{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,20]],"date-time":"2025-10-20T18:38:52Z","timestamp":1760985532616},"reference-count":36,"publisher":"Japan Oil Chemists' Society","issue":"3","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Oleo Sci."],"published-print":{"date-parts":[[2017]]},"DOI":"10.5650\/jos.ess16150","type":"journal-article","created":{"date-parts":[[2017,2,9]],"date-time":"2017-02-09T22:09:38Z","timestamp":1486678178000},"page":"285-295","source":"Crossref","is-referenced-by-count":6,"title":["Characterization of a Novel Rhamnose-containing Acidic Glycosphingolipid from the Ascidian &lt;i&gt;Haloc&lt;\/i&gt;&lt;i&gt;ynthia aurantium&lt;\/i&gt;"],"prefix":"10.5650","volume":"66","author":[{"given":"Hisao","family":"Kojima","sequence":"first","affiliation":[{"name":"Department of Bioinformatics, College of Life Sciences, Ritsumeikan University"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ryota","family":"Shinohara","sequence":"additional","affiliation":[{"name":"Department of Bioinformatics, College of Life Sciences, Ritsumeikan University"},{"name":"Division of Pharmacology, Graduate School of Medicine, Kobe University"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Saki","family":"Itonori","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masahiro","family":"Ito","sequence":"additional","affiliation":[{"name":"Department of Bioinformatics, College of Life Sciences, Ritsumeikan University"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"3621","reference":[{"key":"1","doi-asserted-by":"crossref","unstructured":"1) Hakomori, S. Cell adhesion\/recognition and signal transduction through glycosphingolipid microdomain. Glycoconj. J. 17, 143-151 (2000).","DOI":"10.1023\/A:1026524820177"},{"key":"2","doi-asserted-by":"crossref","unstructured":"2) Saito, M.; Kitamura, H.; Sugiyama, K. Occurrence of gangliosides in the common squid and pacific octopus among protostomia. Biochim. Biophys. Acta 1511, 271-280 (2001).","DOI":"10.1016\/S0005-2736(01)00282-6"},{"key":"3","doi-asserted-by":"crossref","unstructured":"3) Saito, M.; Kitamura, H.; Sugiyama, K. Occurrence and tissue distribution of c-series gangliosides in the common squid Todarodes pacificus. Comp. Biochem. Physiol. B Biochem. Mol. Biol. 131, 433-441 (2002).","DOI":"10.1016\/S1096-4959(01)00517-6"},{"key":"4","doi-asserted-by":"crossref","unstructured":"4) Itonori, S., Sugita, M. Glycophylogenetic aspects of lower animals. in Comprehensive Glycoscience from Chemistry to Systems Biology 3: Biochemistry of Glycoconjugate Glycans; Carbohydrate-Mediated Interactions. (Kamerling, J.P. ed.), Elsevier, Oxford, pp. 253-284 (2007).","DOI":"10.1016\/B978-044451967-2\/00050-7"},{"key":"5","unstructured":"5) Hori, T.; Sugita, M.; Ando, S.; Tsukada, K.; Shiota, K.; Tsuzuki, M.; Itasaka, O. Isolation and characterization of a 4-O-methylglucuronic acid-containing glycosphingolipid from spermatozoa of a fresh water bivalve, Hyriopsis schlegelii. J. Biol. Chem. 258, 2239-2245 (1983)."},{"key":"6","doi-asserted-by":"crossref","unstructured":"6) Sugita, M.; Nakae, H.; Yamamura, T.; Takamiya, Y.; Itasaka, O.; Hori, T. The occurrence of glycosphingolipids containing mannose in the sea-water bivalve, Meretrix lusoria (Hamaguri). J. Biochem. 98, 27-34 (1985).","DOI":"10.1093\/oxfordjournals.jbchem.a135268"},{"key":"7","doi-asserted-by":"crossref","unstructured":"7) Sugita, M.; Inoue, T.; Itasaka, O.; Hori, T. The localization of 4-O-methylglucuronic acid-containing glycosphingolipid on the cell surface of bivalve spermatozoa by use of an immunological method. J. Biochem. 