Intracellular Phospholipase A1 and Acyltransferase, Which Are Involved in Caenorhabditis elegans Stem Cell Divisions, Determine the sn-1 Fatty Acyl Chain of Phosphatidylinositol

Phosphatidylinositol (PI), an important constituent of membranes, contains stearic acid as the major fatty acid at the sn-1 position. This fatty acid is thought to be incorporated into PI through fatty acid remodeling by sequential deacylation and reacylation. However, the genes responsible for the reaction are unknown, and consequently, the physiological significance of the sn-1 fatty acid remains to be elucidated. Here, we identified acl-8, -9, and -10, which are closely related to each other, and ipla-1 as strong candidates for genes involved in fatty acid remodeling at the sn-1 position of PI. In both ipla-1 mutants and acl-8 acl-9 acl-10 triple mutants of Caenorhabditis elegans, the stearic acid content of PI is reduced, and asymmetric division of stem cell-like epithelial cells is defective. The defects in asymmetric division of these mutants are suppressed by a mutation of the same genes involved in intracellular retrograde transport, suggesting that ipla-1 and acl genes act in the same pathway. IPLA-1 and ACL-10 have phospholipase A1 and acyltransferase activity, respectively, both of which recognize the sn-1 position of PI as their substrate. We propose that the sn-1 fatty acid of PI is determined by ipla-1 and acl-8, -9, -10 and crucial for asymmetric divisions.

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Monensin blocks the transfer of very long chain fatty acid containing lipids to the plasma membrane of leek seedlings. Evidence for lipid sorting based on fatty acyl chain lenght

Biochimica et Biophysica Acta (BBA) - Biomembranes ◽

10.1016/0005-2736(91)90154-z ◽

1991 ◽

Vol 1070 (1) ◽

pp. 127-134 ◽

Cited By ~ 17

Author(s):

Pascal Bertho ◽

Patrick Moreau ◽

D. James Morré ◽

Claude Cassagne

Keyword(s):

Plasma Membrane ◽

Fatty Acid ◽

Acyl Chain ◽

Fatty Acyl ◽

Chain Fatty Acid ◽

Fatty Acyl Chain ◽

Long Chain Fatty Acid ◽

Lipid Sorting ◽

Long Chain

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Solubilization and separation of two distinct carnitine acyltransferases from hepatic microsomes: characterization of the malonyl-CoA-sensitive enzyme

Biochemical Journal ◽

10.1042/bj3100989 ◽

1995 ◽

Vol 310 (3) ◽

pp. 989-995 ◽

Cited By ~ 24

Author(s):

N M Broadway ◽

E D Saggerson

Keyword(s):

Acyl Chain ◽

Gel Filtration ◽

Physiological Role ◽

Fatty Acyl ◽

Exchange Chromatography ◽

Mitochondrial Outer Membrane ◽

Fatty Acyl Chain ◽

Acyltransferase Activity ◽

Carnitine Acyltransferase ◽

Malonyl Coa

Conditions have been developed for the solubilization of hepatic microsomal carnitine acyltransferase activity in good yield, with excellent long-term stability and with retention of malonyl-CoA sensitivity. Solubilized microsomal carnitine acyltransferase activity can be separated into malonyl-CoA-sensitive and -insensitive activities either by gel filtration on Superdex 200 or by anion-exchange chromatography on Resource Q. On gel filtration the apparent molecular masses of the malonyl-CoA-sensitive and -insensitive activities are approx. 300 kDa and 60 kDa respectively. The malonyl-CoA-sensitive and -insensitive activities have different fatty-acyl-chain-length specificities and different stabilities in the detergent octyl glucoside. Together these findings indicate that the malonyl-CoA-sensitive and -insensitive activities are due to different enzymes. The malonyl-CoA sensitivity of the inhibitable enzyme is markedly increased on reconstitution into soybean L-alpha-lecithin liposomes, demonstrating that phospholipids play a crucial role in the inhibition by this metabolite. Evidence is also provided that the malonyl-CoA-sensitive microsomal carnitine acyltransferase is a different enzyme from the malonyl-CoA-sensitive carnitine palmitoyltransferase found in the mitochondrial outer membrane. The possible physiological role of the two microsomal acyltransferases is discussed.

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Phosphoproteomic Analysis across the Yeast Life Cycle Reveals Control of Fatty Acyl Chain Length by Phosphorylation of the Fatty Acid Synthase Complex

Cell Reports ◽

10.1016/j.celrep.2020.108024 ◽

2020 ◽

Vol 32 (6) ◽

pp. 108024

Author(s):

Fernando Martínez-Montañés ◽

Albert Casanovas ◽

Richard R. Sprenger ◽

Magdalena Topolska ◽

David L. Marshall ◽

...

