small amount of ultra-long-chain fatty acids (C28:1, 0.44%; C30:1, 0.06%; C32:1, trace). In the fungal cells, 98.87% of nervonic acid was localized at the sn-1,3 position of triacylglycerol. Nervonic acid production was maximum (186.3 mg·L(-1)) when the fungus was cultured in potato dextrose (PD) medium containing yeast extract, CaCl2, and MgSO4·7H2O.
Topics: Base Sequence; Culture Media; Fatty Acids, Monounsaturated; Fermentation; Glucose; Japan; Mortierella; Soil Microbiology; Triglycerides
PubMed: 24919474
DOI: 10.5650/jos.ess14029 -
Journal of Natural Products May 1994The novel alpha-hydroxy fatty acids 2-hydroxy-13-docosenoic acid [1a], 2-hydroxy-14-tricosenoic acid [2a], and 2-hydroxy-15-tetracosenoic acid [3a] were identified in...
The novel alpha-hydroxy fatty acids 2-hydroxy-13-docosenoic acid [1a], 2-hydroxy-14-tricosenoic acid [2a], and 2-hydroxy-15-tetracosenoic acid [3a] were identified in the Caribbean urchin, Tripneustes esculentus. The double-bond positions of the novel alpha-hydroxy fatty acids were determined by derivatization with dimethyl disulfide and shown to correlate with the corresponding non-hydroxylated mono-unsaturated fatty acids, 13-docosenoic acid, 14-tricosenoic acid, and 15-tetracosenoic acid also present in T. esculentus. The total fatty acid composition of the urchins is also reported where cis-5-olefinic fatty acids such as 5,9-octadecadienoic acid and 5,11-eicosadienoic acid were found to predominate in the mixture. Cholesterol was the predominant sterol in T. esculentus.
Topics: Aldehydes; Animals; Cholesterol; Chromatography, Thin Layer; Fatty Acids; Gas Chromatography-Mass Spectrometry; Phospholipids; Sea Urchins
PubMed: 8064293
DOI: 10.1021/np50107a008 -
Lipids May 2013Phospholipids (PL) and glycolipids (GL) FA in the edible Rhodophyta Grateloupia turuturu, from Brittany, France, were investigated over four seasons. The major lipid...
Phospholipids (PL) and glycolipids (GL) FA in the edible Rhodophyta Grateloupia turuturu, from Brittany, France, were investigated over four seasons. The major lipid class was GL in all seasons (around 45 %). More than 80 FA occurred in polar lipids, with chains from C12 to C26, identified as methyl esters and N-acyl pyrrolidides by gas chromatography-mass spectrometry (GC-MS). PUFA occurred at up to 47.1 % (summer) in PL, and up to 43.6 % (summer) in GL. The major PUFA were 20:5n-3 (12.2 % in PL and 29.0 % in GL) and 20:4n-6 (25.6 % in PL and 10.4 % in GL). The unusual 18:3n-7 acid was identified in PL up to 2.2 %. Several minor unsaturated FA were identified in PL and are previously unreported in seaweeds, namely 14-tricosenoic, 15-tetracosenoic, 5,11-octadecadienoic and 5,9-nonadecadienoic. Also unprecedented in seaweeds, ten 2-hydroxy and three 3-hydroxy FA occurred mainly in PL, 13.9 % in spring with the 3-hydroxyhexadecanoic acid as the major one (8.1 % winter). Three n-9 monounsaturated 2-hydroxy FA occurred in PL. The 2-hydroxy-15-tetracosenoic acid was characterized as the dimethyl disulfide adduct of its methyl ester. The 2-hydroxy-16-pentacosenoic and 2-hydroxy-17-hexacosenoic acids were identified by comparison of mass spectra and GC mobilities with those of the 2-hydroxy-15-tetracosenoic acid, and of other homogeneous FA series. These rare n-9 monounsaturated 2-hydroxy FA are unprecedented in seaweeds.
Topics: Fatty Acids; Fatty Acids, Unsaturated; Gas Chromatography-Mass Spectrometry; Hydroxylation; Lipid Metabolism; Lipids; Phospholipids; Rhodophyta; Seasons; Seaweed
PubMed: 23515999
DOI: 10.1007/s11745-013-3783-5