Glycerophospholipids are important structural and functional components of biological membranes and constituents of serum lipoproteins and the pulmonary surfactant. In addition, glycerophospholipids act as precursors of lipid mediators such as platelet-activating factor and eicosanoids. Cellular membranes contains a distinct composition of various glycerophospholipids such as phosphatidic acid (PA), phosphatidylcholine (PC), phosphatidylethanolamine (PE), phosphatidylserine (PS), phosphatidylglycerol (PG), phosphatidylinositol (PI), cardiolipin (CL), lysophosphatidic acid (LPA) and lysobisphosphatidic acid (also known as bis(monoacylglycerol) hydrogen phosphate - BMP).
Glycerophospholipids are first formed by the de novo (Kennedy) pathway using fatty acids activated as acyl-CoA donors. However, the acyl groups of glycerophospholipids are highly diverse and distributed in an asymmetric manner. Saturated and monounsaturated fatty acids are usually esterified at the sn-1 position, whereas polyunsaturated acyl groups are esterified at the sn-2 position. Subsequent acyl chain remodeling (Lands cycle) generates the diverse glycerophospholipid composition and asymmetry characteristic of cell membranes.
In the de novo pathway of glycerophospholipid biosynthesis, lysophosphatidic acid (LPA) is initially formed from glycerol 3-phosphate (G3P). Next, LPA is converted to PA by a LPA acyltransferase (AGPAT, also known as LPAAT), then PA is metabolized into two types of glycerol derivatives. The first is diacylglycerol (DAG) which is converted to triacylglycerol (TAG), PC, and PE. Subsequently, PS is synthesized from PC or PE. The second is cytidine diphosphate-diacylglycerol (CDP-DAG), which is processed into PI, PG, CL, and BMP. Each glycerophospholipid is involved in acyl chain remodeling via cleavage by phospholipases followed by reacylation by an acyltransferase.
Most of the glycerophospholipids are synthesized at the endoplasmic reticulum (ER), however, some, most notably cardiolipin, and BMP are synthesized in the mitochondrial and endosomal membranes respectively. Since the most of the glycerophospholipids are found in all membrane compartments, there must be extensive network of transport of glycerophospholipids from one membrane compartment to another via various mechanisms including diffusion through the cytosol, formation of transportation complexes, and diffusion via membrane contact sites (MCS) (Osman et al. 2011, Lebiedzinska et al. 2009, Lev 2010, Scherer & Schmitz 2011, Orso et al. 2011, Hermansson et al. 2011, Vance & Vance 2008).
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Yamashita A, Tanaka K, Kamata R, Kumazawa T, Suzuki N, Koga H, Waku K, Sugiura T.; ''Subcellular localization and lysophospholipase/transacylation activities of human group IVC phospholipase A2 (cPLA2gamma).''; PubMedEurope PMCScholia
Ye GM, Chen C, Huang S, Han DD, Guo JH, Wan B, Yu L.; ''Cloning and characterization a novel human 1-acyl-sn-glycerol-3-phosphate acyltransferase gene AGPAT7.''; PubMedEurope PMCScholia
Nair TS, Kozma KE, Hoefling NL, Kommareddi PK, Ueda Y, Gong TW, Lomax MI, Lansford CD, Telian SA, Satar B, Arts HA, El-Kashlan HK, Berryhill WE, Raphael Y, Carey TE.; ''Identification and characterization of choline transporter-like protein 2, an inner ear glycoprotein of 68 and 72 kDa that is the target of antibody-induced hearing loss.''; PubMedEurope PMCScholia
Chen YQ, Kuo MS, Li S, Bui HH, Peake DA, Sanders PE, Thibodeaux SJ, Chu S, Qian YW, Zhao Y, Bredt DS, Moller DE, Konrad RJ, Beigneux AP, Young SG, Cao G.; ''AGPAT6 is a novel microsomal glycerol-3-phosphate acyltransferase.''; PubMedEurope PMCScholia
Nissilä E, Ohsaki Y, Weber-Boyvat M, Perttilä J, Ikonen E, Olkkonen VM.; ''ORP10, a cholesterol binding protein associated with microtubules, regulates apolipoprotein B-100 secretion.''; PubMedEurope PMCScholia
Shiao YJ, Lupo G, Vance JE.; ''Evidence that phosphatidylserine is imported into mitochondria via a mitochondria-associated membrane and that the majority of mitochondrial phosphatidylethanolamine is derived from decarboxylation of phosphatidylserine.''; PubMedEurope PMCScholia
Zhao Y, Chen YQ, Li S, Konrad RJ, Cao G.; ''The microsomal cardiolipin remodeling enzyme acyl-CoA lysocardiolipin acyltransferase is an acyltransferase of multiple anionic lysophospholipids.''; PubMedEurope PMCScholia
West J, Tompkins CK, Balantac N, Nudelman E, Meengs B, White T, Bursten S, Coleman J, Kumar A, Singer JW, Leung DW.; ''Cloning and expression of two human lysophosphatidic acid acyltransferase cDNAs that enhance cytokine-induced signaling responses in cells.''; PubMedEurope PMCScholia
Prasad SS, Garg A, Agarwal AK.; ''Enzymatic activities of the human AGPAT isoform 3 and isoform 5: localization of AGPAT5 to mitochondria.''; PubMedEurope PMCScholia
Bertrand T, Augé F, Houtmann J, Rak A, Vallée F, Mikol V, Berne PF, Michot N, Cheuret D, Hoornaert C, Mathieu M.; ''Structural basis for human monoglyceride lipase inhibition.''; PubMedEurope PMCScholia
Tomsig JL, Creutz CE.; ''Copines: a ubiquitous family of Ca(2+)-dependent phospholipid-binding proteins.''; PubMedEurope PMCScholia
Cao J, Li JL, Li D, Tobin JF, Gimeno RE.; ''Molecular identification of microsomal acyl-CoA:glycerol-3-phosphate acyltransferase, a key enzyme in de novo triacylglycerol synthesis.''; PubMedEurope PMCScholia
Labar G, Bauvois C, Borel F, Ferrer JL, Wouters J, Lambert DM.; ''Crystal structure of the human monoacylglycerol lipase, a key actor in endocannabinoid signaling.''; PubMedEurope PMCScholia
Long JZ, Cisar JS, Milliken D, Niessen S, Wang C, Trauger SA, Siuzdak G, Cravatt BF.; ''Metabolomics annotates ABHD3 as a physiologic regulator of medium-chain phospholipids.''; PubMedEurope PMCScholia
Lev S.; ''Non-vesicular lipid transport by lipid-transfer proteins and beyond.''; PubMedEurope PMCScholia
Maury E, Prévost MC, Nauze M, Redoulès D, Tarroux R, Charvéron M, Salles JP, Perret B, Chap H, Gassama-Diagne A.; ''Human epidermis is a novel site of phospholipase B expression.''; PubMedEurope PMCScholia
Gaigg B, Simbeni R, Hrastnik C, Paltauf F, Daum G.; ''Characterization of a microsomal subfraction associated with mitochondria of the yeast, Saccharomyces cerevisiae. Involvement in synthesis and import of phospholipids into mitochondria.''; PubMedEurope PMCScholia
Duncan RE, Sarkadi-Nagy E, Jaworski K, Ahmadian M, Sul HS.; ''Identification and functional characterization of adipose-specific phospholipase A2 (AdPLA).''; PubMedEurope PMCScholia
Horibata Y, Hirabayashi Y.; ''Identification and characterization of human ethanolaminephosphotransferase1.''; PubMedEurope PMCScholia
Shadan S, Holic R, Carvou N, Ee P, Li M, Murray-Rust J, Cockcroft S.; ''Dynamics of lipid transfer by phosphatidylinositol transfer proteins in cells.''; PubMedEurope PMCScholia
Kang HW, Wei J, Cohen DE.; ''PC-TP/StARD2: Of membranes and metabolism.''; PubMedEurope PMCScholia
Ishizaki J, Suzuki N, Higashino K, Yokota Y, Ono T, Kawamoto K, Fujii N, Arita H, Hanasaki K.; ''Cloning and characterization of novel mouse and human secretory phospholipase A(2)s.''; PubMedEurope PMCScholia
Grataroli R, Dijkman R, Dutilh CE, van der Ouderaa F, De Haas GH, Figarella C.; ''Studies on prophospholipase A2 and its enzyme from human pancreatic juice. Catalytic properties and sequence of the N-terminal region.''; PubMedEurope PMCScholia
Kramer RM, Hession C, Johansen B, Hayes G, McGray P, Chow EP, Tizard R, Pepinsky RB.; ''Structure and properties of a human non-pancreatic phospholipase A2.''; PubMedEurope PMCScholia
