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| Myristic acid (IUPAC name: tetradecanoic acid) is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. Its salts and esters are commonly referred to as myristates or tetradecanoates. The name of the acyl group derived from myristic acid is myristoyl or tetradecanoyl. The acid is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair. |
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Read full article at Wikipedia
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| InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16) |
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Chlamydomonas reinhardtii
(NCBI:txid3055)
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See:
PubMed
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Daphnia magna
(NCBI:txid35525)
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See:
Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
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Homo sapiens
(NCBI:txid9606)
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Found in
blood serum
(BTO:0000133).
See:
MetaboLights Study
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
EC 3.1.1.1 (carboxylesterase) inhibitor
Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of carboxylesterase (EC 3.1.1.1 ).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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View more via ChEBI Ontology
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1-tetradecanecarboxylic acid
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ChEBI
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14
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ChEBI
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14:0
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ChEBI
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14:00
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ChEBI
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acide tétradécanoïque
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ChEBI
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C14
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ChEBI
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CH3‒[CH2]12‒COOH
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IUPAC
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Myristic acid
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KEGG COMPOUND
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MYRISTIC ACID
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PDBeChem
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Myristic acid
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KEGG COMPOUND
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Myristinsäure
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ChEBI
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n-Tetradecan-1-oic acid
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ChemIDplus
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n-tetradecanoic acid
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NIST Chemistry WebBook
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n-Tetradecoic acid
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ChemIDplus
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Tetradecanoic acid
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KEGG COMPOUND
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tetradecoic acid
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ChEBI
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242115
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Gmelin Registry Number
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Gmelin
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508624
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Reaxys Registry Number
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Reaxys
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544-63-8
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CAS Registry Number
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KEGG COMPOUND
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544-63-8
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CAS Registry Number
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ChemIDplus
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544-63-8
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CAS Registry Number
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NIST Chemistry WebBook
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Roomruangwong C, Kanchanatawan B, Sirivichayakul S, Anderson G, Carvalho AF, Duleu S, Geffard M, Maes M (2017)
IgM-mediated autoimmune responses to oxidative specific epitopes, but not nitrosylated adducts, are significantly decreased in pregnancy: association with bacterial translocation, perinatal and lifetime major depression and the tryptophan catabolite (TRYCAT) pathway.
Metabolic brain disease 32, 1571-1583 [PubMed:28600633]
[show Abstract]
Immunoglubulin (Ig)M responses directed to oxidative specific epitopes (OSEs) and nitric oxide (NO)-adducts are significantly associated with major depression and physio-somatic symptoms. End of term serum IgM responses to OSEs and NO-adducts were assayed in pregnant women with (n = 24) and without prenatal depression (n = 25) as well as in 24 non-pregnant women. Associations of IgM/IgA responses to Gram-negative gut commensal bacteria (leaky gut index) and IgA/IgM responses to tryptophan catabolites (TRYCATs) were analyzed. IgM responses to OSEs, but not NO-adducts, were significantly reduced at the end of term. There were no significant associations between IgM responses to OSEs and perinatal depression, whilst IgM responses to NO-adducts, especially NO-cysteinyl, were significantly associated with a lifetime major depression. IgM responses to OSEs and NO-cysteinyl were significantly associated with IgA/IgM responses to Gram-negative bacteria, especially Morganella morganii, Klebsiella pneumoniae and Citrobacter koseri. IgM responses to NO-adducts and OSEs, especially malondialdehyde and myristic acid, and C-reactive protein (CRP) were inversely associated with TRYCAT pathway activity, whilst a lifetime depression and Pseudomonas putida were positively associated. The attenuation of natural IgM-mediated responses to OSEs at the end of term may indicate lowered activity of this part of the compensatory (anti-)inflammatory reflex system and may be partly explained by lowered bacterial translocation. Increased IgM responses to NO-cysteinyl is a biomarker of lifetime depression and may be induced by bacterial translocation. Natural IgM-mediated autoimmune responses, increased nitrosylation and higher CRP levels may have negative regulatory effects on the TRYCAT pathway. | Wada Y, Sakiyama S, Sakai H, Sakane F (2016)
Myristic Acid Enhances Diacylglycerol Kinase δ-Dependent Glucose Uptake in Myotubes.
