Fatty acid 2-Hydroxylation in mammalian sphingolipid biology

Hiroko Hama1
1Department of Biochemistry and Molecular Biology, Medical University of South Carolina, Charleston, SC 29425

Tài liệu tham khảo

Pruett, 2008, Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols, J. Lipid Res., 49, 1621, 10.1194/jlr.R800012-JLR200 Deuel, 1951, Chemistry of the Phosphatides and Cerebrosides, vol. 1, 405 Kishimoto, 1963, Occurrence of 2-Hydroxy Fatty Acids in Animal Tissues, J. Lipid Res., 4, 139, 10.1016/S0022-2275(20)40339-6 Hoshi, 1973, Synthesis of cerebronic acid from lignoceric acid by rat brain preparation. Some properties and distribution of the α-hydroxylation system, J. Biol. Chem., 248, 4123, 10.1016/S0021-9258(19)43848-9 Akanuma, 1979, Synthesis of ceramides and cerebrosides containing both alpha-hydroxy and nonhydroxy fatty acids from lignoceroyl-CoA by rat brain microsomes, J. Biol. Chem., 254, 1050, 10.1016/S0021-9258(17)34166-2 Kishimoto, 1979, Fatty acid alpha-hydroxylation and its relation to myelination, Mol. Cell. Biochem., 28, 93, 10.1007/BF00223361 Shigematsu, 1990, Alpha-hydroxylation of lignoceroyl-CoA in rat brain microsomes: involvement of NADPH-cytochrome c reductase and topical distribution, Int. J. Biochem., 22, 1427, 10.1016/0020-711X(90)90233-S Shigematsu, 1987, Alpha-hydroxylation of lignoceroyl-CoA by a cyanide-sensitive oxygenase in rat brain microsomes, Int. J. Biochem., 19, 41, 10.1016/0020-711X(87)90121-2 Alderson, 2004, The human FA2H gene encodes a fatty acid 2-hydroxylase, J. Biol. Chem., 279, 48562, 10.1074/jbc.M406649200 Eckhardt, 2005, A mammalian fatty acid hydroxylase responsible for the formation of alpha-hydroxylated galactosylceramide in myelin, Biochem. J., 388, 245, 10.1042/BJ20041451 Edvardson, 2008, Mutations in the fatty acid 2-hydroxylase gene are associated with leukodystrophy with spastic paraparesis and dystonia, Am. J. Hum. Genet., 83, 643, 10.1016/j.ajhg.2008.10.010 Shanklin, 1998, Desaturation and related modifications of fatty acids, Annu. Rev. Plant Physiol. Plant Mol. Biol., 49, 611, 10.1146/annurev.arplant.49.1.611 Alderson, 2005, A novel method for the measurement of in vitro fatty acid 2-hydroxylase activity by gas chromatography-mass spectrometry, J. Lipid Res., 46, 1569, 10.1194/jlr.D500013-JLR200 Alderson, 2006, FA2H-dependent fatty acid 2-hydroxylation in postnatal mouse brain, J. Lipid Res., 47, 2772, 10.1194/jlr.M600362-JLR200 Wanders, 2003, Phytanic acid alpha-oxidation, new insights into an old problem: a review, Biochim. Biophys. Acta, 1631, 119, 10.1016/S1388-1981(03)00003-9 Mukherji, 2002, Utilization of sterol carrier protein-2 by phytanoyl-CoA 2-hydroxylase in the peroxisomal alpha oxidation of phytanic acid, Chem. Biol., 9, 597, 10.1016/S1074-5521(02)00139-4 Searls, 2005, Studies on the specificity of unprocessed and mature forms of phytanoyl-CoA 2-hydroxylase and mutation of the iron binding ligands, J. Lipid Res., 46, 1660, 10.1194/jlr.M500034-JLR200 Mizutani, 2008, 2-Hydroxy-ceramide synthesis by ceramide synthase family: enzymatic basis for the preference of FA chain length, J. Lipid Res., 49, 2356, 10.1194/jlr.M800158-JLR200 Uchida, 2007, Fatty acid 2-hydroxylase, encoded by FA2H, accounts for differentiation-associated increase in 2-OH ceramides during keratinocyte differentiation, J. Biol. Chem., 