Keyword(s):

Life Cycle ◽

Fatty Acid ◽

Chain Length ◽

Fatty Acid Synthase ◽

Acyl Chain ◽

Fatty Acyl ◽

Fatty Acyl Chain ◽

Acyl Chain Length

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Regulating effect of β-ketoacyl synthase domain of fatty acid synthase on fatty acyl chain length in de novo fatty acid synthesis

Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids ◽

10.1016/j.bbalip.2015.12.002 ◽

2016 ◽

Vol 1861 (3) ◽

pp. 149-155 ◽

Cited By ~ 5

Author(s):

Wei Cui ◽

Yan Liang ◽

Weixi Tian ◽

Mingjuan Ji ◽

Xiaofeng Ma

Keyword(s):

Fatty Acid ◽

Fatty Acid Synthesis ◽

Fatty Acid Synthase ◽

De Novo ◽

Acyl Chain ◽

Acid Synthesis ◽

Fatty Acyl ◽

Fatty Acyl Chain ◽

Acyl Chain Length ◽

Ketoacyl Synthase

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Effects of an early life diet containing large phospholipid-coated lipid globules on hepatic lipid metabolism in mice

Scientific Reports ◽

10.1038/s41598-020-72777-y ◽

2020 ◽

Vol 10 (1) ◽

Author(s):

Onne A. H. O. Ronda ◽

Bert J. M. van de Heijning ◽

Ingrid Martini ◽

Albert Gerding ◽

Justina C. Wolters ◽

...

Keyword(s):

Fatty Acid ◽

Early Life ◽

Acid Metabolism ◽

Acyl Chain ◽

Later Life ◽

Fatty Acyl ◽

Dietary Lipids ◽

Bile Acid Metabolism ◽

Fatty Acyl Chain ◽

Acid Uptake

Abstract We recently reported that feeding mice in their early life a diet containing a lipid structure more similar to human milk (eIMF, Nuturis) results in lower body weights and fat mass gain upon high fat feeding in later life, compared to control (cIMF). To understand the underlying mechanisms, we now explored parameters possibly involved in this long-term effect. Male C57BL/6JOlaHsd mice, fed rodent diets containing eIMF or cIMF from postnatal (PN) day 16–42, were sacrificed at PN42. Hepatic proteins were measured using targeted proteomics. Lipids were assessed by LC–MS/MS (acylcarnitines) and GC-FID (fatty-acyl chain profiles). Early life growth and body composition, cytokines, and parameters of bile acid metabolism were similar between the groups. Hepatic concentrations of multiple proteins involved in β-oxidation (+ 17%) the TCA cycle (+ 15%) and mitochondrial antioxidative proteins (+ 28%) were significantly higher in eIMF versus cIMF-fed mice (p < 0.05). Hepatic l-carnitine levels, required for fatty acid uptake into the mitochondria, were higher (+ 33%, p < 0.01) in eIMF-fed mice. The present study indicates that eIMF-fed mice have higher hepatic levels of proteins involved in fatty acid metabolism and oxidation. We speculate that eIMF feeding programs the metabolic handling of dietary lipids.

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NodFE-Dependent Fatty Acids That Lack an α-β Unsaturation Are Subject to Differential Transfer, Leading to Novel Phospholipids

Molecular Plant-Microbe Interactions ◽

10.1094/mpmi.1998.11.1.33 ◽

1998 ◽

Vol 11 (1) ◽

pp. 33-44 ◽

Cited By ~ 14

Author(s):

Otto Geiger ◽

John Glushka ◽

Ben J. J. Lugtenberg ◽

Herman P. Spaink ◽

Jane E. Thomas-Oates

Keyword(s):