Ma Z, Wang X, Nowatzke W, Ramanadham S, Turk J.; ''Human pancreatic islets express mRNA species encoding two distinct catalytically active isoforms of group VI phospholipase A2 (iPLA2) that arise from an exon-skipping mechanism of alternative splicing of the transcript from the iPLA2 gene on chromosome 22q13.1.''; PubMedEurope PMCScholia
Zhao Y, Chen YQ, Bonacci TM, Bredt DS, Li S, Bensch WR, Moller DE, Kowala M, Konrad RJ, Cao G.; ''Identification and characterization of a major liver lysophosphatidylcholine acyltransferase.''; PubMedEurope PMCScholia
Clark JD, Lin LL, Kriz RW, Ramesha CS, Sultzman LA, Lin AY, Milona N, Knopf JL.; ''A novel arachidonic acid-selective cytosolic PLA2 contains a Ca(2+)-dependent translocation domain with homology to PKC and GAP.''; PubMedEurope PMCScholia
Wright MM, McMaster CR.; ''PC and PE synthesis: mixed micellar analysis of the cholinephosphotransferase and ethanolaminephosphotransferase activities of human choline/ethanolamine phosphotransferase 1 (CEPT1).''; PubMedEurope PMCScholia
Yang L, Lewkowich I, Apsley K, Fritz JM, Wills-Karp M, Weaver TE.; ''Haploinsufficiency for Stard7 is associated with enhanced allergic responses in lung and skin.''; PubMedEurope PMCScholia
Hiroyama M, Takenawa T.; ''Isolation of a cDNA encoding human lysophosphatidic acid phosphatase that is involved in the regulation of mitochondrial lipid biosynthesis.''; PubMedEurope PMCScholia
Kazachkov M, Chen Q, Wang L, Zou J.; ''Substrate preferences of a lysophosphatidylcholine acyltransferase highlight its role in phospholipid remodeling.''; PubMedEurope PMCScholia
Cao J, Liu Y, Lockwood J, Burn P, Shi Y.; ''A novel cardiolipin-remodeling pathway revealed by a gene encoding an endoplasmic reticulum-associated acyl-CoA:lysocardiolipin acyltransferase (ALCAT1) in mouse.''; PubMedEurope PMCScholia
Osman C, Voelker DR, Langer T.; ''Making heads or tails of phospholipids in mitochondria.''; PubMedEurope PMCScholia
Weinstock M, Groner E.; ''Rational design of a drug for Alzheimer's disease with cholinesterase inhibitory and neuroprotective activity.''; PubMedEurope PMCScholia
Chen J, Engle SJ, Seilhamer JJ, Tischfield JA.; ''Cloning and recombinant expression of a novel human low molecular weight Ca(2+)-dependent phospholipase A2.''; PubMedEurope PMCScholia
Hung V, Zou P, Rhee HW, Udeshi ND, Cracan V, Svinkina T, Carr SA, Mootha VK, Ting AY.; ''Proteomic mapping of the human mitochondrial intermembrane space in live cells via ratiometric APEX tagging.''; PubMedEurope PMCScholia
Jain S, Zhang X, Khandelwal PJ, Saunders AJ, Cummings BS, Oelkers P.; ''Characterization of human lysophospholipid acyltransferase 3.''; PubMedEurope PMCScholia
Roderick SL, Chan WW, Agate DS, Olsen LR, Vetting MW, Rajashankar KR, Cohen DE.; ''Structure of human phosphatidylcholine transfer protein in complex with its ligand.''; PubMedEurope PMCScholia
Schuurs-Hoeijmakers JH, Geraghty MT, Kamsteeg EJ, Ben-Salem S, de Bot ST, Nijhof B, van de Vondervoort II, van der Graaf M, Nobau AC, Otte-Höller I, Vermeer S, Smith AC, Humphreys P, Schwartzentruber J, FORGE Canada Consortium, Ali BR, Al-Yahyaee SA, Tariq S, Pramathan T, Bayoumi R, Kremer HP, van de Warrenburg BP, van den Akker WM, Gilissen C, Veltman JA, Janssen IM, Vulto-van Silfhout AT, van der Velde-Visser S, Lefeber DJ, Diekstra A, Erasmus CE, Willemsen MA, Vissers LE, Lammens M, van Bokhoven H, Brunner HG, Wevers RA, Schenck A, Al-Gazali L, de Vries BB, de Brouwer AP.; ''Mutations in DDHD2, encoding an intracellular phospholipase A(1), cause a recessive form of complex hereditary spastic paraplegia.''; PubMedEurope PMCScholia
Gallego-Ortega D, Ramirez de Molina A, Ramos MA, Valdes-Mora F, Barderas MG, Sarmentero-Estrada J, Lacal JC.; ''Differential role of human choline kinase alpha and beta enzymes in lipid metabolism: implications in cancer onset and treatment.''; PubMedEurope PMCScholia
Nakanishi H, Shindou H, Hishikawa D, Harayama T, Ogasawara R, Suwabe A, Taguchi R, Shimizu T.; ''Cloning and characterization of mouse lung-type acyl-CoA:lysophosphatidylcholine acyltransferase 1 (LPCAT1). Expression in alveolar type II cells and possible involvement in surfactant production.''; PubMedEurope PMCScholia
Zvonok N, Williams J, Johnston M, Pandarinathan L, Janero DR, Li J, Krishnan SC, Makriyannis A.; ''Full mass spectrometric characterization of human monoacylglycerol lipase generated by large-scale expression and single-step purification.''; PubMedEurope PMCScholia
Horibata Y, Sugimoto H.; ''StarD7 mediates the intracellular trafficking of phosphatidylcholine to mitochondria.''; PubMedEurope PMCScholia
Nakajima K, Sonoda H, Mizoguchi T, Aoki J, Arai H, Nagahama M, Tagaya M, Tani K.; ''A novel phospholipase A1 with sequence homology to a mammalian Sec23p-interacting protein, p125.''; PubMedEurope PMCScholia
Mayr JA, Haack TB, Graf E, Zimmermann FA, Wieland T, Haberberger B, Superti-Furga A, Kirschner J, Steinmann B, Baumgartner MR, Moroni I, Lamantea E, Zeviani M, Rodenburg RJ, Smeitink J, Strom TM, Meitinger T, Sperl W, Prokisch H.; ''Lack of the mitochondrial protein acylglycerol kinase causes Sengers syndrome.''; PubMedEurope PMCScholia
Higashino Ki K, Yokota Y, Ono T, Kamitani S, Arita H, Hanasaki K.; ''Identification of a soluble form phospholipase A2 receptor as a circulating endogenous inhibitor for secretory phospholipase A2.''; PubMedEurope PMCScholia
Aguado B, Campbell RD.; ''Characterization of a human lysophosphatidic acid acyltransferase that is encoded by a gene located in the class III region of the human major histocompatibility complex.''; PubMedEurope PMCScholia
Chiba H, Michibata H, Wakimoto K, Seishima M, Kawasaki S, Okubo K, Mitsui H, Torii H, Imai Y.; ''Cloning of a gene for a novel epithelium-specific cytosolic phospholipase A2, cPLA2delta, induced in psoriatic skin.''; PubMedEurope PMCScholia
Lopez I, Arnold RS, Lambeth JD.; ''Cloning and initial characterization of a human phospholipase D2 (hPLD2). ADP-ribosylation factor regulates hPLD2.''; PubMedEurope PMCScholia
Levine T.; ''Short-range intracellular trafficking of small molecules across endoplasmic reticulum junctions.''; PubMedEurope PMCScholia
Yamashita A, Nakanishi H, Suzuki H, Kamata R, Tanaka K, Waku K, Sugiura T.; ''Topology of acyltransferase motifs and substrate specificity and accessibility in 1-acyl-sn-glycero-3-phosphate acyltransferase 1.''; PubMedEurope PMCScholia
Takeuchi K, Reue K.; ''Biochemistry, physiology, and genetics of GPAT, AGPAT, and lipin enzymes in triglyceride synthesis.''; PubMedEurope PMCScholia
Pickard RT, Strifler BA, Kramer RM, Sharp JD.; ''Molecular cloning of two new human paralogs of 85-kDa cytosolic phospholipase A2.''; PubMedEurope PMCScholia
Buckland AG, Kinkaid AR, Wilton DC.; ''Cardiolipin hydrolysis by human phospholipases A2. The multiple enzymatic activities of human cytosolic phospholipase A2.''; PubMedEurope PMCScholia
Zhang Y, Liu X, Bai J, Tian X, Zhao X, Liu W, Duan X, Shang W, Fan HY, Tong C.; ''Mitoguardin Regulates Mitochondrial Fusion through MitoPLD and Is Required for Neuronal Homeostasis.''; PubMedEurope PMCScholia
Yang Y, Cao J, Shi Y.; ''Identification and characterization of a gene encoding human LPGAT1, an endoplasmic reticulum-associated lysophosphatidylglycerol acyltransferase.''; PubMedEurope PMCScholia
Hua JC, Berger J, Pan YC, Hulmes JD, Udenfriend S.; ''Partial sequencing of human adult, human fetal, and bovine intestinal alkaline phosphatases: comparison with the human placental and liver isozymes.''; PubMedEurope PMCScholia
Larsson Forsell PK, Kennedy BP, Claesson HE.; ''The human calcium-independent phospholipase A2 gene multiple enzymes with distinct properties from a single gene.''; PubMedEurope PMCScholia