282, 13211, 10.1074/jbc.M611562200 Dahiya, 1985, Glycosphingolipids of fetal and adult sheep colonic mucosa, Lipids, 20, 331, 10.1007/BF02534198 Dahiya, 1986, Glycosphingolipid patterns of fetal and adult small intestinal mucosa in the sheep, Biochim. Biophys. Acta, 875, 220, 10.1016/0005-2760(86)90171-2 Dahiya, 1986, Distribution of glycosphingolipids of monkey small and large intestinal mucosa, Lipids, 21, 107, 10.1007/BF02534429 Schaeren-Wiemers, 1995, The UDP-galactose:ceramide galactosyltransferase: expression pattern in oligodendrocytes and Schwann cells during myelination and substrate preference for hydroxyceramide, J. Neurochem., 65, 2267, 10.1046/j.1471-4159.1995.65052267.x Futerman, 2004, The cell biology of lysosomal storage disorders, Nat. Rev. Mol. Cell Biol., 5, 554, 10.1038/nrm1423 Sugita, 1973, Fatty acid composition of free ceramides of kidney and cerebellum from a patient with Farber's disease, Lipids, 8, 401, 10.1007/BF02531715 Sugita, 1974, High performance liquid chromatography of ceramides: application to analysis in human tissues and demonstration of ceramide excess in Farber's disease, J. Lipid Res., 15, 223, 10.1016/S0022-2275(20)36799-7 Matsuda, 2004, Mutation in saposin D domain of sphingolipid activator protein gene causes urinary system defects and cerebellar Purkinje cell degeneration with accumulation of hydroxy fatty acid-containing ceramide in mouse, Hum. Mol. Genet., 13, 2709, 10.1093/hmg/ddh281 Kolter, 2005, Principles of lysosomal membrane digestion: stimulation of sphingolipid degradation by sphingolipid activator proteins and anionic lysosomal lipids, Annu. Rev. Cell Dev. Biol., 21, 81, 10.1146/annurev.cellbio.21.122303.120013 Kyogashima, 2008, Chemical and apoptotic properties of hydroxy-ceramides containing long-chain bases with unusual alkyl chain lengths, J. Biochem., 144, 95, 10.1093/jb/mvn050 Ji, 1995, Induction of apoptotic DNA fragmentation and cell death by natural ceramide, FEBS Lett., 358, 211, 10.1016/0014-5793(94)01428-4 Foulon, 2005, Breakdown of 2-hydroxylated straight chain fatty acids via peroxisomal 2-hydroxyphytanoyl-CoA lyase: a revised pathway for the alpha-oxidation of straight chain fatty acids, J. Biol. Chem., 280, 9802, 10.1074/jbc.M413362200 Kishimoto, 1959, Isolation and determination methods for brain cerebrosides, hydroxy fatty acids, and unsaturated and saturated fatty acids, J. Lipid Res., 1, 72, 10.1016/S0022-2275(20)39095-7 Kishimoto, 1959, Composition of cerebroside acids as a function of age, J. Lipid Res., 1, 79, 10.1016/S0022-2275(20)39096-9 Hajra, 1962, Biosynthesis of the cerebroside odd-numbered fatty acids, J. Lipid Res., 3, 327, 10.1016/S0022-2275(20)40405-5 Mead, 1963, A 1 carbon degradation of the long chain fatty acids of brain sphingolipids, J. Biol. Chem., 238, 1634, 10.1016/S0021-9258(18)81113-9 Norton, 1984, Isolation and characterization of myelin Dick, 2008, A novel locus for an autosomal recessive hereditary spastic paraplegia (SPG35) maps to 16q21-q23, Neurology, 71, 248, 10.1212/01.wnl.0000319610.29522.8a Zoller, 2008, Absence of 2-hydroxylated sphingolipids is compatible with normal neural development but causes late-onset axon and myelin sheath degeneration, J. Neurosci., 28, 9741, 10.1523/JNEUROSCI.0458-08.2008 Downing, 1992, Lipid and protein structures in