Identification of glucosylceramides containing sphingatrienine in maize and rice using ion trap mass spectrometry

Lipids

Volumn 45, Issue 5, 2010, Pages 451-455

  Sugawara, Tatsuya ^a   Duan, Jingjing ^a   Aida, Kazuhiko ^b   Tsuduki, Tsuyoshi ^c   Hirata, Takashi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Kanagawa 243 0041   (Japan)

^c TOHOKU UNIVERSITY   (Japan)

Author keywords

Glycosphingolipids; HPLC (High performance liquid chromatography); Mass spectrometry (MS); Plant lipids; Sphingoid bases

Indexed keywords

4 HYDROXY ,8 SPHINGENINE; 4,8 SPHINGADIENINE; FATTY ACID; GLUCOSYLCERAMIDE; SPHINGANINE; SPHINGATRIENINE; SPHINGENINE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION TRAP MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY; MAIZE; NONHUMAN; PROTEIN ANALYSIS; REVERSED PHASE LIQUID CHROMATOGRAPHY; RICE; SEPARATION TECHNIQUE;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCOSYLCERAMIDES; ORYZA SATIVA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPHINGOSINE; ZEA MAYS;

EMBRYOPHYTA; SPHINGOIDEA; ZEA MAYS;

EID: 77953232358     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-010-3417-0     Document Type: Article

References (29)