O'Regan S, Traiffort E, Ruat M, Cha N, Compaore D, Meunier FM.; ''An electric lobe suppressor for a yeast choline transport mutation belongs to a new family of transporter-like proteins.''; PubMedEurope PMCScholia
Valentin E, Singer AG, Ghomashchi F, Lazdunski M, Gelb MH, Lambeau G.; ''Cloning and recombinant expression of human group IIF-secreted phospholipase A(2).''; PubMedEurope PMCScholia
Abe A, Shayman JA.; ''Purification and characterization of 1-O-acylceramide synthase, a novel phospholipase A2 with transacylase activity.''; PubMedEurope PMCScholia
Nakashima A, Hosaka K, Nikawa J.; ''Cloning of a human cDNA for CTP-phosphoethanolamine cytidylyltransferase by complementation in vivo of a yeast mutant.''; PubMedEurope PMCScholia
Orsó E, Grandl M, Schmitz G.; ''Oxidized LDL-induced endolysosomal phospholipidosis and enzymatically modified LDL-induced foam cell formation determine specific lipid species modulation in human macrophages.''; PubMedEurope PMCScholia
Kobayashi T, Stang E, Fang KS, de Moerloose P, Parton RG, Gruenberg J.; ''A lipid associated with the antiphospholipid syndrome regulates endosome structure and function.''; PubMedEurope PMCScholia
Uyama T, Ikematsu N, Inoue M, Shinohara N, Jin XH, Tsuboi K, Tonai T, Tokumura A, Ueda N.; ''Generation of N-acylphosphatidylethanolamine by members of the phospholipase A/acyltransferase (PLA/AT) family.''; PubMedEurope PMCScholia
Schouten A, Agianian B, Westerman J, Kroon J, Wirtz KW, Gros P.; ''Structure of apo-phosphatidylinositol transfer protein alpha provides insight into membrane association.''; PubMedEurope PMCScholia
Murakami M, Masuda S, Shimbara S, Ishikawa Y, Ishii T, Kudo I.; ''Cellular distribution, post-translational modification, and tumorigenic potential of human group III secreted phospholipase A(2).''; PubMedEurope PMCScholia
Simbeni R, Pon L, Zinser E, Paltauf F, Daum G.; ''Mitochondrial membrane contact sites of yeast. Characterization of lipid components and possible involvement in intramitochondrial translocation of phospholipids.''; PubMedEurope PMCScholia
Gelb MH, Valentin E, Ghomashchi F, Lazdunski M, Lambeau G.; ''Cloning and recombinant expression of a structurally novel human secreted phospholipase A2.''; PubMedEurope PMCScholia
Turkish AR, Henneberry AL, Cromley D, Padamsee M, Oelkers P, Bazzi H, Christiano AM, Billheimer JT, Sturley SL.; ''Identification of two novel human acyl-CoA wax alcohol acyltransferases: members of the diacylglycerol acyltransferase 2 (DGAT2) gene superfamily.''; PubMedEurope PMCScholia
Hishikawa D, Shindou H, Kobayashi S, Nakanishi H, Taguchi R, Shimizu T.; ''Discovery of a lysophospholipid acyltransferase family essential for membrane asymmetry and diversity.''; PubMedEurope PMCScholia
Lord CC, Thomas G, Brown JM.; ''Mammalian alpha beta hydrolase domain (ABHD) proteins: Lipid metabolizing enzymes at the interface of cell signaling and energy metabolism.''; PubMedEurope PMCScholia
Golczak M, Kiser PD, Sears AE, Lodowski DT, Blaner WS, Palczewski K.; ''Structural basis for the acyltransferase activity of lecithin:retinol acyltransferase-like proteins.''; PubMedEurope PMCScholia
Henneberry AL, McMaster CR.; ''Cloning and expression of a human choline/ethanolaminephosphotransferase: synthesis of phosphatidylcholine and phosphatidylethanolamine.''; PubMedEurope PMCScholia
Hiraoka M, Abe A, Shayman JA.; ''Cloning and characterization of a lysosomal phospholipase A2, 1-O-acylceramide synthase.''; PubMedEurope PMCScholia
Chakraborty TR, Vancura A, Balija VS, Haldar D.; ''Phosphatidic acid synthesis in mitochondria. Topography of formation and transmembrane migration.''; PubMedEurope PMCScholia
Köhn L, Kadzhaev K, Burstedt MS, Haraldsson S, Hallberg B, Sandgren O, Golovleva I.; ''Mutation in the PYK2-binding domain of PITPNM3 causes autosomal dominant cone dystrophy (CORD5) in two Swedish families.''; PubMedEurope PMCScholia
Heravi J, Waite M.; ''Transacylase formation of bis(monoacylglycerol)phosphate.''; PubMedEurope PMCScholia
Matsutani A, Takeuchi Y, Ishihara H, Kuwano S, Oka Y.; ''Molecular cloning of human mitochondrial glycerophosphate dehydrogenase gene: genomic structure, chromosomal localization, and existence of a pseudogene.''; PubMedEurope PMCScholia
Pan YH, Yu BZ, Singer AG, Ghomashchi F, Lambeau G, Gelb MH, Jain MK, Bahnson BJ.; ''Crystal structure of human group X secreted phospholipase A2. Electrostatically neutral interfacial surface targets zwitterionic membranes.''; PubMedEurope PMCScholia
Wakimoto K, Chiba H, Michibata H, Seishima M, Kawasaki S, Okubo K, Mitsui H, Torii H, Imai Y.; ''A novel diacylglycerol acyltransferase (DGAT2) is decreased in human psoriatic skin and increased in diabetic mice.''; PubMedEurope PMCScholia
Flores-Martin J, Rena V, Angeletti S, Panzetta-Dutari GM, Genti-Raimondi S.; ''The Lipid Transfer Protein StarD7: Structure, Function, and Regulation.''; PubMedEurope PMCScholia
Lin S, Ikegami M, Moon C, Naren AP, Shannon JM.; ''Lysophosphatidylcholine Acyltransferase 1 (LPCAT1) Specifically Interacts with Phospholipid Transfer Protein StarD10 to Facilitate Surfactant Phospholipid Trafficking in Alveolar Type II Cells.''; PubMedEurope PMCScholia
Carvou N, Holic R, Li M, Futter C, Skippen A, Cockcroft S.; ''Phosphatidylinositol- and phosphatidylcholine-transfer activity of PITPbeta is essential for COPI-mediated retrograde transport from the Golgi to the endoplasmic reticulum.''; PubMedEurope PMCScholia
Shindou H, Hishikawa D, Nakanishi H, Harayama T, Ishii S, Taguchi R, Shimizu T.; ''A single enzyme catalyzes both platelet-activating factor production and membrane biogenesis of inflammatory cells. Cloning and characterization of acetyl-CoA:LYSO-PAF acetyltransferase.''; PubMedEurope PMCScholia
Kryger G, Harel M, Giles K, Toker L, Velan B, Lazar A, Kronman C, Barak D, Ariel N, Shafferman A, Silman I, Sussman JL.; ''Structures of recombinant native and E202Q mutant human acetylcholinesterase complexed with the snake-venom toxin fasciculin-II.''; PubMedEurope PMCScholia
Taylor WA, Hatch GM.; ''Identification of the human mitochondrial linoleoyl-coenzyme A monolysocardiolipin acyltransferase (MLCL AT-1).''; PubMedEurope PMCScholia
Schlame M, Haldar D.; ''Cardiolipin is synthesized on the matrix side of the inner membrane in rat liver mitochondria.''; PubMedEurope PMCScholia
Li J, Dong Y, Lü X, Wang L, Peng W, Zhang XC, Rao Z.; ''Crystal structures and biochemical studies of human lysophosphatidic acid phosphatase type 6.''; PubMedEurope PMCScholia
Saito K, Nishijima M, Kuge O.; ''Genetic evidence that phosphatidylserine synthase II catalyzes the conversion of phosphatidylethanolamine to phosphatidylserine in Chinese hamster ovary cells.''; PubMedEurope PMCScholia
This CandidateSet contains sequences identified by William Pearson's analysis of Reactome catalyst entities. Catalyst entity sequences were used to identify analagous sequences that shared overall homology and active site homology. Sequences in this Candidate set were identified in an April 24, 2012 analysis.
Dihydroxyacetone phosphate (DHAP) is converted to glycerol-3-phosphate (G3P) by glycerol-3-phosphate dehydrogenase (GPD1) or by glycerol-3-phosphate dehydrogenase-like (GPD1L) enzymes (Ou et al. 2006, Valdivia et al. 2009). The active forms of both enzymes are homodimers. This reaction may be found in white adipose tissues where glycerol-3-kinase activity is not observed in sufficient levels. GPD1/GPD1L reduces dihydroxyacetone phosphate with NADH donating electrons to this reduction.
At the endoplasmic reticulum (ER) membrane, phosphatidylserine synthase 1 (PTDSS1) converts phosphatidylcholine (PC) into phosphatidylserine (PS) by facilitating the exchange of L-Serine (L-Ser) with the choline (Cho) head group (Saito et al. 1998, Tomohiro et al. 2009).