the permeability barrier of mammalian epidermis, J. Lipid Res., 33, 301, 10.1016/S0022-2275(20)41520-2 Feingold, 2007, Thematic review series: skin lipids. The role of epidermal lipids in cutaneous permeability barrier homeostasis, J. Lipid Res., 48, 2531, 10.1194/jlr.R700013-JLR200 Holleran, 2006, Epidermal sphingolipids: metabolism, function, and roles in skin disorders, FEBS Lett., 580, 5456, 10.1016/j.febslet.2006.08.039 Makita, 1964, Biochemistry of Organ Glycolipids. Ii. Isolation of Human Kidney Glycolipids, J. Biochem., 55, 269, 10.1093/oxfordjournals.jbchem.a127880 Igisu, 1984, Glycolipids of the spinal cord, sciatic nerve, and systemic organs of the twitcher mouse, J. Neuropathol. Exp. Neurol., 43, 22, 10.1097/00005072-198401000-00002 Sprong, 1998, UDP-galactose:ceramide galactosyltransferase is a class I integral membrane protein of the endoplasmic reticulum, J. Biol. Chem., 273, 25880, 10.1074/jbc.273.40.25880 Bouhours, 1983, Developmental changes of hematoside of rat small intestine. Postnatal hydroxylation of fatty acids and sialic acid, J. Biol. Chem., 258, 299, 10.1016/S0021-9258(18)33256-3 Bouhours, 1985, Developmental changes of monohexosylceramide and free ceramide in the large intestine of the rat, J. Biochem., 98, 1359, 10.1093/oxfordjournals.jbchem.a135403 Bouhours, 1993, Developmental changes of glycosphingolipid composition of epithelia of rat digestive tract, Adv. Lipid Res., 26, 353 Riboni, 1992, Changes of the human liver GM3 ganglioside molecular species during aging, Eur. J. Biochem., 203, 107, 10.1111/j.1432-1033.1992.tb19834.x Pascher, 1976, Molecular arrangements in sphingolipids. Conformation and hydrogen bonding of ceramide and their implication on membrane stability and permeability, Biochim. Biophys. Acta, 455, 433, 10.1016/0005-2736(76)90316-3 Pascher, 1977, Molecular arrangements in sphingolipids. The crystal structure of cerebroside, Chem. Phys. Lipids, 20, 175, 10.1016/0009-3084(77)90033-0 Lofgren, 1977, Molecular arrangements of sphingolipids. The monolayer behavior of ceramides, Chem. Phys. Lipids, 20, 273, 10.1016/0009-3084(77)90068-8 Boggs, 1988, Influence of structural modifications on the phase behavior of semi- synthetic cerebroside sulfate, Biochim. Biophys. Acta, 938, 361, 10.1016/0005-2736(88)90134-4 Rapport, 1969, Immunochemical reactions of lipids, Prog. Allergy, 13, 273 Birkle, 2003, Role of tumor-associated gangliosides in cancer progression, Biochimie, 85, 455, 10.1016/S0300-9084(03)00006-3 Hakomori, 1996, Tumor malignancy defined by aberrant glycosylation and sphingo(glyco)lipid metabolism, Cancer Res., 56, 5309 Kiguchi, 1992, Glycosphingolipids of various human ovarian tumors: a significantly high expression of I3SO3GalCer and Lewis antigen in mucinous cystadenocarcinoma, Cancer Res., 52, 416 Ladisch, 1989, Aberrant fatty acyl alpha-hydroxylation in human neuroblastoma tumor gangliosides, J. Biol. Chem., 264, 12097, 10.1016/S0021-9258(18)80178-8 Nilsson, 1986, Detection of a ganglioside antigen associated with small cell lung carcinomas using monoclonal antibodies directed against fucosyl-GM1, Cancer Res., 46, 1403 Hakomori, 1984, Novel fucolipids accumulating in human adenocarcinoma. I. Glycolipids with di- or trifucosylated type 2 chain, J. Biol. Chem., 259, 4672, 10.1016/S0021-9258(17)43099-7 Yang, 1971, A