Lipids 51, 897-903 [PubMed:27206979]
[show Abstract]
Decreased expression of diacylglycerol kinase (DGK) δ in skeletal muscles attenuates glucose uptake and is closely related to the pathogenesis of type 2 diabetes. Therefore, up-regulation of DGKδ expression is thought to protect and improve glucose homoeostasis in type 2 diabetes. We recently determined that myristic acid (14:0), but not palmitic (16:0) or stearic (18:0) acid, significantly increased DGKδ2 protein expression in mouse C2C12 myotubes. In the current study, we analyzed whether myristic acid indeed enhances glucose uptake in C2C12 myotubes. We observed that myristic acid caused ~1.4-fold increase in insulin-independent glucose uptake. However, palmitic and stearic acids failed to enhance glucose uptake. DGKδ-specific siRNA decreased myristic acid-dependent increase of glucose uptake. Moreover, overexpression of DGKδ2 enhanced glucose uptake in C2C12 cells in the absence of myristic acid treatment. Taken together, these results strongly suggest that myristic acid enhances basal glucose uptake in myotubes in a DGKδ2 expression-dependent manner. | Rioux V, Pédrono F, Legrand P (2011)
Regulation of mammalian desaturases by myristic acid: N-terminal myristoylation and other modulations.
Biochimica et biophysica acta 1811, 1-8 [PubMed:20920594]
[show Abstract]
Myristic acid, the 14-carbon saturated fatty acid (C14:0), usually accounts for small amounts (0.5%-1% weight of total fatty acids) in animal tissues. Since it is a relatively rare molecule in the cells, the specific properties and functional roles of myristic acid have not been fully studied and described. Like other dietary saturated fatty acids (palmitic acid, lauric acid), this fatty acid is usually associated with negative consequences for human health. Indeed, in industrialized countries, its excessive consumption correlates with an increase in plasma cholesterol and mortality due to cardiovascular diseases. Nevertheless, one feature of myristoyl-CoA is its ability to be covalently linked to the N-terminal glycine residue of eukaryotic and viral proteins. This reaction is called N-terminal myristoylation. Through the myristoylation of hundreds of substrate proteins, myristic acid can activate many physiological pathways. This review deals with these potentially activated pathways. It focuses on the following emerging findings on the biological ability of myristic acid to regulate the activity of mammalian desaturases: (i) recent findings have described it as a regulator of the Δ4-desaturation of dihydroceramide to ceramide; (ii) studies have demonstrated that it is an activator of the Δ6-desaturation of polyunsaturated fatty acids; and (iii) myristic acid itself is a substrate of some fatty acid desaturases. This article discusses several topics, such as the myristoylation of the dihydroceramide Δ4-desaturase, the myristoylation of the NADH-cytochrome b5 reductase which is part of the whole desaturase complex, and other putative mechanisms. | Li J, Gu B, Meng Q, Yan Z, Gao H, Chen X, Yang X, Lu W (2011)
The use of myristic acid as a ligand of polyethylenimine/DNA nanoparticles for targeted gene therapy of glioblastoma.
Nanotechnology 22, 435101 [PubMed:21955528]
[show Abstract]
To establish a gene delivery system for brain targeting, a low molecular weight polyethylenimine (PEI(10 K)) was modified with myristic acid (MC), and complexed with DNA, yielding MC-PEI(10 K)/DNA nanoparticles successfully. The nanoparticles were observed to be successfully taken up by the brains of mice. The transfection efficiency of the nanoparticles was then investigated, and both the in vitro and in vivo gene expression of MC-PEI(10 K)/DNA nanoparticles is significantly higher than that of unmodified PEI(10 K)/DNA nanoparticles. The anti-glioblastoma effect of MC-PEI(10 K)/pORF-hTRAIL was demonstrated by the survival time of intracranial U87 glioblastoma-bearing mice. The median survival time of the MC-PEI(10 K)/pORF-hTRAIL group (28 days) was significantly longer than that of the PEI(10 K)/pORF-hTRAIL group (24 days), the MC-PEI(10 K)/pGL(3) group (21 days) and the saline group (22 days). Therefore, our results suggested that MC-PEI(10 K) could be potentially used for brain-targeted gene delivery and in the treatment of glioblastoma. | Voon PT, Ng TK, Lee VK, Nesaretnam K (2011)
Diets high in palmitic acid (16:0), lauric and myristic acids (12:0 + 14:0), or oleic acid (18:1) do not alter postprandial or fasting plasma homocysteine and inflammatory markers in healthy Malaysian adults.