At the endoplasmic reticulum (ER) membrane, phosphatidylcholine (PC) is hydrolysed, and has one of its acyl chains cleaved off, by cytosolic phospholipase A2 alpha/beta/delta/epsilon/zeta (PLA2G4A/B/D/E/F) (Ghomashchi et al. 2010). This produces 2-acyl lysophosphatidylcholine (LPC). Cytosolic phospholipase A2 enzymes show not only PLA2 hydrolysing activity to form the 1-acyl lysophospholipid but also have a degree of PLA1 activity, producing a 2-acyl lysophospholipid.
At the endoplasmic reticulum (ER) membrane, lysophospholipid acyltransferase 7 (MBOAT7) aka LPIAT acylates 1-acyl lysophosphatidylinositol (LPI) to form phosphatidylinositol (PI) (Gijon et al. 2008, Lee et al. 2008).
At the plasma membrane, phosphatidylethanolamine (PE) is hydrolyzed, removing one of its acyl groups, to 1-acyl phosphatidylethanolamine (LPE) by secretory phospholipase A2 proteins (Singer et al. 2002, Ishizaki et al. 1999). These include: Group IB (PLA2G1B) (Grataroli et al. 1982); Group IIA (PLA2G2A) (Seilhamer et al. 1989); Group IID (PLA2G2D) (Ishizaki et al. 1999); Group IIE (PLA2G2E) (Suzuki et al. 2000); Group IIF (PLA2G2F) (Valentin et al. 2000); Group III (PLA2G3) (Murakami et al. 2003, Murakami et al. 2005); Calcium-dependent Group V (PLA2G5) (Chen et al. 1994); Group X (PLA2G10) (Cupillard et al. 1997, Pan et al. 2002); and Group XIIA (PLA2G12A) (Gelb et al. 2000, Murakami et al. 2003).
At the endoplasmic reticulum (ER) membrane, lysophospholipid acyltransferases acylate 1-acyl lysophosphatidylcholine (LPC) to form phosphatidylcholine (PC). The lysophospholipid acyltransferases involved are: lysophosphatidylcholine acyltransferase 1 (LPCAT1) (Nakanishi et al. 2006, Chen et al. 2006); lysophosphatidylcholine acyltransferase 2 (LPCAT2) (Shindou et al. 2006); lysophospholipid acyltransferase 5 (LPCAT3) (Hishikawa et al. 2008, Zhao et al. 2008, Gijon et al. 2008, Jain et al. 2009, Kazachkov et al. 2008); lysophospholipid acyltransferase LPCAT4 (LPCAT4) aka LPEAT2 (Cao et al. 2008, Ye et al. 2005); or lysophospholipid acyltransferase 2 (MBOAT2) aka LPCAT4 (Hishikawa et al. 2008, Gijon et al. 2008).
Phosphatidic acid (PA) transport within the mitochondrion occurs as free diffusion through the aqueous phase and not mediated by phospholipid transfer proteins. This event is inferred from rats (Chakraborty et al. 1999, Wojtczak et al. 1990).
At the endoplasmic reticulum (ER) membrane, monoglyceride lipase (MGLL) hydrolyzes 2-monoacylglycerol (2-MAG) to form a fatty acid and glycerol (Dinh et al. 2004, Zvonok et al. 2008, Bertrand et al. 2010, Labar et al. 2010).
Dilysocardiolipin (DLCL) transports via membrane contact sites between the endoplasmic reticulum (ER) and the inner mitochondria membranes (IM) (Zhao et al. 2009, Buckland et al. 1998).
At the endoplasmic reticulum (ER) membrane, phosphatidylserine (PS) is hydrolyzed, and has one of its acyl chains cleaved off, by cytosolic phospholipase A2 alpha/beta/delta/epsilon/zeta (PLA2G4A,B,D/E/F) (Ghomashchi et al. 2010), or by group XVI phospholipase A2 (PLA2G16) (Duncan et al. 2008). This produces 1-acyl lysophosphatidylserine (LPS).
At the inner mitochondrial membrane (IM), the trifunctional enzyme HADH (3-hydroxyacyl-CoA dehydrogenase), an octamer of four alpha (HADHA) and four beta (HADHB) subunits, acylates monolysocardiolipin (MLCL) to cardiolipin (CL) (Taylor & Hatch 2009).
At the endoplasmic reticulum (ER) membrane, a 2-monoacylglycerol (2-MAG) molecule and a diacylglycerol (DAG) molecule are transacylated by patatin-like phospholipase domain-containing proteins 2/3 (PNPLA2/3). This forms triacylglycerol (TAG) and glycerol (Jenkins et al. 2004).
At the endoplasmic reticulum (ER) membrane, phosphatidylserine (PS) is hydrolyzed, and has one of its acyl chains cleaved off, by cytosolic phospholipase A2 alpha/delta/zeta (PLA2G4A/D/F) (Ghomashchi et al. 2010). This produces 2-acyl lysophosphatidylserine (LPS). Cytosolic phospholipase A2 enzymes show not only PLA2 hydrolyzing activity to form the 1-acyl lysophospholipid but also have a degree of PLA1 activity, producing a 2-acyl lysophospholipid.
At the inner mitochondrial membrane (IM), calcium-independent phospholipase A2 gamma (PLA2G6) hydrolyzes, removing one of the acyl chains, cardiolipin (CL) to form monolysocardiolipin (MLCL). This reaction is inferred from rats. PLA2G6 has also been characterized in humans (Larsson et al. 1998, Ma et al. 1999, Larsson Forsell et al. 1999).
At the endoplasmic reticulum (ER) membrane, phosphatidate phosphatase 1-3 (LPIN) dephosphorylates phosphatidic acid (PA) to form diacylglycerol (DAG) (Grimsey et al. 2008, Donkor et al. 2007).
At the endoplasmic reticulum (ER) membrane, phosphatidylinositol (PI) is hydrolyzed, and has one of its acyl chains cleaved off, by a phospholipase A2 to form 1-acyl lysophosphatidylinositol (LPI). The phospholipases are either cytosolic phospholipase A2 alpha/beta/zeta (PLA2G4A/D/F) (Ghomashchi et al. 2010), group XVI phospholipase A2 (PLA2G16) (Duncan et al. 2008), or Phospholipase B-like 1 (PLBD1) (Xu et al. 2009). PLBD1 also acts as a phospholipase A2 but in addition has the propensity to hydrolyze the lysophospholipid formed in its initial reaction.
At the endoplasmic reticulum (ER) membrane, phosphatidylinositol (PI) is hydrolyzed, and has one of its acyl chains cleaved off, by membrane-associated phospholipase A2 gamma 2A (PLA2G2A) (Singer et al. 2002) or by cytosolic phospholipase A2 gamma (PLA2G4C) (Ghomashchi et al. 2010), to form 1-acyl lysophosphatidylinositol (LPI).
At the Golgi membrane, cholinephosphotransferase 1 (CHPT1) converts CDP-choline (CDP-Cho) and diacylglycerol (DAG) to phosphatidylcholine (PC) and cytidine monophosphate (CMP) (Wright et al. 2002, Henneberry et al. 1999, Henneberry et al. 2002, Henneberry et al. 2000).
At the endoplasmic reticulum (ER) membrane, 2-acyl lysophosphatidylcholine (LPC) is hydrolyzed to glycerophosphocholine (GPCho) by membrane-bound cytosolic phospholipase A2 gamma (PLA2G4C) (Yamashita et al. 2005, Ghomashchi et al. 2010, Yamashita et al. 2009).
At the endoplasmic reticulum (ER) membrane, phosphatidic acid (PA) is hydrolyzed, and has one of its acyl chains cleaved off, by phospholipase A2 alpha/beta/delta/zeta (PLA2G4A/B/D/F) to form 1-acyl lysophosphatidic acid (LPA) (Ghomashchi et al. 2010).
At the endoplasmic reticulum (ER) membrane, active membrane-bound ethanolamine-phosphate cytidylyltransferase (PCY2) dimer condenses phosphoethanolamine (PETA) and cytidine triphosphate (CTP) to produce CDP-ethanolamine (CDP-ETA) (Zhu et al. 2008, Nakashima et al. 1997).
In the cytosol, phosphoethanolamine (PETA) is dephosphorylated to ethanolamine (ETA) by phosphoethanolamine/phosphocholine phosphatase (PHOSPHO1) (Roberts et al. 2004).
At the endoplasmic reticulum (ER) membrane, lysophospholipid acyltransferases acylate 2-acyl lysophosphatidylcholine (LPC) to form phosphatidylcholine (PC). The lysophospholipid acyltransferases involved are: lysophosphatidylcholine acyltransferase 1 (LPCAT1) (Nakanishi et al. 2006, Chen et al. 2006); lysophosphatidylcholine acyltransferase 2 (LPCAT2) (Shindou et al. 2006); lysophospholipid acyltransferase 5 (LPCAT3) (Hishikawa et al. 2008, Zhao et al. 2008, Gijon et al. 2008, Jain et al. 2009, Kazachkov et al. 2008); lysophospholipid acyltransferase LPCAT4 (LPCAT4) aka LPEAT2 (Cao et al. 2008, Ye et al. 2005); or lysophospholipid acyltransferase 2 (MBOAT2) aka LPCAT4 (Hishikawa et al. 2008, Gijon et al. 2008).
