Dietary cyclic fatty acids derived from linolenic acid do not exhibit intrinsic toxicity in the rat during gestation

Abstract Background Cottonseed is one of the major sources of vegetable oil. Analysis of the dynamic changes of fatty acid components and the genes regulating the composition of fatty acids of cottonseed oil is of great significance for understanding the biological processes underlying biosynthesis of fatty acids and for genetic improving the oil nutritional qualities. Results In this study, we investigated the dynamic relationship of 13 fatty acid components at 12 developmental time points of cottonseed (Gossypium hirsutum L.) and generated cottonseed transcriptome of the 12 time points. At 5–15 day post anthesis (DPA), the contents of polyunsaturated linolenic acid (C18:3n-3) and saturated stearic acid (C18:0) were higher, while linoleic acid (C18:2n-6) was mainly synthesized after 15 DPA. Using 5 DPA as a reference, 15,647 non-redundant differentially expressed genes were identified in 10–60 DPA cottonseed. Co-expression gene network analysis identified six modules containing 3275 genes significantly associated with middle-late seed developmental stages and enriched with genes related to the linoleic acid metabolic pathway and α-linolenic acid metabolism. Genes (Gh_D03G0588 and Gh_A02G1788) encoding stearoyl-ACP desaturase were identified as hub genes and significantly up-regulated at 25 DPA. They seemed to play a decisive role in determining the ratio of saturated fatty acids to unsaturated fatty acids. FAD2 genes (Gh_A13G1850 and Gh_D13G2238) were highly expressed at 25–50 DPA, eventually leading to the high content of C18:2n-6 in cottonseed. The content of C18:3n-3 was significantly decreased from 5 DPA (7.44%) to 25 DPA (0.11%) and correlated with the expression characteristics of Gh_A09G0848 and Gh_D09G0870. Conclusions These results contribute to our understanding on the relationship between the accumulation pattern of fatty acid components and the expression characteristics of key genes involved in fatty acid biosynthesis during the entire period of cottonseed development.

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Polyunsaturated ω-3 fatty acids inhibit ACE2-controlled SARS-CoV-2 binding and cellular entry

Scientific Reports ◽

10.1038/s41598-021-84850-1 ◽

2021 ◽

Vol 11 (1) ◽

Author(s):

Anna Goc ◽

Aleksandra Niedzwiecki ◽

Matthias Rath

Keyword(s):

Fatty Acids ◽

Polyunsaturated Fatty Acids ◽

Eicosapentaenoic Acid ◽

Linolenic Acid ◽

Cathepsin L ◽

Saturated Fatty Acids ◽

Monounsaturated Fatty Acids ◽

In Vivo Experiments ◽

Lipid Compounds

AbstractThe strain SARS-CoV-2, newly emerged in late 2019, has been identified as the cause of COVID-19 and the pandemic declared by WHO in early 2020. Although lipids have been shown to possess antiviral efficacy, little is currently known about lipid compounds with anti-SARS-CoV-2 binding and entry properties. To address this issue, we screened, overall, 17 polyunsaturated fatty acids, monounsaturated fatty acids and saturated fatty acids, as wells as lipid-soluble vitamins. In performing target-based ligand screening utilizing the RBD-SARS-CoV-2 sequence, we observed that polyunsaturated fatty acids most effectively interfere with binding to hACE2, the receptor for SARS-CoV-2. Using a spike protein pseudo-virus, we also found that linolenic acid and eicosapentaenoic acid significantly block the entry of SARS-CoV-2. In addition, eicosapentaenoic acid showed higher efficacy than linolenic acid in reducing activity of TMPRSS2 and cathepsin L proteases, but neither of the fatty acids affected their expression at the protein level. Also, neither reduction of hACE2 activity nor binding to the hACE2 receptor upon treatment with these two fatty acids was observed. Although further in vivo experiments are warranted to validate the current findings, our study provides a new insight into the role of lipids as antiviral compounds against the SARS-CoV-2 strain.

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Prepubertal Dietary and Plasma Phospholipid Fatty Acids Related to Puberty Timing: Longitudinal Cohort and Mendelian Randomization Analyses

Nutrients ◽

10.3390/nu13061868 ◽

2021 ◽

Vol 13 (6) ◽

pp. 1868

Author(s):

Tuck Seng Cheng ◽

Felix R. Day ◽

John R. B. Perry ◽

Jian’an Luan ◽

Claudia Langenberg ◽

...