The American journal of clinical nutrition 94, 1451-1457 [PubMed:22030224]
[show Abstract]
BackgroundDietary fat type is known to modulate the plasma lipid profile, but its effects on plasma homocysteine and inflammatory markers are unclear.ObjectiveWe investigated the effects of high-protein Malaysian diets prepared with palm olein, coconut oil (CO), or virgin olive oil on plasma homocysteine and selected markers of inflammation and cardiovascular disease (CVD) in healthy adults.DesignA randomized-crossover intervention with 3 dietary sequences of 5 wk each was conducted in 45 healthy subjects. The 3 test fats, namely palmitic acid (16:0)-rich palm olein (PO), lauric and myristic acid (12:0 + 14:0)-rich CO, and oleic acid (18:1)-rich virgin olive oil (OO), were incorporated at two-thirds of 30% fat calories into high-protein Malaysian diets.ResultsNo significant differences were observed in the effects of the 3 diets on plasma total homocysteine (tHcy) and the inflammatory markers TNF-α, IL-1β, IL-6, and IL-8, high-sensitivity C-reactive protein, and interferon-γ. Diets prepared with PO and OO had comparable nonhypercholesterolemic effects; the postprandial total cholesterol for both diets and all fasting lipid indexes for the OO diet were significantly lower (P < 0.05) than for the CO diet. Unlike the PO and OO diets, the CO diet was shown to decrease postprandial lipoprotein(a).ConclusionDiets that were rich in saturated fatty acids prepared with either PO or CO, and an OO diet that was high in oleic acid, did not alter postprandial or fasting plasma concentrations of tHcy and selected inflammatory markers. This trial was registered at clinicaltrials.gov as NCT00941837. | Crow JA, Herring KL, Xie S, Borazjani A, Potter PM, Ross MK (2010)
Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids.
Biochimica et biophysica acta 1801, 31-41 [PubMed:19761868]
[show Abstract]
Two major isoforms of human carboxylesterases (CEs) are found in metabolically active tissues, CES1 and CES2. These hydrolytic enzymes are involved in xenobiotic and endobiotic metabolism. CES1 is abundantly expressed in human liver and monocytes/macrophages, including the THP1 cell line; CES2 is expressed in liver but not in monocytes/macrophages. The cholesteryl ester hydrolysis activity in human macrophages has been attributed to CES1. Here, we report the direct inhibitory effects of several endogenous oxysterols and fatty acids on the CE activity of THP1 monocytes/macrophages and recombinant human CES1 and CES2. Using THP1 whole-cell lysates we found: (1) 27-hydroxycholesterol (27-HC) is a potent inhibitor of carboxylesterase activity (IC50=33 nM); (2) 24(S),25-epoxycholesterol had moderate inhibitory activity (IC(50)=8.1 microM); and (3) cholesterol, 7-ketocholesterol, 22(R)-hydroxycholesterol, 24(S)-hydroxycholesterol, and 25-hydroxycholesterol each had little inhibitory activity. 27-HC was a partially noncompetitive inhibitor of recombinant CES1 (K(iapp)=10 nM) and impaired intracellular CES1 activity following treatment of intact THP1 cells. In contrast, recombinant CES2 activity was not inhibited by 27-HC, suggesting isoform-selective inhibition by 27-HC. Furthermore, unsaturated fatty acids were better inhibitors of CES1 activity than saturated fatty acids, while CES2 activity was unaffected by any fatty acid. Arachidonic acid (AA) was the most potent fatty acid inhibitor of recombinant CES1 and acted by a noncompetitive mechanism (K(iapp)=1.7 microM); when not complexed to albumin, exogenous AA penetrated intact THP1 cells and inhibited CES1. Inhibition results are discussed in light of recent structural models for CES1 that describe ligand binding sites separate from the active site. In addition, oxysterol-mediated inhibition of CES1 activity was demonstrated by pretreatment of human liver homogenates or intact THP1 cells with exogenous 27-HC, which resulted in significantly reduced hydrolysis of the pyrethroid insecticide bioresmethrin, a CES1-specific xenobiotic substrate. Collectively, these findings suggest that CE activity of recombinant CES1, cell lysates, and intact cells can be impaired by naturally occurring lipids, which may compromise the ability of CES1 to both detoxify environmental pollutants and metabolize endogenous compounds in vivo. | Veeresh Babu SV, Veeresh B, Patil AA, Warke YB (2010)
Lauric acid and myristic acid prevent testosterone induced prostatic hyperplasia in rats.