At the inner mitochondrial membrane (IM), phosphatidylglycerol (PG) is hydrolyzed, and has one of its acyl chains cleaved off, by phospholipase A2 beta (PLA2G4B) to form 1-acyl lysophosphatidylglycerol (LPG) (Ghomashchi et al. 2010, Singer et al. 2002).
At the endoplasmic reticulum (ER) membrane, membrane-bound cytosolic phospholipase A2 gamma (PLA2G4C) hydrolyzes 1-acyl lysophosphatidylethanolamine (LPE) to produce glycerophosphoethanolamine (GPETA) (Yamashita et al. 2005, Yamashita et al. 2009).
At the endoplasmic reticulum (ER) membrane, choline/ethanolaminephosphotransferase (CEPT1) converts CDP-choline (CDP-Cho) and diacylglycerol (DAG) to phosphatidylcholine (PC) and cytidine monophosphate (CMP) (Wright et al. 2002, Henneberry et al. 1999, Henneberry et al. 2002, Henneberry et al. 2000).
Monolysocardiolipin (MLCL) transports via membrane contact sites between the endoplasmic reticulum (ER) and the inner mitochondria membranes (IM) (Cao et al. 2004, Zhao et al. 2009, Taylor & Hatch 2009).
At the inner mitochondrial (IR) membrane, phosphatidylglycerol (PG) is hydrolysed, and has one of its acyl chains cleaved off, by phospholipase A2 beta (PLA2G4B) (Ghomashchi et al. 2010) to form 2-acyl lysophosphatidylglycerol (LPG). Phospholipase A2 enzymes show not only PLA2 hydrolysing activity to form the 1-acyl lysophospholipid but also have a degree of PLA1 activity, producing a 2-acyl lysophospholipid.
At the inner mitochondrial membrane (IM), tafazzin (TAZ) converts monolysocardiolipin (MLCL) and phosphatidylethanolamine (PE) to cardiolipin (CL) and 1-acyl lysophosphatidylethanolamine (LPE) (Xu et al. 2003, Xu et al. 2006, Malhotra et al. 2009). Although this reaction is reversible, the net effect of the phospholipase A and acyltransferase reactions drives it towards the formation of LPE and CL.
At the plasma membrane, phosphatidylinositol (PI) is hydrolyzed, removing one of its acyl groups, to 1-acyl lysophosphatidylinositol (LPI) by secretory phospholipase A2 proteins (Singer et al. 2002, Ishizaki et al. 1999). These include: Group IB (PLA2G1B) (Grataroli et al. 1982); Group IIA (PLA2G2A) (Seilhamer et al. 1989); Group IID (PLA2G2D) (Ishizaki et al. 1999); Group IIE (PLA2G2E) (Suzuki et al. 2000); Group IIF (PLA2G2F) (Valentin et al. 2000); Calcium-dependent Group V (PLA2G5) (Chen et al. 1994); Group X (PLA2G10) (Cupillard et al. 1997, Pan et al. 2002); and Group XIIA (PLA2G12A) (Gelb et al. 2000, Murakami et al. 2003).
At the plasma membrane, phosphatidylcholine (PC) is hydrolyzed, removing one of its acyl groups, to 1-acyl lysophosphatidylcholine (LPC) by membrane-associated phospholipase B1 (PLB1) (Maury et al. 2002, Gassama-Diagne et al. 1992).
At the plasma membrane, phosphatidylserine (PS) is hydrolyzed, removing one of its acyl groups, to 1-acyl lysophosphatidylserine (LPS) by secretory phospholipase A2 proteins (Singer et al. 2002, Ishizaki et al. 1999). These include: Group IB (PLA2G1B) (Grataroli et al. 1982); Group IIA (PLA2G2A) (Seilhamer et al. 1989); Group IID (PLA2G2D) (Ishizaki et al. 1999); Group IIE (PLA2G2E) (Suzuki et al. 2000); Group IIF (PLA2G2F) (Valentin et al. 2000); Calcium-dependent Group V (PLA2G5) (Chen et al. 1994); Group X (PLA2G10) (Cupillard et al. 1997, Pan et al. 2002); and Group XIIA (PLA2G12A) (Gelb et al. 2000, Murakami et al. 2003).
At the endoplasmic reticulum (ER) membrane, phosphatidylcholine (PC) is hydrolyzed and has one of its acyl chains cleaved off by a phospholipase A2 to form 1-acyl lysophosphatidylcholine (LPC). The phospholipases are either cytosolic phospholipase A2 alpha/beta/delta/zeta (PLA2G4A/B/D/F) (Ghomashchi et al. 2010, Clarke et al. 1991, Sharp et al. 1994, Song et al. 1999, Chiba et al. 2004), 85 kDa calcium-independent phospholipase A2 (PLA2G6) (Larsson et al. 1998, Ma et al. 1999, Larsson Forsell et al. 1999), group XVI phospholipase A2 (PLA2G16) (Duncan et al. 2008), or Phospholipase B-like 1 (PLBD1) (Xu et al. 2009). PLBD1 acts as a phospholipase A2 but in addition has the propensity to hydrolyze the lysophospholipid formed in its initial reaction.
At the plasma membrane, phosphatidylcholine (PC) is hydrolyzed, removing one of its acyl groups, to 1-acyl lysophosphatidylcholine (LPC) by secretory phospholipase A2 proteins (Singer et al. 2002, Ishizaki et al. 1999). These include: Group IB (PLA2G1B) (Grataroli et al. 1982); Group IIA (PLA2G2A) (Seilhamer et al. 1989); Group IID (PLA2G2D) (Ishizaki et al. 1999); Group IIE (PLA2G2E) (Suzuki et al. 2000); Group IIF (PLA2G2F) (Valentin et al. 2000); Group III (PLA2G3) (Murakami et al. 2003, Murakami et al. 2005); Calcium-dependent Group V (PLA2G5) (Chen et al. 1994); Group X (PLA2G10) (Cupillard et al. 1997, Pan et al. 2002); and Group XIIA (PLA2G12A) (Gelb et al. 2000, Murakami et al. 2003).
At the endoplasmic reticulum (ER) membrane, 1-acyl lysophosphatidylcholine (LPC) is hydrolyzed to glycerophosphocholine (GPCho) by cytosolic phospholipase A2 alpha/beta/delta/epsilon/zeta (PLA2G4A/B/D/E/F) (Yamashita et al. 2005, Ghomashchi et al. 2010, Yamashita et al. 2009, Sharp et al. 1994) or by Phospholipase B1-like (PLBD1) (Xu et al. 2009). PLBD1 also acts as a phospholipase A2 but in addition has the propensity to hydrolyze the lysophospholipid formed in its initial reaction.
At the endoplasmic reticulum (ER) membrane, diacylglycerol (DAG) is acylated and forms triacylglycerol (TAG) by the action of diacylglycerol O-acyltransferase 1 (DGAT1) tetramer or by diacylglycerol O-acyltransferase 2 (DGAT2) (Wakimoto et al. 2003, Oelkers et al. 1998, Cases et al. 2001).
At the inner mitochondrial (IM) membrane, phosphatidate cytidylyltransferase 2 (CDS2) converts phosphatidic acid (PA) and cytidine triphosphate (CTP) into cytidine diphosphate-diacylglycerol (CDP-DAG). Both ER and mitochondrial membranes have the capability to synthesise cytidine diphosphate-diacylglycerol (CDP-DAG) with phosphatidate cytidylyltransferase 1 and 2 (CDS1 and CDS2) (Lykidis et al. 1997, Schlame & Haldar 1993). However, transport of CDP-DAG between organelles cannot be ruled out (Stuhne-Sekalec et al. 1986).
At the endoplasmic reticulum (ER) membrane, phosphatidylglycerol (PG) is hydrolyzed, and has one of its acyl chains cleaved off, by cytosolic phospholipase A2 alpha/beta/delta/zeta (PLA2G4A/B/D/F) (Ghomashchi et al. 2010) to form 1-acyl lysophosphatidylglycerol (LPG).
At the endoplasmic reticulum (ER) membrane, patatin-like phospholipase domain-containing proteins 2/3 (PNPLA2/3) hydrolyze diacylglycerol (DAG), removing an acyl group to form 2-monoacylglycerol (2-MAG) (He et al. 2010, Jenkins et al. 2004, Basantani et al. 2011).
At the endoplasmic reticulum (ER) membrane, membrane-bound cytosolic phospholipase A2 gamma (PLA2G4C) hydrolyzes 2-acyl lysophosphatidylethanolamine (LPE) to produce glycerophosphoethanolamine (GPETA) (Yamashita et al. 2005, Yamashita et al. 2009).
At the endoplasmic reticulum (ER) membrane, 1-acyl lysophosphatidylcholine (LPC) is hydrolyzed to glycerophosphocholine (GPCho) by membrane-bound cytosolic phospholipase A2 gamma (PLA2G4C) (Yamashita et al. 2005, Ghomashchi et al. 2010, Yamashita et al. 2009).