Keyword(s):

Fatty Acids ◽

Linolenic Acid ◽

Mendelian Randomization ◽

Saturated Fatty Acids ◽

Plasma Phospholipid ◽

Height Velocity ◽

Breast Development ◽

Dietary Intakes ◽

Linear Regression Models ◽

Peak Height Velocity

Dietary intakes of polyunsaturated, monounsaturated and saturated fatty acids (FAs) have been inconsistently associated with puberty timing. We examined longitudinal associations of prepubertal dietary and plasma phospholipid FAs with several puberty timing traits in boys and girls. In the Avon Longitudinal Study of Parents and Children, prepubertal fat intakes at 3–7.5 years and plasma phospholipid FAs at 7.5 years were measured. Timings of Tanner stage 2 genital or breast development and voice breaking or menarche from repeated reports at 8–17 years, and age at peak height velocity (PHV) from repeated height measurements at 5–20 years were estimated. In linear regression models with adjustment for maternal and infant characteristics, dietary substitution of polyunsaturated FAs for saturated FAs, and higher concentrations of dihomo-γ-linolenic acid (20:3n6) and palmitoleic acid (16:1n7) were associated with earlier timing of puberty traits in girls (n = 3872) but not boys (n = 3654). In Mendelian Randomization models, higher genetically predicted circulating dihomo-γ-linolenic acid was associated with earlier menarche in girls. Based on repeated dietary intake data, objectively measured FAs and genetic causal inference, these findings suggest that dietary and endogenous metabolic pathways that increase plasma dihomo-γ-linolenic acid, an intermediate metabolite of n-6 polyunsaturated FAs, may promote earlier puberty timing in girls.

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Uptake of α-Linolenic Acid and Its Conversion to Long Chain Omega-3 Fatty Acids in Rats Fed Microemulsions of Linseed Oil

Lipids ◽

10.1007/s11745-012-3731-9 ◽

2012 ◽

Vol 47 (12) ◽

pp. 1155-1167 ◽

Cited By ~ 9

Author(s):

D. Sugasini ◽

B. R. Lokesh

Keyword(s):

Fatty Acids ◽

Linolenic Acid ◽

Linseed Oil ◽

Omega 3 Fatty Acids ◽

Omega 3 ◽

Long Chain

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XII.—Studies on the oxidation of unsaturated fatty oils and unsaturated fatty acids. Part I. The formation of acrolein by the oxidation of linseed oil and linolenic acid

Journal of the Chemical Society Transactions ◽

10.1039/ct9160900138 ◽

1916 ◽

Vol 109 (0) ◽

pp. 138-145 ◽

Cited By ~ 12

Author(s):

Arthur Henry Salway

Keyword(s):

Fatty Acids ◽

Linolenic Acid ◽

Unsaturated Fatty Acids ◽

Linseed Oil

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Alpha linolenic acid in maternal diet halts the lipid disarray due to saturated fatty acids in the liver of mice offspring at weaning

Lipids in Health and Disease ◽

10.1186/s12944-015-0012-7 ◽

2015 ◽

Vol 14 (1) ◽

Cited By ~ 14

Author(s):

Limor Shomonov-Wagner ◽

Amiram Raz ◽

Alicia Leikin-Frenkel

Keyword(s):

Fatty Acids ◽

Linolenic Acid ◽

Maternal Diet ◽

Saturated Fatty Acids ◽

Alpha Linolenic Acid

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“Cell Membrane Theory of Senescence” and the Role of Bioactive Lipids in Aging, and Aging Associated Diseases and Their Therapeutic Implications

Biomolecules ◽

10.3390/biom11020241 ◽

2021 ◽

Vol 11 (2) ◽

pp. 241

Author(s):

Undurti N. Das

Keyword(s):