95, 737-742 (1984).","DOI":"10.1093\/oxfordjournals.jbchem.a134664"},{"key":"8","doi-asserted-by":"crossref","unstructured":"8) Sutherland, I.W. Bacterial Exopolysaccharides. in Comprehensive Glycoscience From Chemistry to Systems Biology 2: Analysis of Glycans; Polysaccharide Functional Properties. (Kamerling, J.P. ed.), Elsevier, Oxford, pp. 521\u2013558 (2007).","DOI":"10.1016\/B978-044451967-2\/00133-1"},{"key":"9","doi-asserted-by":"crossref","unstructured":"9) Waldron, K.W.; Faulds, C.B. Cell wall polysaccharides: composition and structure. in Comprehensive Glycoscience from Chemistry to Systems Biology 1: Introduction to Glycoscience Synthesis of Carbohydrates. (Kamerling, J.P. ed.), Elsevier, Oxford, pp. 181-200 (2007).","DOI":"10.1016\/B978-044451967-2\/00005-2"},{"key":"10","doi-asserted-by":"crossref","unstructured":"10) Previato, J.O.; Wait, R.; Jones, C.; Mendon\u00e7a-Previato, L. Structural analysis of novel rhamnose-branched oligosaccharides from the glycophosphosphingolipids of Leptomonas samueli. Glycoconj. J. 11, 23-33 (1994).","DOI":"10.1007\/BF00732429"},{"key":"11","doi-asserted-by":"crossref","unstructured":"11) Costantino, V.; Fattorusso, E.; Imperatore, C.; Mangoni, A. Glycolipids from sponges. 13. Clarhamnoside, the first rhamnosylated alpha-galactosylceramide from Agelas clathrodes. Improving spectral strategies for glycoconjugate structure determination. J. Org. Chem. 69, 1174-1179 (2004).","DOI":"10.1021\/jo034865h"},{"key":"12","doi-asserted-by":"crossref","unstructured":"12) Shenkar, N.; Swalla B.J. Global diversity of Ascidiacea. PLoS One 6, e20657 (2011).","DOI":"10.1371\/journal.pone.0020657"},{"key":"13","doi-asserted-by":"crossref","unstructured":"13) Lemaire, P.; Smith, W.C.; Nishida, H. Ascidians and the plasticity of the chordate developmental program. Curr. Biol. 18, R620-R631 (2008).","DOI":"10.1016\/j.cub.2008.05.039"},{"key":"14","doi-asserted-by":"crossref","unstructured":"14) Putnam, N.H.; Butts, T.; Ferrier, D.E.; Furlong, R.F.; Hellsten, U.; Kawashima, T.; Robinson-Rechavi, M.; Shoguchi, E.; Terry, A.; Yu, J.K.; Benito-Guti\u00e9rrez, E.L.; Dubchak, I.; Garcia-Fern\u00e0ndez, J.; Gibson-Brown, J.J.; Grigoriev, I.V.; Horton, A.C.; de Jong, P.J.; Jurka, J.; Kapitonov, V.V.; Kohara, Y.; Kuroki, Y.; Lindquist, E.; Lucas, S.; Osoegawa, K.; Pennacchio, L.A.; Salamov, A.A.; Satou, Y.; Sauka-Spengler, T.; Schmutz, J.; Shin-I, T.; Toyoda, A.; Bronner-Fraser, M.; Fujiyama, A.; Holland, L.Z.; Holland, P.W.; Satoh, N.; Rokhsar, D.S. The amphioxus genome and the evolution of the chordate karyotype. Nature 453, 1064-1071 (2008).","DOI":"10.1038\/nature06967"},{"key":"15","doi-asserted-by":"crossref","unstructured":"15) Hirose, E.; Kimura, S.; Itoh, T.; Nishikawa, J. Tunic morphology and cellulosic components of pyrosomas, doliolids, and salps (thaliacea, urochordata). Biol. Bull. 196, 113-120 (1999).","DOI":"10.2307\/1543173"},{"key":"16","doi-asserted-by":"crossref","unstructured":"16) Dehal, P.; Satou, Y.; Campbell, R.K.; Chapman, J.; Degnan, B.; De Tomaso, A. et al. The draft genome of Ciona intestinalis: insights into chordate and vertebrate origins. Science 298, 2157-2167 (2002).","DOI":"10.1126\/science.1080049"},{"key":"17","doi-asserted-by":"crossref","unstructured":"17) Nakashima, K.; Yamada, L.; Satou, Y.; Azuma, J.; Satoh, N. The