Inhibitors of acyl-CoA:cholesterol acyltransferase (ACAT). 2. Modification of fatty acid anilide ACAT inhibitors: bioisosteric replacement of the amide bond

A facultatively anaerobic, non-spore-forming, non-motile, catalase- and oxidase-positive, Gram-reaction-negative, coccoid to short rod-shaped strain, designated FLN-7T, was isolated from activated sludge of a wastewater biotreatment facility. The strain was able to hydrolyse amide pesticides (e.g. diflubenzuron, propanil, chlorpropham and dimethoate) through amide bond cleavage. Strain FLN-7T grew at 4–42 °C (optimum 28 °C), at pH 5.0–8.0 (optimum pH 7.0) and with 0–5.0 % (w/v) NaCl (optimum 1.0 %). The major respiratory quinone was ubiquinone-10. The major cellular fatty acid was C18 : 1ω7c. The genomic DNA G+C content of strain FLN-7T was 66.4±0.5 mol%. The major polar lipids were phosphatidylglycerol, phosphatidylethanolamine, diphosphatidylglycerol, phosphatidylcholine and an unidentified glycolipid. Phylogenetic analysis based on 16S rRNA gene sequences revealed that strain FLN-7T was a member of the genus Paracoccus and showed highest 16S rRNA gene sequence similarities with Paracoccus aminovorans JCM 7685T (99.2 %), P. denitrificans DSM 413T (97.8 %), P. yeei CDC G1212T (97.3 %) and P. thiocyanatus THI 011T (97.1 %). Strain FLN-7T showed low DNA–DNA relatedness with P. aminovorans KACC 12261T (36.5±3.4 %), P. denitrificans KACC 12251T (30.5±2.6 %), P. yeei CCUG 46822T (26.2±2.4 %) and P. thiocyanatus KACC 13901T (15.5±0.9 %). Based on the phylogenetic analysis, DNA–DNA hybridization, whole-cell fatty acid composition and biochemical characteristics, strain FLN-7T was clearly distinguished from all recognized species of the genus Paracoccus and should be classified in a novel species, for which the name Paracoccus huijuniae sp. nov. is proposed. The type strain is FLN-7T ( = KACC 16242T = ACCC 05690T).

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The Biosynthesis and Metabolism of the N-Acylated Aromatic Amino Acids: N-Acylphenylalanine, N-Acyltyrosine, N-Acyltryptophan, and N-Acylhistidine

Frontiers in Molecular Biosciences ◽

10.3389/fmolb.2021.801749 ◽

2022 ◽

Vol 8 ◽

Author(s):

Suzeeta Bhandari ◽

Kirpal S. Bisht ◽

David J. Merkler

Keyword(s):

Amino Acids ◽

Fatty Acid ◽

Acid Amide ◽

Aromatic Amino Acids ◽

Amide Bond ◽

Future Research ◽

Cellular Functions ◽

Fatty Acid Amides ◽

Biological Source ◽

Fatty Acid Amide

The fatty acid amides are a family of lipids composed of two chemical moieties, a fatty acid and a biogenic amine linked together in an amide bond. This lipid family is structurally related to the endocannabinoid anandamide (N-arachidonoylethanolamine) and, thus, is frequently referred to as a family of endocannabinoid-related lipids. The fatty acid amide family is divided into different classes based on the conjugate amine; anandamide being a member of the N-acylethanolamine class (NAE). Another class within the fatty acid amide family is the N-acyl amino acids (NA-AAs). The focus of this review is a sub-class of the NA-AAs, the N-acyl aromatic amino acids (NA-ArAAs). The NA-ArAAs are not broadly recognized, even by those interested in the endocannabinoids and endocannabinoid-related lipids. Herein, the NA-ArAAs that have been identified from a biological source will be highlighted and pathways for their biosynthesis, degradation, enzymatic modification, and transport will be presented. Also, information about the cellular functions of the NA-ArAAs will be placed in context with the data regarding the identification and metabolism of these N-acylated amino acids. A review of the current state-of-knowledge about the NA-ArAAs is to stimulate future research about this underappreciated sub-class of the fatty acid amide family.

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A rapid posttranslational myristylation of a 68-kD protein in D. discoideum.

The Journal of Cell Biology ◽

10.1083/jcb.111.2.401 ◽

1990 ◽

Vol 111 (2) ◽

pp. 401-407 ◽

Cited By ~ 26

Author(s):

A M da Silva ◽

C Klein

Keyword(s):

Protein Synthesis ◽

Fatty Acid ◽

Amide Bond ◽

Acyl Moiety ◽

Half Time ◽

Developmentally Regulated ◽

Unusual Finding

Cells incubated with [3H]myristate were shown to rapidly and specifically acylate a 68-kD protein, p68, in a developmentally-regulated manner. The fatty acid incorporated into p68 was identified as myristate, and is linked to the protein via an amide bond, apparently to an NH2-terminal glycine. The acylation of p68 in D. discoideum displays some unusual properties. Unexpectedly, myristylation of p68 is a posttranslational event and occurs in the presence of inhibitors of protein synthesis. Another unusual finding was that although p68 is a stable protein, the acyl moiety is removed with a half time of approximately 15 min.

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Two Novel Lyso-Ornithine Lipids Isolated from an Arctic Marine Lacinutrix sp. Bacterium

Molecules ◽

10.3390/molecules26175295 ◽

2021 ◽

Vol 26 (17) ◽

pp. 5295

Author(s):

Venke Kristoffersen ◽

Marte Jenssen ◽

Heba Raid Jawad ◽

Johan Isaksson ◽

Espen H. Hansen ◽

...