sphingolipid having a novel type of ceramide and lacto-N-fucopentaose 3, J. Biol. Chem., 246, 1192, 10.1016/S0021-9258(19)76958-0 Ugorski, 1989, Glycosphingolipids of human urothelial cell lines with different grades of transformation, Glycoconj. J., 6, 303, 10.1007/BF01047850 Iwamori, 2007, Characteristic expression of Lewis-antigenic glycolipids in human ovarian carcinoma-derived cells with anticancer drug-resistance, J. Biochem., 141, 309, 10.1093/jb/mvm031 Kiguchi, 2006, Characteristic expression of globotriaosyl ceramide in human ovarian carcinoma-derived cells with anticancer drug resistance, Cancer Sci., 97, 1321, 10.1111/j.1349-7006.2006.00326.x Herrero, 2008, Levels of SCS7/FA2H-mediated fatty acid 2-hydroxylation determine the sensitivity of cells to antitumor PM02734, Cancer Res., 68, 9779, 10.1158/0008-5472.CAN-08-1981 Hannun, 1996, Functions of ceramide in coordinating cellular responses to stress, Science, 274, 1855, 10.1126/science.274.5294.1855 Okazaki, 1989, Sphingomyelin turnover induced by vitamin D3 in HL-60 cells. Role in cell differentiation, J. Biol. Chem., 264, 19076, 10.1016/S0021-9258(19)47268-2 Hannun, 2008, Principles of bioactive lipid signalling: lessons from sphingolipids, Nat. Rev. Mol. Cell Biol., 9, 139, 10.1038/nrm2329 Alderson, 2009, Fatty acid 2-hydroxylase regulates cAMP-induced cell cycle exit in D6P2T Schwannoma cells, J. Lipid Res., 50, 1203, 10.1194/jlr.M800666-JLR200 Clark, 1998, Involvement of MAP kinase in the cyclic AMP induction of myelin basic protein gene expression, Int. J. Dev. Neurosci., 16, 323, 10.1016/S0736-5748(98)00045-8 Friessen, 1997, Cyclin-dependent kinase inhibitor p27kip1 is expressed at high levels in cells that express a myelinating phenotype, J. Neurosci. Res., 50, 373, 10.1002/(SICI)1097-4547(19971101)50:3<373::AID-JNR3>3.0.CO;2-F Atanasoski, 2006, Cell cycle inhibitors p21 and p16 are required for the regulation of Schwann cell proliferation, Glia, 53, 147, 10.1002/glia.20263 Kannagi, 1983, Factors affecting expression of glycolipid tumor antigens: influence of ceramide composition and coexisting glycolipid on the antigenicity of gangliotriaosylceramide in murine lymphoma cells, Cancer Res., 43, 4997 Nakakuma, 1989, Monoclonal antibody to galactosylceramide: discrimination of structural difference in the ceramide moiety, FEBS Lett., 258, 230, 10.1016/0014-5793(89)81660-6 Binnington, 2002, Effect of globotriaosyl ceramide fatty acid alpha-hydroxylation on the binding by verotoxin 1 and verotoxin 2, Neurochem. Res., 27, 807, 10.1023/A:1020261125008 Angstrom, 1998, The lactosylceramide binding specificity of Helicobacter pylori, Glycobiology, 8, 297, 10.1093/glycob/8.4.297 Stromberg, 1990, Characterization of the binding of propionibacterium granulosum to glycosphingolipids adsorbed on surfaces. An apparent recognition of lactose which is dependent on the ceramide structure, J. Biol. Chem., 265, 11244, 10.1016/S0021-9258(19)38583-7 Stromberg, 1990, Characterization of the binding of Actinomyces naeslundii (ATCC 12104) and Actinomyces viscosus (ATCC 19246) to glycosphingolipids, using a solid-phase overlay approach, J. Biol. Chem., 265, 11251, 10.1016/S0021-9258(19)38584-9 Stromberg, 1988, Studies on the binding of bacteria to glycolipids. Two species of Propionibacterium apparently recognize separate