Transport of phosphatidylserine (PS) occurs via membrane contact sites between the endoplasmic reticulum (ER) membrane and the inner mitochondrial (IM) membrane. This event has been inferred from rats (Vance 1990, Vance 1991).
At the inner mitochondrial membrane (IM), tafazzin (TAZ) converts cardiolipin (CL) and 1-acyl lysophosphatidylcholine (LPC) to monolysocardiolipin (MLCL) and phosphatidylcholine (PC) (Xu et al. 2003, Xu et al. 2006, Malhotra et al. 2009).
At the endoplasmic reticulum (ER) membrane, lysophospholipid acyltransferase 7 (MBOAT7) aka LPIAT acylates 2-acyl lysophosphatidylinositol (LPI) to form phosphatidylinositol (PI) (Gijon et al. 2008, Lee et al. 2008).
At the endoplasmic reticulum (ER) membrane, CDP-diacylglycerol-inositol 3-phosphatidyltransferase (CDIPT) converts cytidine diphosphate-diacylglycerol (CDP-DAG) and inositol (Ins) into phosphatidylinositol (PI) and cytidine monophosphate (CMP) (Lykidis et al. 1997).
At the endoplasmic reticulum (ER) membrane, phosphatidylglycerol (PG) is hydrolyzed, and has one of its acyl chains cleaved off, by membrane-associated phospholipase A2 gamma 2A, PLA2G2A (Singer et al. 2002), to form 1-acyl lysophosphatidylglycerol (LPG).
At the endoplasmic reticulum (ER) membrane, phosphatidate cytidylyltransferase 1 (CDS1) converts phosphatidic acid (PA) and cytidine triphosphate (CTP) into cytidine diphosphate-diacylglycerol (CDP-DAG). Both ER and mitochondrial membranes have the capability to synthesize cytidine diphosphate-diacylglycerol (CDP-DAG) with phosphatidate cytidylyltransferase 1 and 2 (CDS1 and CDS2) (Lykidis et al. 1997). However, transport of CDP-DAG between organelles cannot be ruled out (Stuhne-Sekalec et al. 1986).
At the endoplasmic reticulum (ER) membrane, phosphatidylethanolamine (PE) is hydrolyzed, and has one of its acyl chains cleaved off by membrane-associated phospholipase A2 gamma 2A, PLA2G2A, to form 2-acyl lysophosphatidylethanolamine (LPE) (Yamashita et al. 2005, Ghomashchi et al. 2010, Yamashita et al. 2009). Cytosolic phospholipase A2 enzymes show not only PLA2 hydrolyzing activity to form the 1-acyl lysophospholipid but also have a degree of PLA1 activity, producing a 2-acyl lysophospholipid.
At the inner mitochondrial (IM) membrane, CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase (PGS1) converts cytidine diphosphate-diacylglycerol (CDP-DAG) and glycerol-3-phosphate (G3P) to phosphatidylglycerophosphate (PGP) and cytidine monophosphate (CMP). This event is inferred from rats. The enzyme PGS1 has been characterized in humans (Ota et al. 2004).
At the endoplasmic reticulum (ER) membrane, phosphatidylserine synthase 2 (PTDSS2) converts phosphatidylethanolamine (PE) into phosphatidylserine (PS) by facilitating the exchange of L-Serine (L-Ser) with the ethanolamine (ETA) head group (Saito et al. 1998, Tomohiro et al. 2009).
At the inner mitochondrial (IM) membrane, phosphatidylserine decarboxylase proenzyme (heterodimer of two chains from the same protein) (PISD) decarboxylates phosphatidylserine (PS) to phosphatidylethanolamine (PE). This event has been inferred from rats and limited data for a human PISD (Forbes et al. 2007).
At the endoplasmic reticulum (ER) membrane, phosphatidylcholine (PC) is hydrolyzed, and has one of its acyl chains cleaved off, by membrane-associated phospholipase A2 gamma 4C, PLA2G4C (Yamashita et al. 2005, Ghomashchi et al. 2010, Yamashita et al. 2009), to form 2-acyl lysophosphatidylcholine (LPC). Cytosolic phospholipase A2 enzymes show not only PLA2 hydrolysing activity to form the 1-acyl lysophospholipid but also have a degree of PLA1 activity, producing a 2-acyl lysophospholipid.
At the endoplasmic reticulum (ER) membrane, phosphatidylinositol (PI) is hydrolyzed, and has one of its acyl chains cleaved off, by cytosolic phospholipase A2 delta/epsilon (PLA2G4D/E) Ghomashchi et al. 2010). This produces 2-acyl lysophosphatidylinositol (LPI). Cytosolic phospholipase A2 enzymes show not only PLA2 hydrolyzing activity to form the 1-acyl lysophospholipid but also have a degree of PLA1 activity, producing a 2-acyl lysophospholipid.
At the endoplasmic reticulum (ER) membrane, phosphatidylserine (PS) is hydrolyzed, and has one of its acyl chains cleaved off, by membrane-associated phospholipase A2 gamma 2A, PLA2G2A, to form 1-acyl lysophosphatidylserine (LPS) (Singer et al. 2002).
Cardiolipin (CL) transports via membrane contact sites between the endoplasmic reticulum (ER) and the inner mitochondria membranes (IM) (Osman et al. 2011, Vance 1990, Gaigg et al. 1995, Zhao et al. 2009, Simbeni et al. 1991, Ardail et al. 1993, Shiao et al., 1995).
At the inner mitochondrial membrane (IM), tafazzin (TAZ) converts cardiolipin (CL) and 1-acyl lysophosphatidylethanolamine (LPE) to monolysocardiolipin (MLCL) and phosphatidylethanolamine (PE) (Xu et al. 2003, Xu et al. 2006, Malhotra et al. 2009).
At the endoplasmic reticulum (ER) membrane, two 2-monoacylglycerol (2-MAG) molecules are transacylated by patatin-like phospholipase domain-containing proteins 2/3 (PNPLA2/3) to form diacylglycerol (DAG) and glycerol (Jenkins et al. 2004).
At the endoplasmic reticulum (ER) membrane, lysophospholipid acyltransferases acylate 1-acyl lysophosphatidylglycerol (LPG) to form phosphatidylglycerol (PG). The lysophospholipid acyltransferases involved are: lysophosphatidylcholine acyltransferase 1 (LPCAT1) (Nakanishi et al. 2006, Chen et al. 2006), lysophospholipid acyltransferase LPCAT4 (LPCAT4) aka LPEAT2 (Cao et al. 2008, Ye et al. 2005); or acyl-CoA:lysophosphatidylglycerol acyltransferase (LPGAT1) (Yang et al. 2004).
At the inner mitochondrial membrane (IM), the phospholipase A2 group IV alpha (PLA2G4A) protein hydrolyzes monolysocardiolipin (MLCL) and produces dilysocardiolipin (DLCL) (Buckland et al. 1998, Sharp et al. 1994).
At the inner mitochondrial membrane (IM), cardiolipin synthase (CRLS1) acylates 2-acyl lysophosphatidylglycerol (LPG) to form phosphatidylglycerol (PG) (Nie et al. 2010).
In the cytosol, glycerophosphocholine phosphodiesterase (GPCPD1, also known as GDE5) hydrolyzes glycerophosphocholine (GPCho) to produce choline (Cho) and glycerol-3-phosphate (G3P). This event has been inferred from mice. GPCPD1 has also been characterized in humans (Ota et al. 2004).
At the endoplasmic reticulum (ER) membrane, triacylglycerol (TAG) is hydrolyzed, removing one of its acyl groups to form diacylglycerol (DAG) by patatin-like phospholipase domain-containing protein 2/3 (PNPLA2/3) (He et al. 2010, Jenkins et al. 2004, Basantani et al. 2011).
The biosynthetic pathway of lysobisphosphatidic acid, also known as bis(monoacylglycerol) hydrogen phosphate (BMP), is still not fully understood with the in vivo enzymes responsible yet to be fully identified. It appears to involve multiple steps including hydrolysis of phosphatidylglycerol (PG) by a phospholipase A2, acylation, and a reorientation of the phosphoryl ester (Poorthuis & Hostetler 1978, Heravi & Waite 1999, Hullin-Matsuda et al. 2007, Gallala & Sandhoff 2010).
Lysobisphosphatidic acid, also known as bis(monoacylglycerol) hydrogen phosphate (BMP), is enriched in late endosomes and not found in the endoplasmic reticulum (ER) or mitochondria where phosphatidylglycerol (PG) is synthesised. Late endosomes form membrane contact sites with the ER, providing a means for PG to enter the late endosome and be converted to BMP (Levine 2004, Eden et al. 2010, Kobayashi et al. 1998, Hullin-Matsuda et al. 2007, Kobayashi et al. 1999).
At the endoplasmic reticulum (ER) membrane, choline/ethanolaminephosphotransferase 1 (CEPT1) or ethanolaminephosphotransferase 1 (EPT1) converts CDP- ethanolamine (CDP-ETA) and diacylglycerol (DAG) to phosphatidylethanolamine (PE) and cytidine monophosphate (CMP) (Horibata et al. 2007, Wright et al. 2002, Henneberry et al. 1999, Henneberry et al. 2002, Henneberry et al. 2000).