European journal of pharmacology 626, 262-265 [PubMed:19786012]
[show Abstract]
Numerous plants have proven to improve uncontrolled growth of the prostate gland and improve urinary tract symptoms associated with benign prostatic hyperplasia. Major components of those plants were lauric acid and myristic acid. Our study investigated whether lauric acid or myristic acid prevent testosterone induced prostatic hyperplasia in rats. Rats were divided into negative control and testosterone induced prostatic hyperplasia rats (positive control, low dose lauric acid treated, high dose lauric acid treated, low dose of myristic acid treated, high dose of myristic acid treated, finasteride treated). Testosterone and drug treatment were carried out for 14 days. Body weights were recorded before and after treatment. On 15th day, rats were sacrificed, prostates were weighed and histopathological studies were carried out. Lauric acid/myristic acid treatment showed significant inhibition of prostate enlargement and protection of histoarchitecture of prostate when compared with positive control group. In conclusion, the study showed that lauric acid/myristic acid reduced the increase of both prostate weight and prostate weight:body weight ratio, markers of testosterone induced prostatic hyperplasia in rats. | Becker LC, Bergfeld WF, Belsito DV, Hill RA, Klaassen CD, Marks JG, Shank RC, Slaga TJ, Snyder PW, Alan Andersen F (2010)
Final report of the amended safety assessment of myristic acid and its salts and esters as used in cosmetics.
International journal of toxicology 29, 162S-86S [PubMed:20634506]
[show Abstract]
This report addresses the safety of the inorganic salts and esters of various fatty alcohols of myristic acid. Most of the esters are used as skin conditioning agents in many types of cosmetics in a range of concentrations. Myristate esters are readily hydrolyzed to the corresponding alcohols and acids, which are then further metabolized. Myristate salts readily dissociate in any likely cosmetic formulation. The Cosmetic Ingredient Review (CIR) Panel recognized that much of the data supporting the ingredients in this group were previously reviewed in safety assessments for related ingredients. Where specific data did not exist, the Panel considered structure-activity relationships in determining the safety of these ingredients as used in cosmetics. The Panel determined that myristic acid and its salts and esters are safe as cosmetic ingredients in the current practices of use and concentration. | Bradbury KE, Skeaff CM, Green TJ, Gray AR, Crowe FL (2010)
The serum fatty acids myristic acid and linoleic acid are better predictors of serum cholesterol concentrations when measured as molecular percentages rather than as absolute concentrations.
The American journal of clinical nutrition 91, 398-405 [PubMed:19955401]
[show Abstract]
BackgroundThe use of serum fatty acid biomarkers in nutritional epidemiology is increasingly common; however, there is an absence of scientific evidence to substantiate whether the measurement of fatty acids as molecular percentages (which is the conventional approach) or as absolute concentrations is more informative.ObjectiveTo advance understanding about this fundamental concept, we examined the ability of serum myristic acid and linoleic acid, expressed as molecular percentages or as concentrations, to predict dietary fat and serum cholesterol concentrations.DesignA cross-sectional analysis of a population-based survey of New Zealand adults (n = 2732) was undertaken. The association of myristic and linoleic acids in serum cholesterol ester and phospholipid with dietary fat or serum cholesterol was assessed.ResultsIntake of saturated fat, dairy fat, and polyunsaturated fat was predicted similarly with the use of both units of measurement. After adjustment for confounders, mean total cholesterol decreased by 0.18 mmol/L from the lowest to the highest quintile of serum cholesteryl-linoleate as a molecular percentage (P = 0.027). In contrast, mean total cholesterol increased by 1.09 mmol/L from the lowest to the highest quintile of serum cholesteryl-linoleate concentration (P < 0.001). The molecular percentage and concentration of serum cholesteryl-myristate were positively associated with total cholesterol (P < 0.001). Results for serum phospholipid fatty acids were similar.ConclusionSerum myristic acid and linoleic acid measured as molecular percentages, but not as concentrations, predict serum total cholesterol in a manner that distinguishes between the differential cholesterolemic effects of dietary saturated and polyunsaturated fats. | Tada M, Ichiishi E, Saito R, Emoto N, Niwano Y, Kohno M (2009)
Myristic Acid, A Side Chain of Phorbol Myristate Acetate (PMA), Can Activate Human Polymorphonuclear Leukocytes to Produce Oxygen Radicals More Potently than PMA.