epitopes on lactose of lactosylceramide, FEBS Lett., 232, 193, 10.1016/0014-5793(88)80415-0 Tang, 2001, Requirement of ceramide for adhesion of Helicobacter pylori to glycosphingolipids, FEBS Lett., 504, 31, 10.1016/S0014-5793(01)02759-4 Llado, 2008, Minerval Induces Apoptosis in Jurkat and Other Cancer Cells, J. Cell. Mol. Med., 10.1111/j.1582-4934.2008.00625.x Martinez, 2005, The repression of E2F-1 is critical for the activity of Minerval against cancer, J. Pharmacol. Exp. Ther., 315, 466, 10.1124/jpet.105.088716 Martinez, 2005, Membrane structure modulation, protein kinase C alpha activation, and anticancer activity of minerval, Mol. Pharmacol., 67, 531, 10.1124/mol.104.000778 Llado, 2009, Pivotal role of dihydrofolate reductase knockdown in the anticancer activity of 2-hydroxyoleic acid, Proc. Natl. Acad. Sci. U. S. A., 106, 13754, 10.1073/pnas.0907300106 Alemany, 2004, 2-hydroxyoleic acid: a new hypotensive molecule, Hypertension, 43, 249, 10.1161/01.HYP.0000107778.85528.b5 Borchert, 2008, 2-hydroxyoleic acid affects cardiomyocyte [Ca2+]i transient and contractility in a region-dependent manner, Am. J. Physiol. Heart Circ. Physiol., 294, H1948, 10.1152/ajpheart.01209.2007 Ahmed, 2009, Deorphanization of GPR109B as a receptor for the beta-oxidation intermediate 3-OH-octanoic acid and its role in the regulation of lipolysis, J. Biol. Chem., 284, 21928, 10.1074/jbc.M109.019455 Bouhours, 1984, Identification of free ceramide in human erythrocyte membrane, J. Lipid Res., 25, 613, 10.1016/S0022-2275(20)37774-9 Hara, 1975, Long chain base and fatty acid compositions of equine kidney sphingolipids, J. Biochem., 78, 527, 10.1093/oxfordjournals.jbchem.a130937 Bouhours, 1979, Free ceramide, sphingomyelin, and glucosylceramide of isolated rat intestinal cells, J. Lipid Res., 20, 879, 10.1016/S0022-2275(20)40019-7 Iwamori, 1979, Analysis and quantitation of free ceramide containing nonhydroxy and 2-hydroxy fatty acids, and phytosphingosine by high-performance liquid chromatography, J. Lipid Res., 20, 86, 10.1016/S0022-2275(20)40654-6 Yasugi, 1991, Composition of long chain bases in ceramide of the guinea pig Harderian gland, J. Biochem., 110, 202, 10.1093/oxfordjournals.jbchem.a123557 Karlsson, 1969, The presence of hydroxy fatty acids in sphingomyelins of bovine rennet stomach, Biochim. Biophys. Acta, 176, 660, 10.1016/0005-2760(69)90239-2 Breimer, 1975, Distribution of molecular species of sphingomyelins in different parts of bovine digestive tract, J. Lipid Res., 16, 189, 10.1016/S0022-2275(20)36725-0 Breimer, 1975, Presence of phytosphingosine combined with 2-hydroxy fatty acids in sphingomyelins of bovine kidney and intestinal mucosa, Lipids, 10, 17, 10.1007/BF02532188 Morrison, 1970, Polar lipids in bovine milk. II. Long-chain bases, normal and 2-hydroxy fatty acids, and isomeric cis and trans monoenoic fatty acids in the sphingolipids, Biochim. Biophys. Acta, 202, 460, 10.1016/0005-2760(70)90116-5 Yasugi, 1990, Composition of long-chain bases in sphingomyelin of the guinea pig Harderian gland, Biochem. Cell Biol., 68, 154, 10.1139/o90-021 Robinson, 1992, Novel molecular species of sphingomyelin containing 2-hydroxylated polyenoic very-long-chain fatty acids in mammalian testes and spermatozoa, J. Biol. Chem., 267, 1746, 10.1016/S0021-9258(18)46009-7 Nilsson, 