1. S Spiegel AH Merrill Jr 1996 Sphingolipid metabolism and cell growth regulation FASEB J 10 1388 1397 1:CAS:528:DyaK28XmsVSgu7w%3D 8903509
2. O Cuvillier 2002 Sphingosine in apoptosis signaling Biochim Biophys Acta 1585 153 162 1:CAS:528:DC%2BD3sXivVOquw%3D%3D 12531549
3. YA Hannun LM Obeid 2008 Principles of bioactive lipid signaling: lessons from sphingolipids Nat Rev Mol Cell Biol 9 139 150 10.1038/nrm2329 1:CAS:528:DC%2BD1cXovFOntg%3D%3D 18216770 (Pubitemid 351158911)
4. RD Duan Å Nilsson 2009 Metabolism of sphingolipids in the gut and its relation to inflammation and cancer development Prog Lipid Res 4 62 72 10.1016/j.plipres.2008.04.003
5. EM Schmelz 2004 Sphingolipids in the chemoprevention of colon cancer Front Biosci 9 2632 2639 10.2741/1422 1:CAS:528:DC%2BD2cXls1entLo%3D 15358586
6. EM Schmelz MC Sullards DL Dillehay AH Merrill Jr 2000 Colonic cell proliferation and aberrant crypt formation are inhibited by dietary glycosphingolipids in 1,2-dimethylhydrazine-treated CF1 mice J Nutr 130 522 527 1:CAS:528:DC%2BD3cXhsFChu7Y%3D 10702579
7. EM Schmelz PC Roberts EM Kustin LA Lemonnier MC Sullards DL Dillehay AH Merrill Jr 2001 Modulation of intracellular β-catenin localization and intestinal tumorigenesis in vivo and in vitro by sphingolipids Cancer Res 61 6723 6729 1:CAS:528:DC%2BD3MXntFaisL4%3D 11559543
8. K Aida M Kinoshita M Tanji T Sugawara M Tamura J Ono N Ueno M Ohnishi 2005 Prevention of aberrant crypt foci formation by dietary maize and yeast cerebrosides in 1,2-dimethylhydrazine-treated mice J Oleo Sci 54 45 49 1:CAS:528:DC%2BD2MXmsVKq
9. M Kinoshita K Aida Y Tokuji T Sugawara M Ohnishi 2009 Effects of dietary plant cerebroside on gene expression in the large intestine of 1, 2-dimethylhydrazine (DMH)-treated mice determined by DNA microarray analysis J Food Lipids 16 200 208 10.1111/j.1745-4522.2009.01141.x 1:CAS:528: DC%2BD1MXptVaqsLw%3D
10. K Tsuji S Mitsutake J Ishikawa Y Takagi M Akiyama H Shimizu T Tomiyama Y Igarashi 2006 Dietary glucosylceramide improves skin barrier function in hairless mice J Dermatol Sci 44 101 107 10.1016/j.jdermsci.2006.08.005 1:CAS:528:DC%2BD28XhtVGju77N 17000082 (Pubitemid 44499011)
11. I Duivenvoorden PJ Voshol PC Rensen W van Duyvenvoorde JA Romijn JJ Emeis LM Havekes WF Nieuwenhuizen 2006 Dietary sphingolipids lower plasma cholesterol and triacylglycerol and prevent liver steatosis in APOE*3Leiden mice Am J Clin Nutr 84 312 321 1:CAS:528:DC%2BD28XosVehs70%3D 16895877
12. M Kinoshita N Hori K Aida T Sugawara M Ohnishi 2007 Prevention of melanin formation by yeast cerebroside in B16 mouse melanoma cells J Oleo Sci 56 645 648 1:CAS:528:DC%2BD2sXhtl2rurfI 17992005
13. P Sperling E Heinz 2003 Plant sphingolipids: structural diversity, biosynthesis, first gene and functions Biochim Biophys Acta 1632 1 15 1:CAS:528:DC%2BD3sXktVyisbg%3D 12782146
14. N Bartke A Fischbeck HU Humpf 2006 Analysis of sphingolipids in potatoes (Solanum tuberosum L.) and sweet potatoes (Ipomoea batatas (L.) Lam.) by reversed phase high-performance liquid chromatography electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) Mol Nutr Food Res 50 1201 1211 10.1002/mnfr.200600140 1:CAS:528:DC%2BD2sXmsFensQ%3D%3D 17103377 (Pubitemid 46032206)
15. RL Shaner JC Allegood H Park E Wang S Kelly CA Haynes MC Sullards AH Merrill Jr 2009 Quantitative analysis of sphingolipids for lipidomics using triple quadrupole and quadrupole linear ion trap mass spectrometers J Lipid Res 50 1692 1707 10.1194/jlr.D800051-JLR200 1:CAS:528:DC%2BD1MXovV2lsr8%3D 19036716
16. T Sugawara K Aida J Duan T Hirata 2010 Analysis of glucosylceramides from various sources by liquid chromatography-ion trap mass spectrometry J Oleo Sci 59 387 394
17. R Duran E Zubia MJ Ortega S Naranjo J Salva 1998 Phallusides, new glucosphingolipids from the ascidian Phallusia fumigate Tetrahedron 54 14597 14602 10.1016/S0040-4020(98)00917-X 1:CAS:528:DyaK1cXnslejt78%3D (Pubitemid 28526868)
18. W Jin KL Rinehart EA Jares-Erijman 1994 Ophidiacerebrosides: cytotoxic glycosphingolipids containing a novel sphingosine from a sea star J Org Chem 59 144 147 10.1021/jo00080a023 1:CAS:528:DyaK2cXntlOgtQ%3D%3D
19. ME Diaz de Vivar AM Seldes MS Maier 2002 Two novel glucosylceramides from gonads and body walls of the Patagonian starfish Allostichaster inaequalis Lipids 37 597 603 10.1007/s11745-002-0938-7 1:CAS:528:DC%2BD38Xlt1Slsbw%3D 12120959
20. P Sperling S Franke S Lüthje E Heinz 2005 Are glucocerebrosides the predominant sphingolipids in plant plasma membranes? Plant Physiol Biochem 43 1031 1038 10.1016/j.plaphy.2005.10.004 1:CAS:528:DC%2BD28XhsFKqtL4%3D 16386430 (Pubitemid 43243622)
21. T Sugawara M Kinoshita M Ohnishi J Nagata M Saito 2003 Digestion of maize sphingolipids in rats and uptake of sphingadienine by Caco-2 cells J Nutr 133 2777 2782 1:CAS:528:DC%2BD3sXntlalu7k%3D 12949364
22. D Warnecke E Heinz 2003 Recently discovered function of glucosylceramides in plants and fungi Cell Mol Life Sci 60 919 941 1:CAS:528:DC%2BD3sXlt1aitLo%3D 12827281
23. Y Ohashi T Tanaka S Akashi S Morimoto Y Kishimoto Y Nagai 2000 Squid nerve sphingomyelin containing an unusual sphingoid base J Lipid Res 41 1118 1124 1:CAS:528:DC%2BD3cXltF2qt78%3D 10884294
24. RG Shu FW Wang YM Yang YX Liu RX Tan 2004 Antibacterial and xanthine oxidase inhibitory cerebrosides from Fusarium sp. IFB-121, an endophytic fungus in Quercus variabilis Lipids 39 667 673 10.1007/s11745-004-1280-9 1:CAS:528:DC%2BD2cXhtVSjurzN 15588024 (Pubitemid 39488885)
25. T Sugawara N Zaima A Yamamoto S Sakai R Noguchi T Hirata 2006 Isolation of sphingoid bases of sea cucumber cerebrosides and their cytotoxicity against human colon cancer cells Biosci Biotechnol Biochem 70 2906 2912 10.1271/bbb.60318 1:CAS:528:DC%2BD2sXktVGrsw%3D%3D 17151482 (Pubitemid 46021548)
26. H Imai M Ohnishi K Hotsubo M Kojima S Ito 1997 Sphingoid base composition of cerebrosides from plant leaves Biosci Biotechnol Biochem 61 351 353 10.1271/bbb.61.351 1:CAS:528:DyaK2sXhs1KjsbY%3D
27. T Sugawara T Miyazawa 1999 Separation and determination of glycolipids from edible plant sources by high-performance liquid chromatography and evaporative light-scattering detection Lipids 34 1231 1237 10.1007/s11745-999- 0476-3 1:CAS:528:DyaK1MXnvFKmsbs%3D 10606047
28. T Sugawara M Kinoshita M Ohnishi T Tsuzuki T Miyazawa J Nagata T Hirata M Saito 2004 Efflux of sphingoid bases by P-glycoprotein in human intestinal Caco-2 cells Biosci Biotechnol Biochem 68 2541 2546 10.1271/bbb.68.2541 1:CAS:528:DC%2BD2MXltlygsA%3D%3D 15618625 (Pubitemid 40218184)
29. Sugawara T, Tsuduki T, Yano S, Hirose M, Duan J, Aida K, Ikeda I, Hirata T (2010) Intestinal absorption of dietary maize glucosylceramide in lymphatic duct cannulated rats. J Lipid Res (in press)