Journal of clinical biochemistry and nutrition 45, 309-314 [PubMed:19902021]
[show Abstract]
Myristic acid (MyA), which is a saturated fatty acid (C14:0) and a side chain of phorbol 12-myristate 13-acetate (PMA), was examined if MyA stimulates human polymorphonuclear leukocytes (PMNs) to release oxygen radicals comparable to PMA by applying electron paramagnetic resonance (EPR)-spin-trapping method. When MyA was added to isolated human PMNs, spin adducts of 5,5-dimethyl-1-pyrroline-N-oxide (DMPO)-OH and DMPO-OOH were time-dependently observed. The amounts of these spin adducts were larger than those of PMNs stimulated by PMA. These results clearly show that MyA is more potent agent to prime human PMNs than PMA, in a point of view of not only O(2) (.-) but also .OH production. This fact calls attention that too much intake of MyA that is known to be contained vegetable oils can lead to crippling effect through uncontrolled production of reactive oxygen species. | Beauchamp E, Rioux V, Legrand P (2009)
[New regulatory and signal functions for myristic acid].
Medecine sciences : M/S 25, 57-63 [PubMed:19154695]
[show Abstract]
Myristic acid is a 14 carbon saturated fatty acid, which is mostly found in milk fat. In industrialized countries, its excessive consumption is correlated with an increase in plasma cholesterol and mortality due to cardiovascular diseases. Nevertheless, one feature of this fatty acid is its ability to acylate proteins, a reaction which is called N-terminal myristoylation. This article describes various examples of important cellular regulations where the intervention of myristic acid is proven. Modulations of the cellular concentration of this fatty acid and its associated myristoylation function might be used as regulators of these metabolic pathways. | Narasimhan B, Mourya V, Dhake A (2006)
Design, synthesis, antibacterial, and QSAR studies of myristic acid derivatives.
Bioorganic & medicinal chemistry letters 16, 3023-3029 (Source: ChEMBL) [PubMed:16554156]
[show Abstract]
A series of esters and amides of myristic acid was synthesized and tested in vitro for antibacterial activity against gram-positive and gram-negative bacteria. All the compounds showed activity comparable to that of the standard drug, ciprofloxacin. The structural characteristics governing antibacterial activity of myristic acid derivatives was studied using QSAR methodology. The results showed that the antibacterial activity could be modeled using the topological descriptor, valence molecular connectivity index. The predictive ability of the models was cross-validated by construction of a test set. The low residual activity and high cross-validated r2 values (r(cv)2) observed indicated the predictive ability of the developed QSAR models. | Seyberth T, Voss S, Brock R, Wiesmüller KH, Jung G (2006)
Lipolanthionine peptides act as inhibitors of TLR2-mediated IL-8 secretion. Synthesis and structure-activity relationships.
Journal of medicinal chemistry 49, 1754-1765 (Source: ChEMBL) [PubMed:16509590]
[show Abstract]
Lipoproteins from gram-positive and -negative bacteria, mycoplasma, and shorter synthetic lipopeptide analogues activate cells of the innate immune system via the Toll-like receptor TLR2/TLR1 or TLR2/TLR6 heterodimers. For this reason, these compounds constitute highly active adjuvants for vaccines either admixed or covalently linked. The lanthionine scaffold has structural similarity with the S-(2,3-dihydroxypropyl)cysteine core structure of the lipopeptides. Therefore, lanthionine-based lipopeptide amides were synthesized and probed for activity as potential TLR2 agonists or antagonists. A collection of analytically defined lipolanthionine peptide amides exhibited an inhibitory effect of the TLR2-mediated IL-8 secretion when applied in high molar excess to the agonistic synthetic lipopeptide Pam3Cys-Ser-(Lys)4-OH. Structure-activity relationships revealed the influence of the chirality of the two alpha-carbon atoms, the chain lengths of the attached fatty acids and fatty amines, and the oxidation level of the sulfur atom on the inhibitory activity of the lipolanthionine peptide amides. | Hill TA, Odell LR, Quan A, Abagyan R, Ferguson G, Robinson PJ, McCluskey A (2004)
Long chain amines and long chain ammonium salts as novel inhibitors of dynamin GTPase activity.