1982, Characterization and quantitative determination of gangliosides and neutral glycosphingolipids in human liver, J. Lipid Res., 23, 327, 10.1016/S0022-2275(20)38163-3 Martensson, 1966, Neutral glycolipids of human kidney isolation, identification, and fatty acid composition, Biochim. Biophys. Acta, 116, 296, 10.1016/0005-2760(66)90012-9 Breimer, 1985, The specific glycosphingolipid composition of human ureteral epithelial cells, J. Biochem., 98, 1169, 10.1093/oxfordjournals.jbchem.a135383 Mikami, 1992, Menstrual cycle-associated expression of 2-hydroxy fatty acyl phytosphingosine-containing GlcCer, LacCer and Gb3Cer in human uterine endometrium, Biochim. Biophys. Acta, 1125, 104, 10.1016/0005-2760(92)90162-O Karlsson, 1973, Separation of monoglycosylceramides (cerebrosides) of bovine kidney into subgroups and characterization by mass spectrometry, Biochim. Biophys. Acta, 306, 317, 10.1016/0005-2760(73)90237-3 Bouhours, 1985, Developmental changes of the lipidic part of the neutral glycosphingolipids of the rat stomach, J. Biol. Chem., 260, 2172, 10.1016/S0021-9258(18)89533-3 Bouhours, 1977, Rat intestinal glycolipids. III. Fatty acids and long chain bases of glycolipids from villus and crypt cells, Biochim. Biophys. Acta, 487, 51, 10.1016/0005-2760(77)90043-1 Breimer, 1982, Studies on differentiating epithelial cells of rat small intestine. Alterations in the lipophilic part of glycosphingolipids during cell migration from crypt villus tip, Biochim. Biophys. Acta, 710, 415, 10.1016/0005-2760(82)90125-4 Umesaki, 1981, Presence of asialo GM1 and glucosylceramide in the intestinal mucosa of mice and induction of fucosyl asialo GM1 by conventionalization of germ-free mice, J. Biochem., 90, 1731, 10.1093/oxfordjournals.jbchem.a133650 Seyfried, 1978, Isolation and characterization of human liver hematoside, J. Lipid Res., 19, 538, 10.1016/S0022-2275(20)41284-2 Angstrom, 1981, Separation and characterization of hematosides with different sialic acids and ceramides from rat small intestine. Different composition of epithelial cells versus non-epithelial tissue and of duodenum versus jejunum-ileum, J. Biochem., 90, 909, 10.1093/oxfordjournals.jbchem.a133579 Bouhours, 1988, Tissue-specific expression of GM3(NeuGc) and GD3(NeuGc) in epithelial cells of the small intestine of strains of inbred rats. Absence of NeuGc in intestine and presence in kidney gangliosides of brown Norway and spontaneously hypertensive rats, J. Biol. Chem., 263, 15540, 10.1016/S0021-9258(19)37622-7 Rauvala, 1976, Gangliosides of human kidney, J. Biol. Chem., 251, 7517, 10.1016/S0021-9258(17)32880-6 Ito, 1969, Proteolytic microdissection of smooth-surfaced vesicles of liver microsomes, J. Cell Biol., 40, 179, 10.1083/jcb.40.1.179 Dunn, 1998, Synthesis of monohydroxylated inositolphosphorylceramide (IPC-C) in Saccharomyces cerevisiae requires Scs7p, a protein with both a cytochrome b5-like domain and a hydroxylase/desaturase domain, Yeast, 14, 311, 10.1002/(SICI)1097-0061(19980315)14:4<311::AID-YEA220>3.0.CO;2-B Mitchell, 1997, Fah1p, a Saccharomyces cerevisiae cytochrome b5 fusion protein, and its Arabidopsis thaliana homolog that lacks the cytochrome b5 domain both function in the alpha-hydroxylation of sphingolipid-associated very long chain fatty acids, J. Biol. Chem., 272, 28281, 10.1074/jbc.272.45.28281