Keyword(s):

Mass Spectrometry ◽

Fatty Acid ◽

Hydroxy Fatty Acid ◽

Bacterial Species ◽

Human Melanoma ◽

Amide Bond ◽

Mass Spectrometry Analysis ◽

Cytotoxic Activities ◽

Production Potential ◽

Spectrometry Analysis

The Lacinutrix genus was discovered in 2005 and includes 12 Gram-negative bacterial species. To the best of our knowledge, the secondary metabolite production potential of this genus has not been explored before, and examination of Lacinutrix species may reveal novel chemistry. As part of a screening project of Arctic marine bacteria, the Lacinutrix sp. strain M09B143 was cultivated, extracted, fractionated and tested for antibacterial and cytotoxic activities. One fraction had antibacterial activity and was subjected to mass spectrometry analysis, which revealed two compounds with elemental composition that did not match any known compounds in databases. This resulted in the identification and isolation of two novel isobranched lyso-ornithine lipids, whose structures were elucidated by mass spectrometry and NMR spectroscopy. Lyso-ornithine lipids consist of a 3-hydroxy fatty acid linked to the alpha amino group of an ornithine amino acid through an amide bond. The fatty acid chains were determined to be iso-C15:0 (1) and iso-C16:0 (2). Compound 1 was active against the Gram-positive S. agalactiae, while 2 showed cytotoxic activity against A2058 human melanoma cells.

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1-(5-Carboxyindazol-1-yl)propan-2-ones as dual inhibitors of cytosolic phospholipase A2α and fatty acid amide hydrolase: bioisosteric replacement of the carboxylic acid moiety

Journal of Enzyme Inhibition and Medicinal Chemistry ◽

10.1080/14756366.2016.1178246 ◽

2016 ◽

Vol 31 (sup1) ◽

pp. 131-140 ◽

Cited By ~ 4

Author(s):

Jan Althaus ◽

Theresa Hake ◽

Walburga Hanekamp ◽

Matthias Lehr

Keyword(s):

Fatty Acid ◽

Fatty Acid Amide Hydrolase ◽

Acid Amide ◽

Acid Moiety ◽

Bioisosteric Replacement ◽

Cytosolic Phospholipase ◽

Dual Inhibitors ◽

Cytosolic Phospholipase A2α ◽

Amide Hydrolase ◽

Fatty Acid Amide

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Temperature Dependence of the Critical Electron Dose for Fatty Acid Monolayers

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100053188 ◽

1982 ◽

Vol 40 ◽

pp. 78-79

Author(s):

Kenneth H. Downing ◽

Robert M. Glaeser

Keyword(s):

Electron Beam ◽

Fatty Acid ◽

Inelastic Scattering ◽

Temperature Dependence ◽

Structural Damage ◽

Direct Result ◽

Second Step ◽

Strong Temperature Dependence ◽

Electron Dose ◽

Covalent Bonds

The structural damage of molecules irradiated by electrons is generally considered to occur in two steps. The direct result of inelastic scattering events is the disruption of covalent bonds. Following changes in bond structure, movement of the constituent atoms produces permanent distortions of the molecules. Since at least the second step should show a strong temperature dependence, it was to be expected that cooling a specimen should extend its lifetime in the electron beam. This result has been found in a large number of experiments, but the degree to which cooling the specimen enhances its resistance to radiation damage has been found to vary widely with specimen types.

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Effect of light intensity on the ultrastructure of the filamentous cyanobacterium, Anabaena variabilis

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100103565 ◽

1988 ◽

Vol 46 ◽

pp. 300-301

Author(s):

C. S. Bricker ◽

S. R. Barnum ◽

B. Huang ◽

J. G. Jaworskl

Keyword(s):

Fatty Acid ◽

Light Intensity ◽

Acid Content ◽

Fatty Acid Content ◽

Anabaena Variabilis ◽

Chloroplast Envelope ◽

Major Constituent ◽

Filamentous Cyanobacterium ◽

Photosynthetic Membrane ◽

Effect Of Light

Cyanobacteria are Gram negative prokaryotes that are capable of oxygenic photosynthesis. Although there are many similarities between eukaryotes and cyanobacteria in electron transfer and phosphorylation during photosynthesis, there are two features of the photosynthetic apparatus in cyanobacteria which distinguishes them from plants. Cyanobacteria contain phycobiliproteins organized in phycobilisomes on the surface of photosynthetic membrane. Another difference is in the organization of the photosynthetic membranes. Instead of stacked thylakolds within a chloroplast envelope membrane, as seen In eukaryotes, IntracytopIasmlc membranes generally are arranged in three to six concentric layers. Environmental factors such as temperature, nutrition and light fluency can significantly affect the physiology and morphology of cells. The effect of light Intensity shifts on the ultrastructure of Internal membrane in Anabaena variabilis grown under controlled environmental conditions was examined. Since a major constituent of cyanobacterial thylakolds are lipids, the fatty acid content also was measured and correlated with uItrastructural changes. The regulation of fatty acid synthesis in cyanobacteria ultimately can be studied if the fatty acid content can be manipulated.

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The effects of low-ratio n-6/n-3 PUFA on biomarkers of inflammation: a systematic review and meta-analysis

Food & Function ◽

10.1039/d0fo01976c ◽

2021 ◽

Author(s):

Yali Wei ◽

Yan Meng ◽

Na Li ◽

Qian Wang ◽

Liyong Chen

Keyword(s):

Systematic Review ◽

Fatty Acid ◽

Polyunsaturated Fatty Acid ◽

Meta Analysis ◽

Chain Polyunsaturated Fatty Acid ◽

Inflammation Markers ◽

Pufa Supplementation ◽

Long Chain

The purpose of the systematic review and meta-analysis was to determine if low-ratio n-6/n-3 long-chain polyunsaturated fatty acid (PUFA) supplementation affects serum inflammation markers based on current studies.

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