Fatty Acids ◽

Fatty Acid ◽

Rhizobium Leguminosarum ◽

Unsaturated Fatty Acids ◽

Fatty Acid Biosynthesis ◽

Acyl Chain ◽

Fatty Acyl ◽

Fatty Acyl Chain ◽

Acid Biosynthesis ◽

Fatty Acid Trans

In Rhizobium leguminosarum, the nodABC and nodFEL operons are involved in the production of lipo-chitin oligosaccharide signals that mediate host specificity. A nodFE-determined, highly unsaturated C18:4 fatty acid (trans-2, trans-4, trans-6, cis-11-octadecatetraenoic acid) is essential for the ability of the signals to induce nodule meristems and pre-infection thread structures on the host plant Vicia sativa. Of the nod genes, induction of only nodFE is sufficient to modify fatty acid biosynthesis to yield trans-2, trans-4, trans-6, cis-11-octadeca-tetraenoic acid, with an absorbance maximum of 303 nm. This unusual C18:4 fatty acid is not only found in the lipo-chitin oligosaccharides but is also associated with the phospholipids (O. Geiger, J. E. Thomas-Oates, J. Glushka, H. P. Spaink, and B. J. J. Lugtenberg, 1994, J. Biol. Chem. 269:11090-11097). Here we report that the phospholipids can contain other nodFE-derived fatty acids, a C18:3 trans-4, trans-6, cis-11-octadecatrienoic acid that has a characteristic absorption maximum at 225 nm, and a C18:2 octadecadienoic acid. Neither this C18:3 nor this C18:2 fatty acid has to date been observed attached to lipo-chitin oligosaccharides, suggesting that an as yet unknown acyl transferase (presumably NodA), responsible for the transfer of the fatty acyl chain to the glycan backbone of the lipo-chitin oligosaccharides, does not transfer all fatty acids synthesized by the action of NodFE to the lipo-chitin oligosaccharides. Rather, it must have a preference for α-β unsaturated fatty acids during transfer.

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Fatty acyl chain structure, orientational order, and the lipid phase transition in Acholeplasma laidlawii B membranes. A review of recent 19F nuclear magnetic resonance studies

Canadian Journal of Biochemistry and Cell Biology ◽

10.1139/o84-147 ◽

1984 ◽

Vol 62 (11) ◽

pp. 1134-1150 ◽

Cited By ~ 16

Author(s):

P. M. Macdonald ◽

B. D. Sykes ◽

R. N. McElhaney

Keyword(s):

Phase Transition ◽

Fatty Acids ◽

Nuclear Magnetic Resonance ◽

Acyl Chain ◽

Orientational Order ◽

Membrane Lipid ◽

Fatty Acyl ◽

Fatty Acyl Chain ◽

Lipid Phase ◽

Lipid Phase Transition

The orientational order parameters of monofluoropalmitic acids biosynthetically incorporated into membranes of Acholeplasma laidlawii B in the presence of a large excess of a variety of structurally diverse fatty acids have been determined via 19F nuclear magnetic resonance (19F NMR) spectroscopy. It is demonstrated that these monofluoropalmitic acids are relatively nonperturbing membrane probes based upon physical (differential scanning calorimetry), biochemical (membrane lipid analysis), and biological (growth studies) criteria. 19F NMR is shown to convey the same qualitative and quantitative picture of membrane lipid order provided by 2H-NMR techniques and to be sensitive to the structural characteristics of the membrane fatty acyl chains, as well as to the lipid phase transition. Representatives of each naturally occurring class of fatty acyl chain structures, including straight-chain saturated, methyl-branched, monounsaturated, and alicyclic-ring-substituted fatty acids, were studied and the 19F-NMR order parameters were correlated with the lipid phase transitions (determined calorimetrically). The lipid phase transition was the prime determinant of overall orientational order regardless of fatty acid structure. Effects upon orientational order attributable to specific structural substituents were discernible, but were secondary to the effects of the lipid phase transition. In the gel state, relative overall order was directly proportional to the temperature of the particular lipid phase transition. Not only the overall order, but also the order profile across the membrane was sensitive to the presence of particular structural substituents. In particular, in the gel state specific fatty acyl structures demonstrated a characteristic disordering effect in the membrane order profile. These various observations can be merged to provide a unified picture of the manner in which fatty acyl chain chemistry modulates the physical state of membrane lipids.

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The Role of Ceramide Metabolism and Signaling in the Regulation of Mitophagy and Cancer Therapy

Cancers ◽

10.3390/cancers13102475 ◽

2021 ◽

Vol 13 (10) ◽

pp. 2475

Author(s):

Megan Sheridan ◽

Besim Ogretmen

Keyword(s):

Cancer Therapy ◽

Acyl Chain ◽

Fatty Acyl ◽

Fatty Acyl Chain ◽

Cancer Cell Proliferation ◽

Bioactive Lipids ◽

Cellular Functions ◽

Proliferation Response ◽

Ceramide Synthases

Sphingolipids are bioactive lipids responsible for regulating diverse cellular functions such as proliferation, migration, senescence, and death. These lipids are characterized by a long-chain sphingosine backbone amide-linked to a fatty acyl chain with variable length. The length of the fatty acyl chain is determined by specific ceramide synthases, and this fatty acyl length also determines the sphingolipid’s specialized functions within the cell. One function in particular, the regulation of the selective autophagy of mitochondria, or mitophagy, is closely regulated by ceramide, a key regulatory sphingolipid. Mitophagy alterations have important implications for cancer cell proliferation, response to chemotherapeutics, and mitophagy-mediated cell death. This review will focus on the alterations of ceramide synthases in cancer and sphingolipid regulation of lethal mitophagy, concerning cancer therapy.

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