Fatty Acids ◽

Cell Membrane ◽

Linolenic Acid ◽

Genomic Stability ◽

Bioactive Lipids ◽

Camp Content ◽

Associated Diseases ◽

Epa And Dha ◽

Oncogene Activation ◽

Anti Inflammatory

Lipids are an essential constituent of the cell membrane of which polyunsaturated fatty acids (PUFAs) are the most important component. Activation of phospholipase A2 (PLA2) induces the release of PUFAs from the cell membrane that form precursors to both pro- and ant-inflammatory bioactive lipids that participate in several cellular processes. PUFAs GLA (gamma-linolenic acid), DGLA (dihomo-GLA), AA (arachidonic acid), EPA (eicosapentaenoic acid) and DHA (docosahexaenoic acid) are derived from dietary linoleic acid (LA) and alpha-linolenic acid (ALA) by the action of desaturases whose activity declines with age. Consequently, aged cells are deficient in GLA, DGLA, AA, AA, EPA and DHA and their metabolites. LA, ALA, AA, EPA and DHA can also be obtained direct from diet and their deficiency (fatty acids) may indicate malnutrition and deficiency of several minerals, trace elements and vitamins some of which are also much needed co-factors for the normal activity of desaturases. In many instances (patients) the plasma and tissue levels of GLA, DGLA, AA, EPA and DHA are low (as seen in patients with hypertension, type 2 diabetes mellitus) but they do not have deficiency of other nutrients. Hence, it is reasonable to consider that the deficiency of GLA, DGLA, AA, EPA and DHA noted in these conditions are due to the decreased activity of desaturases and elongases. PUFAs stimulate SIRT1 through protein kinase A-dependent activation of SIRT1-PGC1α complex and thus, increase rates of fatty acid oxidation and prevent lipid dysregulation associated with aging. SIRT1 activation prevents aging. Of all the SIRTs, SIRT6 is critical for intermediary metabolism and genomic stability. SIRT6-deficient mice show shortened lifespan, defects in DNA repair and have a high incidence of cancer due to oncogene activation. SIRT6 overexpression lowers LDL and triglyceride level, improves glucose tolerance, and increases lifespan of mice in addition to its anti-inflammatory effects at the transcriptional level. PUFAs and their anti-inflammatory metabolites influence the activity of SIRT6 and other SIRTs and thus, bring about their actions on metabolism, inflammation, and genome maintenance. GLA, DGLA, AA, EPA and DHA and prostaglandin E2 (PGE2), lipoxin A4 (LXA4) (pro- and anti-inflammatory metabolites of AA respectively) activate/suppress various SIRTs (SIRt1 SIRT2, SIRT3, SIRT4, SIRT5, SIRT6), PPAR-γ, PARP, p53, SREBP1, intracellular cAMP content, PKA activity and peroxisome proliferator-activated receptor γ coactivator 1-α (PGC1-α). This implies that changes in the metabolism of bioactive lipids as a result of altered activities of desaturases, COX-2 and 5-, 12-, 15-LOX (cyclo-oxygenase and lipoxygenases respectively) may have a critical role in determining cell age and development of several aging associated diseases and genomic stability and gene and oncogene activation. Thus, methods designed to maintain homeostasis of bioactive lipids (GLA, DGLA, AA, EPA, DHA, PGE2, LXA4) may arrest aging process and associated metabolic abnormalities.

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Saccharomyces kluyveri FAD3 encodes an ω3 fatty acid desaturase

Microbiology ◽

10.1099/mic.0.27049-0 ◽

2004 ◽

Vol 150 (6) ◽

pp. 1983-1990 ◽

Cited By ~ 34

Author(s):

Takahiro Oura ◽

Susumu Kajiwara

Keyword(s):

Fatty Acids ◽

Fatty Acid ◽

Linoleic Acid ◽

Linolenic Acid ◽

Functional Characterization ◽

Fatty Acid Desaturase ◽

Fatty Acid Desaturases ◽

Desaturase Gene ◽

Saccharomyces Kluyveri ◽

Fatty Acid Desaturase Gene

Fungi, like plants, are capable of producing the 18-carbon polyunsaturated fatty acids linoleic acid and α-linolenic acid. These fatty acids are synthesized by catalytic reactions of Δ12 and ω3 fatty acid desaturases. This paper describes the first cloning and functional characterization of a yeast ω3 fatty acid desaturase gene. The deduced protein encoded by the Saccharomyces kluyveri FAD3 gene (Sk-FAD3) consists of 419 amino acids, and shows 30–60 % identity with Δ12 fatty acid desaturases of several eukaryotic organisms and 29–31 % identity with ω3 fatty acid desaturases of animals and plants. During Sk-FAD3 expression in Saccharomyces cerevisiae, α-linolenic acid accumulated only when linoleic acid was added to the culture medium. The disruption of Sk-FAD3 led to the disappearance of α-linolenic acid in S. kluyveri. These findings suggest that Sk-FAD3 is the only ω3 fatty acid desaturase gene in this yeast. Furthermore, transcriptional expression of Sk-FAD3 appears to be regulated by low-temperature stress in a manner different from the other fatty acid desaturase genes in S. kluyveri.

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