evolutionary origin of animal cellulose synthase. Dev. Genes Evol. 214, 81-88 (2004).","DOI":"10.1007\/s00427-003-0379-8"},{"key":"18","doi-asserted-by":"crossref","unstructured":"18) Yamada, S.; Matsumuro, Y.; Inoue, T.; Kitamura, T.; Itonori, S.; Sugita, M.; Ito, M.A Novel sulfatide, GlcCer-I6 sulfate, from the ascidian Ciona intestinalis. J. Oleo Sci. 56, 129-136 (2007).","DOI":"10.5650\/jos.56.129"},{"key":"19","doi-asserted-by":"crossref","unstructured":"19) Yu, R.K.; Yanagisawa, M.; Ariga, T. Glycosphingolipid structures. in Comprehensive Glycoscience 1: Introduction to Glycoscience Synthesis of Carbohydrates. (Kamerling, J.P. ed.), Elsevier, Oxford, pp. 73-122 (2007).","DOI":"10.1016\/B978-044451967-2\/00003-9"},{"key":"20","doi-asserted-by":"crossref","unstructured":"20) Ito, M.; Matsumuro, Y.; Yamada, S.; Kitamura, T.; Itonori, S.; Sugita, M. Isolation and characterization of a novel uronic acid-containing acidic glycosphingolipid from the ascidian Halocynthia roretzi. J. Lipid Res. 48, 96-103 (2007).","DOI":"10.1194\/jlr.M600296-JLR200"},{"key":"21","doi-asserted-by":"crossref","unstructured":"21) Tomono, T.; Kojima, H.; Fukuchi, S.; Tohsato, Y.; Ito, M. Investigation of glycan evolution based on a comprehensive analysis of glycosyltransferases using phylogenetic profiling. Biophys. Physicobiol. 12, 57-68 (2015).","DOI":"10.2142\/biophysico.12.0_57"},{"key":"22","doi-asserted-by":"crossref","unstructured":"22) Svennerholm, L. The quantitative estimation of cerebrosides in nervous tissue. J. Neurochem. 1, 42-53 (1956).","DOI":"10.1111\/j.1471-4159.1956.tb12053.x"},{"key":"23","doi-asserted-by":"crossref","unstructured":"23) Dittmer, J.C.; Lester. R.L. A simple, specific spray for the detection of phospholipids of thin-layer chromatograms. J. Lipid Res. 5, 126-127 (1964).","DOI":"10.1016\/S0022-2275(20)40272-X"},{"key":"24","doi-asserted-by":"crossref","unstructured":"24) Itonori, S.; Takahashi, M.; Kitamura, T.; Aoki, K.; Dulaney, J.T.; Sugita, M. Microwave-mediated analysis for sugar, fatty acid, and sphingoid compositions of glycosphingolipids. J. Lipid Res. 45, 574-581 (2004).","DOI":"10.1194\/jlr.D300030-JLR200"},{"key":"25","doi-asserted-by":"crossref","unstructured":"25) Gaver, R.C.; Sweeley, C.C. Methods for methanolysis of sphingolipids and direct determination of long-chain bases by gas chromatography. J. Am. Oil Chem. Soc. 42, 294-298 (1965).","DOI":"10.1007\/BF02540132"},{"key":"26","doi-asserted-by":"crossref","unstructured":"26) Ciucanu, I.; Kerek, F. A simple and rapid method for the permethylation of carbohydrates. Carbohydr. Res. 131, 209-217 (1984).","DOI":"10.1016\/0008-6215(84)85242-8"},{"key":"27","doi-asserted-by":"crossref","unstructured":"27) Taylor, R.L.; Conrad. H.E. Stoichiometric depolymerization of polyuronides and glycosaminoglycuronans to monosaccharides following reduction of their carbodiimide-activated carboxyl group. Biochem. 11, 1383-1388 (1972).","DOI":"10.1021\/bi00758a009"},{"key":"28","doi-asserted-by":"crossref","unstructured":"28) Itonori, S.; Hiratsuka, M.; Sonku, N.; Tsuji, H.; Itasaka, O.; Hori, T.; Sugita, M. Immunogenic properties of mannose-containing ceramide disaccharide and immunochemical detection of its hapten in the two kinds of crustacean, Euphausia superba and Macrobrachium nipponense. Biochim. Biophys. Acta 1123, 263-268 (1992).","DOI":"10.1016\/0005-2760(92)90005-G"},{"key":"29","doi-asserted-by":"crossref","unstructured":"29) Kojima, H.; Shimizu, T.; Sugita, M.; Itonori, S.; Fujita, N.; Ito, M. Biochemical