Bioorganic & medicinal chemistry letters 14, 3275-3278 (Source: ChEMBL) [PubMed:15149689]
[show Abstract]
We examined a number of ligands with the view of inhibiting the GTPase activity of dynamin. Dynamin contains a pleckstrin homology (PH) domain that interacts with lipids. We report a series of simple lipid-like molecules that display moderate inhibitory activity. Inhibitory activity is linked to chain length and quaternarization of the terminal amine. A change in the counterion, Cl versus Br or I, had little effect on potency. However, introduction of a hydrophobic collar proximal to the charged site was beneficial to dynamin GTPase inhibitory action. The most potent compound was myristoyl trimethyl ammonium bromide (MTMAB, IC(50) 3.15 microM). | Machmüller A, Machmüller A, Soliva CR, Kreuzer M (2003)
Methane-suppressing effect of myristic acid in sheep as affected by dietary calcium and forage proportion.
The British journal of nutrition 90, 529-540 [PubMed:13129458]
[show Abstract]
The efficiency of myristic acid (14 : 0) as a feed additive to suppress CH4 emissions of ruminants was evaluated under different dietary conditions. Six sheep were subjected to a 6 x 6 Latin square arrangement. A supplement of non-esterified 14 : 0 (50 g/kg DM) was added to two basal diets differing in their forage:concentrate values (1 : 1.5 and 1 : 0.5), which were adjusted to dietary Ca contents of 4.2 and 9.0 g/kg DM, respectively. Comparisons were made with the unsupplemented basal diets (4.2 g Ca/kg DM). The 14 : 0 supplementation decreased (P<0.001) total tract CH4 release depending on basal diet type (interaction, P<0.001) and dietary Ca level (P<0.05, post hoc test). In the concentrate-based diet, 14 : 0 suppressed CH4 emission by 58 and 47 % with 4.2 and 9.0 g Ca/kg DM, respectively. The 14 : 0 effect was lower (22 %) in the forage-based diet and became insignificant with additional Ca. Myristic acid inhibited (P<0.05) rumen archaea without significantly altering proportions of individual methanogen orders. Ciliate protozoa concentration was decreased (P<0.05, post hoc test) by 14 : 0 only in combination with 9.0 g Ca/kg DM. Rumen fluid NH3 concentration and acetate:propionate were decreased (P<0.05) and water consumption was lower (P<0.01) with 14 : 0. The use of 14 : 0 had no clear effects on total tract organic matter and fibre digestion; this further illustrates that the suppressed methanogenesis resulted from direct effects against methanogens. The present study demonstrated that 14 : 0 is a potent CH4 inhibitor but, to be effective in CH4 mitigation feeding strategies, interactions with other diet ingredients have to be considered. | Yasuda Y, Tochikubo K, Hachisuka Y, Tomida H, Ikeda K (1982)
Quantitative structure-inhibitory activity relationships of phenols and fatty acids for Bacillus subtilis spore germination.
Journal of medicinal chemistry 25, 315-320 (Source: ChEMBL) [PubMed:6802973]
[show Abstract]
Phenols and fatty acids were found to inhibit L-alanine-initiated germination of Bacillus subtilis spores without altering their heat resistance. Inhibitory effect was defined as the concentration necessary to cause 50% inhibition of the germination rate. The quantitative structure-inhibitory activity relationships for 39 phenols and 7 fatty acids were analyzed. The pH dependency of inhibition showed that the nonionized form of the molecule was responsible for inhibition. Hydrophobicity, which was expressed by the partition coefficient or the distribution coefficient of the compounds, was important for inhibition. In addition to hydrophobicity, the electronic effect, which was expressed by the dissociation constant, played a partial role in phenols. The correlation equation of the fatty acids was similar to those of the alcohols and other hydrophobic compounds, which had been reported earlier. That of the phenols, however, appeared to be different, indicating a different and more complex mechanism of inhibition. The type of inhibition by both compounds was mixed rather than competitive or noncompetitive. |
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2010-04-22