At the plasma membrane, phosphatidylglycerol (PG) is hydrolyzed, removing one of its acyl groups, to 1-acyl lysophosphatidylglycerol (LPG) by secretory phospholipase A2 proteins (Singer et al. 2002, Ishizaki et al. 1999). These include: Group IB (PLA2G1B) (Grataroli et al. 1982); Group IIA (PLA2G2A) (Seilhamer et al. 1989); Group IID (PLA2G2D) (Ishizaki et al. 1999); Group IIE (PLA2G2E) (Suzuki et al. 2000); Group IIF (PLA2G2F) (Valentin et al. 2000); Group III (PLA2G3) (Murakami et al. 2003, Murakami et al. 2005); Calcium-dependent Group V (PLA2G5) (Chen et al. 1994); Group X (PLA2G10) (Cupillard et al. 1997, Pan et al. 2002); and Group XIIA (PLA2G12A) (Gelb et al. 2000, Murakami et al. 2003).
At the endoplasmic reticulum (ER) membrane, phosphatidylglycerol (PG) is hydrolyzed, and has one of its acyl chains cleaved off, by cytosolic phospholipase A2 delta/zeta (PLA2G4D/F) (Ghomashchi et al. 2010) to form 2-acyl lysophosphatidylglycerol (LPG). Cytosolic phospholipase A2 enzymes show not only PLA2 hydrolyzing activity to form the 1-acyl lysophospholipid but also have a degree of PLA1 activity, producing a 2-acyl lysophospholipid.
At the endoplasmic reticulum (ER) membrane, 2-acyl lysophosphatidylcholine (LPC) is hydrolyzed to glycerophosphocholine (GPCho) by cytosolic phospholipase A2 alpha/beta/delta/epsilon/zeta (PLA2G4A/B/D/E/F) (Yamashita et al. 2005, Ghomashchi et al. 2010, Yamashita et al. 2009, Sharp et al. 1994) or by Phospholipase B1-like (PLBD1) (Xu et al. 2009). PLBD1 also acts as a phospholipase A2 but in addition has the propensity to hydrolyze the lysophospholipid formed in its initial reaction.
At the Golgi membrane, phosphatidylinositol (PI) is exchanged for phosphatidylcholine (PC) within the phosphatidylinositol transfer protein beta isoform (PITPNB) complex (Tilley et al. 2004, Yolder et al. 2001, Carvou et al. 2010, Schouten et al. 2002, Vordtriede et al. 2005, Shadan et al. 2008).
Transport of phosphatidylethanolamine (PE) occurs via membrane contact sites between the mitochondrial membrane and the endoplasmic reticulum (ER) membrane. The event is inferred from rats (Vance 1990, Vance 1991).
At the outer mitochondrial (OM) membrane, 1-acyl lysophosphatidic acid (LPA) is acylated to phosphatidic acid (PA) by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferases epsilon (AGPAT5) (Prasad et al. 2011).
At the endoplasmic reticulum (ER) membrane, phosphatidylethanolamine (PE) is hydrolyzed, and has one of its acyl chains cleaved off, by phospholipase A2 to form 1-acyl lysophosphatidylethanolamine (LPE). The phospholipases are either cytosolic phospholipase A2 alpha/beta/delta/epsilon/zeta (PLA2G(4A/B/D/E/F) (Ghosh et al. 2006, Yamashita et al. 2009, Yamashita et al. 1999, Ghomashchi et al. 2010), 85 kDa calcium-independent phospholipase A2 (PLA2G6) (Larsson et al. 1998, Ma et al. 1999, Larsson Forsell et al. 1999), group XVI phospholipase A2 (PLA2G16) (Duncan et al. 2008), or Phospholipase B-like 1 (PLBD1) (Xu et al. 2009). PLBD1 acts as a phospholipase A2 but in addition has the propensity to hydrolyze the lysophospholipid formed in its initial reaction.
At the endoplasmic reticulum (ER) membrane, phosphatidylethanolamine (PE) is hydrolyzed, and has one of its acyl chains cleaved off, by membrane-associated phospholipase A2 gamma 2A, (PLA2G2A) or by calcium-independent phospholipase A2-gamma (PNPLA8), to form 1-acyl lysophosphatidylethanolamine (LPE) (Murakami et al. 2005, Kramer et al. 1989, Singer et al. 2002).
At the endoplasmic reticulum (ER) membrane, phosphatidylcholine (PC) is hydrolyzed, and has one of its acyl chains cleaved off, by a membrane-associated phospholipase A2 to form 1-acyl lysophosphatidylcholine (LPC). The phospholipases are either phospholipase A2 group II alpha (PLA2G2A) (Seihamer et al. 1989, Singer et al. 2002), cytosolic phospholipase A2 group IV gamma (PLA2G4C) (Yamashita et al. 2005, Pickard et al. 1999, Ghomashchi et al. 2010, Yamashita et al. 2009), or calcium-independent phospholipase A2-gamma (PNPLA8) (Murakami et al. 2005, Underwood et al. 1998).
At the inner mitochondrial membrane (IM), tafazzin (TAZ) converts monolysocardiolipin (MLCL) and phosphatidylcholine (PC) to cardiolipin (CL) and 1-acyl lysophosphatidylcholine (LPC) (Xu et al. 2003, Xu et al. 2006, Malhotra et al. 2009). Although this reaction is reversible, the net effect of the phospholipase A and acyltransferase reactions drives it towards the formation of LPC and CL.
In the cytosol, ethanolamine (ETA) is phosphorylated to phosphoethanolamine (PETA) by choline kinase (CHK) dimer or by ethanolamine kinase 1/2 (ETNK1/2) (Lykidis et al. 2001, Gallego-Ortega et al. 2009). CHK dimer consists of either choline kinase alpha subunit (CHKA) or beta subunit (CHKB) homodimer, or of CHKA:CHKB heterodimer.
At the endoplasmic reticulum (ER) membrane, lysocardiolipin acyltransferase 1 (LCLAT1) aka ALCAT1 acylates dilysocardiolipin (DLCL) to produce monolysocardiolipin (MLCL) (Zhao et al. 2009).
In the cytosol, choline kinase alpha subunit (CHKA) homodimer, choline kinase beta subunit (CHKB) dimer, or CHKA:CHKB heterodimer phosphorylates choline (Cho) to produce phosphocholine (PCho) (Malito et al. 2006, Gallego-Ortega et al. 2009).
At the endoplasmic reticulum (ER) membrane, active membrane-bound choline-phosphate cytidylyltransferase A (PCYT1A) or B (PCYT1B) homodimer condenses phosphocholine (PCho) and cytidine triphosphate (CTP) to produce CDP-choline (CDP-Cho) (Lykidis et al. 1998).
Glycerol-3-phosphate (G3P) is acylated to 1-acyl lysophosphatidic acid (LPA) by the enzymes glycerol-3-phosphate acyltransferase 1 (GPAT, also known as GPAM) and glycerol-3-phosphate acyltransferase 2 (GPAT2), at the outer mitochondrial (OM) membrane (Shindou & Shimizu 2009, Chen et al. 2008, Takeuchi & Reue 2009).
In the cytosol, glycerophosphocholine phosphodiesterase (GPCPD1, also known as GDE5) hydrolyzes glycerophosphoethanolamine (GPETA) to produce ethanolamine (ETA) and glycerol-3-phosphate (G3P). This event has been inferred from mice. GPCPD1 has also been characterized in humans (Ota et al. 2004).
At the ER membrane, phosphatidylcholine (PC) is exchanged for phosphatidylinositol (PI) within the phosphatidylinositol transfer protein beta isoform (PITPNB) complex (Tilley et al. 2004, Yolder et al. 2001, Carvou et al. 2010, Schouten et al. 2002, Vordtriede et al. 2005, Shadan et al. 2008).
At the inner mitochondrial membrane (IM), cardiolipin synthase (CRLS1) converts phosphatidylglycerol (PG) and cytidine diphosphate-diacylglycerol (CDP-DAG) into cardiolipin (CL) (Lu et al. 2006, Houtkooper et al. 2006).
Dihydroxyacetone phosphate (DHAP) is converted to 1-acyl glycerone 3-phosphate (GO3P) by the enzyme dihydroxyacetone phosphate acyltransferase (GNPAT) (de Vet et al. 1999, Ofman et al. 1994). This reaction step links Glycerolipid metabolism to Ether lipid metabolism.
The phosphatidylinositol transfer protein beta isoform (PITPNB) bound to phosphatidylinositol (PI) complex transports from the endoplasmic reticulum (ER) membrane to the Golgi membrane (Carvou et al. 2010, Shadan et al. 2008).
Phosphatidylcholine (PC) is hydrolyzed to phosphatidic acid (PA) and choline (Cho) by the enzymes phospholipase D1/2 (PLD1/2), at the endoplasmic reticulum (ER) membrane (Lopez et al. 1998, Hammond et al. 1995).
At the inner mitochondrial (IR) membrane, cardiolipin synthase (CRLS1) acylates 1-acyl lysophosphatidylglycerol (LPG) to form phosphatidylglycerol (PG) (Nie et al. 2010).