studies on sphingolipids of Artemia franciscana: novel neutral glycosphingolipids. J. Lipid Res. 52, 308-317 (2011).","DOI":"10.1194\/jlr.M010173"},{"key":"30","doi-asserted-by":"crossref","unstructured":"30) Weske, B.; Dennis, R.D.; Helling, F.; Keller, M.; Nores, G.A.; Peter-Katalinic, J.; Egge, H.; Dabrowski, U.; Wiegandt, H. Glycosphingolipids in insects. Chemical structures of two variants of a glucuronic-acid-containing ceramide hexasaccharide from a pupae of Calliphora vicina (Insecta: Diptera), distinguished by a N-acetylglucosamine-bound phosphoethanolamine sidechain. Eur. J. Biochem. 191, 379-388 (1990).","DOI":"10.1111\/j.1432-1033.1990.tb19133.x"},{"key":"31","doi-asserted-by":"crossref","unstructured":"31) Vinogradov, E.; Petersen, B.O.; Duus, J.\u00d8.; Radziejewska-Lebrecht, J. The structure of the polysaccharide part of the LPS from Serratia marcescens serotype O19, including linkage region to the core and the residue at the non-reducing end. Carbohydr. Res. 338, 2757-2761 (2003).","DOI":"10.1016\/j.carres.2003.08.011"},{"key":"32","doi-asserted-by":"crossref","unstructured":"32) Aiello, A.; Fattorusso, E.; Mangoni, A.; Menna, M. Sulcaceramide, a novel triglycosylceramide from the marine ascidian Microcosmus sulcatus. Eur. J. Org. Chem. 2002, 1047-1050 (2002).","DOI":"10.1002\/1099-0690(200203)2002:6<1047::AID-EJOC1047>3.0.CO;2-2"},{"key":"33","doi-asserted-by":"crossref","unstructured":"33) McNeil, M.; Daffe, M.; Brennan, P.J. Evidence for the nature of the link between the arabinogalactan and peptidoglycan of mycobacterial cell walls. J. Biol. Chem. 265, 18200-18206 (1990).","DOI":"10.1016\/S0021-9258(17)44738-7"},{"key":"34","doi-asserted-by":"crossref","unstructured":"34) Maehashi, E.; Sato, C.; Ohta, K.; Harada, Y.; Matsuda, T.; Hirohashi, N.; Lennarz, W.J.; Kitajima, K. Identification of the sea urchin 350-kDa sperm-binding protein as a new sialic acid-binding lectin that belongs to the heat shock protein 110 family: implication of its binding to gangliosides in sperm lipid rafts in fertilization. J. Biol. Chem. 278, 42050-42057 (2003).","DOI":"10.1074\/jbc.M307493200"},{"key":"35","doi-asserted-by":"crossref","unstructured":"35) White, D.; Weerachatyanukul, W.; Gadella, B.; Kamolvarin, N.; Attar, M.; Tanphaichitr, N. Role of sperm sulfogalactosylglycerolipid in mouse sperm-zona pellucida binding. Biol. Reprod. 63, 147-155 (2000).","DOI":"10.1095\/biolreprod63.1.147"},{"key":"36","unstructured":"36) Schmelz, E.M; Bushnev, A.S; Dillehay, D.L; Sullards, M.C; Liotta, D.C; Merrill, A.H. Jr. Ceramide-beta-D-glucuronide: synthesis, digestion, and suppression of early markers of colon carcinogenesis. Cancer Res. 59, 5768-72 (1999)."}],"container-title":["Journal of Oleo Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/jos\/66\/3\/66_ess16150\/_pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,7,23]],"date-time":"2022-07-23T22:42:10Z","timestamp":1658616130000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/jos\/66\/3\/66_ess16150\/_article"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017]]},"references-count":36,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2017]]}},"URL":"https:\/\/doi.org\/10.5650\/jos.ess16150","relation":{},"ISSN":["1345-8957","1347-3352"],"issn-type":[{"value":"1345-8957","type":"print"},{"value":"1347-3352","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017]]}}}