At the endoplasmic reticulum (ER) membrane, lysophospholipid acyltransferases acylate 2-acyl lysophosphatidylglycerol (LPG) to form phosphatidylglycerol (PG). The lysophospholipid acyltransferases involved are: lysophosphatidylcholine acyltransferase 1 (LPCAT1) (Nakanishi et al. 2006, Chen et al. 2006), lysophospholipid acyltransferase LPCAT4 (LPCAT4) aka LPEAT2 (Cao et al. 2008, Ye et al. 2005); or acyl-CoA:lysophosphatidylglycerol acyltransferase (LPGAT1) (Yang et al. 2004).
In the cytosol, the phosphoethanolamine/phosphocholine phosphatase (PHOSPHO1) dephosphorylates phosphocholine (PCho) to choline (Cho) (Roberts et al. 2004).
The complex between phosphatidylcholine (PC) and phosphatidylinositol transfer protein beta isoform (PITPNB) transports from the Golgi membrane to the ER membrane (Carvou et al. 2010, Shadan et al. 2008).
At the inner mitochondrial (IM) membrane, PTPMT1 (phosphatidylglycerophosphatase and protein-tyrosine phosphatase 1) catalyzes the dephosphorylation of phosphatidylglycerophosphate (PGP) to phosphatidylglycerol (PG). The biochemical properties of human PTPMT1 have not been determined; this reaction is inferred from the one catalyzed by the homologous mouse protein (Zhang et al. 2011).
At the endoplasmic reticulum (ER) membrane, phosphatidic acid (PA) is hydrolyzed, and has one of its acyl chains cleaved off, by membrane-associated phospholipase A2 gamma 2A (PLA2G2A), to form 1-acyl lysophosphatidic acid (LPA) (Singer et al. 2002).
At the outer mitochondrial (OM) membrane, phosphatidic acid (PA) is hydrolyzed, and has one of its acyl chains cleaved off, by phospholipase A2 alpha/beta/delta/zeta (PLA2G4A/B/D/F) to form 1-acyl lysophosphatidic acid (LPA) (Ghomashchi et al. 2010).
At the plasma membrane, phosphatidic acid (PA) is hydrolyzed, removing one of its acyl groups, to 1-acyl lysophosphatidic acid (LPA) by secretory phospholipase A2 proteins (Singer et al. 2002, Ishizaki et al. 1999). These include: Group IB (PLA2G1B) (Grataroli et al. 1982); Group IIA (PLA2G2A) (Seilhamer et al. 1989); Group IID (PLA2G2D) (Ishizaki et al. 1999); Group IIE (PLA2G2E) (Suzuki et al. 2000); Group IIF (PLA2G2F) (Valentin et al. 2000); Calcium-dependent Group V (PLA2G5) (Chen et al. 1994); Group X (PLA2G10) (Cupillard et al. 1997, Pan et al. 2002); and Group XIIA (PLA2G12A) (Gelb et al. 2000, Murakami et al. 2003).
In the endoplasmic reticulum (ER) membrane, phospholipase D1-4,6 (PLD1-4,6) transphosphatidylates phosphatidylcholine (PC) with glycerol to displace choline (Cho) and form phosphatidylglycerol (PG). This reaction is inferred from rats, but PLD enzymes are present in humans (Hammond et al. 1995, Steed et al. 1998, Cao et al. 1997).
At the endoplasmic reticulum (ER) membrane, phosphatidylethanolamine (PE) is hydrolyzed, and has one of its acyl chains cleaved off by cytosolic phospholipase A2 alpha/delta/epsilon/zeta (PLA2G4A/D/E/F) (Ghomashchi et al. 2010). This produces 2-acyl lysophosphatidylethanolamine (LPE). Cytosolic phospholipase A2 enzymes show not only PLA2 hydrolyzing activity to form the 1-acyl lysophospholipid but also have a degree of PLA1 activity, producing a 2-acyl lysophospholipid.
Acetylcholinesterase (ACHE) oligomers (comprising monomers, dimers and tetramers), anchored to the extracellular side of the plasma membrane, hydrolyze acetylcholine (AcCho) to form choline (Cho) and acetate (Weinstock & Groner 2008, Velan et al. 1991, Kryger et al. 2000).
Acetylcholine from the synaptic cleft is degraded into inactive molecules, Cho and acetate by ACHE, which is located in the synaptic cleft (Weinstock & Groner 2008).
At the endoplasmic reticulum (ER) membrane, 1-acyl-lysophosphatidic acid (LPA) is acylated to phosphatidic acid (PA) by the enzymes 1-acyl-sn-glycerol-3-phosphate acyltransferases (AGPAT1 through 11), and lysophosphatidylcholine acyltransferase (LPCAT1) (Aguado and Campbell 1998).
See recent review by Agarwal (2012, in press).
AGPAT1, 2, 3 and LPCAT1 have been characterized biochemically (AGPAT1, 2: Yamashita et al. 2007, West et al. 1997, Aguado and Campbell 1998, Gale et al. 2006; AGPAT3: Agarwal et al. 2006; LPCAT1: Nakanishi et al. 2006, Chen et al. 2006). Two additional proteins, AGPAT4 and AGPAT5, are inferred to have such activity based on studies of homologous mouse enzymes (Lu et al. 2005). These enzymes differ in their tissue specific patterns of expression in the body and in their preferences for specific acyl CoA molecules (Shindou and Shimizu 2009; Takeuchi and Reue 2009).
Choline (Cho) transports from the extracellular space through the plasma membrane via the choline transporter-like proteins (SLC44A1-5 also known as CTL1-5) to the cytosol (Okuda & Haga 2000, Traiffort et al. 2005, O'Regan et al. 2000).
CTL1 is broadly expressed on leukocytes and endothelial cells (Wille et al. 2001). CTL2 is highly expressed in human inner ear and is the target of antibody-induced hearing loss (Nair et al. 2004).
Glycerol-3-phosphate (G3P) is acylated to 1-acyl lysophosphatidic acid (LPA) by the enzymes glycerol-3-phosphate acyltransferase 4 (AGPAT6) at the endoplasmic reticulum (ER) membrane (Cao et al., 2006; Chen et al., 2008).
Glycerophospholipids are first formed by the de novo (Kennedy) pathway using fatty acids activated as acyl-CoA donors. However, the acyl groups of glycerophospholipids are highly diverse and distributed in an asymmetric manner. Saturated and monounsaturated fatty acids are usually esterified at the sn-1 position, whereas polyunsaturated acyl groups are esterified at the sn-2 position. Subsequent acyl chain remodeling (Lands cycle) generates the diverse glycerophospholipid composition and asymmetry characteristic of cell membranes.
In the de novo pathway of glycerophospholipid biosynthesis, lysophosphatidic acid (LPA) is initially formed from glycerol 3-phosphate (G3P). Next, LPA is converted to PA by a LPA acyltransferase (AGPAT, also known as LPAAT), then PA is metabolized into two types of glycerol derivatives. The first is diacylglycerol (DAG) which is converted to triacylglycerol (TAG), PC, and PE. Subsequently, PS is synthesized from PC or PE. The second is cytidine diphosphate-diacylglycerol (CDP-DAG), which is processed into PI, PG, CL, and BMP. Each glycerophospholipid is involved in acyl chain remodeling via cleavage by phospholipases followed by reacylation by an acyltransferase.
Most of the glycerophospholipids are synthesized at the endoplasmic reticulum (ER), however, some, most notably cardiolipin, and BMP are synthesized in the mitochondrial and endosomal membranes respectively. Since the most of the glycerophospholipids are found in all membrane compartments, there must be extensive network of transport of glycerophospholipids from one membrane compartment to another via various mechanisms including diffusion through the cytosol, formation of transportation complexes, and diffusion via membrane contact sites (MCS) (Osman et al. 2011, Lebiedzinska et al. 2009, Lev 2010, Scherer & Schmitz 2011, Orso et al. 2011, Hermansson et al. 2011, Vance & Vance 2008).
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Acetylcholine from the synaptic cleft is degraded into inactive molecules, Cho and acetate by ACHE, which is located in the synaptic cleft (Weinstock & Groner 2008).
AcCho is synthesised in the cytoplasm of cholinergic neurons from acetyl-CoA and Cho by CHAT enzyme.
See recent review by Agarwal (2012, in press).
AGPAT1, 2, 3 and LPCAT1 have been characterized biochemically (AGPAT1, 2: Yamashita et al. 2007, West et al. 1997, Aguado and Campbell 1998, Gale et al. 2006; AGPAT3: Agarwal et al. 2006; LPCAT1: Nakanishi et al. 2006, Chen et al. 2006). Two additional proteins, AGPAT4 and AGPAT5, are inferred to have such activity based on studies of homologous mouse enzymes (Lu et al. 2005). These enzymes differ in their tissue specific patterns of expression in the body and in their preferences for specific acyl CoA molecules (Shindou and Shimizu 2009; Takeuchi and Reue 2009).
CTL1 is broadly expressed on leukocytes and endothelial cells (Wille et al. 2001). CTL2 is highly expressed in human inner ear and is the target of antibody-induced hearing loss (Nair et al. 2004).